casual discrimination and indifference to their lived experiences, but I’ve found this mindset common even among folks participating in the industry through the vehicle of significant privilege. For a long time, my own career thinking focused on reaching financial independence such that I would feel in control of my future.
My father retired a few years ago, having worked as a professor at the University of North Carolina Asheville for the significant majority of his adult life. Since then I’ve spent more time than expected reflecting on his retirement and his preceding career. In particular, reflecting on the idea that my career is something I can deliberately develop over a forty year horizon. Not four IPOs, not fourteen two-year stints, but forty years.
It’s strange to realize that I lost sight of the forty-year career model, because for a long time it was the only model I knew. Growing up, a white collar career was my only reference point for participating in America’s dwindling middle class. It never occurred to me that alternatives existed, despite the majority of my aunts and uncles being entrepreneurs who started and worked in their own small businesses. If you have the good fortune to start on the long-term career conveyor belt, do your best to avoid tripping, and ride it to success, home ownership and eventually retirement.
I did have exactly that good fortune to start on the conveyor belt, moving to San Francisco at 23, but what I found wasn’t the career conveyor belt that I expected. A different set of ideas reigned. Rather than careers, the zeitgeist reminded me of studying Death of a Salesman in high school, “Why, boys, when I was seventeen I walked into jungle and when I was twenty-one I walked out. And by God I was rich!”
Meeting my new coworkers, they structured their jobs as lottery tickets bought with their lifeblood, trading tips on managing the symptoms of work until the pearly gates of liquidity opened. We talked about coworkers and friends leaving the industry with burnout and frustration. We talked about the engineer who exercised their equity at a beloved startup and years later remained on an IRS payment plan for taxes on equity in a defunct company.
At Digg, one mentor gave me the savvy advice that the fastest path to financial success was working for four years at three different just-about-to-IPO companies. A surefire way to retire by forty. (This is, for the record, pretty good advice.)
At Uber, another friend told me I was looking at a frustrating situation the wrong way, the way they viewed their work was, “Each day I walk into work, and this slot opens up above my head, and money falls out of it into my hands, then the slot closes. I go about my day, and the next day I come back, and the slot reopens; more money falls out.”
This is a surprisingly dark way to view your life’s work. So as I pondered my father’s retirement, the question that caught hold of me was: 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’d focus on pace, people, prestige, profit and learning.
The biggest barrier to a forty year career is burnout, and preventing burnout is twofold. First, work on work you find meaningful. Second, manage your pace.
For a long time my default approach to any situation was to take personal responsibility for it, and relatedly I have never worked a job where I didn’t experience aspects of burnout. When I joined Stripe, one of my stated goals was to approach my work in a way where I was doing my best work three, five, ten years rather than peaking early. To work at a pace I could sustain, instead of a blitz followed by a slow fizzling out.
Energy management is essential for your mental health. And, let’s be real, the quality of your overall work is going to mirror your mental health, so getting this right matters for your overall performance. Less obviously, building continued depth and expertise requires remaining in the same environment for multiple years, which makes long-term energy management an essential part of skill development.
You will be continuously stymied until you learn to manage your pace.
There is no simple formula for what pace will be sustainable for you. It depends on your obligations and environment outside of work, the particulars of your role and team, and so many other factors.
There is, however, a simple formula for checking if what you’re doing is sustainable: how long does it take on a vacation or weekend until you stop feeling anxious, and how anxious do you start feeling when you think about returning to work on Monday? If work anxiety is a constant companion, then change your situation even if it feels like a step back in the short-term: your success depends on sustained impact, not spikes.
The biggest part of how I feel heading into the office each week, as well as picking which office to head into over the course of my career, are the folks I’ll be working with. Your coworkers being an important part of your day-to-day experience is unsurprising, and what I’ve found increasingly true is that your current coworkers also have an outsized influence on your career long after you’ve stopped working together.
These relationships are invaluable. They’ll be the folks who enter you through the streamlined referral process. They’ll be the folks you can trust when they tell you about a company’s culture. They’ll be the folks that suggest your name for an important role. They’ll give you advice on difficult situations. They’ll be the folks who are advisors or investors in your startup, if you choose to start one.
It requires some deliberate focus to approach each new role with the intention of building the network of folks you know and work with well, but the compounding value of doing so is huge. And to be fair, your relationships expand beyond your coworkers: there are innumerable ways to meet and develop relationships with folks. Positive relationships enable serendipity, and that serendipity is the source of the most interesting opportunities.
If you’re struggling to build your network, spend time at a couple large companies. You’ll organically meet hundreds or thousands of folks, who will scatter over time across the industry.
There is a well-worn refrain that Silicon Valley’s meritocracy is the great equalizer, eliminating the role of prestige, but my lived experience is that prestige matters a great deal. Companies start their searches for scarce roles by recruiting from FAANG, and hiring processes bias outcomes to the advantage of candidates at elite companies and colleges. This is done with good intent–why wouldn’t you draft off the well-respected hiring processes at such companies and well-respected curriculums at such colleges–and creates a pervasive career lubricant for folks from such institutions.
If you’re a company leader, you have effectiveness and moral obligations to reduce the role of prestige in your systems, and we do that by developing good process. However, many desirable things that you want over the course of your career will be gated by mechanisms that favor folks with prestige. You can be justly upset by that fact, but upset is an insufficient catalyst for change, and ultimately you’ll have to develop your own prestige to gain access to those scarce opportunities and resources.
The good news, though, is that prestige is imminently manufacturable! Some examples I’ve seen:
This is something I’ve gotten quite deliberate about myself over the last couple of years, starting with rebooting my gone-silent blog in 2016 (from 1 post in 2015 to 76 in 2018), contributing to well-known and fast growing companies, speaking on my first podcast (thank you Intercom!) in 2018 and subsequently speaking on 11 more, speaking at half a dozen Bay Area company’s internal events, presenting at QConSF 2018, Velocity SJ 2019, and SRECon EMEA 2019, and finally publishing An Elegant Puzzle.
This was a lot of work, and candidly I got the pace wrong in 2019 in particular, working at a pace that’s been unsustainable for me, but the general premise applies: there are accessible forms of prestige that you can build through deliberate, hard work.
It’s hard, but it’s possible. In retrospect, many folks’ prestige seems inevitable, but is the result of deliberate, intentional action over an extended period. With each bit of prestige you accumulate, gathering the next bit gets easier.
Prestige makes everything more attainable: a universal lubricant.
For most folks, growing older also means being responsible for more people: a partner, children, aging parents, extended families or local communities. Similarly, folks get more deliberate about selecting roles as they’re further into their careers, avoiding situations that likely to lead rapidly to burnout, have toxic elements, or otherwise take a bad turn. Some folks I’ve worked with have encountered ageism as well, finding that folks are less and less interested in hiring them as they get more experienced.
As you get deeper into your career, you’ll move into increasingly senior roles, and there are considerably fewer such roles available. Gone are the days of leaving your job one day and jumping into another the next (although, yes, I have found that folks generally underestimate their employability). I was recently chatting with a well-respected senior engineering leader and she mentioned her job process took ten months from start to finish! Admittedly, the role she took is quite an amazing role, but still, ten months, and it’s not the longest such story I’ve heard.
The process takes longer, and time depends upon money. Consequently, the best roles are only accessible if you’re already financially stable, whether it’s stability from an existing role that’s you can interview from, or from savings and investments that allow you to pause between roles to rest and explore.
Danielle Morrill’s Post-Startup Life describes the particular variant of financial independence espoused by the Financial Independence, Retire Early aka FIRE community, which is one approach to increasing your financial position over time through passive investing and a high savings rate that’s particularly accessible for younger folks working in technology. I won’t recap the entire approach here, but generally I’ve found it to be a simple, boring and gimmick-free approach to increase your financial flexibility over time.
The key here isn’t “getting rich”, but creating the flexibility for yourself and the folks who depend on you, because that flexibility allows you to be deliberate about creating opportunities to invest into yourself and your career.
Financial security is a prerequisite to own your pace and learning.
One section in Coders at Work, I believe it was Joe Armstrong’s, described spending four hours a week thinking about the future. Each week, their thinking would compound on the previous week’s, letting them see further and further into the future. Over time they were dreaming far beyond their contemporaries.
Conversely, in hypergrowth roles, I’ve found little time for deep reflection, but instead worked on dozens of concurrent problems across many facets of the team and company. I wasn’t always developing mastery in any of them, but I was building familiarity and learning to leverage experts in each area.
I think of these as “learning deep” and “learning broad” respectively, and a forty year career has ample space and need for extended periods of both.
Each year I try to pick some personal goals and professional goals–sometimes these overlap entirely and sometimes not at all–and use those goals to deliberately schedule both kinds of learning. For 2019, I set myself the professional goals of getting An Elegant Puzzle published, speaking at three public conferences, reading books on a handful of specific topics, and starting a small business to learn more there. These are mostly on track, except the last which is extremely not on track (maybe 2020). These have been great forcing functions to develop myself, and next year I’ll develop myself either deeper in those areas or perhaps in a different direction entirely.
Each year identify one or two new things–things that you’re uncomfortable with–and do them! You’ll continue growing yourself, adding more and more pieces to your toolkit. You don’t need to do everything new each year, but do enough to maintain your habit of learning. If you’re at a loss at how to do this, broaden your idea of what’s possible, for example, Charity’s The Engineer/Manager Pendulum facilitates just such an approach.
One last comment on learning: learning doesn’t come just from doing new things. It also requires time carved out to reflect on how you did those new things and how you might adjust your future approach. Space to reflect is a precursor to improvement, which once again brings us back to the most important aspect of career management: managing your pace.
As you invest into your pace, the people you know, the prestige you build, the profits to fuel financial security, and your deep and broad learning, something magical starts to happen: each of these makes the others easier. This to me is the joy of a forty year career: things that seem hard early on become easy a decade in, and I can only imagine what it will look like two or three decades in.
I’m excited to find out how my next twenty-some years unfold.
For now, I’ll be over here working on my pace.