If you’re a business owner or CEO, odds are you feel like you can do almost anything yourself.

That’s part of what got you here. You’re capable, competent, and confident enough to take control when things get hard.

But here’s the truth most high performers don’t like to hear: You can go it alone — it just costs more, takes longer, and leaves less room for errors.

The Backstory

In 2012, I ran the Heartland 100.  It’s an out-and-back, 100-mile ultramarathon through gravel roads in the Flint Hills of central Kansas. It took me just under 26 hours of continuous effort.

The belt buckle I earned still sits in its wrapper. I’ve never worn it. It reminds me not of the finish line, but of the process, and the people who helped me reach it.

By rule, runners could have one pacer after mile 44. I surrounded myself with serious endurance athletes: multiple Ironman finishers, seasoned ultrarunners, and a crew chief who’d represented the U.S. in the 24-hour world ultrarunning championships and had to run more than 155 miles in a single day just to make that team.

They didn’t baby me. They understood pain, strategy, and how to stay sharp when the body starts to shut down.

That crew didn’t make the race easier. They made finishing possible.

This year, I returned to Heartland, not to run, but to volunteer and work the aid station that was located at the 44 mile marker on the way out to the turnaround point. It was also located at the 56-mile marker on the way back to the finish.

The weather was brutal. Temperatures exceeded 90 degrees, and there was no shade. I watched racers come in dizzy, blistered, and beaten down.

My unofficial job: talking people out of quitting.

Here’s what I learned.

Some runners came solo. They had no crew, no pacer, just grit. Some of them finished. But it was harder, riskier, and their margin for error was tiny. When exhaustion fogged their judgment, nobody was there to spot mistakes, like missing a turn in the dark or skipping nutrition until it was too late.

Others had crews. But, they were the wrong ones. A well-meaning mom, boyfriend, or friend saw them suffering and offered sympathy instead of strategy.

“It’s okay to stop. You’ve done great.” That’s how caring, well-meaning people talked strong runners into quitting.

Then there were the ones with experienced pacers and smart crews — people who’d been through it before. They didn’t offer excuses. They offered direction. “Fix your feet. Get calories in. Keep moving.”

And those runners? They finished.

Lesson for Leaders

Business works the same way.

Yes, you can do it yourself. Plenty of founders have.
But the higher you climb, the thinner the air gets — and the smaller your margin for error.

You don’t need cheerleaders. You don’t need people who “believe in you.” You need people who know the terrain, can read the warning signs, and keep you on course when fatigue sets in.

If you surround yourself with people who give comfort when you need clarity, they’ll talk you out of doing what you need to do to get to YOUR finish in time.

If you surround yourself with people who’ve been there before, they’ll get you through the ugly middle when you can’t see straight.

Call to Action

Audit your circle.

Ask yourself:

  • Am I trying to do this solo out of pride or practicality?
  • Who in my crew actually knows how to help at this stage — not just wants to help?
  • Who would tell me the hard truth when I’m at mile 44 of my business?

Going solo can work. So can the wrong team, for a while.  But if you’re chasing something big, something that takes endurance, risk, and pain tolerance, your success will depend on who’s beside you when things get ugly. Choose wisely.

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