Cate and I almost didn’t build this course.

A few months ago, we had a spurt of AI learning and were feeling confident about our progress. Then we spent a few weeks focused on our first DRI Your Career cohort and resurfaced suddenly feeling behind. The tools are changing every week, sometimes every day.

That feeling of being behind (and also Cate’s reminder that on top of being engineering leaders, we are also experienced coaches who have helped tons of people navigate mindset shifts) became fuel for the course. Turns out, a lot of people are wondering the same thing: whether they’re behind, and whether the years they poured into their engineering career still matter.

This post is a little peek behind the scenes of what it was like for Cate and I to build a Navigating the AI Shift course while continuing to navigate this shift ourselves.

Building our course platform

My own building with AI journey has been one of awe and also often frustration. In my last post about being a human engineer in an AI era, I shared some of my earlier projects, and as my own confidence grows with each project, so does my intuition about what I can build and how I can most easily build it.

Late last year, Cate and I had been collaborating on the content of our first course, and I had taken on the task of researching a few different course platforms to figure out where we’d want to host the course.

I happened to have a few precious hours at a coffee shop. Tired of copy/pasting our course content from Google Docs into chatgpt for feedback, I moved it all into local files and opened up Claude Code to iterate on the with full context. Wait a sec, I thought, since all the content is all here, why can’t I just build the platform to host the course? We had very basic needs — login, modules with written content, an audio file, and the ability to submit exercises. “I think I’m going to try to build a basic platform for our course,” I texted Cate, and within a few hours, while Cate was asleep in Ireland, I had basic functionality up and running.

Since then, Cate has joined me in the github repository, and we’ve had our fair share of breaking production, botched database migrations, and oh-shit moments. After a middleware refactor a few months ago, we realized a week or so later that our course landing pages (where people BUY the course) weren’t accessible to logged-out users, so basically everyone. Whoops.

Through it all, we’ve been figuring out what it actually takes to work together with AI as a third collaborator. The async rhythm across an 8-hour time zone gap, where Cate’s evenings overlap my mornings. The social media manager tool that Cate built to analyze our shares and tell us what’s working and what’s not. The places AI dramatically accelerates us, and the places it’ll happily lead us into a pile of slop, and our experience and judgement are so valuable.

We’ve also seen how important it is to have a space to share half-baked ideas with each other without judgment. I get lots of “Ok I have an unhinged idea” texts from Cate and then shortly after, invitations to new github repos.

From skeptic to enthusiast

Six months ago, Cate’s relationship to AI looked quite different. We were collaborating on our first course, DRI Your Career, when she asked: “Should we have a disclaimer about how we used AI to build this?”

Her question reflected where a lot of thoughtful people were six months ago — dipping their toes into using the tools, but unsure about the optics and the expectations. It also reflected her own situation as a busy engineering director dealing with a huge influx of AI-generated docs to review, and not wanting to inadvertently do that to others.

Fast forward to last month: Cate sent me a present, a custom Chief of Staff repository — a tool she built with Claude Code to help me manage the growing chaos of my many projects. She’d seen me juggling fractional work, course development, content, other side projects, and just... built me something to help me stay on top of everything.

That arc from hesitance to fluency mirrors the journey we’re wanting to support others in taking. You might be cautious of AI because of the slop that you’ve no doubt been subject to at work. Or you might have some subconscious fear about what it all means for your job and the type of work you love doing. You’ll start with something small to get over that initial hump and be well on your way to a kind of fluency where the tools just become part of how you work.

Navigating the shift ourselves

For weeks, we agonized over whether we had the credibility to build an AI course. And how we could build something that wouldn’t be outdated the moment we announced it. But it turns out that as coaches and engineering leaders actively navigating this transition and all the feelings that come up, we are uniquely well-suited to help others on this journey.

Every module in this course reflects something we worked through ourselves and continue to work through.

We built this course because the most valuable thing in our own AI journey was having a space to experiment, be a beginner, and develop real opinions based on the work we actually needed to get done. A space where it was safe to be bad at something new.

And from that space of exploration and learning together, we’ve been able to figure out how to build in a way that is delightful, joyful, and more powerful that we could have ever imagined over a year ago when we first started working together.

A lot of people feel behind. But that feeling is not supportive to actual learning — it pushes you toward avoidance and shame at the moment you’d benefit most from leaning into curiosity and joy. This technology is genuinely new for everyone. So start trying things, share what you don’t know, and build your own confidence in the skills you’ve already developed and the ones you’ll build next.

And if you’d love a little coaching support and scaffolding, you know where to find us.

Sign up for Navigating the AI Shift.

Also, Cate and I recently chatted with Luca over at Refactoring. We discussed all things DRI Your Career, from exploring what you want from your career, how to be intentional about it, how to use feedback to assess how you're doing, to how AI is changing and not changing the picture. We hope you enjoy it!

Refactoring

How to Own Your Career 🦝 — with Jean Hsu and Cate Huston

Today’s sponsor is Intent by Augment…

Listen now

a month ago · 19 likes · Luca Rossi

Being a human engineer in the AI era can be... challenging.

You want to upskill to stay employable, but the top-down AI mandates really make you want to dig your heels into the ground. The years you’ve poured into coding feel trivialized, under-appreciated. You watch someone demo a vibe-coded app built in twenty minutes and feel a complicated mix of awe and grief.

There’s a collective mourning happening that isn’t being talked about openly enough. The loss of craft. The loss of the joy of building something by hand and knowing exactly how it all works. A resistance to being commoditized — to seeing our jobs as, as Cate put it, pampered raccoons whose time has come to an end. And underneath it all, the fear of being left behind, of feeling already behind.

If you’ve been feeling this way, you are not alone, though it can feel that way. It’s a reasonable response to a real situation. The tools changed overnight. The job description is still catching up. And the public conversation — which mostly oscillates between “everything is fine, just use the tools” and “engineers are obsolete” — hasn’t been particularly helpful.

But I want to share something about what got me through this, because fear turned out to be a terrible motivator. Curiosity and delight were much better ones.

Where I started

Almost exactly one year ago, I was emerging from my post-partum year and still taking care of Baby K half-time, and I knew getting up to speed with AI was on my plate. I caught up over tea with an engineering leader friend who worked at an AI company, and I just felt so behind. The conversation was full of terms and workflows I didn’t recognize. How would I ever catch up?

He was encouraging and said, just jump in whenever you can, and you can pick up from there.

But jumping in felt hard. I had years of experience telling me that building is time-consuming, especially on my own and especially with 3 kids to care for — that I should wait until I have the right idea before committing. And my own tendency to want to over-optimize side projects to find the one right thing — the project that could also be a business, that could also be my life’s purpose — held me back for a bit. What should I build? How do I start? What if I waste time?

To get past that, I had to choose something so absurd that I couldn’t imagine ever monetizing it. Something that just delighted me and a few friends — a Trader Joe’s snackbox builder. It seems trivial now, but it was an important first step for me to just start somewhere.

Building reps, not masterpieces

There’s a classic study where a ceramics teacher divided the class in two. One group would be graded on quantity — make as many pots as possible. The other group would be graded on quality — make one perfect pot. At the end of the semester, the best pots all came from the quantity group. While the quality group was theorizing about perfection, the quantity group was learning from their mistakes, getting their hands dirty, building up reps.

That’s what I needed to do. Just build something. Anything.

To prevent myself from getting in my own way, I constantly reminded myself of this idea: it didn’t matter what I built, as long as it was something I wanted to exist in the world. It didn’t matter if it scaled, if it persisted beyond a few months. I was just building reps in the practice of building, and truthfully I was building apps as well as my own confidence.

Before I knew it, I had built a simple app for community lending with auth and email notifications. Then another for local food resources. And by the time we were planning to launch our first cohort of DRI Your Career, I realized — I could build the platform too.

Some days, I marvel at Claude’s ability to build something in a session that would have taken me days, if not weeks. Other days, I mourn the satisfying morsels of work that used to break up my days of engineering management with little dopamine hits — refactoring, deleting unused code, tidying things up. Those small reprieves are gone now.

But on the flip side, there’s a lot that’s become newly available to me. As a parent who doesn’t have loads of free time during nights and weekends, AI has made side projects feasible in a way they never were before. I now have the opposite problem: too many projects, not enough hours. Which is a much better problem to have than the paralysis I started with.

Fear is not the motivator

I know it’s a hard place to be right now — especially in this job market. It can be so easy to put it off, even though you know it’s something you’ll eventually have to do. But fear is not the best motivator — learning from a place of fear will feel like a chore, like being dragged along whether you’re ready or not. Tapping into intrinsic curiosity, delight, and the joy of building has been far more effective for me.

If you’re reading things online about other people’s elaborate agentic workflows and orchestrators and feeling overwhelmed and behind, take a breath. Your skills are not obsolete. If you’re an engineer, you are already well-equipped to navigate this shift with skills you already have. The judgment, the systems thinking, the ability to decompose problems and know what good looks like — those are the skills that travel. But navigating it alone, especially from a place of anxiety, is harder than it needs to be.

Navigating the AI Shift

Cate and I have been navigating this shift ourselves — and we found that the most valuable thing wasn’t reading yet another article about a workflow that’ll change next month. It was having a non-judgmental space to work through the identity threat, to be a beginner, to talk to someone about wins and absurd losses, and to develop real opinions based on our own experience.

So we built Navigating the AI Shift as the course to help others have a space as well. We start with the identity threat — creating space for and coaching you through the feelings before asking you to do anything about it. Then we support you in building something real: a personal project that’s yours. By the end, you’ll have clarity on which of your skills carry over, a project you can point to, and a plan for bringing what you’ve learned back to your team.

The course can be taken in 4 or 8 weeks, depending on your schedule and how much time you’re able to carve out. It’s entirely async, with personalized feedback from us throughout.

If you’re feeling behind and don’t know where to start in navigating this AI shift, we’d love to have you. Early bird pricing is available until April 30, 2026.

Sign up for Navigating the AI Shift.

This week I’m sharing something Cate Huston wrote that I keep coming back to. If you’ve ever felt deflated by a performance review, or confused about what it actually means for your career, this reframes it in a way I wish I’d heard years ago.

It’s also the clearest articulation of why we built DRI Your Career: no one else is going to own your growth for you.

— Jean

The following is written by Cate Huston and cross-posted from cate.blog.

Every review season is an emotional rollercoaster. Anxiety. Self assessments. Anticipation. Disappointment. As an IC, I felt like how much it impacted me was a personal failure. As a manager, I learned that review season trauma is pervasive.

The worst thing about all of it, I think, is how much people take it out on each other rather than seeing the system for what it is. The games. The performative work. People stepping on each other to get ahead. We’ve all known people who do this. We’ve all seen them get away with it. But they leave a trail of resentment and people who would be happy to see them fail behind them. Do you want to be that person? Before you buy into that as a way to get ahead, it’s worth asking yourself what timeframe do you want to live on? It’s easier to build something that lasts when people trust and want to work with you.

What performance reviews actually are

Performance reviews are the scorecard of capitalism. They measure your value to that specific organization at that specific moment. No more, no less.

It’s not a measure of your worth as a person. Not a measure of your talent or your potential. Just: what are you worth to this organization right now, given the current market conditions, the current priorities, and the current budget.

The goalposts move with market forces. It’s not (just) that the system is unfair -- although it can be. It’s that capitalism changes the rules. When talent was a scarce resource, companies promoted in order to retain. Now companies are promoting fewer people not because they suddenly care more about excellence, but because the market shifted, and they can. In the era of mass layoffs, attrition is less likely to be seen as a problem; it’s an exit the company didn’t have to pay severance on.

Getting angry at your manager doesn’t change this. Often they’re the messenger, not the system. Most of them are doing the best they can within constraints they didn’t set and can’t change.

The conflation problem

Performance reviews exist for a reason, and it’s not a bad thing that people get some minimum amount of feedback at least once a year. The problem is that when growth feedback and position feedback come bundled together, it gets emotionally charged.

Growth feedback is useful. “Here’s what you could get better at” is information you can actually do something with. Position feedback is “you’re not deemed as valuable to the org as you would like to be” (or think you should be). That second part carries all the emotional weight. When both kinds of feedback arrive at the same time, people hear the second part louder.

If review season is the only time you hear feedback about your work, that’s a problem. That’s a process-driven minimum, not good management. (Better ongoing is a whole other conversation I won’t get into here.)

