Look Before You Leap: How to Trust Yourself in Tough Decisions

Over twenty-one years ago, I took a bold leap of faith, leaving a thriving career in finance—complete with three promising opportunities—for a life as a ski patroller and, later, a backcountry manager. How did I find the courage to trust myself in a decision that traded financial rewards for profound personal fulfillment? Navigating the self-doubt that comes with such a life-altering choice required both instinct and strategy, often without realizing I was using them. We all face tough decisions, and I’m here to share insights from my journey to help you navigate yours with confidence.

Weighing the Pros and Cons

When the chance to become a ski patroller—a dream I’d planned to chase in retirement—came unexpectedly early, I started by weighing the pros and cons. I was young, owned a beautiful home, and was gaining recognition in a career I shared with my brother and father. The finance and insurance industries were intellectually stimulating, but I struggled to balance success with personal fulfillment. My family wasn’t getting the attention they deserved, and I felt out of sync with my own sense of purpose.

Ski patrolling offered a chance to live my passion for adventure and service in challenging environments. Yes, it meant a significant pay cut and leaving behind the polished office life, but it also meant living in a mountain paradise. Now, I’m steps away from trails for hiking and fly fishing, five blocks from downhill skiing, and a short drive from cross-country skiing and mountain biking. Most importantly, I could leave work at work, giving me time to build deeper relationships with my wife and children. As we used to say at Angel Fire Resort, “My job is better than your vacation.”

By projecting what life as a ski patroller might look like, I found clarity. Most of my expectations proved true, and this thoughtful weighing of pros and cons gave me the confidence to take the next step.

Seeking Wise Counsel

When the surprise job offer came, I turned to the wisest person I know: my wife. Seeking advice from someone affected by your decision can be tricky—they’re not impartial—but sometimes they offer the most valuable perspective. Her insights were both invigorating and sobering. She highlighted the financial strain of the pay cut, noting we’d need to dip into savings for the first couple of years—a reality that took us time to recover from. She also pointed out that my current career was straining our family, with no real connection to our kids and a workaholic pace that was unsustainable. Just weeks earlier, my doctor had warned me I was “the healthiest person he knew who was going to die before forty.”

Her candid words were a wake-up call, offering perspective I hadn’t fully grasped. They helped me see the challenges of staying in finance and the potential of the path ahead, guiding me toward a decision rooted in clarity.

Trusting Your Intuition

Even after weighing pros and cons and seeking wise counsel, I still had to make the leap. No decision comes with complete information; at best, we work with an incomplete puzzle. That’s where intuition steps in. Merriam-Webster defines intuition as both “quick and ready insight” and “the power of knowing things without conscious reasoning.” To me, it’s like reaching into a bag, unsure of what you’re seeking, and pulling out exactly what you need. With practice, you get better at trusting that instinct.

My gut told me to “go for it,” despite the butterflies and nausea that came with such a monumental choice. Trusting my intuition felt as significant as proposing to my wife—the last time I’d leaned so heavily on my gut. Choosing to pursue ski patrolling, and later becoming a backcountry manager, was a deliberate act of faith in myself. That intentionality bolstered my confidence in the decision.

Building Confidence Through Practice

Mastering decision-making takes practice. Over time, applying these steps—weighing pros and cons, seeking advice, and trusting intuition—becomes second nature. Small decisions offer low-stakes opportunities to refine this process, while honest self-reflection and feedback from others help you learn from successes and missteps. Whether the stakes are high or low, a mindful framework can transform how you approach choices, building confidence in your ability to make sound decisions.

A Quick Note of Celebration

I recently had a fantastic conversation with Caitlin Lowe on her podcast, Silver on the Sage. You can listen to it on your favorite streaming platform or here. While you’re at it you can help fund Silver on the Sage on Patreon.

Also, my book, The Long Walk Home: When the Power Dies, is now available for pre-order as an ebook at retailers like Amazon, Kobo, Apple Books, Barnes & Noble, Google Play, and more. The paperback will be available starting Thursday, November 20th, wherever books are sold (you may need ot order it though). The book will be available as an audiobook too, but I don’t have the details on that yet. I’m still working out details for signed copies and will share more updates soon.