What Do I Do Now? A Midlife Career Change May Be Just the Challenge You Need

The other night I had dinner with my friend Kim, who in midlife is endeavoring to change her career. She has spent decades as a successful photographer, but she knows it’s time to do something different. What, however, is she qualified to do, besides photography? “I’m good at parties,” she told me with a shrug. “And parallel parking.” We refilled our wineglasses and laughed really hard as we dreamed up the various careers in which that particular combination might be useful.

Here’s a humbling exercise: Ask yourself what you’re good at, aside from the skills you use at work. After my conversation with Kim, I put this question to a handful of friends and got responses ranging from “finding restaurants for people” to “spotting terrific old chairs.” The more I think about my own answer to this question, the more confused I seem to get. Which apparently does not happen to everyone — but more about politics in a minute.

A year ago this month I left a job, and a career, that brought me great satisfaction for more than two decades. Can serendipity be a strategy? It certainly worked for me. I happened to find a field in which my skills and the requirements of the job were a Venn diagram with near total overlap. Like most of my friends, I spent my 20s and 30s marching determinedly along my given path, working hard, with purpose, and by the time I reached my 40s, I was able to enjoy the fruits of my labor. Isn’t that the way the American Dream goes?

Here’s what you learn when you wake up from that dream: hubris is the unpleasant by-product of success. If you are really good at your job for a long enough time, you begin to believe that you can be good at any job and therefore can easily jump from one thing to another, switching horses in midstream. Examples of this flawed thinking are everywhere, from the harmlessly frivolous (Dancing With the Stars) to the dangerously serious (the current presidency). As it turns out, humility is its own kind of skill; developing it hurts, but falling on your face hurts more.

Over the years a number of 20-somethings have come to me for advice, which I have dutifully given: Work hard, meet lots of people, say yes to many things. Don’t whine, put a smile on your face, remind yourself that studying Foucault for four years in college might not prove to be particularly relevant in the working world. Swallow your pride and ask a lot of questions.

What I should be telling the young and ambitious is this: being really good at one thing is fantastic until it isn’t. The day may come — in my experience, will come — when you know you want to do, want to be, something else. For example, 20-somethings, one day you might want to appear on Dancing With the Stars. I’m not sure if Sean Spicer is a fool or a genius for turning down this opportunity for his first post-Administration gig. Maybe he’s not aware that Apolo Ohno placed first on the show?

Or maybe you’ll want to run for President. Never mind that it was a President — Abraham Lincoln — who popularized the admonition about switching horses in midstream. If you are a real estate tycoon and loudmouthed TV star who made a name for yourself with a combination of instinct, bravado and riding the wave of chaos you create everywhere you go, then who cares what Abe Lincoln said? The White House is the logical next career step.

Or, 20-somethings, maybe you’ll do both! At the same time! After all, doesn’t today’s White House sort of resemble Dancing With the Stars, if you squint hard and use your imagination? With experts and amateurs working together, trying to make it all look graceful while the audience alternatively laughs and cries?

So, folks, an assignment: Ask yourself what you’re good at. As for me, aside from what I most recently did for a living — writing, editing, managing people and showing up to meetings on time — my greatest strengths seem to be making vacation packing lists and remembering which houses in my town are on the market. So I have entered this next phase of my life with gratitude (for what I’ve accomplished), humility (about all that I don’t know) and fear (see random greatest strengths). I used to be filled with optimism; if Donald Trump could become President, anything seemed possible. But with each passing month, and each new fiasco, my optimism dims. If he wanted to try something new, wouldn’t Dancing With the Stars have been a wiser choice?