This weekend, I kayaked around Anacapa Island while two friends swam around it.

If you've never seen Anacapa, it's a small island off the California coast – beautiful, rugged, and bigger than it looks when you're trying to get all the way around it.

One of the swimmers has done plenty of marathon swims before. I know her rhythm and know what to expect. The other was attempting her first marathon swim, and she absolutely crushed it. Her pace was steady, her form held together, and she stayed focused for more than five hours in the water.

But as anyone who has done something hard knows, the last hour is different.

The wind picked up. The water got choppy. The final bend around the island seemed to stretch forever. At one point she joked that she was getting angry. She was smiling when she said it, but still, it was hard.

That night, over pizza, salad, and constant interruptions from my parents' dog, we talked about the swim. I assumed she felt proud. After all, she had just completed her first marathon swim and done something most people would never even attempt.

Instead, she said something that caught me off guard:

"It didn't feel successful because it didn't feel good."

The more we talked about it, the more I realized we were measuring the same accomplishment in completely different ways. If you had asked me beforehand what success looked like, I would have said finishing the swim, hitting a certain time, or simply making it around the island. Her definition was different. For her, success meant feeling good while doing it.

And while I don't think she's wrong, I couldn't stop thinking about how difficult that standard is.

What meaningful growth actually feels good while it's happening?

Every time I've tried to learn a new AI tool recently, I've felt slow, confused, and frustrated. The same thing happens when you're building a company, learning a skill, training for an event, or taking on a challenge you've never attempted before. The experience itself often doesn't feel great.

In fact, that's often the point.

We tend to assume that progress should feel comfortable and that success should feel smooth. But when I think about the moments that have actually changed me, very few of them felt good while they were happening. Most felt uncertain, awkward, frustrating, or difficult. The discomfort wasn't evidence that I was failing. It was evidence that I was stretching beyond what I already knew how to do.

So if you're working on something ambitious right now and it doesn't feel great all the time, that might not be a warning sign. It might be proof that you're exactly where you need to be.

Success is interesting because we get to define it for ourselves. The question is whether we're using a definition that helps us grow.