Eight weeks to build a foundation for retirement — in your own words, tested against your own life, shared with a small group going through the same transition.
A free 10-minute assessment shows you where you stand on the six things that actually matter in retirement — and where to focus first.
Retirement planning has been reduced to a number. A savings target. A withdrawal rate. But the real challenge isn't running out of money. It's waking up on a Tuesday with no idea who you are anymore.
In a Forbes Health survey of 1,000+ retirees, 32% admitted they didn't feel prepared for the day-to-day reality of being retired. The money was figured out. The life wasn't.
Trailhead maps the pillars of a fulfilling retirement that no spreadsheet can capture.
What gets you out of bed when nobody's expecting you at the office? 1 in 5 retirees say they've lost their sense of purpose entirely. Discover what drives you beyond a title.
You were "the VP" or "the engineer" for decades. Who are you now? Rebuild your sense of self on your own terms.
Retirement reshuffles every relationship. Strengthen the ones that matter and build the community you need.
Will your body and mind keep up with the life you want to live? Design the habits that keep you sharp, not just alive.
Total freedom can feel like total emptiness — 27% of retirees report feeling unmotivated and overwhelmed. Build a daily rhythm that energizes you without the 9-to-5.
What will people say you stood for? Decide now, while you can still shape it. Not just assets — wisdom, impact, stories, and the mark you made.
There's no coach. That's the point. A coach costs $200–$400 a session and creates dependency. Trailhead gives you the framework a coach would walk you through — to use on your own schedule, with people in the same chapter of life.
Start with an honest assessment. Get a personalized blueprint. Build toward the life you want.
Score yourself across all 6 pillars. See where you're thriving and where you're adrift.
Start the 8-week curriculum. Every lesson is built to meet you where you are, with private reflection, real-world experiments, and cohort discussion. Your scores tell the course where you've already done work and where there's more to do.
Each week's lessons end in real-world experiments and cohort sharing. By Week 8, you'll have a foundation for the chapter ahead — built in your own words, tested against your own life.
I'm Jon Davis. I'm not a coach — I'm a business professor and a CPA who retired at the start of the pandemic and quickly discovered that the financial side of retirement had been planned for years and the rest had not. Looking for something to replace the work I'd left, I completed a coaching training program (CTI). The work gave me a foundation for my own transition — and showed me how much was missing for everyone else going through the same thing.
Trailhead is the program I wish I'd had. I tested every lesson on myself first. The program is what survived.
— Jon Davis, Founder
Testimonial coming soon.
Testimonial coming soon.
Testimonial coming soon.
Three to four lessons per week across the six pillars, plus integration and launch weeks. Lessons require private reflection, action steps in your own life, shared discussion with the others in your group, and accountability from the group.
Your assessment scores show you where you're strong and where the gaps are. The curriculum allows you to go deeper on the pillars where you need the most work and to polish the areas where you're already strong — so the time you spend maps to the pillars that matter most for you.
Six to twelve people doing the eight weeks together. You'll share your work, read theirs, and find out you're not navigating this alone.
Trailhead is built as an eight-week transformation, not a content collection. Each week asks for real reflection, real writing, real conversations with others. By the end, what you've built is yours, in your own words.
The work you do is yours. The reflections you write, the experiments you run, the materials you build — all of it stays with you, even after the cohort ends. We'll continue to host the platform and your cohort's archive for as long as we're operating, and we'll give you advance notice if anything changes.
Trailhead exists because the work that comes after work doesn't get easier without a plan. Your career got the structured thinking. The chapter that follows deserves the same.
A single coaching session costs $200–$400. Trailhead is $299 for eight weeks of structured curriculum, a cohort of peers, and the materials you build are yours to keep.
Start the Free Assessment Already convinced? Enroll now →