The real question: Are you actually growing?

Forget position for a moment. Forget the level, the title, the rating. Ask yourself:

• What have you done this year you couldn’t do before?

• What have you learned?

• What feedback are you getting and are you able to action it?

• What do people come to you for advice on?

• What problems do you see coming that others don’t yet?

If there are deficits, you need to shore them up. If there are bright spots, consider how you can build on them or apply them more broadly.

The core mistake people make when looking for increased responsibility is thinking more about where they “should” be rather than what is actually being asked of them and what the organization really needs. They ask for the diff to get to where they want rather than focusing on impact. Approach these conversations from a place of genuine curiosity about growth and impact, and you’ll learn a lot more.

Outside the drama of review season, these can be great conversations to have with your manager. Just about growth. Not about position. Once your manager starts “managing your expectations” you’re getting a whole lot less information that could be useful to you.

The market goes up and down, and is well outside of your control. Your own capability and growth -- that is within your control, and expending your energy on that has a bigger payoff longer term.

What you can actually control (and what to do about it)

You can control your work and how you approach it. That’s it. That’s what’s in your control.

If you feel undervalued in your current job, maybe it makes sense to check the market. Actually check it. Interview. Get an offer. Or choose not to pursue it because you realize it’s not worth the effort. Either way, you get data.

Sometimes the market validates you; it turns out you could get promoted or paid more elsewhere. Sometimes it shows you the state of things broadly is rough. Both are useful to know.

Own your growth

Caring too much about position in this market will make you miserable.

Companies are less interested than ever in fostering career development. So you need to fill that gap -- and more. This means:

• Building your own support system beyond your manager

• Developing a clearer point of view on what you need to learn

• Going toward it

The performance review is the scorecard of capitalism. When you can separate your strengths and career goals from that scorecard, you can step into your own growth -- whether that aligns with what the organization wants, or it does not. Make this market the push to be the DRI of your own career. No one else is going to do it for you.

If this resonated, DRI Your Career is the course Cate and I built to help you separate what the system tells you from what you actually want. Join us! Our next cohort starts April 15th.

When Cate Huston and I first launched DRI Your Career, we had a thesis: coaching is powerful, but the price point puts it out of reach for most people — especially now, with L&D budgets slashed. So we built an async, self-paced course and hoped people would do the deep introspective work without a live facilitator pushing them.

We thought it would definitely provide value (I mean, we wouldn’t have designed something we didn’t think would work), but the results honestly blew us away.

Here’s what surprised us.

People got deeply introspective — on paper

We’re used to live coaching sessions where you can feel the energy shift in real time. We hypothesized that people could do that same work asynchronously, through writing exercises and documents we reviewed. Especially with the accountability of knowing we would review the exercises if they submitted them on time, unlike when you read a book and get to the end-of-chapter exercises and skip to the next chapter! What we didn’t expect was how introspective people got — not just about their work, but their lives.

Cate’s morning ritual became reading through everyone’s documents. I batched them up and reviewed every few days. We never saw anyone on a Zoom call, and yet we felt like we got to know each person deeply through their writing.

It didn’t drain us

This was a big one. We’ve both run workshops, led offsites, done live coaching — and we love that work, but it takes a lot out of us. We were very intentional about designing something that was sustainable for us too. No energy-intensive facilitation days, made even more challenging due to timezone differences, just reading and commenting on documents at our own pace, on our own time.

Cate joked during our wrap-up: “Imagine having 50 coaching clients. I would die. But 50 documents is fine.” We wanted to reach more people without burning ourselves out in the process. The async format isn’t just better for participants who are busy and don’t want to show up for another Zoom meeting, it’s also better for us as the people running it.

The exercises hit differently than we expected

Our values exercise is deceptively simple: here’s a long list of values, highlight any that jump out to you, then narrow down to five. But from the feedback we got, that whittling process — having to choose, having to let go of values that feel important but aren’t most important — was one of the most valuable parts of the course.

The peak learning exercise was another favorite. Hearing people write about the periods that fueled their greatest growth brought out these vivid, specific memories. It reminded me how much I love coaching: people already have the answers. They just need the right prompt to surface them.

We learned and adapted as we went

One thing we added mid-course was asking people where they wanted feedback. The exercises are deeply personal reflections, and sometimes we’d read something and wonder if a comment or question would be appreciated. Adding that small prompt (”where do you feel stuck? where do you want feedback?”) gave us more confidence that our comments were landing where they were useful.

We also decided to record a wrap-up podcast and a short visualization as a parting gift. The async nature of the course allowed us to iterate on it as it was running.

It changed us too

During the first cohort, Cate quit her job.

She’d been an engineering director, and in some of the modules she shared are about how great that role can be. But the foreshadowing was really that she kept telling me “Jean, you’re living your best life.” Her side projects reached escape velocity, and she decided to go toward the less traveled path of fractional CTO work and building out DRI Your Career.

As for me, I was already in the thick of building my own portfolio career, so nothing dramatically changed. But going through the material again reinforced something I keep coming back to: I trust myself to piece together a rewarding career from varied, interesting work.

What we believe after running it

The market was wild when we launched. It’s only gotten wilder. But the pattern we keep seeing — in our own lives and in our participants’ work — is that the people who navigate uncertainty best aren’t the ones with the most options. They’re the ones who know what matters to them.

That’s what the course is really about. Not figuring it out once and for all, but building a toolkit you can return to in different seasons of your life.

We’re so pleased to run this course again with our second cohort. In building out a portfolio career and balancing how I want to spend my time and meet my financial needs, I often come back to this question of “Would I take this on if I had pizza money?” Offering the DRI Your Career experience every quarter for more and more folks to get clarity around what they want is definitely a Hell Yes!

Here are some quotes from engineers in our first cohort!

Cate & Jean’s course was great. I was able to fit it in even around a busy schedule, and I got value and insights in areas I didn’t expect, and concrete next steps I’ll be able to use to get unstuck.

An excellent and well-thought out program about how to manage an engineering career in modern times. Jean and Cate present the material with clarity and compassion and their desire to help you grow really shines through every part of the program.

It’s a great way to find out what you care about in your life and career. It fits into your schedule and can help you figure out perspective on your values. Well worth the time!

Our next DRI Your Career cohort starts April 15th. If you’re feeling uncertain or directionless and want some structured space to work on it — plus accountability from us — sign up here.

Our morning starts with a power outage.

We go downstairs to get K ready for preschool. After a swift and well-planned fridge expedition to reduce fridge temperature change, I make all three of us eggs for breakfast on the gas stove, while Naveed deals with a diaper change.

No power means no internet, so we make plans to head to the new community-first co-working space I just joined a few weeks ago. We pack up our work stuff, drop off K and head to the space.

No one else is there, so we have our pick of the 6 desks. I’ve been keeping track of everything I need to do across all my different projects using Todoist, so I start with my daily ritual of reviewing the latest overdue items and moving a few to Today (my planning is a work in progress).

I check in with Cate (my collaborator for the DRI Your Career courses) on priorities. She’s in Ireland, which makes for an interesting workflow — our staggered work schedules often make it feel like the work is marching relentlessly non-stop. The first cohort of The EM Survival Guide starts tomorrow, and there are the usual last-minute things — triple-checking Module 1 before it’s released, adding folks to Slack, etc.

I had recently updated our email system last week. Now, instead of manually clicking a button to send module release email notifications to all participants, there’s a cron job that runs and automatically sends notification emails for any recently released modules. Unfortunately, I had to step out to pick my kids and left the system in a state where it accidentally sent an email to all 50 DRI Your Career participants for a long-previously-released module that hadn’t been marked as “sent.” Whoops! I sent my sincerest apologies in slack.

Now that we have multiple courses, I’m feeling a bit nervous about unexpected email sends, so I have Claude get to work adding an email admin panel for us that shows upcoming emails, with dates, and number of participants. We can do a quick check to make sure nothing untoward is about to happen!

I open up the pull request, tag Cate on it, and merge it (yolo!). Cate has just joined me in this course platform repo, so our workflow has evolved from me and Claude just pushing directly to main, to pull requests for everything, even if we merge it ourselves.

The other day, I sent Cate this message:

Which is something I feel every week we work on DRI Your Career courses. Everything is so so fast — from platform development, executing on existing courses, new course ideation and creation. It is exhilarating and fun, but I’m also hoping we don’t burn ourselves out. I trust that we will know when to dial it back and communicate with each other directly.

I have a bunch of PRs from Cate to review, mostly merged and more of an FYI-I-did-this-while-you-were-sleeping. We have two repos going now, one for the platform the courses run on, and one as a development repo for course content. We used to do it all in google docs, but after a day-long working session with Buster last week on upcoming journaling courses, I moved all our content off gdocs and into github repos.

While co-working with Buster, it was fascinating to see someone else’s inclinations and workflows working with these constantly changing tools. It highlighted how my get-shit-done impatience, while very effective at times, can also hold me back from doing the systems-level work that makes getting things done at scale faster. Taking the time to set Claude up with full context so it can do its best work is an upfront investment that has been paying off already for all my other projects.

No fractional client work today. I’m mostly helping a client with hiring manager interviews for some EM hires. There are some weeks when I have 6+ interviews, and some weeks where I have just 1. On days without client work, I enjoy the spaciousness to work on my own projects.

Someone else comes into the coworking space, one of the founders. She tells me about the carpet tiles she bought off Facebook Marketplace. We’re trying to furnish the space on a shoestring budget, and I am so excited to be part of this community where everyone pitches in and contributes. I built the desks and kitchenette with another member just last week.

I check in with my friend and collaborator Jen on updates on Noodle Labs work and some product ideas we’ve been throwing around. She’s also in a different timezone, so most of our collaboration happens in voice memos, texts, and Slack messages.

I tell her I’m going to try out some agentic workflows to help me manage my life and household stuff and will start to form an opinion about if that’s a direction we want to explore further.

Working in tech, it’s easy to lose track of what mainstream audiences are ready for and want. We continue to carve out time to explore and discuss problem areas that we’re excited to work on and could be bootstrapped as a business.

As a continued evolution of workflows and probably also to procrastinate my top two priorities for the day (Review EM Survival Guide Module 1 content one last time, and Review high-level structure of Navigating AI Adoption course), I decide that today’s the day I’m going to move all my Tech and Tea posts into a repo so that Claude can access it all.

I start to work on this post, and use Claude to help me brainstorm directions, but continue to be mostly dissatisfied by any generated writing, so here I am. I struggle to find the balance between honing prompts so that Claude can write more like me, and writing it myself because well, I enjoy it. What’s the point of AI if it doesn’t help us do the things we don’t want to do, so that we can do more of what we want to do?

I get a notification that our power is back on (yay!), so Naveed and I pack up and head back home. I take a few minutes to remove some random items from the new trinket trade box outside our house. We warm up some pita and falafels I had made as a trial run for community fridge meals, and I come back to this post as I continue to procrastinate the two items I marked as priorities.

I do need to get to those at some point. I also need to print labels for the spaghetti and meat sauce I made last night and deliver those 10 meals to the local community fridge.

My Todoist is a strange mix of “work” project tasks like “Review prompts for Life Transitions courses” and “Take a pass at AI course structure” and random creative projects like “deliver community fridge meals” and “replant tree.”

Some days I feel like I’ve taken on too much, too many projects with too many collaborators. Then Cate posts on Linkedin that she’s 6 weeks into her “portfolio career” and I think to myself, oh yes that’s what I’m doing too, a portfolio career. If I can build a work life that is a novel and ever-evolving mix of things I want to do and building things I want to exist in the world, that’s what success looks like to me. Some months it may be more fractional engineering leadership, and some months it may be mostly days like this.

It feels weird and a bit vulnerable to share about workflows, because they are changing so quickly. Every week, my workflows get a little better in ways that feel obvious in retrospect but would have been unimaginable a few months ago. And yet — when I look at what other people are doing with AI, the more sophisticated setups, the people who seem several steps ahead, I feel behind. But then I remember that three months ago, the things I do now casually would have felt impossibly advanced.

