“I’m Winston Wolf. I solve problems.” — Pulp Fiction
I had a conversation recently with a founder I’ve been coaching for a while. Nothing dramatic happened—no big exit, no new venture just launched.
But something was different.
He Was Showing Up Differently
He sounded lighter. More clear. He was describing conversations he used to dread that now felt easy. He was building relationships, asking great questions, and genuinely enjoying it. Not performing—participating.
He told me about:
• Hosting a major industry event and enjoying being recognized for leadership
• Connecting deeply with people at a wellness startup launch
• Taking in two hours of a live Eckhart Tolle presentation with no notes, no urgency to “get everything down”
• Exploring franchise opportunities—not to escape his day job, but out of real curiosity
• Giving up alcohol, not with fanfare, but because it just made sense
• Reworking his schedule to include tennis, yoga, strength training—and sleeping better than ever
Leading by Letting Go
He also told me he’s ready to step away from the business he sold to private equity—his “day job,” as he called it—with clarity, not bitterness. He’s actively developing his team, handing them more responsibility, and watching them thrive without him in the room.
None of this came from trying harder. It came from letting go of the pressure. The pressure to prove, to perform, to control every outcome, to find and solve every problem.
And when that pressure dropped? Possibility showed up.
He’s not “on fire.” He’s not “crushing it.” He’s not selling someone on his 7-step plan.
He’s just building a life that actually fits him now—and noticing what’s worth leaning into.
A Subtle but Life-Changing Shift
Sometimes the shift we need isn’t tactical. It’s internal. It’s not about having a plan. It’s about having space.
This shift doesn’t just happen to founders. It can happen to anyone.
When you are looking for problems, you find them.
When you are looking for possibilities, you find them, too.
If that’s a shift you’d like to explore, there are two ways to spend two days getting exposed to viewing from possibility.
First, as a one-on-one retreat. Second, as a group event in Denver October 20-21.
If either of those possibilities appeal to you, like this post so more people can see it, and send me a DM.