On Regret, Resilience, and Dealing with the Messiness of Life

What I wish I knew...

“Was it worth it?”

“Would you do anything different?”

“What advice would you give your younger self?”

I get these questions a lot. And despite knowing that they are coming, I often struggle to give an answer on the spot. I could offer something trite and cliché, but these demand something deeper. An almost glimpse into my soul, the essence of who I am as a person. Especially in my case.

These questions don’t just pop up out of nowhere. They are a result of my experience as a whistleblower. My new book, Win the Inside Game starts by detailing the moment where I was standing in a hallway, faced with a singular decision that would shape the direction of my life. Before explaining how I eventually got to the point where I risked my livelihood and career to take on some of the biggest names and companies in sport.

My whistleblowing journey took nearly 10 years of my life. It started when I was fresh out of graduate school, taking on my first real job. What would I tell the early 20s Steve who thought he hit the jackpot in working for Nike and coaching Olympians? What would I say to myself when I stared down the possibility of never working in running again, of saying goodbye to the sport I loved?

There are no good answers, but here’s my best attempt. What advice would I give:

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Dear younger Steve,

Depending on when you read this, you are either on top of the world, about to start your dream job, or living through what surely feels like a nightmare. Maybe you are debating whether or not to hit send on that e-mail to anti-doping authorities, despite everyone around you telling you to let it go and that standing up will ruin your career before it gets started. Maybe you are in the depths of the craziness, with the FBI knocking on your door. (Perhaps I just messed with the space time continuum and am the reason that Biff Tannen is now mayor of Hill Valley…Okay, Back to the Future references aside…)

Regardless of what’s going on. Here’s what I wish I knew.

1. You will go against your values. What matters is how you respond.

You are going to screw up. That’s normal. We all do and will. When we’re young we walk around with this simplistic view of the world; good and evil, right and wrong. At some point along the way that gets shattered. First, with other people. You may see a ‘good person’ go against that grain. Then, with ourselves. We do or say something that goes against everything we’ve been taught, and perhaps, everything we’ve stood for.

You won’t be the first or the last. In fact, those who think they will never do anything wrong are most susceptible to doing so. Part of growing up is recognizing the complexity and messiness. Both within the world and within yourself. We all mess up. We all take the wrong turn. But what matters next is the vital point.

What are you going to do? Research tells us that most people justify, rationalize, or double down. They default towards protection. We have an inbuilt psychological immune system that’s job is to keep that story that we are a good, decent person alive. And when evidence is presented that points in the other direction, our brain goes on a mission to make sure our image of our self is protected. Just look at the lengths frauds in business or cheats in sport go to rationalize their decision making process.

Our natural inclination is to protect our ego, to keep our sense of self in tact. That may save us of some guilt or anxiety in the short term, but it prevents the most important part of all of this: learning, adapting, and growing. When we rationalize, we prevent reflection. When we double down, we close off pathways that reverse course and make it right.

Regardless of what happens, of how bad you may feel, focus on what comes next. How do you respond? That’s the defining piece that will shape your future.

2. Who you surround yourself with matters more than you know

The old saying that you become the five people you spend the most time with has some truth.

We tend to think of our beliefs as fundamental aspects of who we are. We have strong ethical, moral, or core values that define who we are. That's the child's storybook version. It sounds good. Reality and the latest science tell a different story. Your tribe does more to determine your morality than your morality does to determine your tribe. As researchers summarized when studying how political affiliation influences our beliefs, "We will switch our moral compass depending on how it fits with what we believe politically."

When our identity becomes intertwined with our groups, then we go where our tribe goes. Other research tells us that the closer we feel to someone, the more pull they have over our ethical behaviors. The point is this. We like to think that we’ll be the holdout. The person who stands firm, sticking to what they believe in no matter where they are. But research tells us that is highly unlikely. Sure, there are a few exceptions, but the vast majority of us will be nudged in the direction of our boss, teammates, coworkers, or friends. It’s hard to resist the pull.

What that means is one of the most important decisions you can make is who is in your circle. Who are your coworkers, friends, or teammates? Choose wisely. It turns out your mom was right to rhetorically ask you if you’d jump off the bridge if your best friend did. Little did she know, it’s not just teens who have this proclivity. We all do.

