Jason Fried

February 21, 2024

You couldn't know

Have you ever been asked "What do you wish you knew then that you know now?"

I have. And I hate the question.

It's usually framed in a way that encourages you to pretend to place yourself in the nascent days of your career, or early adulthood. Back when you didn't know much, when you were trying to figure things out.

Essentially it's asking you which mistakes you wish you didn't make. To squint and identify the things you could have bypassed if you were armed with the wisdom of hindsight.

My take? I think you’d have made the same mistakes, and I don’t think you could have avoided anything that happened.

Why? First, it assumes you'd even listen to your 50 year old self when you were 20. Next it assumes you'd even be ready and able to accept the advice you didn't recognize as relevant. Last it assumes you'd be able to avoid the things you didn't see coming.

I don't think you could, would, or should.

Learning is experiencing and doing. It’s not dodging, following, or forgoing.

You had to go through the shit to learn the shit. Sidestepping it would have just landed you in some other shit. And then you'd have wished you had listened to different advice.

You wouldn’t have your sage advice today if you hadn’t had the stupid experiences then! In fact, answering the question would erase present you from existence. Because if you were different then, you wouldn’t be the you you know now.

Are there mistakes I wish I hadn’t made? One one hand, absolutely — plenty — but on the other hand, I had to make them to be who I am now. There’s no version of me that’s present me today with a different set of events in the past. I like who I am now, even with portions of my past I’m less satisfied with peering through present day goggles.

But it’s a fantasy to think that if I’d just had magical advice from some old dude named me, then I wouldn’t have made those mistakes back then.

Cut yourself some slack.


About Jason Fried

Hey! I'm Jason, the Co-Founder and CEO at 37signals, makers of Basecamp and HEY. Subscribe below to follow my thinking on business, design, product development, and whatever else is on my mind. Thanks for visiting, thanks for reading.