The Math on Regret: Why the Fear of Failure Costs More Than You Think

By Tony Grayson Tech Executive (ex-Oracle, AWS, Meta) & Former Nuclear Submarine Commander

The "pinnacle moment" described in the article: Receiving the Stockdale Award from Admiral John Richardson in 2016. Standing here, at the height of my naval career, I had to decide whether to stay comfortable or take the risk to start over.

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.

Just like Bezos explains here, projecting yourself to age 80 changes the math on risk.

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:

1. The risk of trying and failing, OR the risk of never trying and always wondering.

2. The risk of looking foolish temporarily, OR the risk of playing it safe permanently.

3. 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.

Tony Grayson

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.

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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