Curious about the Second Harvest retreats?
Fill out the form below or if you have more question, connect with your hosts, Richard and Devon.
A retreat designed for your next chapter
The world's a weird place right now, and it might not be obvious what your next move will be. There’s a good chance that you’re already been successful at something, but your journey feels unfinished. You're not alone. There's a whole community of people just like you doing work to create something better for themselves and the people they care about. We’ve lived through big changes ourselves. We've experienced the death of a spouse, divorce, starting and running great businesses, shutting down failing businesses and even exiting businesses. We've switched careers, moved countries and raised children to adulthood. We share your challenges and celebrate them too. We've learned that change is easier when you’ve got good people around you. Let's meet in Jamestown, connect with like-minded folks, and figure this stuff out together.
Limited spots— apply now
We keep these events small and intimate to ensure everyone gets times the attention and support they need to craft their next chapter, so act now to reserve your spot.
Prefer to talk to us?
You can book time with either Devon or Richard to discuss details or get to know us
Why do I need to apply?
Get answers
Get real, candid insights into what to expect, directly from the hosts
Meet the venue
Find your fit
Limited spots
As much as we'd like, not everyone can be accommodated
What participants have experienced
New retreats, but
seasoned leadership—
Guided by a team with 60+ years of collective experience and an expert local team
What we'll cover on the calls
- What makes Second Harvest different from other events?
- How do I get there from where I am?
- Who will be hosting the sessions?
- What activities will be included?
- Can I bring a spouse/partner/friend?
- What kind of people will attend?
- What’s the investment, and what’s included?
- What can I expect to leave the event with?
FAQs
Second Harvest is for people in the middle of life who look successful on paper but feel misaligned inside. They are typically in their 40s–60s. They’ve built careers, businesses, families, or reputations. They are competent, responsible, and respected. They’ve done what was expected of them and done it well. What’s changed is not their ability, but their relationship to how they’re spending their time. They feel a quiet exhaustion rather than a crisis. Motivation still exists, but meaning feels thinner. The old goals don’t pull like they used to. They don’t want another productivity system, self-help framework, or motivational push. They’re not broken and they’re not looking to be fixed. They’re thoughtful, curious, and self-aware enough to know something needs to shift. They value depth over hype, real conversation over performance, and experiences that feel human rather than transactional. They’re willing to slow down, reflect honestly, and take responsibility for what comes next. They’re not trying to escape their life. They’re trying to redesign it.
Second Harvest creates the space and structure for people to step out of their routines and look clearly at where their energy, time, and attention are going. Through small groups, honest conversations, and carefully chosen experiences, we help participants reconnect to what actually matters to them now, not who they used to be or who they think they should be. The outcome isn’t a dramatic reinvention or a list of goals. It’s clarity, steadiness, and a grounded sense of direction they can take back into their real life and act on immediately.