Midlife MavericksThere is a kind of regret that does not show up until your forties. The deal that went wrong, the boss you stayed with too long: those sting and then they fade, because you learned something and the scar is proof. The regret that lingers is the move you talked yourself out of for sensible reasons.
My dad always said he regretted the mistakes he did not make. It took me until now to understand him. I have been pulling together a conference talk about career mistakes, a handful of real ones, each with a story and a lesson. Somewhere in the middle of writing it, I realised I had not made nearly enough of them. That was the actual problem.
Quote of the Week
Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.
Samuel Beckett, Worstward Ho (1983)
The biggest mistake is not making enough mistakes
We are told the smart move is to learn from other people’s mistakes. Watch from a distance and skip the pain. It sounds wise. Do you actually know one person who learns that way? Real learning comes from your own scars, not someone else’s cautionary tale. The deeper problem in most careers is that we make too few mistakes to ever lose the fear of getting it wrong.
My eldest taught me this before she could talk. Learning to stand, she would spend the whole day at it. Stand, fall, stand, fall, get back up. Endless reps, no loss of enthusiasm. Once she had standing, she moved to small supported steps and ran the same loop. Failure all day long, and not a flicker of embarrassment about it. Somewhere between toddler and forty-something, we lose that. We swap the reps for caution and call it maturity.
The safe path sends the invoice late
We believe the safe path is free. That is the lie. It delays the invoice by ten or fifteen years, then charges the whole thing at once, in the currency of what if. The relocation you turned down. The business you almost started. None of it felt like a mistake at the time. It felt like staying put.
I am not arguing for recklessness. But playing it safe is a decision with consequences, and we almost never price it as one. We treat the bold move as the risky one and the safe move as the default. We call it neutral. It is a risk you have agreed not to look at.
Owning it is the hard part
A mistake only becomes useful when you can say it plainly. That was me. I got it wrong. Not the market shifted, not my manager dropped it. The accountability is what turns a wound into a story you can tell out loud, and the women who can tell those stories without the fog of blame are the ones other people trust.
I know why you haven’t started the business yet. It is the fear of getting it wrong in public, at an age where getting it wrong feels harder to recover from. I feel that too. I decided a long time ago that I would rather collect scars than what ifs.
I have one on my right leg, very visible. Box jumps at CrossFit. I fell, and it was a proper bloodbath, leggings caked in red. I stuck a plaster on it and carried on jumping. Claudia 2, Box 0. I smile every time I see it, and I run my business the same way. You try things, and you keep going when they don’t work.
The fear of making mistakes and the fear of owning them come from the same place. What will they think of me. The way out is the same for both. You do the thing, and you keep going when it goes wrong.
Your move this week
Pick one move you talked yourself out of. The relocation, the role you didn’t go for. Write down the reason you said no, then put one question to it: was that a real constraint, or fear dressed up as prudence? Sometimes it was a genuine constraint, and you can finally put the regret down. Sometimes it was fear, and a smaller version of the move is still sitting there, available today.
Find that smaller version. A trip instead of the relocation. One paid project instead of the whole career change. The point is to stop adding to the pile of moves you never made.
Reply and tell me the move you talked yourself out of, and whether it was a constraint or fear in disguise. I read every one. What is the smaller version of it that is still available to you this week?
See you Wednesday,
C
