Out of Office > On the Trail
A high-impact coaching experience in partnership with Lake Forest Open Lands
This is not a nature walk.
This is a reset for high-functioning professionals who know they need more clarity—but don’t need another conference room to find it.
Led by executive coach Dave O’Connor, Out of Office, On the Trail is a private, small-group coaching experience designed for senior-level leaders navigating transition, burnout, or big decisions. It’s where business insight meets personal realignment—on your feet, in nature, with a clear framework guiding each step.
Expect a potent blend of thought partnership, reflection prompts, and real-time coaching moments tailored to help you make better decisions, see your blind spots, and walk away lighter, sharper, and more confident.
“Dave helps me trust my wisdom, come to clear solutions, and leverage both for planning my personal goals and my business’s future.”
- Craig Bergmann, Lake Forest-based landscape designer and owner of Craig Bergmann Landscape Design
Each 90-minute session includes walking, sitting, standing and dialogue intentionally limited to five participants to protect the intimacy, confidentiality, and potency of the coaching experience. The mobility impaired are welcome and encouraged to communicate necessary accommodations in the contact form required for checkout.
Join us, and get out of your inbox and into a better version of yourself.
Our 2025 experience is currently closed.
But the season isn’t over—discover our Fall invitations here.
Questions?
Interested in working together? Fill out some info and we will be in touch shortly! We can't wait to hear from you!