What Would You Do If Failure Wasn’t an Option?

We’ve all asked ourselves big “what if” questions at some point. What if I had more time? What if I had more money? But here’s one that flips the script: What would you do if failure wasn’t an option?

It’s a simple question, but once you sit with it, the weight of it hits. Imagine if every choice you made was guaranteed to work out. What would you chase? Where would you pour your energy? And maybe most importantly—what’s holding you back right now?

This blog takes you through that thought exercise, mixing in some personal reflections, passions, and stories. My (Randy) hope is that by the end, you’ll be asking yourself the same question and maybe even taking a step toward your own “failure-free” dream.

Why This Question Matters

When you remove the possibility of failure, excuses disappear.

• Fear of wasting time? Gone.

• Worry about money? Irrelevant.

• Concern about what others might think? Doesn’t matter.
  
  

What you’re left with is the pure essence of desire—the things that truly light you up. Sometimes those dreams are career-focused, other times they’re hobbies or experiences. Either way, this question strips away the noise and gets to the heart of what you really want.

My Lifelong Passion: Cars, Racing, and Community

For me, the first thing that comes to mind is cars. It’s been a passion since I was a kid. My dad used to bring home old cars every summer, ones that barely ran, and we’d spend time fixing them up. Nothing fancy—mostly cosmetic repairs—but it sparked something in me.

From go-karts as a kid to a love for classic muscle cars as an adult, cars have always had a way of pulling me in. There’s just something about the rumble of an engine, the smell of an old interior, the art of taking a corner just right.

If failure weren’t an option, here’s where I’d dive headfirst:

• Racing Cars: Not recklessly, but with precision and passion. I still remember the thrill of driving a Porsche GT3 on a track—braking at the right cones, nailing the turns, hearing a pro in my ear coaching me through every lap. Three laps flew by faster than I could blink, but it was pure joy.
  
  

• Classic Car Auctions: I’ve been going to Mecum Auctions for nearly a decade. It’s like Disneyland for car lovers. Imagine driving a 1969 Camaro onto the auction block, windows down, red with black interior, hearing the auctioneer’s chant echo through the arena.
  
  

• Car Shows and Clubs: Whether it’s a Sunday diner show with ’57 Chevys or waving at another Miata on the road, the car community is like its own language—a shared nod, a flash of headlights, a knowing smile. This isn’t just about machines. It’s about connection, nostalgia, and freedom.
  
  

The Challenge of Timing

Of course, life isn’t as simple as dreaming. Responsibilities exist—grandkids to watch, commitments already made, priorities that matter deeply. That’s why this exercise is so powerful: it reminds you to find space for what matters without dismissing what you already value.

The truth is, chasing these dreams doesn’t have to mean quitting everything else. It could look like:

• Volunteering once a year at an auction.

• Joining a local car club and showing up to a few events.

• Spending a weekend helping in the pit crew of a local race team.
  
  

Failure-free living doesn’t always mean going “all in.” Sometimes, it’s about making room for just enough of what lights you up.

Lessons from Family and Role Models

One of the most inspiring parts of this conversation is realizing how joy and passion show up in others:

• My wife absolutely loves her work as a wedding coordinator. Even on the toughest days, she finds purpose in what she does. That’s the dream—loving your work so much it doesn’t feel like work.
  
  

• My kids remind me of the importance of being flexible. Careers go through honeymoon phases and grind phases. The key is being willing to pivot when something no longer feels right. That’s what I’ve always encouraged them to do—stay open to new opportunities.
  
  

• Athletes like Scottie Scheffler show us that passion fuels discipline. He calls golfing “going to work,” but it’s clear he loves every swing. That kind of mindset is contagious.
  
  

The lesson? When passion aligns with purpose, work becomes joy.

The Risk of Regret

Here’s a sobering question: Would you regret not pursuing your dream?

If I’m being honest, yes—I probably would regret not leaning into the car world more. Not because I think I need to make it a career, but because life is too short to leave those passions unexplored.

Regret rarely comes from trying and failing. It usually comes from not trying at all. That’s why this question—what would you do if failure wasn’t an option?—isn’t just fun. It’s important.

Practical Ways to Explore Your Dream

Dreaming is powerful, but acting is transformative. Here are a few small, practical ways to bridge the gap between imagination and reality:

• Find Your Tribe: Join a local club, whether it’s classic cars, Miatas, or racing enthusiasts. Shared passion creates instant community.
  
  

• Leverage Your Network: Remember old connections, like my former coworker Dan who drives cars at Mecum. Sometimes the door you’re looking for is one introduction away.
  
  

• Start Small: Volunteer at one event. Attend one car show. Test-drive one track experience. You don’t need to overhaul your life to feel fulfilled.
  
  

• Share the Passion: Whether it’s with kids, grandkids, or friends, passing on knowledge makes the journey richer. Even pop quizzes about cars can spark a love that lasts generations.
  
  

• Be Open to Timing: Maybe it’s not this month, or even this year. But intention sets things in motion. Opportunities tend to show up when you’re looking for them.
  
  

Bringing It Back to You

So now it’s your turn. Close your eyes and really ask yourself:

• If failure wasn’t an option, what would I do?

• What hobby, career, or adventure would I chase without hesitation?

• Who in my life could I ask this question to—and what doors might that open for them?
  
  

It might be starting a business. It might be moving across the country. It might be something as simple as learning to play guitar or writing that book you’ve been putting off. Whatever it is, give yourself permission to dream without limits.

Final Thoughts

The point of this exercise isn’t to fantasize about an impossible life. It’s to uncover what you really want—then take steps toward it, however small.

For me, that looks like classic cars, racing tracks, and auctions. For you, it might be something entirely different. What matters is allowing yourself to say it out loud, picture it, and move closer to it.

Because at the end of the day, the biggest failure isn’t trying and falling short. It’s never trying at all.

So, I’ll leave you with the same question we asked on the podcast:

👉 What would you do if failure wasn’t an option?

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