3. Learn how to care deeply but be able to let go. The thing that makes you great is what eventually gets in the way

There's no doubt about it. You've got to care to perform well. To get the most out of yourself, you need to care a lot about the thing you're pursuing. You cared a lot about running so you ran 100+ miles per week. You cared a lot about coaching, so you read every physiology book you could find and talked to every successful coach who would answer. That drive is important. But, it will also get in the way.

Working hard, caring deeply, obsessing over the thing narrows us. We become attached to the thing, our motivation shifts from internal curiosity to external. We start worrying about the result, the payoff. We start to see every performance as proving ourselves again and again. When we fall short, it’s not that we failed at skateboarding or running or riding. It becomes “I am a failure.”

The antidote? Let go. Just enough. One day you’ll learn it’s the secret to great performers. You’ll learn from Sara Hall about how she stopped chasing a record and focused on the experience and feeling of racing. You’ll hear from a sports psychologist who will tell you of an Olympian who broke through by finding hobbies. And research backs this up. Contrary to popular opinion, going all-in, burning the boats behind you, being relentlessly obsessive does not make you a better performer. Research from athletics to entrepreneurs shows it mostly backfires. All-in makes you fragile. Caring, but with just enough space frees you up to take risks, to enjoy the experience, and to see what you’re capable of, without it being a threat to your sense of self.

4. Separate your identify from what you do

You are a runner. You are a coach. That’s how you identify yourself, and how the small niche of runners in the world identify you. It’s something that you take pride in. It’s a badge of honor.

It feels great right now, but it will become a problem. When you tie your identity too closely to what you do, anytime you fail at running, you will take it as a failure of your true self. It won’t be that I failed at running. Instead, it will be Steve failed.

If you can’t separate yourself from what you do, the losses will hit particularly hard. A downward spiral will soon follow, as you beat yourself up looking for an answer to why you aren’t better. If you fall into the trap of “hard work” being the answer, you’ll double down your efforts, which will be entirely counterproductive, and put your deeper into a hole.

Instead, embrace your complexity. Understand that running is something that you are really good at. It’s a passion. Embrace how much you care about the sport. But always remember it isn’t who you are.

5. Don’t chase. Accolades, achievements, medals will never be fulfilling. It’s all bullshit.

It’s never enough. For anyone. If you chase the external, you will always end up never satisfied, always wanting more. The richest man in the world will lie about his accolades playing video games…why? It’s never enough, even if you have accomplished a lot and have more money than God.

It's the great trick of life, to convince you that chasing the external is what matters. It’s not. Even the father of capitalism, Adam Smith, warned us of this so many years ago, saying that we need to balance striving with tranquility and contentment.

A meta-analysis of over 100 studies found that when individuals' extrinsic aspirations dominated their intrinsic ones, it was “universally detrimental” to their well-being. It's not that we need to have solely intrinsic motives. We aren't Jesus or the Buddha. It's the balance that matters. When we tip too far to the external, we languish instead of thrive. When winning is all that matters, it might work in the short term, but over the long haul, we increasingly play out of a place of fear. And perform worse.

You’ll see this in your career. People who have achieved at the highest level, but are miserable. You can still strive, obtain the accolades, but those are byproducts to finding things that interest you, pursuing them with zeal, and enjoying the journey along the way.

6. Remind yourself of and stick to your principles

When you are challenged, stuck in an uncertain situation, you will need something to fall back on. A light that acts as a beacon, guiding you through the fog.

Principles are that guide. Developing them seems challenging, but is rather simple. Find what you value, what truly matters. Those are your principles.

Take your time and make sure you perform a particularly deep dive on this subject. Don’t settle for the superficial. Don’t rely on others to tell you what matters. Find what sticks in your core.

This will require some deep reflection, but it is well worth it. When you are at your lowest lows, if you stick to your principles, you will always find a path forward.

These will be tested, you will falter and fail to live up to them, but try to reorient and make sure you align yourself with what you value. Everyone has principles when life is easy, it’s when you are challenged that having a firm foundation will pay off.

7. Life works out if you let it. Don’t force things.

You are going to experience some tremendous highs and some depressing lows. You’ll question why you do this sport, your job, and much more. At times, life will appear meaningless.

Life works out.

