The 10-Year Regret Test: One Question That Changed My Business (and Life)
A 7-year business anniversary reflection on the decision that changed everything for me
Seven years ago, I stood at a crossroads that may look and sound familiar to you.
My skills and talents had recently been "no longer needed" for the second time in my career. The first time, I chalked it up to bad luck. The second time? I couldn't ignore the pattern anymore.
I could see exactly what my next 15 - 20 years would look like if I went back.
Chasing sales goals that felt increasingly meaningless.
Selling initiatives I didn't believe in, explaining to teams why we needed to focus on problems that wouldn't actually "move the needle.” All because someone far removed from the actual business decided it was important.
The stress and grind was taking its toll, mentally and physically.
The Exploration Phase
So I started exploring the possibility of launching my own business.
I talked to business owner after business owner, hoping someone would talk me out of it. They didn't. If anything, their stories made it harder to walk away from the idea.
I did a test consulting project. It went well.
And then came the moment of decision.
The Moment of Truth
I started listing all the reasons it didn't make sense to start my own business:
Our kids were entering high school, which meant college tuition wasn't far behind.
My wife had left her career years earlier to focus on raising our kids.
I had no side gig to scale up and no clear path forward.
I'd be starting from absolute zero.
My wife looked at me and said:
"If you don't give it a shot, are you going to look back in 10 years and regret it?"
Then she added something that stopped me cold:
"I'd rather be broke and have you alive than dead from a heart attack in the next 5 - 10 years. Because that's the path you're on right now."
That question, the 10-year regret test, combined with the stark reality of where I was headed gave me immediate clarity.
The Deeper Calling
But there was something else happening too.
After months of conversations and that successful test project, I felt God speaking clearly to me.
I was standing at the edge of a cliff. I could either step off and trust that He would provide (and catch me).
Or I could turn around, do what I'd always done and get another management position. And eventually find myself in the same spot. Stressed. Unfulfilled. Feeling like there had to be something more to life and business.
What I Couldn't Have Known
The past seven years of building my business should have been more stressful than any management role. By any objective standard, the work has been harder.
But I've never experienced the level of stress I felt in that final management position. Even in the tough times (and there have been plenty), I've had an unwavering peace about staying in business and persisting.
I’ve discovered that's what happens when you're building something aligned with your values instead of constantly working against them.
The difference isn't the difficulty of the work. It's that I'm no longer playing an unwinnable game in a system designed around values I don't share.
I'm building something that matters to me, serving people I genuinely want to help, and doing it in a way that feels rewarding.
How to Apply the 10-Year Regret Test
Think about a business decision you've been avoiding or agonizing over. Apply the 10-year regret test:
"If I don't [make this change / launch this offer / let go of this client / invest in this tool or opportunity], will I look back in 10 years and regret it?"
Sometimes the answer will be "no, this feels important now but probably won't matter in 10 years." That's valuable clarity.
But sometimes the answer will be "yes, I'll most likely regret not trying." That's your signal.
Now, to be clear, the question won't eliminate the fear or make the decision easy. But it will help you see past your current situation to what truly matters for your future.
A Message for Those at the Crossroads
And if you're standing at your own cliff edge right now (whether it's launching something new, repositioning your business, or making a values-aligned change that feels risky), know this:
Building something aligned with who you are is hard work. But it's completely different from the soul-crushing stress of working against your values.
Next Steps
Sometimes a conversation brings clarity you've been missing. If you're facing a significant business decision and need help thinking it through, I'd be honored to help. Book a free Now What? Clarity Session where we'll look at where you are, what you're considering and help you identify your next right move.
Mike Schuster helps those who escaped the rat race to build a business of meaning and purpose clarify their message and develop a marketing approach to fuel growth and momentum without the hype or hustle.