Reader Mailbag: Struggling to do it all

A reader writes in with questions about technical up-skilling, finding balance in life and work, and getting in touch with their identity outside of work.

I’m excited to bring you the first version of Tech and Tea: Reader Mailbag. This reader wrote in touching on so many of the struggles I hear from friends who are further along in their careers, and this is exactly the type of conversations I want to have more of. Enjoy!

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Dear Jean,

I recently took a sabbatical to disconnect from work: to think about who I am and build up confidence in my identity outside of work. I would have gone longer on this time off if I hadn't been forced to return to work (perhaps artificially or self-imposed), but at least in doing so I deliberately chose to pursue something different. I transitioned from a management role back into an individual contributor role after being a manager for many years.

But now that I’ve returned to work, I still have that nagging feeling of “is this really what I want to be doing with my time?” Particularly in the context of:

• Remote work - my employer has embraced a distributed approach to work (no return to office mandates) but in doing this I've lost a human and social connection to partaking in full time employment;

• Mental health challenges - I'm in a much better state now as a result of taking a more balanced approach to work and life, but how long can I sustain that?

• The struggle to do it all - this is a biggie for me. I have an amazing partner and two young kids. My career to date was built off the back of their support and me working too hard. I want to be more present and balanced, so that I don't miss out on the little things in life that bring joy - that make this all worth doing.

So what's top of mind for me?

• How long can I stay in a technical role when my technical (coding) skills are so under-nourished? If I need to up-skill to stay in the job, how will I make time for that whilst not compromising on my goal to be balanced? 

• Is it always going to be a case of ‘grass is greener’ and if I do jump to another role, will I just miss what I had?

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First of all, what a treat to read through your email and see how many similarities there are between us. You are grappling with a lot of the same issues that a lot of engineers / engineering leaders struggle with after reaching a certain point in their career, especially for those who have a family. With competing priorities at play, it can be hard to figure out what you want in your career. 

I remember losing myself in code late into the night in college and in my early startup days, and loving it. Some days, I still think there will be a phase of work that wholly consumes me in that way, and to be honest, a part of me yearns for it. And other times, it's so clear that having space to be present for my family is the most important for me in this phase of life. I don't know if that period of all-consuming work flow is still in the cards for me. I’m open to it, and not attached to it.

In this season of life, my work supports the life I want, not the other way around.

The tech industry sure has a way of making that seem lazy or complacent, that you should be spending all your time upskilling, pushing your growth edges, working your day job and doing other projects on the side. And if that's what you want, then by all means go for it. But if it turns out that some parts of that don't feel right for you, that's ok too. My gripe with the tech industry is that it can make people feel not enough, or not working hard enough, when they don't want that, even though most people I know are earnestly trying to figure out how they can find better balance in their work and lives, not hustling at a YC startup rocket ship working nights and weekends.

There is also this myth that you get on a one-way career path and it's not normal to get off. I like the idea of a jungle gym a bit better. Unless you are one of the fortunate ones to benefit from a tech windfall, your career could be many decades long, and it’ll look different at different times. There may be a few years when being an individual contributor is a good fit for you, and maybe some years, you'll feel the itch to go back into management, or coaching, or running your own business, or something outside of tech entirely. Or you’ll feel the desire to take some time off to prioritize other things, and then return to tech in some way.

As our lives and needs evolve, so too does what we need from our jobs, and so it's only natural that you might gravitate towards something different. I wouldn't see that as a sign that you're indecisive in your career, or having trouble settling down on a path. 

At the same time, one of the common things people in more senior roles need from their jobs is a baseline level of pay that supports their lifestyle and what their family needs. Navigating these seemingly conflicting needs — desire to see what else is out there and a need for financial stability — can make it hard to figure out what direction to go in.

A while back, I remember asking someone what their ideal role would be, and their answer took me by surprise. They said they wanted to be in a role where they could be a complete beginner — that ideally, people’s expectations of them would be similar to a new grad’s, and they could ask any and all questions they had, no matter how basic. The more senior in a career you get, the more stories people make up around “I should know this already” or “What will people think if I ask them for help?” The explicit expectation that you don’t know anything at all can be appealing.

But we don’t need to go so far in that direction, either. Something I have to constantly remind myself of is that the skills and experiences we pick up (whether through explicit upskilling or just gathered through the living of life and the working of work) serve us in ways we couldn’t even imagine, and sometimes in ways we don’t even know. The 3+ years I spent in leadership development and coaching aren’t time that took away from my career as an engineering leader. Those years enhance my experience, uniquely making me the engineering leader I am now.

Back when I was an individual contributor, I was grappling with the evergreen question of should I stay a generalist or specialize in something? Technical breadth or technical depth? It felt like if I chose something to specialize in, I would be choosing something to build the next few decades of my career around, and that felt overwhelming, daunting, impossible. One of the best pieces of advice I received was that even as a generalist, you want to build depth, and that building depth in one area just exercises the muscle of building depth in other areas. Although technical areas of expertise may feel very different, the set of skills you use to build depth in one area help you build depth elsewhere. Like linguists who pick up each subsequent language ever more quickly than the last.

Similarly, moving “back” into an IC role doesn’t mean that you’ve taken a decade leap backwards in your career. You are coming to that IC role with all the experiences and knowledge you gained as a manager — your understanding of stakeholder management, of business needs, of how to communicate with managers. Even if you feel a bit rusty with your technical skills, you bring your own unique version of being an IC to your role, that no one else could.

Do I sometimes wonder what my career would have looked like if I had stayed an IC for longer before moving into management, or if I had climbed an engineering leadership ladder instead of swinging over to leadership development? Sometimes. But I made the best decision I could about my career and how to spend my time at each point in time, and well, that’s the best we can do. When I felt burnt out, I found ways to take a break. When I needed a change, I figured out how to make one. 

You strike me as an introspective person, who reflects on your experiences and thinks about what it is you want. In this industry and in this life, that’s the best we can do — to feel deeply into what we want and what it is we need from our jobs, and try to do the thing that most aligns with that. Sometimes what we want and what we need and what aligns with that is not completely clear, which causes us to struggle with these questions — What am I doing with my life? What do I want? What do I need more of?

It’s healthy to visit these questions, and also I’ve found that for me, it can be healthy to not hunt down their answers aggressively, especially when I’m not in a good place to make big life decisions. The pressure to get to answers sometimes doesn’t allow for the space for those answers to arise. Often, the right thing to do is to put a pin in it and trust my own intuition that when answers become clear, I will know what to do.

So, it’s important to think about these questions you’re pondering, and you don’t need to figure it all out right now. It can be overwhelming to tackle all at once. Find the bits that you have the most energy to work towards right now, and just focus on those.

Best,
Jean

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I’d love to incorporate frequent Reader Mailbag responses into Tech and Tea.

Have a question? Want to let me know what’s top of mind for you? Hit reply or email me at jean@jeanhsu.com and let me know (please include “Reader Mailbag” so I know you’re ok with me sharing an anonymized version of your question).