Everybody's Winging It

A reminder that you're doing just fine

As I continue to make my way through Four Thousand Weeks, I came across this passage:

“I sometimes think of my journey through adulthood to date as one of incrementally discovering the truth that there is no institution, no walk of life, in which everyone isn’t just winging it, all the time. Growing up, I assumed that the newspaper on the breakfast table must be assembled by people who truly knew what they were doing; then I got a job at a newspaper. Unconsciously, I transferred my assumptions of competence elsewhere, including to people who worked in government. But then, I got to know a few people who did — and who would admit, after a couple of drinks that their jobs involved staggering from crisis to crisis, inventing plausible-sounding policies in the back of cars en route to the press conferences at which those policies had to be announced.”

I found this excerpt very reassuring, as I’ve come to unearth more and more of this truth as well.

Sometimes, from where you stand, it may seem like everyone else knows everything. Or that people more advanced in their career know everything there is to know. That the abundant gaps in your knowledge base will be found out, and someone will say, “Wow, did you know Jean never even took a compilers class or programming languages class in college??” or “She got an internship at Google without writing any code in her interviews?” Both true.

For years, I had this thought in the back of my head that I had snuck my way into Google’s backdoor, through two phone interviews, one focused on data structures and algorithms (your standard brute force —> hash map optimization interview), and another design interview for placement on the interviewer’s team. They must have gotten their wires crossed, I was convinced. One of them should have been a coding interview.

When my internship converted to full-time, I carried that question mark with me. Despite the fact that I had gone through two more conversion-to-full-time interviews which included white-boarding. Despite the fact that I had kicked ass during my 12 week internship doing full-stack development, from map-reduces to javascript visualization.

When I quit Google without anything else lined up, to see what else Silicon Valley had to offer, I had a lot of confidence in my ability to figure it out. And anyways, if it didn’t work out, I could always go back to Google. But a tiny voice also whispered, What if you got into Google by accident, and if you try to apply again, they’ll figure it out, and reject you.

Despite having gained the respect of my co-workers, and single-handedly built an experiment that I presented on-stage and launched internally at Google’s TGIF all-hands.

As an aside: I’ve since learned that many people at Google have this story that they snuck their way in. Many highly competent Google engineers fear leaving, avoid interviewing outside the Google bubble, and think that their skillset will not be relevant elsewhere. Stoking this widespread belief is probably pretty beneficial to company retention.

It’s been over a decade since those Google and post-Google days, and I’ve gained a lot of self-confidence in my ability to figure things out or get guidance/help from people around me, even if I haven’t done it before. In fact, doing stuff I haven’t done before is probably my favorite state to be in, which is probably why, despite how nice it sounds to find a big slow company to chill at, I seem to continually gravitate towards early stage startups, where the job is a steady stream of new problems to triage and solve.

Here are some mindsets that helped me:

Everyone else doesn’t know everything

Someone on your team may be great with backend architecture but never touch CSS. Someone else may be able to whip up prototypes faster than you can even wrap your head around the experiment. Someone else may like to dive deep into data and find insights that help the team.

If you’re relatively early in your career or saddled with imposter syndrome, it may seem like everyone’s knowledge includes everything (a superset of combined knowledge of everyone you’ve encountered). Reality looks more like this:

As an engineering leadership coach, I coached a lot of senior leaders, and I honestly was surprised by how little some of them understood about human motivation and relationship-building.

And as I myself moved into a VP of Engineering role, this diagram become even clearer to me. My particular skillset will not be a fit for every company, but not because I’m a bad engineering leader. At more senior levels of engineering leadership, you just won’t find anyone who is strong on every axis, so you need to figure out what’s important for your company, and find someone that’s a good fit for the role.

Everything you’ve learned is applicable

In high school and college, I took on a lot of things that weren’t that obviously related to the career I have now. I was the managing editor of the high school paper, and spent many a night hunched over the near-final version of that month’s paper, catching final typos and alignment errors before it was sent to the printer. In college, I took countless humanities classes about religion, history, and literature, and spent 6 hours a week in college in a cappella rehearsals.

I didn’t do any of those things to bolster my career, but in retrospect, I can see how they have contributed to my strengths. The time I spend (and spent) writing and editing is probably the best way that I can influence the tech industry. It lets me communicate with the team effectively, write and share blog posts and newsletters. Writing has also been really important for my mental well-being. Being in an all-female a cappella group? It taught me a lot about hiring, having a principled rubric (not defaulting to “culture fit”), and how cultural norms shape a group. It also provided a regular much-needed reprieve from the mostly all-male CS spaces I spent the rest of my time.

