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Treat Each Career Struggle As A Phase, Not A Dead End

original Teams & Careers

A while back, a certain “vague worry” came up in conversation, and I gave my own comments in response. Looking back afterward, I felt the content had broader relevance, so I’ve reorganized it below. I hope this helps anyone struggling with how to keep their career motivation up.

The intended reader is someone who:

My own roots are as a thoroughgoing engineer, but I don’t think what follows applies only to engineers. This started from the question: is there a “good method” for keeping motivation up?

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Motivation and the drive for technical growth are both matters of personal values, so all I can really offer is “here’s how I think about it.” I believe it’s good to treat each situation as a “phase” that corresponds to your career plan. Broadly speaking, there may be short periods of doing boring or painful things, but cleanly dividing those into short phases and building up gradually gets you somewhere you couldn’t have reached in a single leap. At the same time, I also believe it’s best not to overdo predicting or planning too far ahead, since that’s genuinely difficult.

I joined a company after graduate school, and in my early twenties I was essentially an errand boy, studying the basics as one member of a large corporation. I arranged procurement of prototype parts, took waveform data while endlessly swapping out candidate components, gathered datasheets and organized documents into something presentable to seniors and veteran engineers. Once I learned how to use CAD, I kept doing precision calculations to meet whatever specs or changes my seniors decided, building PCBs and measuring waveforms again.

In terms of raw development skill, I was probably frighteningly behind many engineers my age who’d come out of technical colleges or robotics competitions. But I treated this whole period simply as “studying.” Asked whether it was fun or not, I think it genuinely was fun. I’d work out for myself why a senior had chosen a particular component value and go ask about it, I’d serve as the hands and feet of an EMC master while learning from him, and out at a remote outdoor test site late at night (back then, a 10-meter measurement site only existed in some shack deep in the mountains!) it would just be the two of us, and he’d generously teach me his secret sauce (laughs). In meetings, I’d sit beside my seniors and learn the company’s overall development flow and how to deal with various vendors.

In my late twenties, I went independent. I made a point of thinking through and designing everything on my own judgment. Because of that I went through terrible experiences repeatedly, and my working hours were the ultimate black-company kind, but without that period of struggling and nearly dying over and over, I don’t think I could have gained confidence in my own skills. (This is too long a story for here — another time.)

What I’m grateful for here above all is that the environment even allowed that kind of stance in the first place. The senior who had trained me on the job happened to become department head right around then, and he pulled me into his department. Things went very smoothly thanks to that coincidence stacking up.

But what if that kind of environment hadn’t come together? Thinking it through, I probably would have had to take some action, which as a template would look like:

I believe a moment for one of these would eventually have come. One positive thing is that, looking back, I can say with confidence that if I’d ended up in an unfavorable situation, I would have taken one of the above actions without hesitation. That’s because the idea above — dividing things into short phases and building up — had already taken root in me not long after I started working.

My early thirties flipped entirely to team management. Having gotten some sense of “what I’m capable of,” I thought moving a team would let me expand what I could do further. I’d also always figured I was suited to management by nature. Some in my generation saw taking on that kind of management role around age 30 negatively — “too early,” “I’d rather keep developing” — but since I was in effect a “playing manager” the whole time (my title hadn’t actually risen), I could enjoy it in the spirit of “well, someone’s got to take responsibility for people, might as well be me.”

I did product planning, talked people around me into things, 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 plant, arranged promotions, and did whatever was needed — whether giving talks or doing sales floor duty at Yodobashi Camera.

Around that time, my mentor pushed me especially hard to become “a people person.” At the time I completely failed to grasp what he meant, and I only understood it as a real, felt thing later, when I became CTO in Japan. He taught me all sorts of things — the basics of planning, presentation technique, estimating development costs, managing internal politics, the right way to engage in outside activities, how free we actually are. That period was when I gained a mentor for life.

And with that, my career at Yamaha ended.

My early thirties, after changing jobs, were pure challenge. How well could I actually hold my own against people building their careers at Apple and Google out of MIT? The conclusion: turns out I could do just fine. Japan’s industrial stagnation runs deep, but I found myself thinking, huh, Japanese engineers really can hold their own globally after all. At the same time, I learned a great deal from them, and it was a period when my mindset properly shifted to a global one. Some of this has been covered in articles, but the expansion of my values over those few years was tremendous. Even now I look back on it fondly. (This too would get long if I started writing it out — another time.)

In my late thirties I’d already decided I would take on a CxO role, but for reasons I still don’t fully understand, a feeling welled up in me that I wanted to somehow contribute to Japan — a country I’d more or less written off (laughs). As one form of that, doing a startup in Japan seemed like a very good idea, so I decided to go back to Japan.

