Why I Hate Everything I've Written

How imposter syndrome affects anyone's mid-life pivot

I had coffee with a friend yesterday, and she mentioned something from a past post of this very newsletter. I started scrolling through my work, looking for the anecdote she was talking about. And I couldn’t believe what I was reading.

Inside the mind of a writer…I spoke last time in a complacency post about how our work is never, ever good enough. Even best-selling author Harlan Coben — whose books have led to Netflix series such as Fool Me Once and Shelter — told us at a recent book festival in Iceland that, “Every writer deals with imposter syndrome. That fuels us a little bit. Only bad writers think they’re good.”

But we are not alone.

When I started my newsletter, I knew the first few posts would be eh—they always are. You get the mediocre stuff out first, see what works, fix it, move on. Perfectionism can be the death of not only starting a newsletter—but of striking out on any new venture. Don’t fall for it.

I know people who never launched their web sites, their businesses, because they got stuck on making it “perfect.” Can you imagine all of those hours wasted??

Only bad writers think they’re good.

—best-selling author and Netflix darling Harlan Coben

You know where this is going:

  • How does this “imposter syndrome” affect crossing the large divide into something new?

  • If you’re feeling some type of way about your work that you’re good at (because you are), how do you get up the nerve to try something new—or just go after it in the first place?

Some practical advice: start by looking through job listings, etc that are totally in your wheelhouse; you could start tomorrow. Then look at the required skills listed—and search those skills. Follow the companies that have jobs using those skills. Continue to cast a wider and wider net.

And then under no circumstances apply.

Yes, you read that right. If you’re different, you’ll never get past the algorithm/keyword/HR death loop. (One exception: applying to jobs does tell LinkedIn, etc what kinds of jobs you’re interested in, so if you’re working on your algorithm, fair.)

Instead, target the CEO if it’s a small company, or maybe another member of the C-suite or a VP that runs the division you’re interested in. This way, you’ll be able to pitch your unique skills and why/how you could change this role for the better. The “Easy Apply” options simply don’t have room for pitching new ideas—not that they’d get past the algorithm with its strict “requirements” anyway.

Perfectionism can be the death of starting anything new. Don’t fall for it.

So…is any of this stuff working? I’m happy to report that yes, it is.

Someone sent me a Reddit post that started with a young adult complaining she’d applied to more than 200 jobs and gotten nowhere. And I know two people personally who are in a similar boat.

But I’ve been doing things a bit differently, and opportunities have materialized. Even if they don’t cross the finish line, they’re serious enough to prove that “thinking outside the box” is working.

Stay tuned for some happy news in my next post…

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