Midlife Work Crisis

A while back, I came across this interesting take on professional careers, and an observation on how they generally fall into 3 stages:

Three crucial skills that leaders must develop to become executives

To summarize, the idea is that for people who make it to executive roles and beyond, they often transition from leader → executive → new career in roughly 10–15 year stints. To be clear, most career arcs don’t follow this trajectory—there are limited senior leadership roles, after all—those that do seem to conform to the time frame and duration. The post title alludes to the skills required to go from one act to the next; well, really, to be able to jump from Act I to II, with the key being a set skills around people and relationship-building and delegation that’s required to make that leap. I don’t have extensive experience in executive leadership to confirm or deny this model1 exactly, but it does line up with all the business management books and articles and podcasts about the topic 2.

The idea of developing a new skillset for another tier of the career ladder isn’t exactly novel, but I was struck by how much the timeline aligns with the often-observed midlife crisis, also at around the 40–50 age range. It raises the question of which is the cause and which is the effect: whether it’s the changes to the job that causes the personal crisis and eventually ends in a red convertible, or whether factors in personal lives shifts the way that people think about their work in their 40s. I also wouldn’t be surprised if it turns out that small changes and quirks in both work and life feed back onto each other to a crisis point.

I guess there’s both an optimistic and pessimistic case to be made in creating a larger-than-usual class of people experiencing their midlife crises. The positive take is that many more people will take the time to find themselves, discover more fulfilling career paths, with some building out businesses that contribute to the system of capitalism that theoretically competes towards better outcomes. The negative take is that people are giving up looking for something different and taking themselves out of the employment pool altogether, and we’re shrinking our overall workforce by losing some of its most valuable, experienced workers, which then places a ton of pressure for everyone else to fill in those gaps.

As I’ve wound down my role at Mystery, I can attest to this feeling of taking a step back to really think about what’s next for myself. In talking with former colleagues, other folks in engineering management with similar or even more years of experience, as well as friends from college—the feeling of wanting to do something completely different is not unique; with some taking real time off to think about what they want to do next, others making a real push to retire early, and many more switching jobs that they’ve held for a decade or longer.

In a time of COVID and the supposed Great Resignation as an exodus from the work status quo, this crisis feels particularly acute, juxtaposed with the cohort of folks in their careers already primed for major changes. Then again, this may just be me reaching exactly this stage of my life and overindexing on my own experience.

  1. It’s also unfortunate that some of the execs I’ve worked have kept these skills undeveloped.

  2. I’ve just taken a pause on the entire genre, as all of it starts sounding the same.

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