The Discipline to Win: Lessons From Trail Miles to Financial Freedom

Lessons from time on the trail have a lot to teach us about money. Every mile in your logbook starts the same way: you lace up, step outside, and put one foot in front of the other until the small efforts add up to real distance. Financial wellness works the same way. You don’t have to sprint; you have to show up—day after day—making steady, often unglamorous choices to pay down debt, build savings, and protect your future. The same discipline that carries you through those long trail miles can carry you all the way to a stronger financial life. 

This year, I’m putting that discipline to the test by joining a group of friends to complete the GWOT 100, a 100mile February fitness challenge led by Team Red, White & Blue (Team RWB) in partnership with GORUCK. Participants run, walk, ruck, bike, or row their way to 100 miles over the month, honoring all who served in the Global War on Terror while improving their own health. 

The way we train for the GWOT 100 is exactly how you win with money. 

Fitness Discipline and Money Discipline Are the Same Muscle 

If you’ve ever trained for a PT test, a ruck march, or a race, you already know what it takes to get out of debt. It’s not about one heroic day; it’s about showing up, even when you don’t feel like it. 

In fitness, discipline looks like: 

• Lacing up your shoes when you’re tired. 
• Choosing a walk, ruck, or gym session instead of more couch time. 
• Sticking to a plan: sets, reps, miles, and recovery. 

In money, the same discipline looks like: 

• Making the minimum payment plus a little extra, every single month.
•  Saying “not today” to impulse buys. 
• Following a simple plan to spend less than you earn and aim the difference at debt and savings. 

The habit is identical: small, repeatable actions that don’t feel impressive in the moment but add up to big results. 

The Power of Small Steps: 100 Miles, 100 Payments 

The GWOT 100 isn’t a one-day ultra; it’s 100 cumulative miles in February. You can walk, run, ruck, row, or cycle those miles in whatever chunks your schedule and body allow. Some days, you might only have time for a single mile. Other days, you might hit five or 10. It all counts toward the same finish line. 

Debt freedom works the same way: 

• One extra $20 to your highest-interest card 
• One subscription you cancel and redirect to savings 
• One side gig hour each week dedicated to paying down a specific balance 

Individually, these actions feel small. Together, they move you 100 “financial miles” closer to zero debt and a healthy emergency fund. Over time, the habit matters more than the size of any single step. 

If you can chip away at 100 miles in a month, you can chip away at $10,000 of debt over the next year or two. The skill set is identical. 

Use Community to Stay in the Fight 

One of the reasons I signed up for the GWOT 100 is that I’m not doing it alone. I’ll be logging those miles with a group of friends and with a virtual community of veterans, military families, and supporters through Team RWB, a nationwide nonprofit that helps veterans lead healthier lives through fitness and connection. Knowing others are out there walking, rucking, and grinding through the same challenge makes it easier to show up on the days when motivation is low. 

You can bring that same idea into your financial life: 

• Share your debt payoff goals with a trusted friend or spouse. 
• Join an online or local community that focuses on budgeting and paying off debt. 
• Celebrate milestones—first $1,000 paid off, first credit card closed, first $500 in savings—just like you’d celebrate a new PR or another five miles in the logbook. 

When you combine discipline with community, you build resilience. The group doesn’t carry you, but it keeps you moving when you’d otherwise stall. For many of us coming from the military, this feels familiar; we were always stronger together than we were alone. 

A Simple “GWOT 100” Plan for Your Money 

If you like the idea of a fitness challenge, try building your own “GWOT 100” for your finances. Here’s a simple framework: 

1. Define the mission 

• Example: “Pay off $1,200 of credit card debt in the next 12 months” or “build a $1,000 starter emergency fund.” 

2. Break it into daily or weekly “miles” 

• $1,200 over 12 months is $100 per month, or about $25 per week. 
• Treat each $25 like a mile in your logbook. 

3. Build the routine 

• Set up automatic transfers on payday toward debt or savings. 
• Review your spending once a week, looking for one thing to cut or reduce. 

4. Track your progress 

• Just as GWOT 100 participants log every mile, log every payment and every new dollar saved. 
• Watch your “miles to go” shrink on paper or in your app. 

5. Bring in your “squad” 

• Ask a friend or fellow veteran to check in with you once a month. 
• Share wins, setbacks, and next steps—just like an after-action review. 

The actions are small; the discipline is big. 

Join the Movement, Then Apply It to Your Money 

If you want to experience this kind of discipline in real time, consider joining Team RWB and signing up for the GWOT 100 yourself. Team RWB offers in-person and virtual events across the country, all focused on helping veterans build healthier lives through movement and community. The GWOT 100 challenge, powered by Team RWB and GORUCK, invites participants to log 100 miles during February—run, walk, ruck, bike, swim, or row—in honor of all who served during the Global War on Terror. 

As I tackle my own GWOT 100 with a group of friends, every mile will be a reminder that the same quiet discipline that carries us across a finish line can also carry us out of debt. You don’t have to be perfect. You just have to keep moving—one workout, one payment, one good decision at a time.