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This past weekend, I got to spend time with one of my favorite people in the world, my former college roommate, Catherine, who is currently swimming the coast of California. Yes, the coast. The whole thing. Her swim brought her through where I live, and I got to support her from a kayak for a couple of miles.

We also had a guest with us who makes shark documentaries and has worked with juggernauts like National Geographic and the BBC. He has a knack for finding sharks, and an equally impressive knack for getting them on camera. He took us to a spot where we saw a 10- to 12-foot great white. Right there, at one of my favorite beaches.

Later, after her swim miles were accomplished, I dipped into the ocean with my diving equipment, not too far from where we’d spotted said shark, he asked if I’d ever been scared. My immediate reaction was no. I wasn’t. Which, when I say it out loud, probably deserves a little more explanation.

The times I’ve seen sharks, they haven’t seemed particularly interested in me. And this weekend, I was in a place I know well. We’d been kayaking in the middle of the day, for just a couple of miles. I felt comfortable. But I’ve also been out there with Catherine under very different circumstances.

I supported her on two earlier training swims. One along the coast between the Golden Gate and Half Moon Bay. The other from the Farallones to the Golden Gate, where we launched at two in the morning. Being in a kayak in the pitch-black ocean, surrounded by sea lions, imagining what might be underneath us – that was scary. Looking back, I’m a little amazed I did it. I was younger, which may explain some things. But mostly, Catherine said we were going to be okay, and I believed her.

At the time, I didn’t think much about what those experiences might mean later. My friend was doing something hard, and I was there to help. Then this weekend, someone asked about my relationship with sharks, and those were the experiences I reached for. I’d been somewhere that felt much scarier. I’d gotten through it. Of course that had something to do with how I felt now.

What’s funny is that I didn’t have to convince myself those old swims counted. I don’t think I give my work history that same credit.

When I look back on trying to start my own company, or my time working in media, I can still get stuck on where I thought those things and dreams would take me. What I expected to happen. Then what didn’t. And then I do the thing where I wonder if I’ve done enough. Been successful enough. If I should be further along by now.

I can spend so much time thinking about what an experience didn’t become that I barely consider what I’m still getting from it. Those years have a lot to do with what I spend time on now. They shaped what I value and what I want more of. Even the things I learned I didn’t want have been useful. I know this. I just seem to forget it whenever I’m evaluating how my life is going.

In the ocean, it was easy. Those earlier swims were part of why I felt comfortable this weekend. I didn’t need them to have led to anything else. With work, I’m still tempted to wait for some future success that will make the earlier attempts feel worth it. Then I’ll be able to look back and say, okay, it all made sense. But I don’t know when that moment comes. Or if I’d even let it count when it did.

And in the meantime, I’m already living a life those experiences helped shape. I still wish some of those things had worked out differently. I probably always will. But I don’t want to keep looking at my life and seeing all the places I should have gotten further. It’s exhausting. And it leaves out so much of what those years actually gave me.

This weekend, I trusted the younger version of me who got in that kayak. I’d like to start trusting the one who tried to build a company, too.