It is an exciting time and a terrifying time to be in tech. On good days, I feel so fortunate to be equipped with the right level of engineering knowledge, entrepreneurial spirit, and low resistance to putting stuff out there to build in this moment in time. My creativity is exploding - my github contribution graph gets ever darker, I have an embarrassing number of domain names registered, I feel energized after a full day of work spread out over many projects. And some days I wonder if I’ll have the time and space and financial means to make it all work, especially in this timeline in tech.

Let me know if this inside look into a day (half day?) of my life as a builder is interesting. I’m happy to share more about workflows or have more day-in-the-life type posts!

If you’ve been wanting to join, here’s your nudge. Prices will increase after tomorrow.

DRI Your Career Updates

Our very first DRI Your Career cohort is almost complete, and it’s been a genuinely lovely group — thoughtful, engaged people all trying to be more intentional about how they navigate their careers. It’s been so rewarding to see people get clearer on their values and what they want out of their jobs, and then translate that clarity into concrete steps.

Cate and I brainstormed a bunch of potential names as we expanded our offerings to include The EM Survival Guide, but in the end, DRI Your Career continued to feel right.

Because ultimately, you can’t outsource your growth — not even to a great manager. No matter the course material, it all comes back to the same core idea: you are responsible for your own development. No one else is going to manage your career for you.

Under the DRI Your Career umbrella live both:

• DRI Your Career, which focuses on taking ownership of your trajectory, and

• The EM Survival Guide, which is about being intentional and effective in the engineering manager role.

Both courses are designed to help you step into that responsibility with more clarity and intention.

Our newer course, The EM Survival Guide, balances space for honest reflection on your strengths with practical frameworks for thriving in a engineering manager role right now.

We also recently created public previews for both courses. Below is a snippet from The EM Survival Guide.

A Preview from The EM Survival Guide

Let’s start with the uncomfortable truth: the expectations on engineering managers have shifted dramatically. In the post-ZIRP era, org size is no longer a status symbol—it’s a liability. The default view of managers has shifted from “necessary leadership layer” to “overhead that needs to prove its value.”

This isn’t going away. We have to accept this reality and work within it.

That means being intentional about the job in a way that wasn’t required before. You can’t coast on good intentions and caring about your team. You need to be demonstrably effective.

What Does a Manager Actually Do?

The job of the manager is the output of the team, over time.

Not the meetings. Not the 1:1s. Not the processes. Those are tools, not the job. Your value as a manager comes from being a force multiplier; helping your team get more done than they would without you.

At their best, engineering managers are force multipliers for their teams. At their worst, they’re overhead. The gap between those two outcomes is what this course is about.

Some days you come in and you’re deep in the details, unblocking a project or pairing on a tricky problem. Other days you’re in back-to-back 1:1s, helping people work through what’s stuck. Other days you’re in meetings with leadership, trying to get clarity on priorities or fight for resources.

All of this can be the job. The question is: are you being deliberate about which mode you’re in and why? Or are you just reacting to whatever’s in front of you?

When you’re constantly in reactive mode, you don’t have the time or energy to think about what the most effective response actually is. What do you do immediately? What do you do in the medium term to ensure this problem won’t surface again? That kind of thinking requires space, and creating that space is itself a skill.

Being a force multiplier means showing up in the way that creates the most leverage for your team in any given moment. Sometimes that’s removing a blocker. Sometimes that’s having a hard conversation. Sometimes that’s doing nothing so someone else can step up. The goal isn’t to be busy; it’s to make your team more effective than they would be without you.

Check out the full previews

You can explore full previews of both courses, which include audio conversations between Cate and me. They are the best way to get a sense for what the courses are like:

• The EM Survival Guide preview

• DRI Your Career preview

We decided on audio-only async content because that’s honestly what we would like in courses we take — not another Zoom meeting to show up for, but something we can fit into walks to break up our day.

Early-bird pricing ends tomorrow, Feb 28.

Hope to see you in one of the courses,

Jean

When I was working a full-time job, this newsletter was my only creative outlet. Writing was where I processed, experimented, made sense of things.

Now that I’m not in a full-time role, something interesting has happened: my weeks themselves feel abundant in creative energy. Instead of pouring all that energy into newsletter posts, I’ve been building, and surprisingly, mostly with other people. Truly shocking as an introvert.

So here’s a little update on what’s been going on over here.

DRI Your Career

After two years of occasional calls and tentative planning conversations, Cate Huston and I finally aligned timelines and motivational energy and shipped our first course DRI Your Career late last year.

Course creation is surprisingly creative work, although it’s not without its tedious moments (hello descript! - amazing audio editing tool but also can be very tedious).

We’ve found our respective strengths pretty quickly. Sometimes one of us runs with something, sometimes we slow down and align first. The collaboration itself has been very creatively satisfying. Take two competent engineering leaders and give them free reign on a project that has no bureaucracy, executive stakeholders, or cross-functional priorities, and let me tell you, we are having a grand ol’ time.

I’ve been enjoying building out the platform the course runs on — with the help of our intern Claude 🤖. There’s something deeply empowering about building exactly what you want, instead of contorting to fit a simple course into an over-featured course platform (I won’t name names).

With the launch of our second course, we decided everything will live under the umbrella brand DRI Your Career — because helping an individual take ownership of their own career development is really what we’re both passionate about. Here are our two courses, with upcoming cohorts starting soon!

• DRI Your Career – next cohort starting April 15

• EM Survival Guide – next cohort starting March 13

The first cohort of DRI is over halfway through now, and I’m genuinely so happy we can offer something like this at a price point that’s much more accessible than 1:1 coaching.

The EM Survival Guide is for the managers who care deeply about their people — and are also exhausted because of it. We’re knee-deep in audio editing and building out materials, and I can’t wait to start the first cohort in under a month!

We have early-bird pricing for both right now. If you want bulk discounts for your company or team or want help expensing tickets, let me know and we’ll make it work.

Noodle Labs

I haven’t shared much about this here yet, but my dear friend Jennifer Dennard and I have combined forces to form Noodle Labs. Our other collaboration is our newsletter Startup Soup — yes, we both love food.

We’d both been doing fractional leadership independently, and in our frequent conversations, we realized: this would be more effective, more fun, and more sustainable if we did it together.

If I had to describe our combined strength in one sentence, it’s this:

We’re super competent and super fast.

This is a weird skill to market, but actually exactly what many early-stage teams need, and what makes our fractional leadership a pretty great deal for clients.

We’re hoping Noodle Labs isn’t a short stint. We have many aspirations that we want to explore, and embedded leadership on early-stage teams is where we’re digging in this year. Jen’s expertise is in Strategic Operations, while mine is Engineering Leadership.

If you know of anyone who is looking for seasoned early-stage leaders to embed in a team, please reach out. We’re having a lot of conversations at the moment, and it’s nice to re-connect with old connections regardless.

Creating Space

This course, a journaling course on 750Words.com, is still near and dear to my heart.

There have been so many seasons of my life where I felt like I had almost no space — no financial space, no mental space, no creative space.

I’ve done a lot of introspection, journaling, and internal work to get to a point where it’s far less difficult to prioritize space for myself. And it’s still sometimes a challenge, but this course is what I hope I can draw on in those periods of scarcity to find my way back to my creative self.

Creating Space is for people who feel the call to creativity but don’t quite know how to create the space for it. The original inspiration for Creating Space was imagining what a lightweight program might look like that was similar to The Artist’s Way but less creativity-is-God-flowing-through-you and more just our lives are better when creativity is injected in different aspects of life.

It’s on its third seasonal cohort, and you can join anytime.

Buster and I are also working on a new course for 750 Words focused on life transitions, so stay tuned.

Trinket Trade Box

And then there’s the smallest project, but maybe the most delightful — a collaboration with my kids.

One late night, instead of doomscrolling, I fell down a trinket trade rabbit hole on Instagram. They are apparently huge in Phoenix and starting to make headway in SF.

I was overtaken by an impulse to set one up for our neighborhood, and in the next few days, we sourced a box, decorated it, and installed it outside our house.

This last rainy weekend, I was delighted to see three adults stroll over with big umbrellas to huddle around the trinket box and make some trades. The kids are also thrilled to witness the exchange of fun little goods. TBD whether our home will end up with net-positive trinkets or not.

Sometimes we all just need a little bit of joy in our day, and I’m happy we can facilitate a little bit for people walking by.

Although these projects can sometimes feel disparate, it all comes back to my original motivation for Tech and Tea — writing about my personal experience navigating a career in the tech industry. Right now my work looks very different from full-time employment, and this season is featuring a lot of creative partnerships with friends, choosing what I build and who I build it with, and building things that don’t necessarily need to scale.

When I first became an engineering manager, the hardest part wasn’t the work itself.

It was the people.

I cared deeply about the people on my team — their growth, their confidence, their stress, their careers. That made me good at the role. But it also made it incredibly tiring, and there were many days when I left the office with little energy left in the tank for my life outside of work.

Being an EM would be much easier if you didn’t care about people.
But then you wouldn’t be a very good EM.

It took me a long time to find the language and frameworks to navigate that tension, to take on the job of people management without depleting myself as a person in the process. If I’m completely honest, there are still days when I wonder what it would be like if I had stayed on an IC track indefinitely.

Over many years of coaching EMs and leadership work, I kept seeing the same patterns of energy drain in myself and others:

• conflict avoidance because you want to be nice

• carrying emotional responsibility for everyone else

• struggling to let go of identity tied to code and fast feedback

• feeling like the only option is to be the “shit umbrella” and absorb it all

All of that is exhausting, and no wonder so many EMs test out the waters and promptly head back to IC land.

One valid outcome of seeing the EM role with clear eyes is realizing: this role isn’t for me — and that’s okay. But so many EMs have no support to navigate this transition, lack clarity about the role itself, and then take on far more than they need to, leading to overwork and often burnout.

At larger companies there’s often some manager training — but it’s usually about compliance or policies, not about the new mindsets and priority shifts needed for engineering management. And in the current post-ZIRP world, where expectations for EMs have shifted, that gap is even more real.

That’s why Cate Huston and I designed The Engineering Manager Survival Guide, a course that gives you practical frameworks, real stories from our careers, and exercises to apply to your specific situation, so you can be effective without burning out.

The Engineering Manager Survival Guide

Over 8 weeks and 4 modules, you’ll get:

• frameworks to help you thrive in your EM role

• audio conversations where Cate and I share stories and reflections

• exercises to help you put what you’re learning into practice

• personal feedback from us on your exercise submissions

The EM survival guide is designed to fit into a busy engineering manager’s schedule. We recommend allocating about 60-90 minutes/week, and it’s completely asynchronous. You can listen on a walk, read between meetings, and do exercises on your time.

The course is designed both for newer engineering managers as well as engineering managers who want to be more intentional about the tradeoffs they’re making with their time, energy, and identity.

This is the course we wish we had when we were in our earlier years as engineering managers, so that we could have learned more quickly how to not just barely survive but thrive in the role.

Our first cohort starts March 13, 2026, and we have early bird pricing until the end of February. Our DRI Your Career course sold out quickly, so get your tickets!

Get your ticket!

P.S. We’d also love your help getting the word out about our new course. Share in your company slack and send it to your EM friends! We can also do corporate group discounts.

This lens is deeply aligned with DRI Your Career, which is all about questioning default paths and making more intentional choices about work and life. Our first cohort is underway, and we just opened up enrollment for a second cohort starting in April.

If you’d like to create a bit of space for yourself but aren’t quite ready for a sabbatical, the winter cohort of my journaling course Creating Space is also open.

Guest post by Nyam Adodoadji

While common in academia and religious contexts, sabbaticals of two months or more for personal endeavors is still not normalized in the tech and corporate worlds. The practice has been gaining traction though as well-known companies like Adobe, Bank of America, and Paypal offer sabbaticals to employees after working there for a certain number of years (although they only offer between 4-6 weeks off). Many professionals are intrigued by the idea of a sabbatical, yet they feel like it’s not a realistic option for them. Below, I share my sabbatical story as well as what to consider if you’re exploring the idea of taking a sabbatical.

Reflect on your why

With forceful vengeance, 2020 and the inception of the pandemic compelled each of us to confront our lives with harsh clarity, and I was no exception. For me that moment of confrontation happened in February 2021. Staring at my computer screen during my remote job, I felt the weight of my 14-year career pattern of crushing workloads, unsupportive managers, and multiple burnout cycles.

Where had my life gone? Was it just going to be one debilitating job after another until I died?

