What am I becoming?
Asked on the first morning of the Northwoods retreat, Plum Lake, August 2026.
Trailhead takes small groups of people into the wilderness and asks them questions they have stopped asking themselves. Then it keeps them in each other’s company for the year after.
What this is
Most of the people who come to Trailhead have already built something. A company, a firm, a practice, a family, a reputation. The building worked. Somewhere along the way, though, “more” quietly stopped being an answer and became a habit. Trailhead is for that moment.
It is not a retreat in the spa sense and it is not a leadership seminar. It is several days somewhere remote enough that your title does not come with you. Morning conversations that ask one hard question each. Afternoons on the water or the trail. Evenings around a fire. The wilderness is not the backdrop. It is the mechanism. When the professional context is stripped away, people say things they have not said out loud in years.
Trailhead grew out of the Entrepreneurs’ Organization community in St. Louis, and it welcomes men and women, members and alumni and friends, anyone navigating the middle of a successful life.
The trail so far
In August 2026, seventeen campers from the EO community and beyond spent five days at Camp Highlands on Plum Lake for the first Trailhead expedition. Peer forums grew out of that trip and still meet. A youth outdoor leadership program launches in January, a monthly journal carries the ideas, and conversations have begun about bringing Trailhead experiences to other cities and other chapters.
Three questions
What am I becoming?
What have I been carrying?
What am I choosing not to see?
Every expedition is built around these morning sessions, one question at a time. The questions do not change much from trip to trip. The answers do.
The Journal
Each month we publish an essay on the work of the second half of life: purpose, discomfort, relationships, money, meaning, and the questions underneath all of it. Honest, sometimes hard to hear, always written from inside the climb.
The Trailhead Letter
A short letter, sent when there is something worth sending. Each new journal entry, reading worth your time, and news when the next group heads for the trees. Never anything said in a Trailhead circle, and never a sales pitch, because there is nothing to sell.
Two commitments
Trailhead is a nonprofit. Go Trailhead, Inc. is a Missouri nonprofit corporation with 501(c)(3) status in process. No one is paid. Expedition costs are shared at cost among campers.
What is said in a Trailhead circle stays in the circle. That is the first thing we say on every expedition and the last thing we say before we leave.
Trailhead · St. Louis, Missouri · info@gotrailhead.com
