An Eighty-Year Career

When I was a kid living at home, I remember my dad, from time to time, wistfully looking forward to retiring. I would often ask him why, since retirement sounded so boring, but I don’t remember ever getting a clear answer. In the years since, as my sense of how big — how interesting! — the world can be, retirement has come to seem like a strange idea. As the default ending for the conventional career narrative, we’ve canonized deferred living en mass. That seems unfortunate. What’s more, retirement appears to discard a career’s worth of experience for decades at a time for millions of people. That seems like a lot of collective human potential going to waste.

I don’t ever want to retire. Instead, I want to have an eighty-year career, one where I get to build upon a lifetime of experience and resources to move the needle on some of the messiest problems we face.

(The longevity aspect of an eighty-year career is a fascinating topic in its own right — will I live long enough to actually have eighty working years? I believe the answer is a plausible yes, but that’s a topic for another time.)

An eighty-year career is nominally twice as long as a typical forty-year career, but given the tail-weighted effectiveness that comes with more experience, connections, and resources, the former could be as much as an order of magnitude more impactful. As a sort of corollary to short-term thinking, an eighty-year career makes it feasible to (and perhaps even encourages) work on problems with long gestation periods or upfront effort — i.e. those that will take many decades to show major progress. For example, at some point in my life, I’d like to work on reversing climate change, designing better cities to improve urban mobility, and understanding human health maintenance (of which health care is one part; while health care is reactive, health maintenance aims to reduce the amount of health care needed by keeping people healthy). In contrast to “not-my-problem”-ism, I’ll have the opportunity to _make_these things (and more!) my problem if I want to. And with decades of compounded personal capital and connections, I would be much-better equipped to make a meaningful amount of progress on them. That’s deeply exciting for me.

But getting there from where I am now is a long-term game as well. While I could conceivably work on those large-scale coordination problems today, I believe that I would be more effective (per unit of time) once I have a strong reputational and financial foundation derived from well-chosen career steps over the course of a decade or so. I’m mindful of that when deciding what to work on and say yes to; while I don’t have a codified set of decision criteria, I’ve been able to refine an intuitive sense of whether a project seems directionally correct. For example, I strongly prefer to work on projects with progressively larger scope or in areas with which I’m not yet familiar — doing stuff I’m already good at isn’t particularly appealing.

An eighty-year career also changes my outlook on personal finances. Dutifully saving up to fund several decades of life without a source of income feels like a quaint and unnecessary exercise in administrivia: as a knowledge worker, it becomes possible to do productive things and earn an income for the rest of my life. A corollary to this is my appetite for financial risk. I’m eagerly looking for high-return (but non-dumb!) investments because, for me, the upside from a few wildly-successful investments — enabling financial independence in the short-term, and building a significant pool of personal capital that I can deploy against those problems in the long-term — is worth much more to me than holding onto the principal in a low-risk retirement-savings account.

I was recently talking to my dad when the topic of his imminent retirement came up again. Weary from decades of grinding in a corporate environment, he had no desire to continue working longer than he needed to, and certainly not for eighty years. I think this was partly a result of a lack of imagination — having settled into a relatively conventional life, he’s looking forward to retirement and doesn’t want to consider alternative things he could do. But it’s partly also a lack of opportunity — as a society, we still don’t have an easy way for knowledge workers to demonstrate their experience and capability in pursuit of a new career path or even the narrative freedom to consider it. We haven’t built education systems that are accessible and understandable for knowledge workers mid-career, awareness of the value-creation opportunities afforded by modern software and remote work, or the health maintenance capabilities to ensure that people remain fit and energized enough to embark on new career epochs in any decade of life. And all of that, I think, would easily fill someone’s eighty-year career.