November 23, 2020.
I recently got an email asking for some perspective that was general enough that I thought it might make more sense to answer as another mailbag post. The lightly edited core of the email was:
These three questions relate a bit, but are sufficiently different that I’ll answer them independently.
When you talk to folks later in their career, they’ve spent so much time crafting their career narrative that it can be hard for them to remember which parts of what they’re saying are real and which parts are the story they’ve practiced telling about themselves for the last decade. For example, earlier this year I tried to write up my own career story in a way that acknowledges just how much luck and privilege has played a part in my accomplishments. It’s still a narrative–we’re all public figures to some extent these days–but hopefully at least a relatively honest one.
The best general career advice I’ve written is A forty year career, which tries to think about what our careers can be if we focus away from liquidity events and towards fulfilling work. Of course, this advice is harder for some folks to follow, who experience a tech industry that is indifferent to their continued participation: "How would I approach my work differently if focused on growth and engagement, and if I measured eras not in equity and IPOs but instead in decades? I’d focus on a small handful of things that build together, with each making the others more impactful as they compound over time."
I also wrote up a more generic article on career advice before that, Some career advice, which isn’t particularly good, but has some generic relevant advice, a few that are particularly relevant for someone ~5 years into their career:
All of those have been important lessons for me, and in particular, the last two have helped me manage my mental wellness more effectively as I’ve come to understand them better.
First, a tangential answer. Titles do matter and it is useful to spend time pursuing them to a limited extent,, especially for folks who don’t look like the stereotypical image of a software engineer. However, it’s also important to remember that titles are not enough. It’s easy to get a senior title in a such a way that you end up stagnating.
Another indirect answer is that unless you have a very clear passion, I’d recommend against specializing too much at this point in your career. I’ve seen folks get framed into a given role and be unable to escape that role for decades. Part of that is, probably, their responsibility for not being more creative in how they switch roles, but there are real forces in play that create career inertia. It’s particularly hard to overcome the financial aspects of that inertia when you have significant responsibilities that make it hard to take a temporary financial hit.
As a final indirect answer–then I’ll actually answer the question–I’d recommend that folks be very cautious about moving from core engineering roles into what I’ll very loosely describe as adjacent roles like TPM, PM, Engineering Management or SRE. If you struggle it can be hard to transition back, but even moreso if you thrive it’s even harder to transition back–how do you step away from all that success? My general advice is to avoid changing roles until you’ve finished what you want to accomplish within your current role–you won’’t always retrace your steps later.
Alright then, so what should you actually focus on?
Like most advice, this is pretty generic, but if folks ever want more concrete advice, I’m glad to give my thoughts, although what you probably really want is advice from someone who actually knows you and your context, which brings us to the third and final question...
Last year I wrote about the strategies I’ve found for Meeting people, which is some general advice on network building. In terms of actually finding mentors, my experience is a bit like what Ritu Vincent’s shared in her StaffEng interview, "What’s been most impactful for me is having a lot of people who I think of as mentors, usually friends, former managers and folks that I’ve worked with. I have a decent number of recurring monthly lunches, coffee chats and dinners with people who’ve worked with me in the past, know me, and I trust. It’s those conversations about career challenges and growth that have gotten me to where I am in my career."
I’ve never found the idea of a capital M Mentor to be super useful for me, but there are dozens of folks in my life who I go to sometimes to get their perspective. The two things that have been most useful for me are meeting folks by working together at medium to large companies (Stripe was… maybe 400 people when I joined an ~2,000 when I left. Uber was ~1,000 when I joined and maybe ~8,000 when I left, Yahoo was 13,000 when I joined and, ahh, 9,000 or so when I left, but I was so early in my career that I didn’t meet many folks), and forming various learning circles and communities. For example, early this year I formed a CTO/VPE learning circle (going really well, although not accepting more folks personally, would strongly encourage more folks to form their own groups like this that meet 1-2 times a week for 1 hour to discuss challenges together) and more recently a TechWriters discord (which isn’t really working yet, pretty low engagement in there, but a supportive place and have met some really impressive folks ambiently through it).
If you are more of a Mentor type, my best advice would be to send a really concise, thoughtful question to a dozen folks you look up to, and then if they respond send them another similarly thoughtful question six months later. Do this three or four times and you have a mentor who does have your context and appreciates how thoughtful you’ve been about their time, and most of those folks at that point would be glad to have a 30 minute video call where they wouldn’t have been engaged enough earlier on.