Why More Certainty Never Calms You Down

The reassurance you keep chasing runs on the same fear it promises to fix.

Every time I think I’ve finally got life figured out, something happens that shows me I don’t.

I wrote the first version of this the week after the 2024 election, when half the people around me were spun up about the result. But you can swap the election for whatever has its hooks in you as you read this. The machinery underneath is identical.

Here’s the pattern I keep catching in myself. Some discomfort shows up: pain, worry, anxiety, a low hum of fear. And I go hunting for the answer, the insight, the piece of information that will finally carry me over the line into peace and contentment.

I’ve run this loop more times than I can count. And every time, I’m convinced this answer is the one.

What I’m actually hunting for, every single time, is certainty.

Certainty that we can afford the house repairs. That college gets covered. That the vacation won’t wreck the budget. That the business keeps working. That my health holds. That there’s enough for retirement. That I’ll be okay when the house goes quiet.

Underneath all of it, if I’m honest, is a scared little kid who just wants someone to tell him it’s all going to be okay. He’s going to be okay. Life is going to work out.

And I don’t think I’m special in this. Everybody’s carrying that kid around. Some of us just hide him behind better resumes.

Here’s the part that finally stopped me.

To need certainty that things will be okay, I first have to believe they might not be. The fear comes preinstalled. The need is built on top of it.

Which means the whole thing is a self-fulfilling machine. I write a story that I’m not safe, that I’m not enough, that life will collapse without my constant management. Then I run around collecting reassurance to quiet a story I authored myself.

You know what the collecting looks like. One more plan. One more scenario gamed out in the shower. One more late night doing math on things that haven’t happened yet.

And no amount of certainty is ever enough for that machine. You can stack evidence to the ceiling. As long as the underlying story says you need rescuing, the machine just asks for more.

Meanwhile, life itself has a few billion years of track record. Things keep unfolding. The whole system keeps running, with zero input from my worry. Who am I to look at that and decide it all hinges on me knowing how next year turns out?

I should be immune to this by now. I coach founders and executives for a living, and I can walk a client through this exact trap in 10 minutes. I’ve put in 30 years of my own inner work: a spiritual teacher, almost 7 years at a Zen center, a master’s in spiritual psychology.

And I still fall in. Regularly. That’s the human thinking machinery doing what it does, and mine apparently came with the deluxe package.

So what interrupts it?

For me, the short circuit is catching the thought and seeing that it isn’t true. The idea that I’m unsafe. The idea that I’m not enough. The idea that everything falls apart the moment I stop gripping. Misunderstandings, all of them. Old programs installed so early I mistook them for facts.

What’s actually true is simpler, and I’ll say it even though part of me still squirms:

I have always been enough. I have never been unsafe. And it’s always going to work out, whatever the circumstances decide to do.

I know that. On my good days, I believe it all the way down. The remembering is the practice, and some days I’m better at it than others.

Now, if only I could remember.

With love, Andy

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