Stop Waiting to “Be Ready.” Or “Have Your Ducks in a Row.” Or Until the Baby is Born, or the House is Built, or the Kids Are Older / More Independent / Less of a Pain in the Ass.

I hear people talk about job security all the time, as if this were a real thing. But people really seem to like the concept, you know? I mean, I can’t think of anything more comforting than 40 years of standing in an elevator every day with Lou from HR. <Wide, delirious eyes.>

I’m not sure why that’s the rationale—it would terrify me to rely on so many external variables to determine whether or not I earn an income. It’s kind of like hoping the cool girls pick you…and then keep you. Forever. And there can never be a falling out. Because otherwise, you’re out on your ass.

The alternative—self-employment—seems to scare people far more, but I don’t think that’s because it’s more scary. (Or even more risky, when you consider the tools that are now available to us.) Rather, I suspect it’s because most people have never done it before…and that feels scary. Not because they aren’t perfectly capable, but because they don’t know themselves to be.

If I could offer a small piece of advice—something that’s worked exceptionally well for me, over the years?

Throw yourself to the wolves.

Stop waiting to “be ready.” Or “have your ducks in a row.” Or until the baby is born, or the house is built, or the kids go to college, or until you “have more time.” More time is a myth. Good intentions are an illusion. Your actions are the only truth you’ve got.

Don’t overthink it.

You’ll figure it out as you go.

You always do.

The wolves are never as vicious once you discover they’re actually Golden Retrievers.

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I run business experiments in remote work, internet publishing, newsletter growth, and using AI to make your projects pay so well your Stripe notifications start sounding like a slot machine at a Reno bowling alley. This is not a newsletter about fish.

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