The plane door swung open. Below stretched a lake, patchwork farms, and gray ribbons of rural southern Michigan roads. To my right sat a stranger—the jumpmaster, credentials unknown beyond his title. When he barked orders, I obeyed.
At his command, I swung my left leg out onto the step, rotated my hips, and gripped the wing strut with both hands. Now perched outside at 3,500 feet, plane roaring at 65 mph, I dangled my feet off the step, flapping like a flag. A static line tethered my parachute pack. Releasing the strut would deploy it—I hoped.
Gripping tighter, doubts flooded me. "Let go!" he shouted. I pretended not to hear, frozen.
* * *
June 1994, fresh out of college. But my deepest fear hit March 2013 as a Sports News writer. An early-morning call: mandatory afternoon meeting, details withheld. I knew—layoff looming. Home with my wife and two young kids (her staying home our priority), financial terror struck. How to provide without a job?
Fear accelerated at 32 feet per second squared. I applied to 18 jobs, got zero responses. Journalism's instability offered no security. Exhausted by fear's grip, I launched my freelance writing business.
Problem: no clue how.
Fear clung like a second skin—failure, rejection, no sales. Isolation amplified it; learning solely from other writers proved disastrous. Instead, confronting physical dangers shattered that illusion. These experiences built resilience for solopreneur challenges. If you're going solo, these lessons may help you too.
Related: 5 things I learned about being a solopreneur
Lesson #1: Understand Boldness and Consequences.
Winter Park, Colorado. Exhausted after covering Knights of Heroes camp for boys who lost fathers in service—two kids evacuated mid-trek from vomiting. Mentors, fighter pilots John “Cosmo” Oglesby and Ryan “Slider” DeKok, lived the camp's "be bold" ethos, embracing risk for resilience.
I craved safety. Years bike-free, a ski slope descent? No thanks—flat pavement first. Yet solopreneurs must leap eventually. Peer pressure from teens won; I joined.
We progressed cautiously. Mid-descent, overconfidence hit: root, hard brake, airborne. Front tire planted; I flew over bars. Helmet, pads—pain minimal, pride bruised.
Lunch: all crashed, swapping gravity tales. More awaited.
“If you live boldly, it rewards more than punishes.”
Slider pale: Cosmo shattered his hip. Clinic bedside, painkillers glazing his eyes, he embodied consequences. Weeks on crutches, months rehabbing. Three years on, he regrets the family burden, quits biking—but not boldness. "It tempers with wisdom. Boldness builds strength and stories."
Related: Afraid of risks? How to be bolder
Lesson #2: Find Kindred Spirits.
Adventures sparked joy and connections. Guides faced parallel hurdles despite vastly different worlds.
Rivers like clients: predictable yet unpredictable (rafting guide). Escape vital (map instructor/homicide detective). Negotiate tough-smart (firearms instructor). Authenticity trumps polish—even F-bombs (glacier ATV owner).
Common thread: passion-fueled pivots from corporate drudgery. Hurdles like planning, marketing identical. Thrivers eye paths, not pitfalls—off-road lesson.
Lesson #3: Focus on Destination, Not Obstacles.
Off-road in Oregon: ravine yawned left, "road" narrow. Speedometer read under 20 mph; panic-locked brakes slid us. Lesson: eyes on path, not peril. Ferris Bueller mashup: life fast; slow turns or crash.
2017: lost major client, 40% income drop, sales drought. Obsessed on loss, spiraled. Off-road redux in Missouri: memorized tracks to speed. Tacoma ahead bounced gleefully through 'mines'—laughing. I crept safely, no thrill.
Overestimated threats. Focus forward rebuilds business.
Related: Think slow and other tips for better problem solving
Lesson #4: Prepare Thoroughly.
Early solopreneur editor: "Good, but needs edge." Adventures honed that. Alaska dog mushing: -40°F redefined cold—eyeballs froze. Returned to Just Short of Magic school.
Window iced shut, snow-buried lot, -20°C. Shrink-wrapped by cold. Owner Eleanor loaned arctic gear atop mine—essential. Trail: prepared, cold vanished; wilderness beauty shone.
Improper dress = fatal. Like business: gear up or perish.
COURTESY OF MATT CROSSMAN
Lesson #5: Embrace Fear Judiciously.
Tree climbing, St. Louis: height terror. Reached 20 feet easy; froze atop pitch. Ropes unseen, trust tested. Pro fears clashed: quit = failure; persist = heights.
$1,500 stake propelled to 55 feet. Tremors hit; visions of kids' grief. Quit safely—"never quit" bad advice. Descent demanded feared leap: trust ropes.
Not fearless now—pitch delays persist. But survival built risk tolerance.
Related: 52+ Ways to Get Out of Your Comfort Zone
Last year: 16-day Europe odyssey, five countries, six flights/hotels, multi-pub assignments. Early me lacked logistics/courage. Retrospect: past scares survivable. Focused forward; worst-case built strength.
Boldness-stupidity line shifts. Chasing it fuels business/life joy.
Skydiving close: clung, released at shouts. Counted "two thousand”—YANK! Floated serene, nailed peat-moss target. Lied "great." Never again—unless paid.
Related: Why stepping out of your comfort zone is worth it, even when it's uncomfortable
This article originally appeared in the Winter 2018 issue of LadiesBelle I/O magazine.