This question propelled me into a year-long process to plan a one year career break that changed my life trajectory. I was hungry to rest, reflect, and create a career that was fulfilling rather than draining.

For some people, the reason for a sabbatical will storm its way to the forefront as mine did; for others, it will be more subtle. In either case, understanding what specifically draws you to the idea of a sabbatical is an important anchor in the planning process. During your sabbatical journey, internal and external challenges will come up. Understanding your motivation will help you stay the course and guide your decisions.

I invite my clients to consider five potential sabbatical themes:

• Rest & rejuvenation: Restoring physical, mental, emotional and/or spiritual rest and cultivating sustainable rhythms of rest.

• Adventure & challenge: Embracing physical, mental or creative challenges that are energizing and invite personal growth in certain areas of life or career.

• Exploration & learning: Creating time to take classes or do focused and integrated study in an area of interest.

• Fun & play: Focusing on experiences that reconnect one to what they enjoy and feels light.

• Connection: Prioritizing deeper connection with family, friends or community or caretaking for a loved one that needs support.

These themes aren’t exhaustive, and more than one theme may be applicable. They’re a starting point to reflect on what you uniquely need from a sabbatical. You can use my free Illuminate Your Muse reflection guide as a resource for this reflection.

A few gentle suggestions as you reflect:

• Pay attention to if a motivation is what you want, or if it’s externally influenced. It’s easy to get tangled in expectations for what a sabbatical “should” be rather than tuning into what you want.

• During this reflection, temporarily set aside pragmatic questions, or if it’s helpful, create a list of them that you can come back to. The invitation of this exercise is to tune into your desires, and often practical questions will prevent you from letting what’s stirring within you come to the surface. You don’t need to make any decisions at this point, but rather use your daydreams to shine a light on what it is you’re needing, then take some time to write down your thoughts.

What holds people back from sabbaticals

Because I was so broken-hearted about the time I had lost living an unfulfilling life during my early adulthood, my heartbreak outweighed any fears or concerns I had about taking a year off from work. Also, having experienced so much burnout in my early career, I’d left multiple jobs without having another one lined up, as I was typically so depleted that I didn’t have capacity to search for a job while in my current job. For better or worse, my career was full of holes, but through community and savings, I’d always made it through these stretches, and I was able to find work again. That being said, I did have significant concerns regarding my sabbatical.

When I had my moment of reckoning in 2021, I was single and 36 years old. I wanted to take a year-long career break, but with housing costs, a late start to saving for retirement, and limited options for health insurance, I wasn’t sure the best approach to take. I worked with my own sabbatical coach, Roshida Dowe, a former corporate lawyer, who used her layoff to launch her sabbatical and, eventually, early retirement. Partnering with her offered both practical and emotional support through the planning process. To resolve the concerns I had:

• I had been saving up to buy a home; however, as I played out the purchase, I realized I’d feel financial pressure to keep working in the high paying roles that were crushing me. Instead, I turned those savings into my sabbatical fund that I kept contributing to throughout 2021.

• It wasn’t an easy decision, but I moved back to my parent’s place in order to save on rent during the year of not working.

• I leveraged the health insurance marketplace via which I got a subsidy for health insurance, since I didn’t have income coming in that year. (This option is obviously outdated given the current happenings in the U.S. government).

Many folks I chat with automatically shut down the idea of taking a sabbatical. “I’d love to do that, but I can’t.” People are understandably concerned about money – how can I not work for a year, and where will money come from to take time off? In the U.S., health insurance is another major concern as it’s often tied to an employer. Others are concerned about the impact to their careers – how will employers view a break from the workforce? Still others have concerns regarding childcare, schooling, housing, possessions, and more existentially, who are they if they aren’t working?

These concerns are legitimate, and that’s why it’s important to carefully plan and problem-solve for them. What I find, though, is that many people don’t get past the initial “I can’t” to imagine how they might. There are all kinds of people with different circumstances who have taken sabbaticals. None of the challenges noted above are insurmountable. What I believe ultimately holds people back is that they’re not willing to be curious and creative about options.

They struggle to think outside of the socialization that we always have to be working. They struggle to give themselves permission to pursue their desire for a break. With these internal struggles, people can always point to excuses as to why a sabbatical is not possible for them, whether it’s that they’re single and the only one providing for themselves financially, or that they’re married and can’t imagine what it would look like to manage a travel break with kids.

I invite folks to be curious about what draws you to the idea of a sabbatical. Exploring your options for taking a break doesn’t require you to make a decision, and certainly not a rushed one. Learn about the stories of others who have taken sabbaticals in order to see how it could be possible for you as well. Rebecca Thomas’ Sabbatical Stories podcast is a good place to hear stories. Also, Taking a Career Break for Dummies by Katrina McGhee is a practical resource for planning and problem solving. McGhee, another sabbatical coach, has coached hundreds of people to take career breaks. If they can do it, you can too!

Finding the courage to take the leap

Your why will be your beacon for forging ahead with your sabbatical. Since taking extended time away from the workforce (outside of things like parental leave) is still a counter-cultural decision, it does take courage to move forward with it. That source of courage and motivation will look different for everyone. I became painfully aware that I didn’t like my life, and I couldn’t escape my mortality. Perhaps it sounds morbid, but whether I took the career break or not, the time would pass anyways, and I’d die anyways. I wanted to give myself the chance to live a life that I loved while I still could.

Facing crushing burnout, some people’s driver is that their mental health is worth taking the time to heal and reset for a more sustainable future. Still others prioritize desires to spend precious time with kids while they’re young or to realize dreams or just enjoy life now, rather than in some unpromised future of retirement at 65. Ultimately, money is a renewable resource; time is not. An intentional sabbatical is an investment in a life well lived.

A couple of reflection questions to unearth your courage:

• Imagine yourself in the future at the end of your life. From the vantage point and wisdom of your future self, what did you do in order to make your sabbatical happen? What was the impact?

• What’s the cost for you NOT to take this break?

• What choice would you make if you chose curiosity and bravery over fear?

Different approaches to structuring time off

People ask me what I did during my sabbatical, and while I did travel, work with a leadership coach, start a newsletter and take a music production class, I spent many of the days that year without much structure. I loved having the space and flexibility to move slowly, reflect and savor time with people. I loved how I got to know my body’s natural rhythms, rather than feeling pressure to conform my days to external demands. For me, having loose structure opened up a gentle flow of life that I needed as a break from the rigid schedules of modern work life in the U.S.

For some people though, not working and suddenly having ample free time feels daunting. They wrestle with feeling guilty about not working on a project or skill acquisition that would be classified as productive. One of the gifts of a sabbatical is unlearning the ideas we’ve ingested from the corporate world that we are workers first, humans second. When you take extended time away from the workforce, it becomes clear just how much of life is oriented around work, rather than actual life.

That being said, some people find structure helpful and will feel aimless without it. I’d recommend a few things when creating daily structure for your sabbatical:

• Create simple routines or rituals to start and end your day: These routines are focused on checking in with and nourishing yourself. They can be as simple as journaling with a morning cup of coffee or taking 15 minutes before picking up your kids or before bed to express what you’re grateful for from the day. Maybe it’s going to the gym or taking a walk, run, or swim. The habit will be different based on what connects for you, but the long-term intention is that you cultivate the habit of reconnecting with yourself daily and that you maintain it post sabbatical.

• Organize your days in alignment with your sabbatical why: Before automatically choosing project(s) to work on during your break, come back to your reason for taking the time off. If your purpose is to rest and recover, explore the seven types of rest and how you can incorporate them into your break. If it’s to learn more deeply in an area, start with one project that you want to focus on or a list of books to read. If it’s to deepen connection with your family and community, explore joining a local club or starting a new weekly family or community gathering time.

• Start with your joy: Your sabbatical is a time for you to reconnect with yourself, and an important aspect of that reconnection is tapping back into your joy. When was the last time you made choices from a place of joy or delight? Understanding, embodying and practicing your joy, what lights you up and energizes you, is a type of power. Via this power, you learn how to refuel yourself, discern what feels draining and take ownership of your well-being.

Normalizing sabbaticals

Even though more tech and corporate companies are offering sabbaticals as a benefit, and more folks are creating their own self-funded sabbaticals, for many corporate employees, there’s still resistance. While there are legitimate pragmatic and emotional questions on how to take a sabbatical, part of the resistance is from modern life, work, and culture in the U.S.

Many of us have been socialized to pursue one particular version of life. Get a good education, get a good job and climb the corporate ladder, get married, buy a house, have kids, retire at 65. For some folks like myself, from immigrant families, this version of life is the epitome of success and stability. Hard work is about survival and deep pride, but modes of rest weren’t always accessible or modeled for us. In addition, for many years U.S. work culture has been driven by employees being dependent solely on one job for income and health insurance. In this model it’s easy for folks to shift into autopilot, until a forced external disruption happens. Employers profit from the idea that there are no other options for finances or life outside of this model, and in turn, it creates a culture of fear or scarcity.

Sabbaticals are a jarring reminder that different ways of living and working are possible. They shine a light on the truth that people have more autonomy and options than they think. Part of the resistance to them becoming normalized is that it cracks open the door for people to reimagine their lives outside of being workers first. It opens people to the power of possibility. It varies by story, but many people experience a deep metamorphosis or change in priorities after taking a sabbatical. That type of change can be rattling for their community or workplaces.

After my sabbatical, I didn’t know exactly how it would come together, but I knew that I didn’t want to live the version of life and career that had been sold to me. While I don’t necessarily see anything wrong with that version of life, I realized clearly that it wasn’t for me. I wanted to do work that stemmed from my vision and that I found passionate, purposeful, powerful and joyful. I wanted ample time for life – family and friends, creative work and travel.

As things stand today, for many folks, taking a sabbatical from the corporate world will require inner vision and grit to go against the grain. It will require financial resources that many people don’t have access to. As more and more people make the choice and share their stories, it opens up the imagination of the collective. As Tricia Hersey, the Nap Bishop and author of “Rest Is Resistance: A Manifesto” professes:

“You were not just born to center your entire existence on work and labor. You were born to heal, to grow, to be of service to yourself and community, to practice, to experiment, to create, to have space, to dream, and to connect.”

Sabbatical Resources

Illuminate Your Muse Sabbatical Reflection Guide

Illuminate Your Muse is a soulful digital guide for mindful, mid-career execs and professionals ready to pause, reflect, and plan a nourishing, intentional career break. Through intuitive prompts, you’ll explore your relationship to rest, reconnect to yourself, and envision what’s next.

https://nyamadodoadji.myflodesk.com/illuminate

The Chrysalis Contemplative

The Chrysalis Contemplative is a 6-month, 1:1 coaching experience to help mid-career tech professionals recover from burnout, craft a career break strategy, reconnect to who you are and create a sustainable life and career that matches.

https://www.nyamadodoadji.com/contemplate

Break Space

Join the community for career breaks and sabbaticals that improve your life, without sabotaging your success. If interested, join any time via this link and use the discount code NYAM30

https://www.gobreakspace.com/join/

2025 was an interesting year that surprised me in many ways. 2024 brought a new baby, and 2025 was our first full year with three kids, continued postpartum recovery, transition to full-time childcare, and work transitions. Common themes for me were creating space for exploration and curiosity, community, family and friends, and of course, food. Here are some of my highlights and things I was grateful for in 2025.

Friends and Community

This theme really took me by surprise, as I’ve long considered myself a hermit-like extreme introvert. But this year, I found myself drawn to my local community, building community, and deepening friendships.

• Community fridges & pantries - I recently learned of two full-size fridges within a few blocks of our place where we can leave extra food. I’m enjoying portioning out extras of soup and stews and feeding the community.

• Community Lending and Buy Nothing groups - this network of Berkeley porch pickups and flow of physical goods in and out of people’s homes continues to fascinate me, and I’m still very interested in more ways to get this system off Facebook.

• Stoop coffee - Inspired by this post, my next-door neighbor and I hosted 3 stoop coffees over the last few months with great turnout. Our bar is intentionally low — it should be something we can start setting up for at 8:50am for a 9:00am start, with quick cleanup as well.

• Mid-autumn festival block party - I co-hosted a neighborhood block party with our neighbor and mandarin teacher. I was surprised to find out it only costs $15 to shut down a block!

• No Kings protests - We attended several throughout the year and found it really moving to see high school kids and elderly alike coming out in strong numbers to protest.

