“Go Big or Go Home”
Why Risk, Not Certainty Is the Path to Freedom
My first big leap of 2026 - Becoming a System and Soul business coach
This phrase came to me as I looked toward the year ahead.
It’s not something I usually say. I’m not an X Games skier about to take on a massive half pipe. And yet, as I reflect on where I am and what’s next, it rings true in a way I can’t quite ignore.
After a year “in between”—grieving the changes that followed a 25+ year career in wilderness therapy and stepping out of an 18-year role as a co-founder and partner at Open Sky, without knowing exactly what’s next—the time has come to go all in.
Just the other day, I was checking in with a client and was reminded of one of our first coaching sessions together, when I encouraged him to take a risk. Almost reflexively, I shared a quote I memorized early in my career as a field guide. It’s been with me for decades, though I seemed to forget it during the more predictable middle stretch of my career.
This quote has followed me for years, even when I wasn’t paying attention:
“Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then providence moves too. …Whatever you can do, or dream you can do, begin it. Boldness has genius, power, and magic in it. Begin it now.”
"Boldness has genius, power, and magic in it."
That line reverberates. It captures the “what do I have to lose?” mindset that settled in toward the end of last year.
Starting something new—especially something that relies entirely on oneself—is not easy. The inner critic is always nearby, whispering (or yelling) that it’s safer to stop, to retreat, to find something familiar and comfortable.
This is how I refuse to give in to that voice.
I also want to be clear: taking risks like this comes from a place of real privilege. I’m deeply grateful for the decisions I’ve made and the foundation set for me by my family.
We’re not desperate for money (yet). I have a spouse with a somewhat steady income (she also works for herself). We refinanced our home before interest rates skyrocketed. I have family support if things truly go sideways.
And still—this is real risk. It’s real money. It’s drawing on savings and retirement. It’s daily sacrifices that show up when a reliable income disappears. Privilege doesn’t remove risk; it simply changes its shape.
So what does this mean, concretely, in the year ahead?
It means moving forward boldly. Taking risks. Trying new things. Stretching myself and putting hard-earned money on the line.
It means committing significant resources to becoming a System and Soul Business Coach—with no guarantee of financial return.
It means putting myself out there - presenting a workshop and also sponsoring a booth at NATSAP's annual conference - hoping to spread the word about GTR Consulting.
It means exploring an investment in a local Durango business, knowing full well it may not succeed.
Any of it could fail. All of it could fail.
“So what?” is how I choose to see it.
After all, failure is feedback. I know I’m standing on a foundation built over nearly 30 years of hard work, combined with privileges and good fortune that are simply part of my lot in life.
And as I often remind myself, to risk nothing is the greatest hazard of all. Or, as another quote from my days guiding young people in the wilderness puts it:
“To laugh is to risk appearing the fool. To weep is to risk appearing sentimental. To reach out for another is to risk involvement. To expose feelings is to risk exposing your true self. But risks must be taken, because the greatest hazard in life is to risk nothing. The person who risks nothing, does nothing, has nothing, is nothing, and becomes nothing. He may avoid suffering and sorrow, but he cannot learn, feel, change, grow, love, or live. Chained by his servitude he is a slave who has forfeited all freedom. Only a person who risks is free.”
Freedom.
That’s the feeling I was longing for once the grief began to lift and the anxiety of uncertainty lingered. Freedom from fear. Freedom from being chained to what might have been. Freedom to move toward what could be. Freedom to go big.
There will be setbacks and successes.
Along the way, some breaks will go my way. Others won’t. I’m reminding myself to practice detachment—to meet success and failure with the same posture. As Jim Murphy cites Rudyard Kipling in Inner Excellence: “Meet with Triumph and Disaster and treat those two imposters just the same.”
Choosing to live fully
If Gain the Ridge Consulting doesn’t work out, it will not be a failure. I will have taken a risk. I will have felt fully alive along the way—risk has a way of doing that. I won’t have regrets.
It will be worthwhile experience: feedback that brings wisdom and compassion and shapes whatever comes next.
And through it all, I will have pursued the joy of freedom—living a life with purpose and meaning, rooted in relationships, and guided by a desire to combine my passion and skills in service of something larger than myself.
That feels like going big. And it feels worth it.
And who knows—I might stick the landing. I certainly have before.
