The Math on Regret: Why the Fear of Failure Costs More Than You Think
- Tony Grayson
- Nov 16, 2025
- 8 min read
Updated: Dec 21, 2025
By Tony Grayson Tech Executive (ex-Oracle, AWS, Meta) & Former Nuclear Submarine Commander
I made one of the hardest decisions of my life standing in a parking lot in Groton, CT.
I’d just completed submarine command and received the 2015 Vice Admiral James Bond Stockdale Award for Inspirational Leadership. It is one of the highest honors a Naval officer can receive. I was at the absolute peak of my military career. Most officers spend their entire professional lives working toward what I’d just accomplished.
And I was about to walk away from it.
Not because I didn’t love it. Not because I couldn’t continue. But because I’d received an offer from Facebook that would change everything.
The safe play was obvious: stay in uniform, leverage the Stockdale Award, and continue climbing a career ladder I’d already proven I could dominate.
The risky play was terrifying: walk away from the pinnacle moment, leave the only professional identity I’d ever known, and start over in an industry where my awards meant nothing—all to spend more time with my family.
I took the risk. And I’ve never regretted it.
The Fear of Failure vs. The Math on Regret
Here’s what nobody tells you about the fear of failure: it’s a distraction.
While you’re busy catastrophizing about what might go wrong, you’re missing the real threat: the slow accumulation of unlived possibilities.
I’ve spent twenty years watching talented people manage their careers like they’re defusing a bomb. Every move is calculated for minimum risk. Every decision is filtered through worst-case scenarios. They are so focused on avoiding failure that they never notice they’re guaranteeing regret.
Because here’s the brutal math: Fear of failure feels massive in the moment, but regret compounds over decades.
Real-World Failure: Lessons from Oracle and AWS
Let me tell you about my failures, because I’ve had plenty.
At Oracle Cloud Infrastructure: I managed a $1.3B infrastructure budget. I greenlit data center expansions that didn’t perform as projected. I built strategies that required complete overhauls before they saw the light of day.
At Amazon Web Services (AWS): I made vendor decisions that cost millions to unwind. I championed technologies that the market rejected.
As a Founder: I burned through capital on facility designs we had to scrap. I pursued partnerships that dissolved. I pitched investors who showed me the door.
This by no means is an inclusive list and not one of those failures keeps me up at night.
You know what does? The acquisition offer I almost didn’t take because I was "comfortable." The executive role I nearly declined because I didn’t feel "ready." The business pivot I delayed for six months because I was overthinking the downside.
Those near misses haunt me more than any actual failure (as long as I learned from the failure).
Scars vs. What-Ifs: Building Your Legacy
You’re going to die with one of two things: A collection of scars, or a collection of "what-ifs."
The Scars make for interesting stories. They become wisdom. They turn into pattern recognition. They’re the tuition you paid for the education you actually use.
The What-Ifs accumulate. They don’t teach you anything because you never experienced them. They don’t become stories because nothing happened. They’re just quiet voices that get louder as you get older.
"I could have started that company." "I should have taken that job." "If only I’d tried when I had the chance."
That’s not a legacy. That’s a eulogy written by fear.
Military Risk Management Applied to Life
When I was in submarine command school, they taught us something critical about risk management: You don’t eliminate risk. You choose which risk you’re willing to accept.
On a submarine, you can’t avoid risk—after all, you’re operating a nuclear reactor underwater. So you train relentlessly, you build redundancies, and you prepare for failures. But you accept that operating involves risk, and you do it anyway because the mission matters.
Your career is the same way. You can’t avoid risk. You can only choose which flavor you want:
The risk of trying and failing, OR the risk of never trying and always wondering.
The risk of looking foolish temporarily, OR the risk of playing it safe permanently.
The risk of a setback you’ll recover from, OR the risk of a regret you’ll carry forever.
Stop managing the downside risk of failure. Start managing the downside risk of never trying.
What Fear Is Actually Protecting
Here’s the thing about fear: it thinks it’s protecting you.
Fear is trying to keep you comfortable. It keeps you from experiencing pain, embarrassment, or loss. But fear has no concept of time. It can’t see thirty years into the future when you’re looking back, wondering what your life would have been like if you’d been braver.
Fear is optimizing for your comfort today at the expense of your fulfillment tomorrow. Don't let it.
The Question That Matters
At the end of your career....hell, at the end of your life...you are going to ask yourself one question:
"Did I go for it?"
Not "Did I succeed at everything?" Not "Did I avoid all failures?" Not "Did I play it safe?"
Just: "Did I go for it?"
Your future self is counting on your current self to answer yes. The risk you didn’t take because you were afraid doesn't become a bullet dodged. It becomes a bullet point in your list of regrets. The opportunity you passed on because the timing wasn’t perfect doesn't become wisdom. It becomes a "what-if."
Your Move
So, here’s my challenge to you:
What’s the one thing you know you should do, but you’ve been avoiding because you’re afraid?
Not afraid because it’s genuinely dangerous. Afraid because it might not work. Afraid because people might judge you. Afraid because you might look foolish.
