8-Week Cohort Program

Eight weeks. Six pillars. A small group going through it with you.

A structured program you work through in a group of 6 to 12 people in the same chapter of life. Written reflections, real-world experiments, and a private discussion forum where your cohort weighs in on each other's work — and you weigh in on theirs.

Reserve Your Spot $299

What's included:

  • 8 weeks of structured curriculum, three to four lessons per week
  • All 6 pillars: Purpose, Identity, Relationships, Health, Structure, Legacy
  • A private cohort of 6 to 12 people working through the program together
  • A discussion forum where your cohort thinks through each lesson alongside you
  • Curriculum and moderation from founder Jon Davis and the Trailhead team
  • A retirement foundation built in your own words by the end of week 8
$299
· one-time
A single coaching session typically costs $200–$400. Trailhead is $299 for eight weeks of structured work and a peer cohort to do it with.
What to Expect

Not a lecture series. A working group.

Small Cohort

6 to 12 people in the same chapter of life, working through the same eight weeks together. You give feedback that helps them think. They give feedback that helps you think. Not anonymous forums — actual peers.

Kept on Pace

Not self-paced. Lessons unlock weekly, your cohort moves through the eight weeks together, and your peers are reading your work in real time. The structure keeps you from falling behind — or rushing ahead.

Real Accountability

A shared commitment, written work that's visible to your peers, and people who'll notice if you stop showing up. Progress happens when you do the work — and a cohort makes you more likely to do it.

The Program

8 weeks of intentional design

Six weeks, six pillars — one at a time. The final two weeks integrate the work and launch you into your next chapter. You'll reflect privately, run small experiments in your real life, and share your work with your group — they respond with structured feedback (we tell them how). By week 8, you'll have a foundation for the chapter ahead, built in your own words.

This isn't therapy. It's not a support group. It's a structured program for people who want to be as intentional about their next chapter as they were about their career.

What People Built in 8 Weeks
— Robert M., retired corporate counsel
— Janet S., retired hospital administrator
— Mike L., retired civil engineer
Reserve Your Spot

Join the next cohort

Cohorts are capped at 12 people. Reserve your spot and we'll email you when your cohort is ready to start.

$ 299  · one-time
Full 8-week program. A coaching session typically runs $200–$400 — Trailhead is the framework a coach would walk you through, structured for self-study.
  • 8 weeks of structured curriculum
  • All 6 pillars of retirement design
  • Private cohort discussion forum
  • Curriculum and moderation from Jon Davis and the Trailhead team
  • A foundation for your retirement built in your own words
🛡️
Two-Week Refund Guarantee

Try the first two weeks. If it's not for you, email us before week 3 begins and we'll refund you in full — no questions asked.

🔐 Secure checkout via Stripe  ·  Two-week refund guarantee (see above)
Not ready to enroll? Take the free assessment first → It takes 10 minutes and shows you where you stand.