Adventure unlocks inspiration.
Coaching turns it into clarity and action.
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The Challenge
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You've followed the map. Navigated the switchbacks. Taken your share of falls. You've reached the summit of your career, scars and all.
You want what comes next to look different, but the next summit that truly matters isn't clear yet.
That uncertainty, that opening, that pull toward something more.
That's where Second Summit Adventures begins.
Why SSA
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Adventure unlocks inspiration.
Coaching provides the compass.
Adventure gets you out of your head. The coaching gets you clear on what's next.
Every SSA experience is built on the Summit to Summit™ framework - four scaffolds that take you from stuck to moving:
Clarity — see what matters now
Structure — build the map forward
Support — climb with a guide, not alone
Momentum — take the first real step
Choose Your Adventure
One day. Three days. Seven days.
Each designed to get clearer on what's next, test your path forward, and reveal summits you can't see from here.
Approach (Mt. Hood Meadows - Winter ‘26)
A full day of skiing and coaching. The mountain inspires. The questions build momentum.
We start with coaching, then move to the mountain with questions on the lifts, clarity between runs, breakthroughs over lunch. We finish the day with a draft of your worthy goal and a 30-day plan to test it.
Blue runs minimum - advanced welcome (snowshoeing available for non-skiers)
Ascent (Bend, OR - Spring/Summer ‘26)
Three days. Solo or with a small group of leaders.
We move through your worthy goal, then go deeper - what are you actually leaving behind? What's the real cost of staying put? What does the path to this summit require?
The activity adapts to the season and your interests - mountain biking, fly fishing, hiking, paddleboarding. Movement creates the space. The framework creates the clarity.
You leave with your worthy goal and your 90-day roadmap.
Summit (Japan - Winter 2027)
Five or twelve days in Japan's mountains. World-class Japow. Solo or up to four leaders.
The bucket-list ski trip: lift-accessed backcountry, chase untouched powder, soak in onsens, eat well. The coaching happens on the mountain and off - we work through your worthy goal, map your support crew, send the emails that matter, and make real progress on the plan.
For leaders at a major turning point who want the time and space to do it right. You leave with your worthy goal, your support crew mapped, and the threshold behind you.
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Meet The Guide
Brad Schwartz
I spent 25 years leading global technology teams at Intel. Three years ago, I left to build Tech Leaders Coach, working with technical leaders on the hard parts of leadership.
The transition was harder than I expected. I'm really glad I had coaches who helped me through it.
Second Summit Adventures is different from my coaching practice. It's where adventure meets the work. Sometimes you need to get out of your office, out of your routine, and into a place where clarity actually has room to happen.
I've been chasing powder, hiking, and biking my whole life. SSA is where I get to combine that with helping leaders figure out what's next.
We offer flexible pricing so cost isn't a barrier if you're ready for this work.
Common Questions
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No - We have alternative adventure options in winter and other activities in spring/summer - snowshoeing, hiking, biking, fly fishing, paddleboarding.
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Absolutely. We customize programs and locations. Reach out for more information.
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If you're at an inflection point, stuck on what's next, or know something needs to change but can't see the path forward - you're ready.
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That’s exactly why you’re here. We’ll work through it together.
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This is a bespoke program - investment depends on your goals and what you need. The core includes coaching, framework worksheets, and follow-up work. We might add individual coaching sessions before or after, adjust adventure logistics, or structure it differently based on what serves you. We'll figure out the right approach in our chemistry call.
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Depends on your company and the topics you want to cover. This qualifies as executive coaching and professional development - many companies will cover it.
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A 30-minute conversation to make sure the timing is right, you're ready for coaching, and the format fits what you need. My goal is for you to see if this is valuable and right for you - not to convince you. If it's a fit, great. If not, I'll point you toward other ways to make progress. No pressure either way.
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Approach and Ascent: as soon as you know you want to do this - spots are limited. Expedition: We're building an interest list and will follow up with specifics in July 2026.
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