What Does Winning Look Like to You in Personal Finance and Life?

“It’s not enough to have lived. We should be determined to live for something.” ~ Winston Churchill

Winning in personal finance and life means defining and pursuing “worthy wins”—goals and habits that actually improve your quality of life, deepen relationships, and align with your core values, not just increase the balance of your 401(k).

In this article, I’ll help explore what a “worthy win” really is—and how it can reshape the way we think about success in money, career, and relationships. You’ll learn a simple framework to filter decisions and habits through what matters most.

Finally, I’ll share some practical examples of wins in my own life that I continuously strive for in hopes of achieving a life well-lived. 

 

Money Is a Blessing—But It Doesn’t Automatically Equal Contentment 

If you’re a professional pilot these days, you may be making more money than you ever thought you would.  Awesome, right?!?  Money is a blessing that can create opportunities, remove obstacles, and, quite frankly, allow you to have more fun! 

However, as you progress in your professional pilot career and you see more money in your 401(k), you may not feel as content as you expected. There’s still stress about spending, health concerns, the busyness of life, and the amount of taxes you’re paying really makes you angry! 

Maybe you’ve hit the “wins” you dreamed of in your twenties—like getting hired at your dream airline—only to find that it’s become a grind. Maybe, after reaching some career goals, you quietly moved the goalposts. Now it seems like someone else has the bigger 401(k), nicer house, and happier family than you—at least on Instagram anyway! 

 

“Worthy Wins”: A Better Definition of Winning 

One of my favorite podcasts, The Jon Gordon Podcast, featured a recent episode where Jon Gordon interviewed John Olinger, a previous executive at Nike and author of the book “Worthy Wins: Pointing Your Life Toward What Matters Most.”  In his book and in the conversation, Olinger explores the difference between meaningful achievements and goals that look impressive but leave you empty

Likely, you’ve heard this line before, as I have.  But maybe as you progress in your professional pilot career and have achieved the goals you set for yourself, you’re ready to put more thought and action into this idea of “what really matters to you?”  What achievements will actually increase my family’s quality of life? 

The podcast discussion emphasizes that worthy wins are not just about big milestones, but also about daily actions and relationships that truly matter. Olinger shares strategies for staying focused on what’s important, avoiding distractions, and making decisions that reflect your core values.

 

Kobe Bryant’s Framework for Excellence

One of my favorite examples from the podcast was John Olinger’s experience at Nike and working with Kobe Bryant.  In addition to working for a decade at Nike as the Brand and Digital Marketing leader, Olinger worked for three years as the Global Brand Director for Kobe Bryant. He says Kobe had a “secret formula” for excellence in life and basketball: extreme clarity about what mattered to him. Kobe wanted to be the greatest basketball player on the planet—period. After his playing days, his focus shifted toward his businesses and being a great father to his daughters. Every habit and decision was filtered through that definition of winning.

Before we get to Kobe’s three rules for how to accomplish the worthy wins in your life, we must first determine and get extremely clear on what the worthy wins are.  I’m guessing that you don’t want to be the greatest athlete in the world. And I also know that many of you don’t obsess over becoming the best pilot in the world either.  However, becoming crystal clear on what winning is to you and me is the first and most important step. 

From my own experience, this clarity is hard to find. When I sit with the question of what really matters, I feel a tug-of-war between what I think I “should” want and what would truly represent a life well lived for my family and me.

 

A Financial Example: Boats, Lake Houses, and Real Life

I live in East Tennessee, where lake life, water sports, and boating are some of the best in the country. One of my best friends regularly shames me for not owning a wake-surf boat pulled by a brand-new, six-figure, four-wheel-drive truck. Honestly, I feel like I should want that too!

In the summer, when I see families heading to the lake with their beautiful boats and new trucks, I feel those twinges of envy. I know my income is likely similar to theirs—maybe even higher. So, the thought creeps in: if they can have it, why shouldn’t I? Furthermore, I deserve that!

The question I keep coming back to is this: Would owning a boat (or an airplane, beach house, lake house, etc.) create worthy wins in my life and relationships? In the boat example, I literally pictured my family and me on the water and hit “play” in my mind—trying to imagine what it would truly feel like over time, not just in the first week.

At one point, I seriously considered buying a lake house. We even took an hour-long joy ride as a family to check out a potential property. The drive was hot and miserable, and the kids griped at each other the whole way. That one experience helped me realize that, at least for now, our family wasn’t ready for this adventure.

In addition to my own life experiences, and research (check out Pilot Money Guys Podcast/Fight #114 with Dr. Michael Finke), I know that if I bought the lake house or the boat and it allowed my family to cultivate meaningful relationships, special moments and memories, it’s worth it! Maybe even a good investment! 

 

Kobe’s Three Rules for Achieving Worthy Wins

Whatever your desire in life or work—being a better parent, spouse, friend, or leader—you can use Kobe’s approach as a framework for your own worthy wins. According to Olinger, Kobe lived by three rules:

 

1. Urgency: Live Like Tomorrow Isn’t Promised

Kobe modeled a powerful sense of urgency in pursuing his goals. He approached each day as if tomorrow weren’t guaranteed.  (Sadly, Kobe died in a helicopter crash with his daughter in January 2020.)