• Food, Friends, and Field Trips - Inspired by an adult field trip I went to at the Oakland Museum of Art earlier this year, a friend and I decided to organize a series of monthly meetups: a museum visit, a hike, a steamed bun-making gathering.

• Close friendships - Last but not least, the past few years have brought a few deep friendships that I never expected I would have in my 30s. I am so grateful for these friends in my life, and also grateful to technology and asynchronous voice memos that have kept us together despite living far apart.

Family

This was our first full year of three kids, and it was full of chaos, unexpected joys, never-ending conflict, the sweetest sibling dynamics, and the occasional moments of peace and quiet. Naveed and I have found (and keep finding) new rhythms and routines to have time together, family time, and solo time, but it isn’t always easy.

• Sibling relationships - it gives me deep heartfelt joy to witness the older kids love and play with Baby K. None of us expected how deep that love would be.

• Tween independence - the 10 and 12 year olds are old enough to go off for a few hours with friends. It always catches me by surprise when that coincides with Naveed taking Baby K to the gym, and I’m suddenly by myself.

• Mama Summer camp - 2025 was the first year of Mama Summer Camp. Highlights included bike rides, field trips, and times tables boot camp (they said this was the most asian mom thing I’ve ever done). I’m hoping to iterate on this in 2026.

• Monopoly week - there was one week this past summer, where we played a full game of monopoly every single night. The night always ended with tears, and someone saying “I’m never playing this game again!” And then asking to play again the next day. Capitalism is wild.

• Road trip - we loaded up a minivan and roadtripped to Big Sur, Santa Barbara, and Sequoia National Park. We ambitiously camped for the first time with all three kids for 5 nights, which went surprisingly well, though we will upgrade our mattress for future trips.

• Chess Mania - our 10 year old has caught the chess bug and would gladly play chess.com all day if he could. We’ve supplemented his interest with some big chess puzzle workbooks. I am a beginner, but have enjoyed the measurable improvement playing online.

Work Exploration

Since Baby K (more a toddler now) started school full-time in August, a large part of my attention has been in exploring how I want work (the paid kind) to fit into my life.

I spent a lot of time thinking about opportunities through the lens of “would I do this if I had pizza money?” - or $365,000 semi-passive income from eating a slice of pizza everyday. Many of the 100% YES responses were the things I built in the next category, and it’s been also satisfying to see the aggregate of those projects start to become meaningful income.

I talked to a few companies about full-time roles, got stealth-interviewed by one company, and quickly gained clarity that I really enjoy and am very good at fractional engineering leadership work and the quick onramp, team debugging, and problem-solving it requires.

• Fractional work - first few engagements ongoing thanks to some referrals from friends and former colleagues. I’ve been surprised that I’m not just tolerating but actually really enjoying fractional work (definitely in that I’d still do it if I had pizza money territory!). I’d love to keep exploring engagements with different types of companies in 2026 (more on this soon).

• Coaching - I picked up a few coaching clients this year, mostly longtime newsletter subscribers or people who had attended my leadership development workshops.

• Writing - I published 16 Tech and Tea posts and 10 Startup Soup posts. I enjoyed having a clearer separation of writing containers for more personal reflections and coaching tools for individuals here and startup content for founders and operators in Startup Soup.

Variety and novelty have emerged as important for me in my work, and I will continue to experiment with combinations of different types of work in 2026.

Building and Creating

Coming out of my post-partum period in 2024, I gave myself permission this year to lean into building and creating whatever I felt drawn to, without too much pressure yet to think about how I would make it work financially. Vibe coding completely changed how quickly green-field ideas became real apps. Collaborations with friends were also a real highlight.

• TJ Snack Box - my first little vibe coding project, which I shared more about here.

• Creating Space - a fun collaboration with Buster Benson of 750 Words. We’ve run it twice now and have plans for new courses in 2026.

• DRI Your Career - a course many years in the making, finally starting in January! Another fun collaboration with long-time internet friend Cate Huston. I also built the platform the course is run on, which was very enjoyable, and makes future courses feel very much within reach.

• Absurd Hypotheticals - a silly little 750 Words collaboration in the form of an advent calendar to satisfy my curiosity around weird hypothetical questions like the $1000 pizza slice question.

• Free Food Resources - My interest in helping people get food they need is strong, and work around food security showed up in a few ways this year, including vibe coding this site.

Food

A year in review wouldn’t be complete with food reflections. Naveed has been saying that I’m a picky eater, which I didn’t understand because I eat almost everything (except most olives, capers, and goat cheese). I’ve realized what he means is that I like the food I eat to be good, which I think is actually accurate, especially if I’m paying 2025 eating-out prices. Some food highlights:

• Granola - big batches of homemade granola, the most Berkeley mom activity. I’ve so enjoyed Christine Koh’s tip to measure out extras of dry ingredients. Subsequent batches of granola come together so quickly, and make an easy and well-received gift.

• Souper Cubes - I’ve been influenced. The freezer used to be where things go to be forgotten and then thrown away 6 months later, but I’m starting to lean into freezing Souper Cubes of meal components - broth, extra rice, pasta sauce, beans. Having easy healthy meals available in 2-3 minutes has reduced the overall tedium of cooking, which has allowed me to enjoy cooking more when I do it.

• Vacuum sealer - I used to be extremely intimidated by the massive cuts of meat at Costco, but with the rising costs of beef, we have ventured into a few different cuts like chuck roast, flap steak, and tri-tip. I am now one of those people who cuts them up at home and vacuum seals them for the freezer.

• Food products - I’ve been experimenting with my friend Jen (same Jen as Startup Soup) in building food-related apps and brainstorming food ideas. We hope to spend more time working together in various ways in 2026. But if you want to check out a prototype we put together, let me know!

Ultimate Frisbee

The last highlight of 2025 that didn’t neatly fit into the other themes is ultimate frisbee. I started playing in middle school and high school, but didn’t play competitively in my 20s. Over the last few years, I’ve often wished that I could play in a few tournaments throughout the year with friends, but without the heavy commitment of weekly practices and travel that competitive club teams require. I recently reflected that I’m well on my way.

• Grandmaster’s - Unlike chess, the grandmaster’s category in ultimate frisbee just means you are of a certain age. In 2025, I played at Nationals with a Mixed Grandmaster’s team and had a blast competing at that level.

• Goaltimate - I also got back into goaltimate (a sort of faster half-court version of ultimate) and am finding the consistent community there very rewarding.

• Rec leagues - rec league teams are often a bit hit-or-miss for me, but my winter league team is almost entirely people I know and play with often at goaltimate. Just a year ago, I was playing winter league about 6 months post-partum and was completely out of breath halfway through points. In my last game just a few weeks ago, I played almost the entire game.

Physically getting back into shape while doing something I love with friends has been amazing for my mental and physical health in 2025. I’m excited to keep it up in 2026 and already have plans to be in Santa Monica in January for a beach tournament!

I hope this update finds you well. 2025 has been challenging in so many ways, and it feels even more important (but also admittedly weird) to make space for gratitude and highlights.

Seasonal rhythms, time off for the holidays, and end-of-year rituals can create an opportune time for reflection and intention-setting. I hope you can carve out a little bit of time for yourself to do so. But also if you’re overwhelmed and don’t want something else you feel like you should be doing, that’s totally fine too.

Feel free to share in the comments: What are you most proud of from 2025? What’s something you’re looking forward to in 2026?

About two years ago, we started talking seriously about creating something together. We’d catch up on life, swap notes on what we were hearing from engineers about their careers, and keep circling the same question:

What would a course look like that actually helped people navigate tech careers with clarity?

The idea took longer to take shape than either of us expected. We tried things, discarded them, and resisted forcing an answer just to ship something. Our day jobs already optimize for speed and productivity — but this was different. We were the DRIs, and we wanted to choose creativity, care, and usefulness over arbitrary deadlines.

At some point we asked a simpler question:

What if we just made the thing we’d actually want to take?

Once that clicked, everything came together quickly.

This course was, in some ways, two years in the making. And when it finally came together, we both had the same feeling: Yes. This is it. This is what we wish we’d had. This is what we’re excited to run.

At the risk of sounding hyperbolic, there isn’t a course out there like it. It’s completely asynchronous, designed for busy introverts like ourselves, complete with raccoon art, personal stories from our own career journeys, and coaching exercises.

What this has to do with your career

When you’re unsure what you want, it’s easy to default to the expected path: the next promotion, the next title, the next checkbox.

But just like designing this course, moving quickly in the wrong direction doesn’t feel energizing — it feels draining. Motivation matters. Engineers know that the people who do their best work aren’t necessarily “10x,” they’re deeply motivated by the problem in front of them.

Pushing toward a goal you don’t actually care about can look like:

• Avoiding work you feel you should want

• Feeling depleted by initiatives that exist mostly for optics

• Taking on a role that doesn’t match how you want to spend your energy

You can do all of this. The question is: at what cost?

DRI Your Career is about creating space to step back, explore what actually matters to you, and move forward with intention — not rush toward someone else’s definition of success.

And when you get clarity over what you want, you may find that it doesn’t look at all like the default career path you had imagined.

We’re running the course over eight weeks starting January 15, 2026.
Early bird pricing ends December 31, and we’re already well over halfway full.

If this resonates, we’d love to have you join us:

Become the DRI of your career

P.S. If you have leftover education budget for 2025, this is a great place to spend it.

“I should try to get promoted to staff.”

“I should be more strategic about leading new initiatives.”

I’ve heard these shoulds many times — from coaching clients, friends, teammates. But the reason they are “should’s” and not “want to’s” is because the tech career ladder was not built when someone sat down and created a system that prioritized individual happiness.

The career ladder exists to fuel companies’ growth, not your personal fulfillment. When your default career goals are to move toward something you don’t actually want, you struggle, feel like you’re failing, and wonder what’s wrong with you.

Nothing’s wrong with you. The career ladder just wasn’t designed for you.

With everything happening in tech right now — layoffs, uncertainty, the complete reshuffling of what our roles will even look like — there’s never been a better time to step back and ask:

What do I actually want?

I’ve been partnering with my long-time friend Cate Huston to build something to help you figure that out. Cate and I are both experienced engineering leaders and leadership coaches who’ve coached countless people through career transitions and inflection points.

We’ve been deep in conversation over the last year discussing the state of the tech industry, Cate’s book The Engineering Leader, what’s worked with engineers (either coaching clients or people on our teams) to help them navigate their own careers, and what types of courses busy introverts (like ourselves!) might actually enjoy.

We’re so excited to finally open up enrollment for DRI Your Career.

What is DRI Your Career?

DRI Your Career is an 8-week course starting on January 15th, 2026 to help you take ownership of your career with clarity, confidence, and intention.

Through this course, you will learn tools, mindsets, and frameworks to become the Directly Responsible Individual of your own growth.

The course is designed for mid to senior-level engineers (or engineering managers) who aren’t finding the default career ladder all that motivating and are ready to figure out what they actually want — and how to move toward it.

Why now?

The tech industry is being flipped upside down and inside out. The old career playbook doesn’t work anymore. But that’s actually good news — because it means you get to write a new one… one that’s actually yours and is based on what you want, not what creates a consistent pipeline of workers for a growing tech industry.

If you’ve been stuck in what you “should” be doing, if you’re wondering what’s next but don’t have a good answer, if you want to feel intentional instead of reactive — this course is for you.

It can be hard to make time to be intentional about your career, and if you’re like me, you might be thinking, wow I really need this, I just wish I had the time.

We get it, and we’ve talked through so many possible versions of this course to land on this format that feels genuinely like something we’d want to take.

We designed the course to fit in your schedule. It’s completely asynchronous, so you can listen to our audio content on a walk or in the car, read the written module content in between meetings, and do each module’s targeted exercises whenever is best for you.

If you are feeling drawn to this course, and need a loving nudge to sign up, consider this your nudge!

Enrollment is open now.

The course will start in mid-January — join us now for early-bird pricing ($349) and use up any development budget you have for 2025!

Enroll today

We hope to see you in the course,

Jean (and Cate)

P.S. We’re so excited to get this course in the hands of people to need it, and we could use your help! Please share this post with friends, coworkers, your team, and networks you’re part of.

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You’re offered $10 million. If you accept, a special turtle is placed somewhere on Earth. Every moment, it moves closer to you, and if it ever touches you, you die instantly. Do you take the money? What precautions do you take?

