I Caught the Same Fish Twice. It's the Best Reminder I've Had All Year.

One of my favorite things is the moment the float plane touches down on Smoothrock Lake — about three hours north of Thunder Bay, no cell service, no road in, just Canadian wilderness, a lot of fish, and whatever you brought with you.

This was our fifth trip. My family and I have been coming every other year since 2017. People who have been fishing together my whole life, on a lake so remote the only internet is back at camp.

Last day. I’m in the boat with my uncle Mike when I hook a 33-inch northern pike on my jig. My dad starts yelling at me to get the fish away from the anchor. I’m yelling back that I’m trying. The fish snaps the line and disappears. I was so disappointed. I thought my chance at getting a big fish this trip had just slipped through my fingers.

I figured if that fish was nearby, maybe others were too. So, I switched to a lure more suited for a pike, made a few casts, and got a bite. When we finally wrestled him into the net, I looked down and saw my original jig lure still in his mouth. Same fish.

I finished the week at 118 fish — not my all-time record, but a good haul with a lot of seesaw to it. Some days I pulled in 28 to 33. Others, single digits. The lake doesn’t care what you caught yesterday. You show up, read the conditions, and adjust.

I’ve been thinking about that fish in the context of the next level of my business I’m trying to get started this year. There’s already plenty I’d do differently — the launch sequencing, the marketing, how I explained what it was before people could actually see it in action. I know this. And I’m also deliberately not making wholesale changes yet, because a few months in isn’t a verdict. Sometimes the lure just needs to change, not the goal.

“The pike didn’t go anywhere.
I just needed a different approach and one more cast.”

The pike didn’t go anywhere. I just needed a different approach and one more cast. That’s the thing about persistence — it only works if you’re also willing to diagnose honestly. Stubbornly repeating the exact same thing isn’t persistence. It’s just noise. The pivot matters as much as the patience.

There’s another lesson that came to the forefront during this week too.

On one of our last evenings, my dad asked me about making the trip an annual thing. He, my mom, and uncle aren’t sure how much longer they’ll be able to do something like this — the float plane, the remote camp, the full week of physical fishing. My oldest nephew is also heading to college in the fall, which means the configuration of who can come and when is already starting to shift. My niece just turned a year and a half, so a whole new chapter is beginning at exactly the same moment another one is changing shape.

When I left Facebook five years ago, one of the pillars I built my next chapter around was friends and family. I knew that 2021 to 2031 was going to be a specific window: the years when my parents were best suited to do trips like this, when my nephews were around before they had their own lives. Smoothrock is part of keeping that promise to myself.

So we’re going back next year. And 2028 is booked as well.

One thing I’ve learned after twenty-five years of navigating technology, politics, and institutional change is that the biggest breakthroughs rarely come from abandoning the mission. More often, they come from changing the approach while staying stubbornly committed to what matters most.

I’ve seen it in election campaigns, inside Facebook, in building Anchor Change, and now in launching the next chapter of my business. The destination usually isn’t wrong. Our first attempt at getting there often is.

That’s true whether you’re rebuilding a product, launching a business, navigating a career transition—or trying to land the same 33-inch northern pike twice.

If there’s something you’ve been circling back to—a project, a relationship, an idea you almost had but lost the line on—it might not need a completely different goal. It might just need a different lure, and the willingness to cast again.