There’s a video of me skiing out of the trees on a narrow trail. Controlled, quick bumps, and I pop out. Seeing only the last 10 seconds, you’d assume the whole run was a breeze.
It wasn’t.
On a sunny Saturday, I was at Sunshine Village with a friend who’s a much stronger skier than I am. From the chairlift, he spotted ski patrol opening a section of a black diamond run that rarely opens.
“We have to go!” he said.
I hesitated. Not because I don’t ski black diamonds, but because every unfamiliar run carries the same quiet question:
What if I get into something I can’t get out of?
Still, I followed.
The spring snow was heavy and deep. Every turn took effort. I fell more than once, got stuck trying to stand back up, and by the time I reached the trees, my legs were burning and my energy was running low.
There’s a moment in experiences like that where you realize you’re fully in it. Turning back isn’t an option, and the path ahead feels uncertain. So, you keep going… not entirely gracefully, but doing the work, sweating through it, and moving forward with determination.
My friend stayed ahead, mostly with insight. Encouraging, but not stepping in. I wasn’t alone, but I still had to find my own way down. He couldn’t ski it for me.
When I finally reached the bottom and said with a sense of victory, “I did it!” It genuinely felt great to conquer the challenge. And that’s the part that doesn’t show up on video.
I see a version of this play out with founders all the time.
From the outside, a decision can lookclean to onlookers. A pivot, a hire, a fire, a hard conversation. It can appear confident, even obvious in hindsight.
What we don’t see is the weight behind it. The second-guessing. The question “What if I get into something I can’t get out of?” The quiet fear of getting it wrong… financially, culturally, relationally. The series of small, imperfect decisions that lead to forward movement.
One of my tech clients hired the wrong person to expand into a new market. The rep was well connected, but didn’t have enough technical aptitude to understand the software application without a solutions engineer in every prospect meeting. The new market had no experience with the brand, so trust needed to be established.
At the time, it felt like turning back wasn’t an option. The founder watched deals drag on for months longer than usual, but held on to hope that the new market would turn a corner, that more coaching and support would lead to deals closing. The signs were clear, but the decision took over a year.
It rarely feels clear when you’re in it.
When the rep was let go, a better-fittingrep was brought in, and industry friends admired the founder for making the change. To them, it seemed quick and decisive.
To the founder, the agonizing process of starting over on the expansion strategy felt like wading through …deep
snow.
I’ve been skiing for over 30 years, and moments like this still put me back into beginner mode. Different conditions. New terrain. No clear path. I love overcoming a challenge like that, but there’s no question; it’s hard and scary.
Leadership has a way of doing the same thing. Experience doesn’t remove fear, uncertainty or doubt, but it changes how you move through it.
And maybe that’s the part worth remembering. The moments that stretch us most are the ones that force us to question our choices, recommit to our plan and make celebration all the sweeter.
*** Subscribe for more tips on leading highly engaged and committed teams. If you have a story about how you wrestled self-doubt and tough leadership situations, I’d love to hear your story! Book a call with me or send me an email.***
CarrieTuttle is the founder and revenue leadership coach at Team Mojo, a firm that develops technical leaders to grow their people AND profit sustainably.