It’s such an absurd question, but the discussion that followed revealed quite a bit about how risk-averse people were, the lengths they were willing to go to ensure their security from turtles, and what tradeoffs they were willing to make or not make.

Since then, I’ve kept collecting these fun and slightly unhinged conversation-starters.

Last Thanksgiving, my cousin shared this gem:

You can squirt five drinks of your choice out of the fingers of your right hand — but they’re the only drinks you can have forever. What do you choose?

And, of course, the pizza question, which you may have seen in this dedicated pizza post:

Someone offers to pay you $1,000 per slice of pizza that you eat in one year. You have to decide upfront how many slices you’re going to eat at the beginning of the year. How many slices would you choose and why?

I love this pizza question so much that it actually makes an appearance in the finance-themed week of Creating Space, where it helps people explore money, enough-ness, and tradeoffs from a totally different angle.

As I’ve been collecting absurd hypotheticals, I’ve wondered what to do with them…until this past month, while chatting with Buster Benson about future Creating Space cohorts and other journaling courses we’d like to work on together.

We decided to create something a little more light-hearted as a fun end-of-year gift to all of you in this community as well as the 750 Words community.

We are excited to gift you…

✨The Absurd Hypotheticals Advent Calendar ✨

Thirty days of absurd questions, starting Wednesday, December 3 through New Year’s. 🙃

Each day, you’ll get a hypothetical question as a writing prompt in 750 Words. Answering some prompts may reveal a little bit about what you truly want, and others may just be a weird thought experiment.

Prompts will only be available on their designated day!

For those of you who are already familiar with 750 Words, we have also included three new badges you can earn through the advent calendar.

You will also be able to discuss each day’s prompt with others in the 750 Words community.

The Absurd Hypotheticals Advent Calendar starts on Wednesday, December 3, so make sure you join the course and mark your calendars if you want to try for the complete set!

Whether you write a handful of times or go for all 30 days, we hope this little advent calendar provides a little bit of levity and reflection for the end of your 2025.

Let's Go!!

If you want to explore these themes more deeply — values, identity, transitions, enoughness, money, creativity — the Fall Cohort of Creating Space is still open for enrollment. You can join anytime and move through it at your own pace.

As the café emptied out around midnight, I’d forge on alone, coding, debugging, making incremental progress each hour. Around 4 a.m., I’d finally head upstairs to sleep a few hours before class (don’t worry, I’d make up another four in the afternoon). I’d lose track of time in that all-consuming flow of building and fixing and figuring things out — and that’s how I knew: Computer Science was it for me.

Over the last fifteen years, I’ve built my career in early-stage startups, and I’ve made some pretty cool software with great people. But it’s only in the last few months that I’ve recaptured that same exhilarating, holed-up, all-consuming joy of building.

But so much has changed. Instead of working on assigned problems (“fill in this function to implement the algorithm”), I get to build whatever I want. Instead of the insecurity of being new to coding, I have two decades of experience building and leading engineering teams, not to mention life experience.

But since Baby K started preschool full-time in August, I’ve rediscovered the joy of building, a part of myself I hadn’t given much space to in years.

With a little time, curiosity, and help from AI coding tools (a.k.a. my friend Claude), I’ve found myself drawn to building community tech — small, useful tools for the people around me.

My last post was about what if hard work felt easier, about leaning into the things that feel joyful and effortless, yet you’re actually learning a ton while letting yourself follow creative and curious impulses. It feels fitting to follow up with personal examples of what that’s looked like for me.

So here’s a little show-and-tell of what I’ve been working on these past few months.

🪴 Community Library

(built in ~2 weeks with Next.js, React, TypeScript, Tailwind CSS, Prisma (PostgreSQL), NextAuth with Google OAuth for authentication, Resend for email notifications, AWS S3 for photo storage, and deployed on Vercel.)

This was the second project I vibe-coded into existence (the first project was TJ Snackbox), but the first one that had some substance.

Community Library is a shared lending library for neighborhoods, a way for people to share household items, camping gear, kids’ stuff, the things that sit in closets 90% of the year.

This site was an upgrade from the Lending Library Spreadsheet I created earlier this year (and wrote about here), and I learned so much about building with Claude and Cursor. I really leaned into using AI, waiting for it to hit a breaking point. Claude planned and executed on building out an MVP app, Google OAuth integration, email sending, photo uploads, caching, performance improvements, and more.

I kept waiting for the whole thing to fall apart, but for the most part it held together. I would tell it what I wanted it to implement or change, and it would execute on it. For a low-stakes site used by a handful of people at any given time, that doesn’t require much ongoing maintenance, it was a perfect experiment in pushing the limits of vibe coding.

The beauty of a community library is it provides tremendous value once people have added items, even with low activity — I love knowing that if I need camping supplies, extra folding tables, or outdoor gear, they are all just a request away.

Feel free to poke around in this test community. If you have a community you’re a part of and would like to set up a Community Library, just let me know and I’ll create one and set you as the admin!

🍎 FreeFoodResources.com

(built in 1 day with Next.js, React,, TypeScript, Tailwind CSS, Neon (PostgreSQL), and OpenAI for AI-powered search)

This one came together shockingly fast just last week. I was putting away groceries while chatting with ChatGPT in voice mode to help define an initial MVP, and within a few hours I had a working prototype that I shipped the next morning.

This project was inspired by a desire to do something to help with the paused SNAP benefits nationwide (other than donating cash to families who didn’t receive their benefits). I kept seeing people share screenshots or bulleted lists on Instagram of local food resources, including this creative state-by-state resource reel. It all felt so ad-hoc that I thought there must be a better way for people to get a comprehensive list of known long-standing organizations as well as newer resources such as restaurants offering free meals.

Free Food Resources is a zip code search tool that helps people find free food resources — food pantries, community fridges, and meal programs.

To get around the empty page problem, I implemented AI-powered web search so the first time someone searches a zip code, it uses OpenAI’s gpt-4o-mini-search-preview model to find and save the results. That first search in each zip code takes over 10 seconds, but any subsequent searches are very fast. Additionally, users can also add more resources, so the database grows organically.

This was a joy to build and get out there.

Lessons learned: If you build anything requiring actual web search, make sure you use a model that is web-search-enabled. Otherwise, it will return results that look completely like real results, but the address or phone number or even the name of the place itself will be completely not real and hallucinated.

Also, Claude got stuck trying to parse an OpenAI API response that was not valid JSON. It kept trying to replace invalid characters one-by-one and getting stuck, yet still continuing down this unsuccessful and brute force route. This went on for quite a while until I redirected it to look for a library that comprehensively sanitizes JSON. While AI is incredibly impressive in some ways, it also can be extremely unimpressive in other ways, and sometimes you need to give it a little nudge or a not-so-gentle shove.

🛒 SNAP Matching Facebook Group Tooling

(built in a few hours with Node.js serverless backend, Facebook Graph API webhooks, Google Sheets API, deployed on Vercel)

This one’s more behind the scenes — internal tooling to help Facebook group admins match sponsors with families needing grocery assistance.

A few days ago, I reached out to an admin on the group. I had donated some funds to a family who hadn’t received their SNAP benefits, and reached out to say, hey this process seems super tedious, are there any tech tools that could help?

The process had been very manual and tedious: spreadsheets, Messenger chats, comments, DMs, physical notebook records.

I built some lightweight tooling to sync information between post comments and a central spreadsheet with Requests and Sponsors, so admins can track who’s been matched and who still needs help. I also set them up for automated DMs with benefits verification info so that people could be verified before being matched with a sponsor.

Some of it was code, but some of it was just connecting existing tools. But it felt really good to help people get financial assistance more smoothly and make the admins’ lives easier.

In an industry where there’s been a huge emphasis on scalability, exponential growth, and maintainable software on growing teams, building community tech by myself — even for just two admins for a FB group — has felt very natural and joyful. I recently joined a Show & Tell group zoom for Relational Tech Project to share my first two projects and hear about other similar projects people are building — for their carpool group, for neighborhood events — and as much criticism as AI gets, it’s enabling small tech in a way that hasn’t been possible before.

Every project I’ve taken on has felt small enough to not be too daunting, and the more I build, the more confident I feel that I can just figure it out. What feels very doable now feels so different than just six months ago, when I wrote about my first vibe coding experience of TJ Snack Box.

If you’ve been wanting to create, to explore, to build, and have felt held back in the past because you’re not an engineer, or setting up a development environment for personal projects feels like too much of a barrier, I encourage you to try it out now.

Pick up a tool — if you’re not technical, Loveable is a good place to start; if you’re technical, Claude Code — and start small.

It’s an exciting time to be a builder.

I’ve been thinking a lot about the difference between work that feels hard and work that just flows.

Sometimes work doesn’t feel effortful, but still leads to big results — it can just feel natural, even joyful. That’s the kind of work I’ve been leaning into lately, and I’m starting to believe it’s not just more sustainable — it can also be more effective.

I was reminded of this when I went into SF a few weeks ago to hear my friend Kate Mason speak about her new book, Powerfully Likeable, at the Ferry Building.

During her conversation with Heather Knight, two things really landed.

First, when asked what it was like to write the book, Kate said, “I know I’m supposed to say it was a slog, but honestly, it was joyful.” Getting her ideas down, things she’d been working through with clients for years, just made sense.

Second, she talked about how powerful it is when your real self and your performative self at work are as close to the same as possible. When you stop trying to lead like someone else — and instead lean into your natural way of working — everything gets easier. And the results are often better, too.

Both of those insights point to the same idea: that ease and alignment aren’t indulgent — they’re a path to real, lasting impact.

These thoughts are so counter to the current state of the tech industry, which feels like it’s glorifying grind culture and mandating long hours with butts in seats more than ever. There’s an implicit assumption that if your work doesn’t feel difficult or draining, you must not be trying hard enough.

But what if that’s completely backwards?

What if the most effective thing you could do is to follow the path that feels most obvious to you — the one that doesn’t feel like a grind at all?

What if the work that flows easily, the things you’d do even if no one asked, is where your real leverage lives?

When “working hard” doesn’t feel hard

I’ve experienced this kind of easeful, high-output work many times — both at companies and on my own.

At my first startup, I wore every hat imaginable, and it all felt obvious and fun. Building out a coaching and leadership development company for engineers felt joyful.

In fact, for a long time I felt shameful that maybe I wasn’t working hard enough. I wondered what I could do if I really pushed myself.

But when I look back, any reasonable person would say I was working incredibly hard. I have just had good luck and judgment to choose several environments where hard work felt like what I wanted to do.

In college, I’d work after dinner and stay up until 3am coding in my dorm basement, then sleep for four hours, go to class, eat lunch, and sleep another four before dinner. That bizarre bimodal sleep/work rhythm felt totally natural at the time. I think back on it fondly — not because it was “hard work,” but because I loved coding and debugging so much, it didn’t feel like work.

I’ve also built my career at early-stage startups, which are known for being a lot of work. But when I’m on the right team, working on something I care about, it feels like I’m just getting what needs to get done, done (and often this does look like putting in extra hours). On the flip side, I’ve also worked on teams where just getting through each work day felt like a grind, regardless of hours worked.

My recent experience with easeful learning

In the year or so after having Baby K, I have had this heavy sense of being behind on the latest in engineering, product development, and AI. I saw emails with tips and tools and tutorials… and avoided opening all of them.

I felt like I should catch up to stay relevant in the changing tech landscape, but that feeling just didn’t translate to action.

Then, a few months ago, I had this silly idea for a Trader Joe’s snack box builder. It made me smile to think about it existing in the world. So I downloaded Cursor, and built and shipped a basic version in two hours.

That tiny spark of joy reminded me how much I love to build. A few weeks ago, I got pulled into building a Community Library app — something I’d been noodling on for months as a shared Google Sheet. Once I had the idea for a real site, it just made sense to build it.

And without realizing it, I started learning all the things I’d been avoiding or feeling like it’d be a slog to learn: Claude Code, agents, auth flows, email automations, SSO integration. Learning those things to bring this idea to life was far more effective (and easy! It felt easy!) than forcing myself to “sit down and learn.”

