50 by 50: Ten Lessons from my 50-Foot Handstand Walk Journey

I make a living challenging and championing leaders as a coach, so entering 2025, in the spirit of walking my talk and with my milestone 50th birthday 10 months away, I decided to take on a challenge.

Thinking of a friend who 8 years ago for his 50th asked his friends to do 50 burpees in honor of his birthday and of one of my sons who used to be a gymnast and had me awe-inspired, I had a crazy idea. What if I could do a 50-foot handstand walk by my 50th birthday?! So my ’50 by 50’ journey began, and while it felt entirely unachievable, it also felt …just right.

Why? Because it scared me. Because it would take time, patience, humility, and a few spectacular wipeouts. And because – somewhere between the bruises, laughter, and breakthroughs – I suspected there might be lessons worth learning upside down.

Turns out, I was right.

1. The Importance of Chosen Challenges

Discomfort is the breeding ground for growth. We take on challenges every day, many of which we don’t choose yet still take on. Opting in to take on challenges acknowledges an active desire for growth. It doesn’t just happen; it comes with choice, work, and dedication.

• Choose something hard enough to stretch you, but meaningful enough to sustain you.

• Discomfort is a FEE, not a FINE. It can be an entry fee to growth instead of a penalty to pay.

• 50 by 50 Application: I didn’t trip and fall into a handstand. I decided to learn one. That choice created accountability and motivation.

• Bonus: When you choose your challenge, failure becomes data – not defeat.

2. 50 is the New 18

Not in the “stone-washed jeans and bad decisions” sense, but in the spirit of discovery. I’m not over the hill – I’m on the hill and get to celebrate the beautiful views and chart my next adventures! Turning 50 gave me permission to approach life like a beginner again.

• Staying young isn’t about age; it’s about curiosity.

• 50 by 50 Application: My first attempt lasted less than a second. My pride lasted about the same. Talking with coaches, watching videos, planning sets of drills, I continually got to imagine the possibilities of walking on my hands!

• Try this: Ask “what if” more often. It’s the best anti-aging serum there is.

3. Lessons in the Long Game

Progress isn’t linear. It can be painfully slow. It takes consistency and trust in the process.

• The long game takes patience, discipline, and humility in equal parts.

• 50 by 50 Application: Early on, I knew stretching and mobility work would be important for the challenge, and I prioritized it. Nevertheless, a few months in, a pain developed in my right wrist. It really hurt. I added more rest, fewer high-intensity days, and ultimately learned that wrist mobility wasn’t my issue (it turned out to be resolved with certain forearm stretches I didn’t know I needed). Plus, I fell. A lot! I even watched videos of babies learning to walk to motivate me to keep going.

• Reflection: Growth feels slow until one day, it feels inevitable.

4. Friends Matter

No one learns to walk 50 feet on their hands alone. The people cheering, spotting, strategizing, and sharing in my many laughs and grumbles are part of the journey.

• Growth is contagious – surround yourself with people who believe in your “impossible.”

• 50 by 50 Application: Friends held my legs for drills, gave me countless tips, took video of me practicing, and celebrated my first 3-foot victory like it was Olympic gold. The day I finally walked past the 50-foot line, a good friend was there taking video with my phone, and I truly believe that those last few feet were powered by his belief in me.

• Bonus: Joy shared is joy multiplied.

5. Believing It’s Possible Makes It Possible

Every breakthrough begins with a belief strong enough to quiet the doubt.

• The moment you shift from “can I?” to “I can,” the body follows.

• 50 by 50 Application: I spent about 2 months handstand walking from a cone to a wall, moving the cone out a few inches with each success. Even when the cone was 12- to 15-feet away from the wall, when I turned away from the wall, I got nowhere. It was only when I started setting up 6 blue cones, each 10 feet apart, so the 6th was at the 50-foot mark that I started to make real progress in distance. I had to believe that today could be the day I hit 50 feet, in order to make 50 feet possible for me in my mind. Up to that point, it was impossible, both on the floor and – more importantly – between my ears.

• Reminder: Confidence isn’t a result – it’s a tool.

6. Fall Gracefully

Falling is unavoidable. But learning to fall and to get back up is an art form.

• Resilience isn’t the absence of failure – it’s the ‘distress tolerance’ muscle built through it.

• 50 by 50 Application: My first real fall shook me. I have some historic back issues (including Degenerative Disc Disease), and I was afraid of getting seriously hurt. So each time I fell and got back up without pain or incident, I was viscerally grateful. From kick downs to cartwheels to tuck-and-roll moves, I now have an ability to fall that far exceeds my new ability to walk on my hands in terms of long-term value. I’m so blessed to know how to fall!

• Practice: When you fall, smile, reset, and kick up again.

7. Progress Loves Structure

Spontaneity is fun. Structure creates success.

• Growth hides in the habits you repeat, not the goals you announce.

• 50 by 50 Application: With and without coaches I engaged, I benefited by drills and routines that we created. Logging sessions, tracking wins both big and small, and working up from basic drills to advanced ones and actual handstand walking were my keys to success.

• Try: Replace “I’ll find time” with “I’ll make time.”

8. The Body Keeps Score – and So Does the Mind

Physical training changes your body. Mental training changes your life.

• Mental fitness and physical fitness are inseparable.

• 50 by 50 Application: As my shoulders strengthened, so did my patience. Both took daily reps.

• Reminder: Every rep of focus builds endurance for everything else in life.

9. Joy Is a Performance Enhancer

Somewhere between effort and obsession, joy can get lost. Don’t let it.

• Joy unlocks flow.

• 50 by 50 Application: When I started smiling mid-handstand (mostly out of disbelief), I found better balance. When coaches and friends at the gym cheered for me, lasting gains followed.

• Tip: Celebrate progress even when – actually, especially when – the goal feels far away.

10. YouTube Has Everything

Holy crap. I think we’ve all learned this lesson at least once. After I searched for and watched one video on handstand tips, about 8 million more like it came my way. And I watched and benefited from more of them than I can count!

• The tools are out there; the question is whether you’ll use them.

• 50 by 50 Application: I learned balance drills from a gymnast in Sweden, warm-up routines from a local Colorado resource (shout out to Ben Dziwulski, CEO at WODprep!), recovery tips from a physical therapist in California, and so much more (including those motivating videos of babies falling time and time again while learning to walk that I mentioned earlier!).

• Action: Take on something hard. The world’s best teachers are one search away.

Ready to Go Upside Down in Your Own Way?

You don’t need to walk on your hands to turn your world around. Try one of these challenges instead or come up with your own:

• 30-Day Cold Plunge Challenge – Build resilience, one shiver at a time.

• 50 Conversations with Strangers – Practice courage and connection.

• Digital Detox Weekends – Reconnect with the people and moments right in front of you.

• Daily Gratitude Note – Train your brain to spot abundance.

• 100 Push-Up Progression – Not because you have to, but because you can.

Pick one. Commit. Learn. Fall. Laugh. Cry. Then laugh some more. And discover what lessons might be waiting for you – just beyond your comfort zone.

Here’s a short video that encapsulates my 50 by 50 journey: