How Far Ahead Should You Plan Your Career

2022-10-10 original Teams & Careers

This topic is for people who have built up some career experience but aren’t confident their current job is leading to growth, or who, if anything, have something else they’d rather be doing. I also think this concern applies broadly, not just to engineers.

To talk about this, I first need to look back at my career by breaking it into “phases.”

I got a job after finishing graduate school, and I spent my early twenties as an errand boy, studying the basics however I could. I arranged procurement of prototype parts, swapped out candidate components endlessly while taking waveform measurements, gathered up datasheets and organized them into documents I could show senior engineers and veterans. Once I learned how to use CAD, I spent my days building PCBs to meet the specs and change requirements my seniors had set, calculating tolerances, then measuring waveforms again. In terms of development skill, I was probably frighteningly behind many engineers my age who came from technical colleges or had robotics competition experience. But I treated this whole period simply as a “study phase.”

My late twenties were an “independence phase.” I made a point of thinking through and executing everything on my own judgment. That got me into terrible trouble more than once, and my working hours were the ultimate in brutal. But without that period of struggling and nearly dying over and over, I don’t think I could have built confidence in my own technical ability. You can’t properly evaluate anything without trying it. That’s a basic principle of engineering. I was very grateful that the environment at the time let me act on that stance in the first place. My OJT senior happened to become a department head right around then, and he pulled me into his department. That kind of coincidence made things go very smoothly.

My early thirties were, in contrast, a “team management phase.” Once I had a sense of what I could do on my own, the next stage was extending that further by moving a team. Some of my peers took a negative view of doing that kind of management work around age 30, saying it was “too soon” or “I’d rather do more development.” But I was essentially a “playing manager in substance” (without an actual promotion in title), so I got to ride on someone else’s coattails (my boss’s) and turn that into my own experience — it was a very fruitful period. I did product planning, persuaded people around me, secured budgets, ran the team, wrote schematics, reviewed source code, handled EMC countermeasures, sorted out legal matters, managed development budgets, coordinated schedules, adjusted specs, occasionally got yelled at by the manufacturing factory, arranged promotions, and did whatever was needed, whether that meant giving a talk or doing sales on the sales floor at Yodobashi. Looking back, I think I was blessed with good bosses in this period too. Mr. A, my mentor as a salaryman. He is my eternal teacher, who taught me the ultimate life skill of how to achieve self-realization and live an interesting, amusing life even as a salaryman.

My early thirties after changing jobs were purely a “challenge phase.” That was when I moved to Silicon Valley with confidence, having acquired a full set of skills. Would I actually measure up? What kind of ability did the people who’d built careers at Apple or Google after graduating from MIT actually have? How well could I compete with them? As I’ve mentioned in other sections, the shift in my values over those few years was significant. Even now, I sometimes find myself impulsively recalling various scenes from that time. It was a wonderful period. I had decided my late thirties would be a “CxO phase,” but during that time, for reasons I couldn’t quite explain even to myself, a feeling of wanting to contribute to Japan — a country I thought I’d basically given up on (lol) — started welling up. Doing a startup in Japan seemed like a great way to act on that, so I decided to return to Japan.

I wasn’t earning nearly enough to become an angel investor, and I thought it was still too early to shift into advisory or support-type work. If I wanted to live as a single engineer, Silicon Valley would undoubtedly make me happier. But instead, the idea of building a company that could itself serve as a reference point fit my motivation at the time very well. As a result, I ended up serving as CTO, and seeing it up close versus actually doing it turned out to be worlds apart. Back in my Miselu days, I had plenty of dissatisfaction and things I wanted to say to my boss J, but I feel like now we could understand each other on a much deeper level and share a good bottle of wine.

My forties have been somewhat a matter of circumstance, but I’d call this the “phase of diversifying activities.” I never got on the track I’d originally envisioned — making a startup a huge success in my late thirties and retiring early (lol) — but as it turned out, this feels like the phase where I’m gradually working through the things I had vaguely in mind when I returned to Japan. In Silicon Valley, there’s a saying that “if you throw a rock, one in two people you hit will be an entrepreneur,” and that reality exists at close range — a high school classmate, the guy from the neighborhood, a parent, a relative. That lets young people see entrepreneurship as something very close to home, and lets them hear all kinds of useful stories about it from an early age. The fact that this kind of social infrastructure isn’t in place is Japan’s biggest weakness, and I’ve been thinking there might be something I could do about it.