Working on the community library app has felt like the most obvious, natural thing to do. With the help of my good ol’ friend Claude, I shipped a working site complete with item upload, loan request flow, and email notifications, in two weeks. The Berkeley library has over 100 people, and people are regularly adding new items

Butts in seats does not mean results

I know what it feels like to brute-force work. I try to do it all the time.

I’ll sit at my desk when I’m tired, click around, skim articles, answer a Slack message, open a doc. Two hours later: technically, I’ve “worked.” Realistically, I’ve accomplished nothing.

If I’d just let go of the “should,” I could’ve gone for a walk, or taken a nap, or called a friend. After any of those, I probably would’ve gotten more done in 15 minutes than in those two wasted hours.

Meanwhile, I launched the Community Library site in a few weeks. For someone else who didn’t really care if this utility existed in the world, building that same app could take months: requirements docs, back-and-forth with a PM, getting edge cases hammered out— even for a competent engineer. All while logging “work” hours that look reasonably productive, but could be so much more effective.

If you’re leading a team, the most effective way to get output is not to mandate effort or hours. It’s to help people find work that feels easy for them — not necessarily work they already know how to do, but work that feels obvious for them to get done by whatever means possible. You can achieve this by tapping into their internal motivation and goals and aligning what the team and company needs with what they want (this also requires being clear about what company needs aka strategic alignment, which is surprisingly often lacking). That’s where you’ll find motivation, momentum, and output you don’t have to measure by the hour.

For more on team motivation that is more effective than hour mandates, check out my post on harnessing scrappy startup energy in my other newsletter Startup Soup — also a fine example of a joyful “work” collaboration with my longtime friend and colleague Jen Dennard!

Ease is the path to sustainable and high output

Honestly, as I get older, my tolerance for doing things I don’t want to do has really dropped off a cliff. So finding the most frictionless way to get from where I am to where I want to be is the only way I’ll get it done.

If you’re trying to find more ease in your work, here are a few questions to play with:

• When has your work felt surprisingly easy and energizing? What were you doing?

• What are the things you’d do even if no one asked you to?

• Is there a “should” that’s been sitting on your to-do list for weeks (or months)? What’s holding you back? Do you actually need to get it done, or can you let go of the “should.” If you do need to do it, is there a more joyful way to approach it?

The more overlap you can find between what energizes you and what needs doing, the more effective (and sustainable) your work will be.

And it might not feel like hard work at all.

This question of how to find the kind of work that feels almost effortless — where output is high but it doesn’t feel like a grind — is something I keep coming back to, especially as I gain more and more clarity around the shape of my own work, which I will share more about soon.

If you are curious about doing some exploration here as well, you would probably enjoy Creating Space, the journaling course I created with Benson. The course isn’t focused on work, but more broadly about creating the space to notice where things flow easily and making more room for that kind of energy in your work and life.

Early bird pricing ($40 with FALLEARLYBIRD) ends at midnight (PT) today if you want to join us for the fall cohort!

If you’re new here: Creating Space is a 6-week course designed by myself and Buster Benson to help you carve out space for yourself through daily journaling. You’ll explore themes like time, physical space, money, and obstacles — and reflect on what emerges when you create some space to check in with yourself. Prompts are delivered via 750 Words, a private, minimalist writing space, and the course is designed to meet you where you are — whether you write every day or just when you can.

Over 50 people joined us for the first run of the course this summer, and following along on everyone’s Creating Space journeys on the community page has been such a joy of my last few months.

Every time a “note of inspiration” came in, I felt grateful and a little awed that this little course Buster and I put out into the world was helping people move through transitions and reconnect with themselves.

Here’s one reflection I shared in the community:

“I’ve gone through these prompts a few times now (pre-course-ideation, course development, and now live with all of you!) and it’s fascinating how new insights and memories come up each time. One realization this time around is how deeply I’ve internalized motherhood as a self-sacrificial endeavor, where others’ needs come first.

My default would be to only carve out space for myself when it doesn’t inconvenience anyone else at all, which actually works ok when you have few obligations and other people’s needs to consider, and there is ample time and space to go around. With three kids, a partner, household obligations, etc...that would mean no space ever. So, I’m working on inconveniencing other people, asking for help, and getting more in touch with what I want!”

We also gathered a bunch of thoughtful feedback and used it to iterate on the course — improving clarity, fixing bugs, and making the experience smoother. It’s still the same core course — 6 weeks, 42 prompts, delivered within space of 750 Words — but with some rough edges smoothed out.

You can start anytime! But there’s something special about moving through the course with others — seeing the same usernames show up each day on the community page, reading their notes of inspiration as they move through the course, and building a journaling habit together.

The course is normally $50, but for the next week, you can join for just $40 using the code FALLEARLYBIRD. The offer ends October 12th, but this cohort will be open until the end of the year at full price.

Sign up here

If you’re curious about creating more space for yourself in your life, and would like a little structure and accountability, I’d love for you to join us.

Hope to see you in the course,
— Jean

She’s making her first short film, After Moonrise, and it’s been such a joy seeing her bring this film to life. In this piece, Vinamrata will explain the twists and turns she took during her sabbatical that brought her to filmmaking, and how you can also create a similar space for yourself.

As a recovering overachiever, a sabbatical is one of the hardest things you’ll do because of the inherent uncertainty required to weather the storm.

The ideas of “success” and “knowing where you’re going” are inextricably linked. There’s some truth to this: if you are working towards a concrete, well-defined direction, you’re more likely to get there. But knowing what you want isn’t as simple as a journaling exercise or reflection; it’s the cumulative effort of micro-moments of realizations that eventually lead you to a bigger answer. And reaching these realizations requires space to try things without knowing where you’re going—weathering uncertainty.

But how exactly does one go about that?

Backstory: Why I took a sabbatical from corporate tech

When I first entered tech, I had a clear vision of what I wanted. Over a decade, I achieved a lot of it, and the remaining (like becoming a venture-backed startup founder), I didn’t want anymore. I felt like I was becoming a different person than who I was when I first started in the industry, and I needed space to figure it out.

There were so many signs of needing that space, but the most obvious was how every day felt like such a…struggle. During work, I felt like going through the same motions. Victories felt more like a relief than a signal that I had achieved something meaningful. I was turning down career advancement opportunities — because I didn’t understand the point. As a former overachiever, this was a clear red flag.

I was also planning my wedding around this time, which made me think a lot about starting a family. While I knew I had time, I also didn’t have… that much time. I figured this would be the few precious years when I could truly focus on myself, which gave me a greater sense of urgency.

Running lots of experiments

I knew that by taking a sabbatical, I’d have to embrace uncertainty. But what if I could control the uncertainty? That’s why, before quitting, I brainstormed projects and experiments that I wanted to try. It turns out that I wanted to do a lot of things: scale my coaching business, create a YouTube channel, write a novel, read more books, undergo more intense therapy, and pursue screenwriting. Writing it down was an exciting reminder of the road ahead of me (which was very helpful when I was just trying to make it through the workweek).

However, during my sabbatical, things changed quickly. It turns out that I didn’t factor in my learning curve or my general burnout. As a result, the list soon felt daunting and discouraging. There were times when I wanted to give in and just pick a thing just so I had something concrete, but I had to remind myself that success wasn’t about output; it was about having the space to try things and eliminate options. Sometimes, that meant giving up on projects halfway through, like my YouTube channel (we won’t go there). It was a messy, painful, and non-linear process, which was very difficult for my brain to accept.

The biggest thing that helped me stay the course was complementing the exploration with inner work, which, in my case, involved working with an IFS-trained therapist. Through this work, I learned to embrace and understand emotions like sadness, fear, and shame, which were crucial signals in helping me process my exploration.

Looking back, I’m really grateful that I gave myself the space to dream, try, and fail. There are times I wonder if I should have had “less of a plan” and let opportunities emerge rather than methodically checking off each item on my list. But I think it ultimately comes down to individual personality. I knew that I needed a plan and checkpoints to feel comfortable taking this risk, and I’m so glad I did that instead of fighting that need.

Narrowing by letting go

Now that I had a few completed experiments, I had to decide: what did I want to narrow in on?

Most people will tell you, “Just listen to your intuition/feelings.” But the reality is much more complicated, because before you can listen, you have to step away from the “shoulds,” which is far more complex.

Ever since I was a kid, I wanted to become an author. During my sabbatical, I finally wrote a draft of a book, something I’d prepared for by writing countless short stories and attending writing workshops and conferences. However, it turns out that I absolutely detested the process. It felt lonely, isolating, and draining, and despite my best efforts, my experience did not get better.

Looking back, it was difficult for me to accept because before I had even started, I had decided I should like this, even though my reality begged to differ. It was a painful truth to accept, because accepting the truth wasn’t just acknowledging my feelings — it also required letting go of a childhood dream and saying goodbye to a past version of myself.

I’m incredibly grateful to the writers I spoke with during this time, who validated my feelings and held space for me to explore my messy emotions. They gently reminded me (many times) to focus on my present experience and feelings, rather than what I promised myself years ago when I didn’t know any better. When I followed their advice, the truth was clear: I didn’t want to be an author, at least not right now.

Instead, I wanted to write screenplays and make films. Growing up across India, Saudi Arabia, New Zealand, and the US, books and movies were the only safe spaces where I could express myself freely and see others do the same. But my novel-writing experience taught me that I wanted something more collaborative, a way to bring stories to life visually, not just on the page. It’s why I loved product management: I got to use my leadership skills to work with a team to build something together. I didn’t want to lose that. Writing and filmmaking scratched both the itch to tell stories and work with a team to bring them to life.

However, there was also resistance to pursuing this path, especially as a non-film school graduate. I had never worked with actors, nor had I ever held a real filmmaking camera in my life. There would be a lot of new stuff to learn, and I would likely suck at it. That’s where resistance came in, telling me to give up before I’d even started because I have a crippling fear of failure. However, this was helpful information, as it helped me understand that what was giving me pause was the discomfort of doing something new, not because I disliked film or writing. In other words, my resistance was a challenge that I could overcome through getting reps, which is exactly what I did, whether by taking classes, reading books, creating work, and seeking out mentors.

Having those moments to slow down and process, rather than immediately jumping into the next thing, was pivotal to successfully navigating this inflection point. It would have been really easy for me to ignore my dislike for novel writing and dive into the next draft, but I would have ended up burning out.

Taking time to slow down and pause might feel like a “waste of time” in the moment, but in the long run, it saved me a lot of pain by focusing my energy on what matters: filmmaking and screenwriting.

The money thing.

Before I could wholeheartedly explore screenwriting and filmmaking, I needed to figure out how to support myself. A creative career could take years (or realistically, a decade) to really take off, and I didn’t want to put pressure on my art.

Initially, I thought about building a coaching business, given my passion for coaching clients and entrepreneurial mindset. At first, it was awesome. I loved building a business and working for myself. But there was a tradeoff: growing a business requires a ton of effort and weathering uncertainty, which I was already doing in my creative career.

I was burning the midnight oil on both ends and drowning quickly.

I realized that what I needed was a balance of stability and flexibility. Luckily, I had just interviewed for a part-time role at a technical marketing agency, where I would make enough to cover my bills, work with people I liked, and have enough time to write. But taking this job would mean deprioritizing my coaching business and, in the long run, a pay cut.

Despite the tradeoff, I took the job, and I’m so glad I did. Having this stability has been game-changing in establishing a consistent routine and freeing up mental space to work on my filmmaking and writing career. But it requires making adjustments in other areas. I no longer have a glamorous, fancy tech job (in fact, I’m a lowly contractor), and I’m not earning big tech salaries.

Some days, this brings me shame. Instead of fighting it, I accept it as a part of my journey. Pursuing this path isn’t just about doing this thing that I love — it’s also embracing a new version of myself and letting go of a former identity, which is painful. The pain is a sign of the shift, not a problem that needs to be solved.

Lessons for anyone considering a major life change

If there’s one thing I’ve learned through this process, it’s that accepting uncertainty requires us to cultivate a more honest and authentic relationship with ourselves.

Learning to accept the uncomfortable emotions that emerged was key in this journey. If you’re going through a significant life change or considering embarking on a sabbatical or other transition, here are some questions that can help you work through emotions that come up:

• What emotions come up when you imagine jumping into the unknown?

• What’s prompting these emotions to come up?

• What do these emotions need from you? What’s prompting this need from them? What does this situation remind them of from their past?

• How do you feel about these emotions? What’s shaping your perspective?

