This post lays out a broad set of challenges that generalists are likely to face in life. It doesn’t spell out all the solutions, because that’s really what the rest of True Generalist is for. But I hope you read something you resonate with, and perhaps feel validated for it.
I also hope it gets you thinking. One of my favorite questions from the life coaching practice is, “What’s hard about this?” If you ask this simple question of yourself, about whatever you’re currently trying to do, big or small, it can be enough to shake you loose from whatever obstacle or environment is blocking your progress. What’s hard about being a generalist?
Illegible competence
The first struggle is that generalists tend to not get as much feedback or appreciation for their work as specialists do—unless their unique array of skills leads them to discover or invent something uniquely valuable.
Specialists have a straightforward way to create value in society and receive status, money, and fulfillment in return. Generalists don’t have such a clear path. A generalist’s competence is mostly illegible/hidden. They say, “I can connect my experience as a musician with my work as a manager”; “I think I could improve our customer onboarding process, based on some principles I learned in the gym”; and so on. But how do you measure the value of that? It’s much harder than measuring the single-track productivity of specialists.
So generalists are sometimes at risk of being undervalued in the labor market. Consequently they feel pressure to match the specialist’s lifestyle so they can compete in specialist metrics a little better.
(On the other hand, however, having illegible value in the labor market can have advantages, too).
Unclear end goals
It’s increasingly common for people to “have no idea what to do with my life.” The modern world is giving us more lifestyle options than any other people in history had, and generalists are especially likely to consider all those options. There’s a wider variety of companies to work for and a multitude of ways to earn a living online, more places to live in, more people to socialize with, more books to read, more ideas to be inspired by.
It can be daunting to choose between so many possible lives and lifestyles. When you sit down and really try to assess all the possibilities available to you, you quickly find yourself overwhelmed, maybe even wishing for less freedom.
CEO obligations
Generalists need to be a bit more structured than the average person if they’re going to balance many different interests in their lives. It takes planning and discipline, and generalists will need to initiate everything themselves, which is harder than following a well-trodden path in career or education.
It can be hard to organize and prioritize different activities; each one has unique demands and a unique structure of progress. Some require daily investment, others monthly; some take a year to reach a milestone, others take only a week; some can be put on pause without losing progress, others quickly deteriorate.
(That said, this is a type of problem that I particularly enjoy working though, and through my coaching I sometimes get to help people organize all their goals in a balanced way).
The planning trap
This struggle is actually kind of the opposite of the previous. Generalists sometimes plan too much. When conscious long-term planning is important in your life, you may get really good at it, and you may enjoy it. But that enjoyment might turn into passive recreation and you might forget to do anything. This is a whole flavor of procrastination: constantly tweaking all your big-picture plans when really you just need to work.
Generalists need to determine when their plans are good enough and it’s time to execute. They must be able to switch off the “Manager” and become the “Worker.” They ask, “Is it a good time to be the Manager here?” “Has the Worker clocked in today?”
The life not lived
“I just don’t have time to do everything.” The right answer to this is often “budget your time better”: quit your addictions; get off YouTube/TikTok/Instagram; consider all the ways you could spend a bit of extra money to save time on things; plan better so there’s less task-switching; and so on. But although there may be a lot of easy gains in time management, we also have to accept that time is finite, and burnout is a real risk.
Sometimes generalists have to make hard decisions about whether to continue this or that project. To take something that inspires genuine interest and let it drop out of your life is a sad thing, but sometimes necessary. To “retire” is a little easier.
Conclusion
If you’re done brooding on the generalist’s struggles and want a pick-me-up, take a look at the generalist’s strengths.