When I started at Range two years ago, part of me wondered, will I be rusty? I’ve been in the leadership development world for 3 years. But I quickly started to see that the skillset I had gained in that world (selling to engineering leaders, writing blog posts, designing courses, facilitating workshops) were so applicable — as VP of Engineering, I ended up hosting Lead Time Chats, running Effective Meetings workshops, coaching team members, networking with and helping build positioning for engineering leaders, and more.

So, if you took time off to care for family members, or took a detour from your current career, or are new to your career after a career change, it can be common to look at your own resume and feel inadequate. But look again. What’s the narrative? What did you learn, and what did you learn about yourself that you’ll carry with you? What’s your story and the uniqueness that your experience brings?

And if you’re considering doing something else but worried that it’ll knock you off your career track, think again too. I imagine that my own life will bring at least one or more major career changes, possibly writing a book, maybe doing something tech-adjacent like coaching again or not in tech at all. But I know now that those changes won’t be hard resets.

Grant me the confidence of a mediocre white man

Controversial perhaps, but I honestly found this extremely effective when I felt unsure about myself. The tech industry and this world we live in is just more forgiving and less critical of white cishet men. I have seen women and other underrepresented folks put their head down, gain years on years of experience and certifications, only to be passed over because they didn’t have all the right credentials. While the same set of mediocre white men fail upward and float around major tech companies in Heads Of roles, sometimes in functions in which they have absolutely no experience beyond perceived potential.

When I took the leap to leave Medium and be a coach, I had worked with coaches before, and I figured a lot of what I did as a manager in a matrix-like organization was coaching, but I hadn’t had any formal training. Slapping a “coach” label on yourself and charging market rates is, I learned, controversial in the coaching world, but anyways, I did it. I saw others around me — namely, white men — do it, so I figured I could give it a shot.

Later, in coach training, I was intrigued that the many female coaches-in-training didn’t feel entitled to the same boldness. I don’t feel like I can charge anything until I’m certified. I’ll start my rates at $50/session and increase it every year as I gain experience.

Meanwhile, I was building a robust coaching practice charging $400-600/session, and regularly raising my rates to test what the market would bear.

I shared this mindset of “What would a mediocre white man do?” with my fellow coaches, and to this day, they will mention it as the best piece of advice they took away from coach training.

Of course, if like me, you don’t fit the demographic of white male, you will not yield the same results because of the systemic biases in our industry and world. I’m sure I have been passed over for many promotions and coaching opportunities because of how I look as a youthful Asian woman. But I have found that it’s an effective hack to getting over the ways you hold yourself back.

—

I’m also reminded of a two-day tech leadership training I ran at a major SF tech company. Tech leads learned some fundamentals about how to define their role, what their superpowers were, how to influence without authority, how to build alignment, and more. At the end of the second day, we asked participants to share what they were taking away from the experience.

One tech lead looked particularly excited as he shared:

“When I came in yesterday, I felt really nervous because I sort of feel like I don’t know what I’m doing, like I’m just winging it. But after these two days in training, what I learned is that all of you are winging it too!”

He was thrilled that it was ok that he was still figuring things out — that that was not his inadequacy, but in fact, the job.

In those moments of feeling like you need to do X before you can do Y, or that you need to fill in particular gaps in your expertise, or that everyone knows more than you do, just remember, you’re doing just fine. Everybody’s winging it.

Lead Time Chats

I’m thrilled to share this episode with you all — I chatted with Range co-founders (and my coworkers!) Jen Dennard and Dan Pupius. They are long-time colleagues of mine from Medium days, and the reason I joined Range. They share their thoughtful observations and insights about the return to work, especially in hybrid workplaces.

How can you implement and roll out policies that don’t disadvantage remote teammates? How do you actually spend in-person time effectively, rather than force people to come in, only to have them be on Zoom with other remote teammates?

Check it out — it’s the last episode of Season 4. I’ll be taking a pause for a bit, to figure out what’s next with Lead Time Chats. If you’ve enjoyed the series, and have feedback or input on what you’d like more of, please let me know!

Things I’ve been enjoying

• Workspace tools for home management - Naveed and I started using Range and Asana to track the many household things that in progress. We have all these great tools for workplaces — why not benefit from them for the household realm!

• Post-meal family walks - I saw this massive thread of health tips, and we started having post-dinner family walks. Sometimes it’s longer, and sometimes it’s just around the block. It’s been a nice routine.

• Digital detox-ish - Inspired by a conversation with coworkers about their social media habits, I deleted Twitter, Facebook, and Instagram apps from my phone. I occasionally still check them on my mobile browser, but I spend a lot less time mindlessly scrolling. We’ll see how long it lasts.

• Light seasonal decorations - One of my worst nightmares is accumulating a ton of seasonal decorations and having to put them up and down constantly. But I did make some crochet pumpkins (free pattern) and am enjoying what the kids call Mama’s Pumpkin Patch.