Square Peg, Round Hole

Lessons from a rough week, a quiet epiphany, and too many fishing metaphors.

When Something Feels Off

I’ve been in a bit of a funk this week.

On paper, I’ve been doing all the right things: talking to potential customers, making outreach lists, following up. But something wasn’t clicking. After each conversation, I didn’t feel energized—I felt flat. Or worse, like I didn’t belong. Like I was selling something to people who didn’t really need or want it.

And the more I pushed forward, the heavier everything started to feel. My motivation tanked. I couldn’t focus. I felt like I was doing it wrong… but I couldn’t explain why.

The 300-Pound Lift

Then something clicked.

I heard a guy on a podcast say: “Don’t try to lift 300 pounds on your first day in the gym.”

As someone who lifts weights, that hit home. I’ve been guilty of that exact mistake—biting off too much, too fast. It dawned on me: maybe I was doing the same thing with my business.

The 99 Product Challenge? That’s a 300-pound barbell. Maybe I’ve been trying to do too much, too soon, again. And when you find yourself stuck under that kind of weight, it’s time to ask:

What’s the smaller lift?

What’s the smaller bet I can place?

What’s the smallest experiment I can run today?

Photo by Anete Lusina on Pexels.com

Where Are the Fish?

The second insight came via another metaphor—fishing.

Someone said, “If no one else is fishing where you are, maybe it’s because there aren’t any fish.”

That stopped me cold. Because I realized I’d been setting up camp in markets where there might not be any demand. No competitors, no noise, no traction… and no bites. That’s not innovation—it’s isolation.

Sure, you don’t want to be elbow-to-elbow with dozens of others fighting for space. But fishing where no one else is fishing? That’s a red flag, not a badge of honor.

So I had to ask myself: What watering holes am I hanging around?

And the honest answer? Some of them are bone dry.

What My Dad Taught Me About Fishing (and Business)

My dad was a diehard fisherman, and he had a saying:

“Never try fly fishing when the fish are biting worms.”

Translation? Don’t do what’s trendy—do what works.

That lesson applies in business too. Don’t waste your time on flashy tactics or over-engineered strategies. Do what’s functional. Do what gets results.

That’s who I am. I’m a pragmatist. I like clean, simple, effective solutions. I like to get shit done.

So yeah, maybe there are all kinds of clever canvases and trendy interview scripts out there for customer discovery. But at the end of the day, you know your business. You know your strengths. You know what works.

Photo by Mabel Amber on Pexels.com

Trust Yourself

This week reminded me of a few key things:

Start with small lifts.
Fish where there’s demand.
Don’t get caught chasing fashion over function.
And most importantly: trust yourself.

You’ve done hard things before. You’ll do them again. You’ve got this.