When Was The Last Time You Did Something Hard?

Most companies go through hard stages. That might be exactly where you want to be.

Mar 03, 2026

Week two in my tenure at The Muse, I was in investor meetings.

The company was mid-Series C fundraise and I was there to show up and contribute. I didn’t know the business. Didn’t know the financials. Was completely new to the space. That didn’t matter. The meetings were happening and hundreds of employees were relying on me to do my part. This was a very heavy feeling.

Our CEO (who is a brilliant CEO) carried the narrative while I scrambled to close my gaps and get up to speed as fast as possible. Late nights, a lot of questions, probably some moments I’ve since blocked out. We ultimately got it done and raised 8 figures. It felt great. But something happened in that chaos that I’m still drawing on today.

I talk to a lot of people who are in the middle of a job search, and I keep hearing a version of: “I only want to go somewhere that has it figured out.” Stable leadership. No ups and downs. I get it. Job searching is exhausting and the last thing you want is to land somewhere chaotic.

But I always want to ask: what company has it all figured out? Every company goes through stages. And some of those stages are hard and gnarly and a little bit ugly. That’s not a red flag. That’s just what companies look like when they’re going through something.

When we filter too hard for comfort, we filter out the experiences that actually move us. The Series C wasn’t something I chose because I wanted to be tested. I was just thrown in. But I came out of it trusting myself more in rooms where I don’t have all the answers.

Fear is a reasonable response to uncertainty. I’m not dismissing it. But fear sometimes has a way of narrowing our options down to only the ones that feel safe, and safe and good are two different things.

Some of the best career growth I’ve seen, in myself and in people I’ve worked with, came from walking into a messy situation and working to figure it out. I’ve come to realize that sometimes fear can rob you of doing these really hard things.

The hard stages are where the good stuff is. Embrace them.

Cool Read or Idea

Nat Eliason wrote this a couple of years ago and it connects directly to what I wrote above. His argument is simple: every hard thing you do becomes proof to yourself that you're capable of more. I find this to be an incredibly powerful way of thinking.

Of course, you are in control of what “hard things” means to you.