A Portfolio Worker's Comfort Is an Illusion Worth Choosing

This is a slightly different kind of topic, but I’ve been asked about it a lot lately, so I’m writing it down. A portfolio worker, by the way, is someone who makes a living by holding multiple jobs and activities at once. The word “portfolio” often comes up in asset management, and a portfolio worker is, true to the name, someone who manages their work the way one manages an investment portfolio.

For me, there’s no such thing as “doing this all week long.” On some days I attend meetings for several different companies. On others I’m holed up somewhere all day doing experiments or verification. Sometimes I end up attending one company’s board meeting in the morning and a different company’s board meeting in the afternoon, purely by coincidence.

How I use the time when I have no meetings or fixed tasks is up to me. I have separate commitments to each company and organization, so I pay close attention to keeping the balance right so there’s no conflict between them. Naturally, even on weekdays there is time when I’m “not attached to anywhere.” I use that time for sales activities, writing, or acquiring new knowledge.

Some of you, hearing about this way of working, may have sensed a kind of precariousness in it. That’s probably an extremely common reaction. A portfolio worker seems to belong everywhere and yet belongs nowhere. Managing a portfolio means managing that ambiguity as well. No one guarantees anything, and it’s entirely possible to lose every source of income in an instant.

But for me, that sense of things shifted completely the moment I became a startup director. My reaction was: “Isn’t that just obvious?”

A director is not an employee. It’s a distinct position, appointed by shareholders to carry out a specific role. If the shareholders say no, you can be dismissed at any time, with no guarantees whatsoever at that point. No unemployment insurance, no severance pay. In exchange, a director has no manager above them. What manages a director are numbers — a sales target, a target for improving profit margins, various targets that are critical to the company. Directors work to hit those targets, and how they go about it is generally left entirely to them.

Being a startup director is a far more unstable position than being a startup employee. That’s because most of the goals a startup takes on are best described as “extremely difficult to achieve, but not impossible.” Taking on something like that while fully aware of what it is means living every day thinking, “It would be entirely reasonable if I got fired tomorrow.”

Seen that way, building a portfolio is, in exactly the same sense as designing a portfolio in fund management, a proper form of “risk management.” I came to realize this when I saw how many engineers in Silicon Valley take on side jobs. While belonging to a startup as their main job, they also belong to another startup on weekends. In some cases, two or three others. In the United States, banning side jobs is disliked to the point of being treated almost like a human rights violation. In America, where employment regulation is weak and labor mobility is high, individuals have to manage their own risk. Belonging to multiple startups is their own way of doing exactly that kind of risk management.

I personally predict that employment mobility in Japan will increase from here on, for better or worse. When that happens, individuals will be required to be even stronger than before. As part of that, I would not be at all surprised if society changes to the point where building one’s own portfolio becomes taken for granted.

Originally published in Japanese at https://clazytech.com/2021/08/511/. Translated with LLM assistance and reviewed before publication.