The 99 Product Challenge

A Late-Night Sailing Lesson

We had just finished a sailboat race the other evening, and I went to start the little outboard motor to get us back into the marina. The motor kicked on for a second, coughed twice, and promptly died.

So there we were—bobbing around in the dark, the whole crew looking at me. Other boats were motoring past us, and I just wanted to get us back to shore. I kept yanking on the starter, again and again, trying to will the thing back to life. It would sputter for a second, then die. Every. Single. Time.

Someone on the boat said, “Hey Tom, I think those guys can give us a tow.”

My first instinct? No way. I’ve got this.

But then reality kicked in: the night wasn’t getting any younger, and we weren’t getting any closer to the dock. So I swallowed my pride and accepted the tow.

They pulled us safely into the marina. We tied up at the dock, and finally—finally—I stopped scrambling. I took a breath. And in that moment of stillness, I looked down and noticed the fuel line wasn’t properly connected to the gas can.

That was it. That was the whole problem.

The Power of a Pause

It’s amazing what we miss when we’re caught up in stress, urgency, and the pressure of being watched. When I was out on the water, with other boats passing by and my crew silently expecting a fix, I couldn’t think clearly. I was too tense to troubleshoot. Too determined to “solve it now” to notice something obvious.

It wasn’t until I gave myself permission to stop—once we were safe, tied up, and no longer in crisis—that I had the clarity to see the problem.

That one breath of distance made all the difference.

This Isn’t Just About Boats

I share this story because I think the same thing happens to many of us, every day. At work. At home. Especially when building something new—like a product or business.

We get wrapped up in the moment. We feel pressure to move fast, solve problems, and deliver results. And when things go sideways, we double down instead of stepping back. We scramble harder. But more effort doesn’t always equal better insight.

Sometimes, what we need most isn’t to push harder.

Sometimes, what we need is space.

When the Pressure Mounts—Pause

If you find yourself stuck, frustrated, or feeling like everyone’s watching—you’re not alone. But that’s your cue. That’s the moment to pause.

Take a breath. Take a step back. Let the moment settle.

You might just notice the unplugged fuel line that’s been holding everything back.