I wasn’t earning nearly enough to become an angel investor (not bragging, laughs), I felt it was still too early to move into advisory or support-type work, and if I were to live purely as an engineer, Silicon Valley would undoubtedly make me happier. Rather than any of that, the idea that fit my motivation at the time was: couldn’t I build a company myself that could serve as a reference point? In Silicon Valley, if you throw a rock, one in two people you hit is an entrepreneur — and that person exists as a reference point among your high school classmates, the older kid from your neighborhood, your parents, your relatives. Because of that, young people come to see starting a company as something very close at hand, and they get to hear all kinds of useful stories about it from a young age. Japan’s greatest weakness is that this kind of social infrastructure isn’t in place, and I thought maybe there was something I could do about that myself.

As a result, the business itself unfortunately didn’t perform all that well (it’s not that easy!), but since then, now in my forties, I’ve been allowed (so far) to advise and speak to various people, so in a changed form, I feel I’ve been able to carry out to some degree what I originally intended.

My forties have had something of a drift to them, but the balance has shifted toward activity as a business manager rather than a pure engineer, and even further toward something like social activity. Engineering obviously still matters to me — I still read schematics, subscribe to Torazu Gihou, buy sketchy items from China and take them apart, and sometimes carve out concentrated blocks of time to code. But for me, that’s like a pro athlete’s jogging or weight training — doing it alone earns you no praise and gives you nothing to be proud of, it’s simply a given. What matters is the further plus alpha beyond that: properly producing social value as output. And the critically important tool for that is management. Right now I’m supporting various affiliated companies across everything from technology strategy to fundraising to hiring plans.

Now, as for how much of these career plans I actually thought through in advance — honestly, I’d say I always thought about one or two phases ahead at most.

When I joined Yamaha, I was aware my technical skills weren’t up to par. I’d studied electrical and electronic engineering, but given the nature of my research, I was in practice almost entirely a software person. So for the first several years after joining, I made a point of thoroughly stealing techniques from everyone around me. And I figured that within about three years I’d become able to design things on my own. As it happened, two and a half years in, I was pulled into a new model project through a transfer and served as lead for electrical design, shipping around four models to market in total. After that, having become someone who had “designed something on my own once,” a kind of independence emerged, and I never again worked as anyone’s assistant.

By the time I started designing on my own, my attention had turned toward America. Part of it was that the US was a huge market in the electronics industry, but as a working adult, seeing the flaws of Japanese-style organizations and Japan’s slowing economic growth, I found myself vaguely wondering what the difference between Japan and America actually was. I kept putting in requests for a transfer to America, but luckily or not, they never went through. Still, there’s no doubt that the various activities born from that mindset and passion expanded my network, and that ultimately led to my move to America. (This too is a long story for another time.)

By the time I moved to America, I had an unshakable conviction about eventually starting a company. I figured I probably couldn’t live any other way anyway. At the time, though, I fully intended to spend the rest of my life in America (I’d even applied for a green card), so going back to Japan and all that was, honestly, unexpected.

The period running TripleW was the worst (the best?) — I wasn’t thinking about the future at all. Laughs. In a good sense, I was fully focused on launching the business, but any thought about my own personal career had completely fallen out of the picture. Was I planning to exit, get rich, and vanish from the mundane world? My career was far from over. Embarrassingly, this is a foolish thing to admit even now, well into my late thirties.

So where am I now? In the first half of my forties, I want to get involved in as many businesses as possible and expand what I’m capable of at the management level. For instance, I’m currently involved in an M&A deal. I’m also involved with a company seeking a large loan from a bank. I’m supporting entrepreneurship among students and founders in their early thirties. Manufacturing, communication, AI, healthcare, music, security, pre-symptomatic care, rehabilitation, atmospheric environment, improving working environments for medical staff, beauty — all of these are themes and areas of activity for me right now.

Through the accumulation of all this, by the time I reach my late forties I want to have become “someone who can act on what needs doing without hesitation.” Unfortunately the “unperturbed forties” aren’t so kind — mine is a hopeless forties dominated by all sorts of illusions, delusions, and confusion. I’d like to evolve a bit more.

Up to now I’ve made products driven by “my own tastes and feelings,” and I’ve also charged straight at “overwhelming social needs.” But society isn’t built that conveniently, and the market exists because all kinds of people are thinking all kinds of things. By broadening the diversity of my viewpoints, I’m hoping that different “tastes and feelings” and “needs” will come into view before me, and that this will let me shed another layer of skin.