Right now, the balance has shifted away from pure work as an engineer and toward activity as a business executive, or even further toward something more like social activism. Engineering obviously still matters — I still read schematics, subscribe to Toranomon Tech (Trakei), buy suspicious gadgets from China and take them apart, and sometimes carve out concentrated blocks of time to code. But for me, that’s like a professional athlete’s jogging or weight training: doing it alone earns you no praise, gives you nothing to be proud of, and is simply the baseline expectation. What matters is the further plus-alpha beyond that — properly producing social value as output. And the critically important tool for doing that is management. These days I support various startups on everything from technical strategy to fundraising to hiring plans. I’m also given opportunities to give talks, and I’ve been allowed to teach students at a university. In that sense, I feel like what I originally envisioned is being realized, just in a different shape.

The phases keep going. Right after I stepped down from TripleW, an angel investor told me, “Being around 40 is prime time, you know.” His point was that technical ability is solid by then, you’ve tasted every kind of hardship there is, and you still have plenty of stamina, drive, and ambition. That’s the kind of age it is. But when it comes to “career,” I actually think prime time always exists. (This has been true in the past and will remain true going forward.) Succeeding once in your career doesn’t mean you get to coast forever. People who sell the startup they built, make a fortune, and then vanish from the world are actually quite rare. Everyone keeps engaging with society afterward. A career, far from ending, just puts you at the starting line of the next phase.

Now, back to the “outlook” I mentioned at the start. Honestly, how far ahead was I really thinking? About “one or two phases ahead at any given time” is the honest answer. I wasn’t reading that far ahead and building a long-term plan.

For example, the big decision to go to America was already on my mind by the time of the “independence phase” mentioned earlier, but honestly, I never thought about it at all as a student. Also, during the period when I was running around doing team management as a salaryman, the idea of starting my own company and becoming independent was very much alive in my mind. But since the path to get there was unclear given my own growth curve at the time, I figured “it’s probably best to just get in there first.” Because I held that view, when an opportunity came rolling in, I could say yes to it without hesitation — and it’s true that I was optimistic, thinking “I’ll figure out what comes after once I get there.”

Around my third year as a working adult, I had the chance to speak at my old high school, and I remember telling the third-year students, “Please try to have an image of yourself five years from now.” The number five didn’t have any particular significance at the time — it was just a message to these soon-to-be college students to think about what they wanted to become or do “after graduating from college.” But looking back now, it seems like a remarkably well-chosen number. Looking too far ahead into the future usually means your assumptions fall apart. In terms of phases, one or two ahead is plenty. In terms of years, three to five is enough.

As a general statement, seeing far into the future is basically impossible. If you look back through the history of the world economy, it’s said that there was essentially no real economic development to speak of until around the year 1600. Of course there was some development day by day even before that, so it wouldn’t be reasonable to say there was no growth at all. But the point is presumably that, compared to the development seen over mere decades or years in the modern era, growth before 1600 was practically nothing. And this trend is likely only to accelerate from here, not slow down. If it ever did slow down, that would probably coincide with a sharp population decline and a great depression, so honestly, it’s better if that never happens. So we should basically understand that the future is not something that can be predicted.

That said, my view is that it’s good to hold a vague sense of a big vision. I had a vague long-term idea that I wanted to live with “technology” as my passport. But it seemed unlikely I could get there in one leap, and I had a sense, even as a student, that I would need to build up a great many things to get there. The important thing is not to let yourself stagnate. Organizations have their own circumstances, but life fundamentally belongs to the individual. If you ever feel stagnation, your career plan is in serious trouble. Someone who can’t properly handle what’s in front of them has no future. But if handling what’s in front of you doesn’t lead toward your goal, then from the standpoint of individual career, there’s no need to force yourself to do it. I think balancing those two points properly is a good way to keep sight of your career.

The content of this post is an excerpt (original text) from the following book. If you’re interested, please pick up a copy.

The Shape of a Happy IoT Startup

Originally published in Japanese at https://clazytech.com/2022/10/1081/. Translated with LLM assistance and reviewed before publication.