A Focused Fool Reflection on Roger Federer’s Quote. How Failure Is About Getting Back Up, and Growing Anyway.
Failure’s PR Problem
I used to think failure was a sign I wasn’t cut out for something. Turns out, it was the application process.
Three days before closing on a house flip that would have netted us a beautiful profit, the buyers walked away. Just like that. We’d already committed to moving back to Michigan for the summer, lined up another property, and I was mentally spending money that suddenly wasn’t coming. Interest rates had just jumped, and what should have been a quick flip now looked like it had been sitting on the market for months, which, in that market, was basically a scarlet letter.
I remember standing in that empty house, calculator in hand, trying to figure out how we’d make the numbers work. The rental income would cover the mortgage, but it wouldn’t give me back my investment. Which meant I’d be heading to Michigan alone, living in a construction site while my family stayed behind. For three months, I’d wake up on an air mattress surrounded by drywall dust, wondering if I’d made a massive mistake.
My kids watched this whole thing unfold. They saw Dad’s “sure thing” turn into Dad scrambling for Plan B, then Plan C.
Roger Federer once said, “I don’t lose. I either win, or I learn.” Meanwhile, I was out here thinking I either win or… hide in the garage eating peanut butter straight from the jar while questioning every life choice I’d ever made.
But here’s what I’ve been thinking about lately: What if failure isn’t just allowed on the path to growth, but required? What if the moments that feel like we’re falling behind are actually the moments we’re being pushed forward?
The Myth of the Clean Climb
Real Growth Looks Like a Clumsy Ladder, Not a Perfect Upward Line
We’ve bought into this lie that successful men have some kind of Midas touch, that they make calculated moves and everything works out according to plan. Social media feeds us a steady diet of highlight reels: the promotion announcements, the family vacation photos, the “crushing it” posts. What we don’t see are the 2 AM strategy sessions, the failed launches, the conversations where someone had to explain to their spouse why the thing they were counting on didn’t happen.
Every meaningful change in my life has involved messing up first. Learning to be a better husband? Failed spectacularly at mind-reading and assuming I knew what my wife needed. Getting in shape? Tried to go from couch to CrossFit athlete in two weeks and pulled something I didn’t know could be pulled. Building a business? Well, you just heard about the house flip.
There’s this concept called a “failure resume,” a document that lists all your mistakes, setbacks, and spectacular crashes alongside the lessons learned. Every man worth knowing has one, even if it’s unspoken. The guys who seem to have it all figured out? They just got comfortable with the fact that figuring it out is a messy, ongoing process.
Growth isn’t linear. It’s spiral-shaped, and every misstep comes back around with a lesson. You keep coming back to the same challenges, but each time you’re a little higher up the mountain, with a better view of where you’ve been and where you’re headed.
What Failure Teaches (That Success Can’t)
Pain Isn’t the Problem. Avoiding It Is.
Success feels good. It validates our decisions, boosts our confidence, and makes us want to keep doing whatever worked. But failure? Failure makes us pay attention. It forces us to examine our assumptions, question our methods, and confront the gap between what we thought would happen and what actually did.
That house flip taught me three things that no successful deal ever could have:
First, where my blind spots were. I was so focused on the potential profit that I got sloppy with risk management. I had all my eggs in one basket and was already spending money I hadn’t earned yet. Success would have reinforced this behavior. Failure exposed it.
Second, what really matters to me. The money was important, sure, but what kept me up at night wasn’t the financial loss. It was being separated from my family. We don’t cry over what we don’t care about. That three-month stretch of living alone clarified my priorities in a way that smooth sailing never would have.
Third, how resilient I actually am. Before this, I thought I was the kind of guy who needed everything to go according to plan. Turns out, I could adapt, problem-solve, and keep moving forward even when Plan A exploded in my face. I discovered I was stronger than I thought, but I needed to get knocked down to find out.
Here’s the thing: success tends to make us comfortable, and comfortable men don’t grow. Failure, on the other hand, creates what psychologists call “post-traumatic growth,” the phenomenon where people emerge from difficult experiences stronger, wiser, and more capable than before.