Interestingly, Buddhist monks do an in-depth study and meditation practice of their own death called Maraṇasati (mindfulness of death, death awareness).  They spend time remembering that death can strike at any time and that we should practice with urgency in every moment, even in the time it takes to draw one breath.

This may sound morbid to many, but we intuitively know that embracing the awareness of your mortality can lead to a more intentional, present, and meaningful life. This mindset encourages us to focus on what truly matters, savor each moment, and act with purpose. Time truly is short!

 

2. Consistency: Get a Little Better Every Day

Kobe believed in consistent improvement—becoming a little better each day. Author James Clear, in Atomic Habits, describes this idea as the “aggregation of marginal gains.” He tells the story of British Cycling hiring Dave Brailsford as performance director after more than 100 years without a Tour de France win.

 

What made him different from previous coaches was his relentless commitment to a strategy that he referred to as “the aggregation of marginal gains,” which was the philosophy of searching for a tiny margin of improvement in everything you do. Brailsford said, “The whole principle came from the idea that if you broke down everything you could think of that goes into riding a bike, and then improve it by 1 percent, you will get a significant increase when you put them all together.” 

 

Patience: Respect the Long Game

Olinger says patience was hard for Kobe but he knew it was important.  Furthermore, patience feels like the antithesis of urgency.  However, Kobe knew he could not become the greatest basketball player on the planet in one day. 

In the same way, you don’t have to pull off huge miracles today to achieve worthy wins in your life. You’re not going to suddenly become the ideal spouse, parent, or steward of your money overnight. But if you keep showing up with urgency and consistency—and give the process time—you’ll move steadily toward your own definition of winning. Give yourself some grace along the way!

 

Examples of Worthy Wins That Are Hard to Measure

Some of the most meaningful wins in life don’t show up on a bank statement or résumé, which makes them harder to measure but no less important.

A few years ago, I hired an executive coach to help me become a better business leader. My background was in the military and as an airline pilot—I’d never run a successful business before, and I felt like I needed professional help.

What surprised me was the very first topic my coach wanted to address: the health of my marriage. I remember thinking, “What does this have to do with running a business or increasing revenue?” His answer was simple: if my marriage wasn’t healthy, nothing else would function at its best.

Through that process, I realized that a major worthy win for me was investing more intentionally in my marriage. The whole point of earning more money is to have more time and margin to enjoy life with my wife—so why not prioritize that now, instead of waiting for some future milestone?

For you, worthy wins might include working extra trips to pay for a dream scuba vacation with your kids, not just to see a bigger number in your checking account. It might be choosing a slightly reduced flying schedule that allows you to be present for key moments at home.

Another worthy win I’m still working on is the way I use my words with my wife, my children, and everyone around me. Truett Cathy, founder of Chick-fil-A, once said, “How do you identify someone who needs encouragement? That person is breathing.” Using our words to sincerely encourage others is a worthy win that costs us very little but pays huge relational dividends.

As an airline or professional pilot, you will inevitably miss significant events in the lives of those you love—birthdays, games, recitals, anniversaries. That’s part of the job. But you can still build deep, meaningful relationships—sometimes even stronger than those who are home every night—if you focus on the quality of the time and engagement you do have, rather than the quantity.

 

Don’t Let the Almighty Dollar Lead You Astray

It’s easy to slip into a mindset where making the most money and never “leaving anything on the table” becomes the main scoreboard. The ability to pick up extra trips can be a blessing: it can fund vacations, college for your kids, or big experiences you genuinely care about.

But that same ability can also consume you. If more money becomes the only win that matters, you risk chasing goals that actually pull you away from the worthy wins you say you value—your health, marriage, friendships, faith, or time with your kids.

So ask yourself: what does winning look like in your life? Is it just a number on your pay stub? Is it a certain balance in your bank or investment accounts? Or is money a means to create time and flexibility so you can pursue the things that lead to real contentment?

Hitting a dollar amount is important—and as financial professionals, that’s a big part of what we help people do. But it’s also the easiest thing to measure. Other forms of return on investment are much harder to quantify: the strength of your relationships, the way you spend your time, your contribution to others, and your spiritual or emotional well-being.

 

Reflection: Define Winning Before You Chase It

One reason I keep returning to this topic is that I carry a healthy fear of achieving things that won’t matter when all is said and done. I don’t want to wake up at 90 and realize I won the wrong game.

So, I regularly ask myself: when I’m 90 years old (Lord willing), and my kids or grandkids ask whether I have any regrets or wish I’d done anything differently, what will I say? My hope is that I can honestly say:

• I did the best I could with what I had.
• I took smart risks.
• I invested in what mattered most—especially relationships.
• I was a good steward of the blessings in my life, including my personal finances.

   

That’s what a worthy win looks like to me. The real challenge—and the real opportunity—is to slow down long enough to define what winning looks like for you, then use your money, time, and talent in service of that vision.

Fly safe!