I know that sounds silly to say, and very unscientific, but it does. You just have to figure out what actually matters to you, and work hard towards that. This doesn’t mean that it will be smooth sailing, in fact, it won’t. You will continue to be tested in every way imaginable. You will suffer; triumph, and face boredom, thrill, complacency and just about every other emotion possible along the way.

The enjoyment comes from the work. Sometimes it leads to phenomenal results, other times, nothing. That’s fine. Just don’t try to force things.

When you force things, you become anxious, you press. You start pushing the boundaries of your principles as the external result begins to supersede the work. Don’t let it.

Like most things in life, the analogy to running is apt. You will soon learn the hard lesson (again) that you can’t force a breakthrough. You can’t shove your way towards running fast. Instead, all you can do is do the work to put yourself in position to succeed, and see what’s there.

Let it come to you. Don’t force it.

8. Embrace the Messiness:

We crave simplicity. We want easy answers, clear-cut solutions, and a world that makes sense. But the truth is, life is messy, complicated, and full of contradictions. We're messy too, full of flaws, imperfections, and misaligned values and actions.

We often try to ignore this messiness, to compartmentalize our lives and present a perfect picture to the world. But that's not how we grow. Real growth, the kind that sticks, comes from confronting the messiness, from acknowledging our flaws and imperfections and figuring out how to make them work together.

Think of it like creating a work of art. If you try to make every brushstroke perfect, you'll end up with something stiff and lifeless. But if you embrace the imperfections, the unexpected turns, and the occasional smudge, you'll create something truly beautiful and unique. That's the power of embracing the messiness. It's in the imperfections that we find our true selves.

9. Own Your Story:

You are the author of your story. In a world that will increasingly intertwine with social media, it can feel like we lose control of our story. That we hand it over to others to control and define. Don't let others define your narrative.

In studying how people navigate life's challenges, psychologists Dan McAdams and Jack Bauer found that how we tell our stories matters. Those who tell redemption stories, where we go from a low to a high, turning our suffering into something positive, score higher on measures of well-being than those who tell “feel good” stories, where everything is generally pretty good. The old adage that the bad makes the good better holds true.

But it’s not just the arc. Bauer found it’s ‘growth themes’ that make the difference. It’s integrating our experiences into a cohesive narrative where we are able to explore, learn, and grow. As he concluded, "It appears that well-being has more to do with interpreting meaning in one's life than with interpreting life as turning out well without a stated reason." It's about finding meaning in and making sense of the struggle.

Own your story. Tell it well.

10. No one gives a shit.

In the future, an NCAA champion is going to share some powerful advice. Listen to her. Phoebe Wright will tell you rather abruptly that “When I get nervous before an Olympic Trials or a big meet, I try to zoom way out, and remember that it’s just track. And in the end, no one really gives a shit about track.”

Phoebe’s not trying to downplay the sport you love. We could substitute any number of pursuits, and the saying would hold true. It’s not that they aren’t important, but you aren’t performing surgery to save someone’s life, you aren’t saving the world from nuclear disaster. You are just running around in circles or writing words on a page.

The message should be clear, keep things in perspective.

It doesn’t mean that running or any of your other interests aren’t important, they are, but they should be important to you. Not for anyone else. You get to decide how much value you assign to each craft you undertake. You do this every day by giving it attention. What that really means is do the hard work and get to the bottom of why you passionately pursue what you do. The answer lies there, not from some external source.

11. Explore more. Go Broad

We're often told to specialize, to find our niche, and to go all-in on mastering a single pursuit. But the truth is, we need breadth as much as depth. We need to explore, dabble, and try on different hats before we can find the one that fits just right.

Think of it like building a house. If you start with a narrow foundation, you'll be limited in what you can build on top. But if you begin with a broad base, you'll have the flexibility to create something truly unique and expansive.

The same applies to our pursuits and identities. When we go broad and explore, we open ourselves up to new possibilities, new perspectives, and new ways of being. We may even discover talents and interests that we never knew we had. And if one path doesn't work out, we'll have plenty of others to come back to. Don't be afraid to wander, dabble, and try new things. It's in the exploration that we discover who we are.

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This post pulls from my new book Win the Inside Game. It's my most personal book yet, trying to use my experience (and lots of research) to show that there's a better way to strive for our potential. It's all about mastering the inner game. Order today and get all sorts of bonuses, including a free e-book on coaching, a masterclass on mental performance, and more.

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