Type 2 Fun and the Business of Leading Well
Over the years, I’ve taken on a few big physical challenges—big for me, at least. They usually involve brothers, blisters, fatigue, and a generous dose of second-guessing. We call it Type 2 Fun. The kind that isn’t fun in the moment, but makes for a great story after the fact.
Rim-to-rim hiking the Grand Canyon. Pedaling for hours on end. Climbing that one mountain we swore we’d never climb again.
Each time, the same two thoughts hit me at the finish line: “I’m never doing that again.” Followed quickly by, “So… what’s next?”
Scaling a business fits squarely in that Type 2 Fun category. It stretches your headspace, tests your stamina, and demands more of you than you think you have. And just like those treks, it brings a rollercoaster of emotions:
Butterflies at the start
Doubt when you realize what you’ve signed up for
Bursts of thrill
Fatigue that hits deeper than expected
Awe when you zoom out
Gratitude for the view
Frustration when progress stalls
Demoralization when it backslides
Elation when it finally clicks
Irritation when the same issue shows up again
And on it goes.
But one truth stands out every time: Who you bring with you matters more than anything else.
You don’t want to drag an anchor up a mountain. And you definitely don’t want to hike next to someone who wakes up each day opposed to the journey.
Yet, that’s exactly what we do in our businesses. We hire misaligned people. We keep them too long. We watch them slow the team, resist the climb, or actively pull in the opposite direction.
Why? In my case—it was pride. I thought I could “coach them up.” Or I didn’t want to deal with the hard conversation. Truth is, you don’t avoid the consequences—you just delay them, and make them worse.
It’s like ignoring a pebble in your shoe. You think you can power through it, but over time, it’ll blister and sideline you. The pain demands attention either way—sooner or later.
What changed for me was learning to lead with clarity, not just grit. That’s where the CARE model came in. A structure that allows you to face misalignment with both compassion and accountability:
Clarify the issue – Be specific, be objective. What’s the actual misalignment?
Ask for their perspective – Let them speak. People need to feel seen before they can hear.
Realign expectations – This isn’t personal. It’s about values, goals, and agreed-upon standards.
Ensure commitment – Make a mutual plan. And follow through. Support them, but don’t carry them.
This isn’t about being nice or being harsh. It’s about leading.
When you use this consistently, it does more than fix performance problems—it builds a culture where expectations are clear, accountability is normal, and people feel respected. And that kind of culture doesn’t avoid problems. It solves them before they fester.
Not everyone wants what you want. That’s not cynicism—it’s stewardship. Your job isn’t to carry people. It’s to lead them. And if they won’t follow, the most respectful thing you can do—for them and for your team—is to let them off the trail.
The smart CEO learns to listen to behavior, not just words. And then they act. Calmly. Clearly. Decisively.
Decide. Act. Review. Lead.