Technology is a universal passport. With it, you can go anywhere. But that’s not the same thing as “acquiring whatever technology happens to be trendy.” Take AI, for example (for some reason I’ve been invited as a speaker to a fair number of AI-related conferences lately. No idea why). I’m personally involved in developing proprietary AI at a certain company, and the gut feeling I’ve gotten from that is: “This field is commoditizing at a terrifying speed.” In other words, I think it’s wise for anyone other than someone who can proudly say “I love AI, I spend my weekends reading papers, I sleep and wake with AI and dream of dying with AI” not to casually dive in.

The above is strictly from the perspective of individual career planning, but there’s a real situation of people running rampant who, with fairly shallow resolve, are grabbing only the short-term cool factor of being an “AI engineer” and seem set to suffer for it later in their careers. Well, I watch that with a warm smile. In reality, there are still all sorts of hurdles left in the world at the stage of social implementation — communications infrastructure, energy issues, or at a different layer entirely, UI/UX problems. I think building strength in those areas is far more likely to become a skill society continuously needs.

As for my fifties, there’s still too much I don’t know, and all I can really say is “I’m probably still going to be somewhere on this planet.” Laughs. Things I can do and things I should do overflow all over the world, so there’s no way our lives could ever get boring.

In that sense, all the phases I’ve built up are connected. Or they look connected, anyway. Maybe it’s just hindsight. I don’t think of myself as someone with especially sharp foresight, but somehow, oddly, none of it went to waste, and I managed to sustain motivation and line things up properly in series.

What mattered through all of it was not letting things stagnate. There are organizational constraints, but life ultimately belongs to the individual. If you ever feel stagnation, your career plan is in serious trouble.

At the same time, I have no real idea what will happen a few years from now. If you look into the history of the global economy, it’s said that “there wasn’t really economic development worthy of the name until around the year 1600.” Of course, human beings developed at least somewhat each day, so it’s not as though there was literally nothing — it just means that compared to the development of the past few decades or few years in the modern era, it was equivalent to a speck of nothing. And this trend will likely only speed up from here, never slow down. If it ever does slow, it will probably happen together with a sharp population decline and a great depression, so honestly I’d rather it not happen at all. So we should understand that, fundamentally, the future is no longer something that can be predicted.

On the other hand, Jeff Bezos said that “a manager’s job is to decide what to plant now, looking three years ahead.” If this could be executed flawlessly every time, it would have to be called supernatural. But in reality, this year, Amazon is said to be losing significant share in the US under Walmart’s offensive. That’s reality.

However much you break things down into small problems — your own career, title, surrounding environment, department transfers, boss, colleagues, sales, product lineup, etc. — it’s extremely difficult to accurately predict and maneuver around any of that a few years out.

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 hold an image of yourself five years from now.” The number five carried no quantitative meaning — the message, for students about to become university students, was to think about what they’d become or want to become “after graduating university.”

A certain famous figure from MIT once said, “look only at the distant goal and the problem right in front of you,” and I find that resonates with me. It means there’s no point in detailed plans for one or two years out. You hold onto a career plan as a distant goal (in my case, something like three to five years out), pour everything into knocking down what’s right in front of you toward that, and every so often check whether you’re properly still facing that “distant goal.”

Someone who can’t properly handle what’s right in front of them has no future. But if what lies beyond doing what’s in front of you isn’t actually facing the goal, then there’s no need to force yourself to do it — not from the standpoint of individual career, anyway.

Balancing those two points properly is, I think, the “good method.”

Right after I stepped down from TripleW, an angel investor gave me the advice: “Your late thirties to early forties is prime time, you know.” That’s actually statistically correct — the age bracket most common among startup founders who exit is, in fact, their forties, and many of those companies were founded around that late-thirties-to-early-forties age. I think this can be put as: a company founded by someone who has already taken one or two painful hits and, having waited for the right moment, fully mobilizes their accumulated experience and network, has the highest odds of success. Impressively on-point advice. I’m genuinely grateful for it.

However, this is undoubtedly true from the “starting a company” angle, while from the “career” angle, I think prime time actually exists at every point, past and future alike. A career doesn’t let you win once and be done. People who buy out the startup they built, get rich, and vanish from ordinary society 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.

Look at your career from a reasonably long-term perspective; conversely, let the events of any given few years unfold somewhat as they will; but arrange things so you can believe that giving everything to what’s in front of you leads to that long-term goal.

This, I think, is the trick to being a happy working adult — and my answer to that worry.

Originally published in Japanese at https://clazytech.com/2020/02/322/. Translated with LLM assistance and reviewed before publication.