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.

Sessions take place from 8:30am - 10:00am on Mondays at Middlefork Savanna George Beach Trail starting on Monday June 16th and ending on Monday August 25th.

Choose from two options:

  • Single Session – $349

  • Three-Session Package – $899

If you’ve been feeling the pressure to lead without a pause button—this is it.
Join us, and get out of your inbox and into a better version of yourself.

Choose Your Path

  • Three-Session Package

    Leverage structure, create momentum, and deepen your insight with three consecutive sessions. (Preferred pricing and flexible scheduling)

    Sign Me Up

  • Single Session

    Kickstart a shift, explore a single challenge or opportunity, or simply shake up your routine with a single session.

    Sign Me Up

Questions?

Interested in working together? Fill out some info and we will be in touch shortly! We can't wait to hear from you!