That thing? That’s exactly what you need to do.
Because twenty years from now, you won’t remember the discomfort of trying. You’ll only remember whether you did.
Be brave today so your future self can be proud tomorrow.
P.S. — What risk are you sitting on right now? Hit reply and tell me. Sometimes just saying it out loud is the first step to taking it.
Frequently Asked Questions: The Math on Regret and Fear of Failure
What is the Math on Regret?
The Math on Regret is the concept that fear of failure feels massive and immediate, while regret compounds silently over decades. Focusing too much on avoiding short-term failure guarantees the long-term downside of accumulated "what-ifs" and unlived possibilities. Fear of failure is optimizing for comfort today at the expense of fulfillment tomorrow.
Why did Tony Grayson leave the Navy at the peak of his career?
After completing submarine command and winning the Vice Admiral James Bond Stockdale Award for Inspirational Leadership, Grayson made the calculated decision to leave a guaranteed career path. He accepted an offer from Facebook (Meta) to pursue a high-risk opportunity and prioritize spending more time with family. He has never regretted the decision.
What is the difference between Scars and What-Ifs?
Scars are results of actual attempts and failures—failed projects, investments that didn't work. They become wisdom, lessons, and stories. What-Ifs are the silent accumulation of chances never taken. They don't teach anything because you never experienced them. What-Ifs are described as "a eulogy written by fear."
What is Jeff Bezos's Regret Minimization Framework?
The Regret Minimization Framework is Jeff Bezos's mental model for making difficult decisions. He projects himself to age 80 and asks which choice he would regret more: trying and failing, or never trying at all. This framework led him to leave Wall Street and start Amazon, realizing the risk of not trying would haunt him far more than failure.
How should military risk management principles apply to career decisions?
In submarine command, you don't eliminate risk—you choose which risk you're willing to accept. Career decisions work the same way: you choose between the risk of trying and failing OR never trying and always wondering. The focus should shift from managing the downside of failure to managing the downside of inaction.
What is the final question the author challenges readers to answer?
The ultimate question is: "Did I go for it?" Not "Did I succeed at everything?" or "Did I avoid all failures?" Just whether you chose courage and action over playing it safe. Your future self is counting on your current self to answer yes.
What failures has Tony Grayson experienced in his career?
At Oracle: data center expansions that didn't perform as projected, strategies requiring complete overhauls. At AWS: vendor decisions that cost millions to unwind, championed technologies the market rejected. As a founder: burned capital on scrapped facility designs, dissolved partnerships, rejected investor pitches. None of these keep him up at night—the near misses haunt him more.
What is fear actually protecting you from?
Fear thinks it's protecting you from pain, embarrassment, or loss. But fear has no concept of time—it can't see thirty years into the future when you're wondering what life would have been like if you'd been braver. Fear is optimizing for your comfort today at the expense of your fulfillment tomorrow. See also: The Intelligence Trap.
What is action bias in leadership?
Action bias is the tendency to favor taking action over inaction, even under uncertainty. In career decisions, it means accepting that the risk you didn't take doesn't become a bullet dodged—it becomes a bullet point in your list of regrets. The opportunity passed because timing wasn't perfect doesn't become wisdom—it becomes a what-if.
What is the Stockdale Award?
The Vice Admiral James Bond Stockdale Award for Inspirational Leadership is one of the highest honors a Naval officer can receive. Named after Medal of Honor recipient and POW James Stockdale, it recognizes junior officers who demonstrate extraordinary leadership. Tony Grayson received this award in 2015/2016 after completing submarine command.
How do you overcome fear of failure?
Recognize that fear of failure is a distraction from the real threat: accumulated regret. Project yourself to age 80 (Bezos's framework) and ask which you'd regret more—trying and failing, or never trying. Accept that you can't avoid risk, only choose which flavor: setbacks you'll recover from, or regrets you'll carry forever. See also: Cognitive Dissonance of Leadership.
Who is Tony Grayson?
Tony Grayson is President & GM of Northstar Enterprise + Defense, former SVP at Oracle ($1.3B budget), AWS, and Meta (30+ data centers). He commanded nuclear submarine USS Providence (SSN-719) and received the Stockdale Award. His transition from Navy to tech exemplifies the "math on regret"—choosing scars over what-ifs.
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Tony Grayson is a recognized Top 10 Data Center Influencer, a successful entrepreneur, and the President & General Manager of Northstar Enterprise + Defense.
A former U.S. Navy Submarine Commander and recipient of the prestigious VADM Stockdale Award, Tony is a leading authority on the convergence of nuclear energy, AI infrastructure, and national defense. His career is defined by building at scale: he led global infrastructure strategy as a Senior Vice President for AWS, Meta, and Oracle before founding and selling a top-10 modular data center company.
Today, he leads strategy and execution for critical defense programs and AI infrastructure, building AI factories and cloud regions that survive contact with reality.
Read more at: tonygraysonvet.com
Let me know what questions and comments you have!