On Restarting Midway Through Your Career

“Screw Mastery” is an ode to new beginnings

Ester Bloom
The Billfold
3 min readJun 22, 2016

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remember the Starting Over house??

I loved this Lenny Letter piece by Hanna Rosin on switching fields in one’s 40s — the age at which, Virginia Woolf once wrote, “one must be a miser; only have time for essentials.”

We like what we’re good at, human beings; and then, when we’re good at things, we do them more. We improve. Even if / when we plateau, it’s generally at a stage of competence. Surrendering that competence and the sense of complacence it brings can be as tough, as dislocating and disorienting and occasionally humiliating, as being in a foreign country. “Everyday I was exhausted,” Rosin writes, from trying to transition from print journalism to podcasts (where the cool kids are!!).

But there were benefits. Even as she flailed, she learned things — about the field, about her own character, and strengths, and weakness. Because she flailed, she learned things.

I learned a ton of new things about myself, in the way you can only do if you are fucking up daily. I learned that I am defensive but trainable. That I have capacity for patience but that my immediate default is speed, bluntness, and ironic distance. That although I am used to working alone, I will happily collaborate. And that I really like working with women, even if they cry more during the day.

She doesn’t come out and say she felt humbled, exactly, but that’s the implication. With mastery, after all, comes pride. Giving up the first can mean watching the other drift away. But, as Marsellus Wallace tells Butch Coolidge (albeit in a very different context) in Pulp Fiction, “Fuck pride.”

“Pride only hurts, it never helps.”

Granted, Marsellus is trying to talk Butch into taking a dive so that Marsellus can recoup massive profits from the bets on the fight. The general principle is sound, though. When we let ourselves be guided too much by pride, we forget the very real, youthful, even giddy pleasure that can come from learning something new. From taking risks. From changing our perception of ourselves and, sometimes, ourselves altogether.

And why not? Many of us find that while we aren’t literally getting beaten down by our jobs, the way those poor bank employees in Changzhi, China, were, we aren’t fulfilled, or even mostly satisfied, either. In 2014, Forbes reported on survey results showing that disappointment with work is characteristic of “most Americans.”

The survey asks workers how they feel about various parts of their experience, including job security, wages, promotion policy, vacation policy, sick leave, health plan and retirement plan. On all of those measures, workers were happier in 1987 than they are now. …

Men are happier in their jobs, with 47.8% saying they’re satisfied versus 46.3% of women. There is also a sign that the glass ceiling persists, observes the report, shown in the differing satisfaction about promotion and compensation. Among men, 26.1% say they’re satisfied with their promotion prospects versus 21.4% of women and 38.3% of men are happy with their wages versus 34.3% of women.

There’s some support, then, for the point made recently by Judith Shulevitz, that being a working mom was easier in the 1980s than it is today.

Important caveat: not everyone can choose to start over. Rosin doesn’t mention whether she had to take a salary cut to go from print to audio, or whether money was even a consideration, but for many of us it is, often a limiting one. Her piece may as well be hashtagged #privilege. Still, if you can afford to try, it’s worth considering her argument for prioritizing the benefits of starting over rather than stability. And maybe we don’t even have to wait until mid-life. (Panoply, call me!!)

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Ester Bloom
The Billfold

Senior Editor, CNBC; former editor @thebillfold; contributing writer @theAtlantic