• How might you find a way to meet the needs of these emotions?

There’s never a right answer, just the answer that feels right in that moment.

To follow along with Vinamrata’s journey, subscribe to The Next Chapter!

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Note from Jean: I would love to highlight more unconventional paths in and out of tech, either through guest posts or interviews. If you have a story that you want to share, reach out to me!

Of course, I had my doubts. I told myself I could always go back to Google if there wasn’t something better out there. But what if they don’t want me back? What if I never find something else?

But there was also another part of me — the steadier, quieter one — that trusted I’d figure it out. I didn’t know what was next, but I was curious enough (and maybe just naive enough) to believe there was something else out there for me. That move led me into the world of early-stage startups — it’s hard to believe that back then, I knew nothing about startups, and now they’ve been my professional life for the last 15 years.

Years later, I left Medium without anything lined up, or as a coworker referred to as “pulling a Jean.” Last year, I did the same when I departed my latest startup.

These transitions, which seem relatively unusual in the corporate tech world, have led me to reflect on the mindsets and tools I rely on during such times, and how I can share them with others.

The part we tend to skip over

We’re taught to be good at execution: set a goal, make a plan, follow the steps. School conditions us this way, and early careers reinforce it.

So when we hit life’s big transitions, we often reach for that same playbook. We want the roadmap so we can strive for the next milestone.

But when we immediately reach for the next thing, we miss the messy, uncomfortable middle, that liminal phase between “the old thing is gone” and “the new thing has emerged.” The space of not knowing yet.

Most people try to leapfrog over that part, because it feels so unsettling.

It’s hard to make space. Not only is it personally uncomfortable, it’s also socially unacceptable outside of “sabbaticals.” People will ask you what’s next, and you’ll feel pressured to give an answer that’s more goal-oriented than “I don’t know.”

But it’s in this space that you get in touch with what you really want in the next phase, rather than what society, capitalism, or the people around you tell you to want.

Savoring the messy middle

Every so often I dream I’m back in college, right before graduation with no idea what’s next. I start to panic — job applications? grad school? a new city? a year off? — but under the anxiety there’s also this electric sense of possibility. I wake up unsettled, but buzzing with: I could do anything. What will I do?

That dream feels a lot like the transition I’m in now. One moment, I’m terrified and wondering what I’m doing, and the next, anything seems possible.

And both can be true, I can feel scared and excited. But as much as possible, I’m trying to stay in that space of exploration and possibility. Because you can know that you need space to figure out what’s next, and still find yourself completely filling that space with worry about finances or employability instead of exploring what you truly want.

What if, instead of meeting the unknown only with anxiety, we also met it with curiosity?

Could we learn to even savor the mess, to savor the unknown and that sense of anticipation?

One thing that’s helped me slow down and delve more into curiosity is always returning to a deep knowing that I’ll be okay. Each time I face uncertainty and come through it, I add another piece of evidence. So when I slip into thoughts of scarcity or desperation, I can look back and remind myself: if I stay patient and curious, clarity will emerge.

Foundational practices for uncertainty

As a somewhat impatient person, waiting for clarity to emerge can sometimes feel torturous. I can feel behind even when I’m just a few days into an exploratory phase. There are so many things outside of my control, but I’ve also learned that there are many things I can control.

When I sense a transition approaching, I have to remind myself to double-down on foundational practices that create a more conducive environment for me to figure out what’s next.

The first is sleep. A few years ago, after listening to a podcast episode with Matthew Walker (author of Why We Sleep), my husband Naveed and I started taking our sleep very seriously. Instead of thinking about what I wanted to do that year, I made the assumption that if I just focused on getting good sleep, good judgment and dynamic attunement to what I want would follow. Sleep became my first foundational practice.

The next foundational practice that has re-emerged this past year for me is journaling — it helps me notice what I’m drawn toward, what repels me, what sparks curiosity.

While I think sleep is probably important for everyone, your own foundational practices that create an environment that helps you navigate uncertainty may be different. It could be yoga, meditation, weightlifting, eating well, or hiking. Start to notice what it is in your life that helps you clear your mind and be more attuned to what you want.

Coaching Toolkit: Practices for Sitting With the Unknown

It’s easy to think of a situation as something happening to you (being laid off, death of a loved one) versus something you’ve decided for yourself (quitting a job, ending a relationship), but in any situation, there are things in your control and things outside of your control.

Navigating the uncertainty of these transitions is uncomfortable, but it’s also a skill you can build. These are the practices I return to when I feel adrift.

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If you’re a Bay Area-based engineering leader, read to the end for a special event!

1. Year one of Mama Summer Camp is complete

A few months ago, while planning out the older kids’ summer schedule, I thought: what if I ran a week of summer camp? With a flexible schedule this year, I ran a successful week of “Mama Summer Camp!” It was a full week of bike rides, hikes, neighborhood explorations, some math and writing, a zoo visit, crafting (when you’re “saving” $500-1000 on summer camp fees, suddenly buying any and all craft supplies feels very reasonable!), and a July 4th BBQ.

Perhaps I’ll just leave you with a review from Alina (12), who said, “it sounds like a negative review, but it’s actually positive”:

“Overall, it has been pretty fun, although there has been some questionable behavior from the summer camp leader. Someone states in one incident during Monopoly, Mama said "My feet are stinky, probably sweaty from biking. Wanna smell them?"

Also, camp plans get canceled or delayed a lot, like the hike or the zoo. There is also a bald man who is not part of the camp who interrupts it a lot. And sometimes they fight. I recommend it.”

2. Nightly Monopoly was a crash course in capitalism

The kids kept asking to play Monopoly, and I don’t think they knew what they were getting themselves into. For about 9 nights straight, we played a full game each night, starting the second Baby K went down for her bedtime at 7:30.

Almost every night, there were tears, dramatic bankruptcies, someone making it rain monopoly cash, and declarations that it was a horrible game and we should never play again. Classic Monopoly.

It was a sometimes exhilarating and sometimes brutal lesson in the realities of capitalism. As for us grownups, it was also a challenging balance — do we play to win at all costs, or to maintain harmonious family dynamics?

3. I’m back on a bike!

After a week in Durango, Colorado, where I marveled at everyone’s enthusiasm for bikes and how toned their calves were (there’s even an instagram account!), I came home and found a used bike for myself.

Since then, I’ve been taking longer rides with the older kids around Berkeley and along the Bay Trail. We’re looking forward to getting Naveed on a bike too and getting a baby seat for full family bike rides.

4. I’m headed to Nationals!?

Earlier this year, I noticed myself feeling curious about the club ultimate frisbee scene. It’s something I never pursued in my 20s, but the appeal of having a team and going to tournaments always attracted me. Ultimately, I decided that joining a club team with weekly practices and social events wasn’t really what I wanted right now in my life.

But then a friend connected me to someone organizing the first-ever Bay Area Grandmasters Mixed team. We’re headed to Colorado next weekend for Nationals. I’m a little intimidated by all the players who’ve been competing for decades, but mostly excited to dive in with a new team.

5. Creating Space is live

The six-week journaling course I built with Buster Benson launched at the end of June. Every morning, I open up 750 Words to write and am dazzled by the 10+ people who have already done their Creating Space writing for the day. I love seeing the community page each day and knowing I created something that helps others create a bit more space in their lives.

The lightweight structure of the course and the sense of support and community built into 750 Words makes for a powerful combination. Buster and I will collect feedback in a few weeks, and figure out what changes we want to make to it before the next run. I’m also dreaming up variations on the course — perhaps something for moms or parents wanting to reconnect with themselves, or a course for people in career transitions. Stay tuned!

6. A summer family roadtrip, we’re doing it!

We’re renting a minivan and hitting the road for a two-week California loop, stopping at a few national parks along the way. It’ll be a mix of camping and hotel stays (ideally with pools). I’m a little nervous about the longer drive days especially with Baby K, but I’ve also just been really looking forward to a long family road trip like this for a long time, and this year felt like THE year. I want to make the most of it while the kids still want to hang out with us!

7. My Berkeley lending library lives on

The Google Sheets Berkeley Lending Library I started last year continues to see plenty of activity, at least with my own items. Our porch constantly has items coming in and going out. The most-loaned item is unexpectedly inflatable loungers.

The spreadsheet has been working fine, but lately I’ve also been thinking about what a dedicated site or app might look like.

8. Favorite summer foods

No summer update would be complete without food. A few hits from our kitchen lately:

• No-bake cheesecake bites - I’ve been making lots of easy recipes for Baby K from Yummy Toddler Foods, although these cheesecake bites are for the grownups for when we want a little treat at night!

• Soba noodle salad - Just One Cookbook is one of my favorite recipe sites, and I made this noodle salad dressing the other day with random fridge veggies…it was so good!

• Egg bites - this is also on weekly rotation here, especially when we can get lactose-free cottage cheese. It is so good, and Baby K seems to not get sick of it either.

• Yakitori skewers - these were featured in our July 4th BBQ this year! We paired it with corn on the cob with miso butter, yum!

I’m always open to easy, high-reward recipes that are on rotation at your homes if you’ve got any to share!

9. I’m starting to think about what’s next work-wise

With Karu starting school in August (!!), more space will open up in my week very soon, and I’ve felt a subtle shift in my own energy and levels of interest. I’m not rushing into anything, but I’m definitely more open to work-related conversations — consulting, coaching, or full-time opportunities. My inbox has been busier, and I’ve noticed my interest in responding has gone up too, almost like my brain is self-regulating my available space.

I’m still in a pretty exploratory space, so if you’re at an early-stage startup or thinking about engineering leadership needs at your company, I’m happy to chat informally and see how I might be helpful. My friend Jen Dennard and I are also writing regularly about startup operations over at Startup Soup.

One Last Thing!

Speaking of work and food, my friend Diana Kimball Berlin and I caught up recently about work and life.

Diana recently joined Gamma and invited me to an engineering leadership dinner she’s hosting in SF at Foreign Cinema next week. She’s also kindly letting me nominate two others to attend!

So if you’re an engineering leader who is available next Tuesday evening (7/22) in SF and want to hang out with me and Diana while eating yummy food, let me know by Friday!

That’s it for now! Wish us luck on roadtripping and camping with a 1 year-old! Let me know what you’ve been up to this summer, or just hit reply and say hi.

She started off confident — she had solid experience and was ready to reenter the tech industry after a break with family. But after months of hearing nothing back, applying into a brutal market that seemed to prefer candidates without visa needs, that confidence began to thin. Not just about her ability to get a job, but about whether she even wanted one in tech anymore.

“It feels like being in a desert with no map,” she told me.

She’d spent years in tech, often the only woman on the team, often feeling like she needed to shout just to be heard. Now, she felt pressure to perform in new ways — to build a personal brand, to constantly self-promote — but it all felt very performative.

When you’re in a place like that — confused, wavering in confidence, a little lost — it’s hard to know what to do next.

This is just one situation where balance coaching can help find a way forward.

Balance Coaching and Mindsets

Balance coaching is one of my favorite Co-Active coaching tools for moments like this.

Simply put, balance coaching helps you name the perspective you’re currently holding — the one that’s shaping your experience — and then explore different ones. Ones that might help you see your situation more spaciously. Ones that give you more agency.

When we’re stuck inside a single lens, everything can feel high-stakes, high-pressure, and low-control. We think the way we’re seeing the world is the world.

But what if you could change the lens?

You’ve probably heard of growth vs. fixed mindset:

• Fixed: I’m either good at this or I’m not.

• Growth: I can improve through effort and learning.

Carol Dweck’s research shows that just introducing language aligned with a growth mindset shift changes how students take on challenging problems. Students who are exposed to language that reinforce a fixed mindset are more likely to give up when encountering challenges.

Other common shifts I’ve seen in coaching:

• Scarcity → Abundance
  → There’s not enough / I’m running out → There’s enough, or I can create more

• Victim → Agent
  → This is happening to me → I have a say in how I respond

• Judgment → Curiosity
  → Why am I like this? → What might this be showing me?

• Self-Criticism → Self-Compassion
  → I’m behind / failing → I’m doing my best in uncertain times

• Perfectionist → Experimenter
  → I need to get it right → I’m here to learn something

Want to try this for yourself?

In the next section, I’ll walk you through balance coaching step-by-step as applied to Sandy’s story — and an experimental AI coaching tool to help you apply it to your own life.

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