Focused Fool Prompt: What’s a recent failure that stung but secretly clarified something important for you?
The Real Danger Is Avoiding Failure
Perfectionism Is Just Fear in a Fancy Jacket
The biggest risk isn’t failing. It’s playing it so safe that you never give yourself the chance to discover what you’re capable of.
I see this with a lot of men in our community. They have ideas, business ventures, career pivots, creative projects, but they’re paralyzed by the possibility of failing publicly. Especially when it comes to providing for their families. The weight of responsibility can make us so risk-averse that we never take the calculated risks that could actually improve our situation.
We’re not taught how to fail with grace. We’re taught to never fail at all. But here’s the problem: if you’re not failing occasionally, you’re not trying hard enough. You’re staying in your comfort zone, which means you’re not growing. And if you’re not growing, you’re not modeling growth for your kids.
Think about it this way: You can’t lead your kids into bravery if you’re still hiding from your own fear. When they encounter their own setbacks, and they will, what are you going to tell them? That failure is the end of the story? Or that it’s just the middle chapter?
My kids didn’t just see the solution. They saw the struggle. The long silences. The short temper. The look I gave their mom that said, “I’m not sure how this ends.” But they also saw me keep working the problem. They saw me pivot, adapt, and ultimately find a way through. They learned that Dad doesn’t always get it right the first time, but he doesn’t give up either.
Failure doesn’t make you less of a man. Avoiding it might.
Failing Forward on Purpose
How to Turn Every Loss into a Launchpad
The goal isn’t more failure. It’s better failure. The kind that teaches.
Here’s how to fail forward:
Name it without shame. When something goes wrong, resist the urge to minimize it or blame external factors. Call it what it is: “I made a mistake,” or “This didn’t work out the way I planned.” I started keeping a simple journal during that difficult period, not to wallow, but to process what was happening without the emotional charge. Sometimes just acknowledging the reality takes the sting out of it.
Extract the lesson. Ask yourself one simple question: “What did this teach me?” Not “Why did this happen to me?” or “Who’s to blame?” but “What can I learn from this?” For me, that house flip taught me to never be more than one deal away from financial trouble. It taught me to have multiple exit strategies. It taught me that my family’s proximity matters more than profit margins.
Adjust and re-engage. Take the lesson and apply it to your next attempt. Don’t quit the mission. Refine the method. After that first house, I didn’t stop flipping properties. I just got more conservative with my cash flow management and stopped counting chickens before they hatched. The very next flip was incredibly profitable, partly because I’d learned from the first one’s mistakes.
Model it for your kids. This might be the most important one. Let them see you navigate setbacks with dignity. Narrate your own growth process: “Dad messed that one up. Here’s what I’m learning,” or “This didn’t go the way I planned, but watch how we work through it together.” They need to see that competent adults don’t have it all mapped out. They just keep moving forward.
The Micro-Failure Challenge: Try something this week that you’re likely to fail at. Not recklessly, but vulnerably. Maybe it’s attempting a new skill, having a difficult conversation, or pitching an idea you’re not sure about. The goal is to normalize the process of trying, failing, learning, and trying again.
The Only Way Through
Roger Federer’s quote makes a lot more sense to me now: “I don’t lose. I either win, or I learn.”
Looking back on that house flip disaster, I can see it wasn’t actually a disaster at all. It was expensive education. That three months of living alone, working through problems one at a time, taught me things about resilience and problem-solving that I never would have learned if everything had gone according to plan.
The second house flip was incredibly profitable, more than the first one would have been. And when we finally sold the rental property a year later, we made more than our original contracted price. But the real win wasn’t financial. It was discovering that I could handle uncertainty, that I could find solutions even when I couldn’t see them initially, and that my family trusted me to work through difficult seasons.
The best men I know aren’t the ones who never fail. They’re the ones who never stop learning.
You’re not failing. You’re training. And sometimes the best training happens when you’re standing in an empty house with a calculator, wondering how you’ll make it work.
The answer, it turns out, is one problem at a time.
What’s one failure that’s secretly been training you for something bigger?
Hit reply and let me know. I read every response.
The Focused Fool Newsletter – Growing As Men. Leading As Fathers.
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