Today marks the 128th running of the Boston Marathon, the world’s oldest marathon. As a kid who looked more like a chunky football player attempting to run, I dreamt of but never truly believed I’d qualify for a race alongside elite runners. But in 2019, that lifelong dream became a reality. (If you’re curious about the life lessons a reformed fat kid learned on the journey to qualify for Boston, check them out here.) 

1. Run Your Own Race – At the start of the Boston Marathon, the energy is electric. Everyone around me sprinted off, tempting me to follow suit. But I stuck to my plan knowing if I followed the crowd, I might not reach the finish line.

• Don’t try to keep up with the Joneses – set YOUR financial goals and live YOUR dreams, not your neighbors.

2. Don’t Blow It All Early – Race day buzz can make you want to sprint from the get-go. But if you expend all your energy early, you’ll be walking before the end…or in the medical tent.

• Spending money today always feels like more fun than saving money for tomorrow. But recognizing that urge and understanding it may mislead you is crucial to getting to your financial finish line.
  

3. Don’t Save Everything for Later – Imagine crossing the finish line only to realize you held back too much and could have done better. 

• Life is short; enjoy it along the way. Attend that baseball game, take that trip, and give to that worthy cause. Don’t put off joy and pursuing a life of true fulfillment until tomorrow because it’s not guaranteed. The book The 5 Regrets of the Dying crystallized this lesson for me.
  

4. Embrace the Good…and Bad Miles – In a marathon, some miles feel fantastic (like hugging my dad at mile 10 and doing the YMCA dance with the crowd at mile 12), while others are grueling (mile 16’s cramp and uphill struggle followed by finishing the race in a downpour). 

• Make sure you have the right expectations. Peaks and valleys are part of a marathon, investing, and life. There’s something valuable we can learn from both the highs and lows.
  

5. Sometimes It Rains – The forecast predicted a sprinkle during the race. Instead, it rained lightly during the race’s first hour and poured for the final 5 miles (as you can see from my soaked clothes in the picture).

• Life throws curveballs too. Have a financial plan and be ready for it not to go as planned. There will always be surprises that we couldn’t foresee.

6. Get a Coach – When I ran two marathons after college, I fell well short of qualifying for the Boston Marathon. But fifteen years later, I got serious about my dream and hired a running coach. The results were life-altering – I qualified for Boston 18 months later.

• My coach’s accountability and expertise took me places I never truly believed I could achieve. A financial coach can do the same. A good coach can help you create a plan and adjust it when life throws unexpected challenges your way.
  

7. Pace Yourself – Imagine running a marathon and wanting to sprint from the start. It can be tempting, but if you burn out early, you’ll struggle later or run out of gas before the finish line. 

• That hot stock pick, or timing the market, always has an intoxicating feel because it could allow us to get to the investing finish line much faster. But the reality is it usually pushes the finish line much farther away. Pacing yourself isn’t fun when everyone’s running by you initially, but there’s no better feeling than when you pass them later.

8. Enjoy the Journey & Don’t Forget to Smile – Pain in a marathon is inevitable. Yet I smiled through most of last year’s race because of the pleasure and privilege I felt to be there – to be in a place for years I told myself I didn’t belong. There was pain but the joy of the overall experience was so much greater than the temporary discomfort.

• Successful long-term investing is painful at times. It’s enduring elevated inflation and interest rates, wars, and presidential elections, and still staying the course. Why do we do it? Because the fruits of achieving our financial goals are much greater than the temporary pain of uncertain markets. It’s why investors must pay the price of admission.
  

9. Success Happens When No One’s Watching – Crossing the Boston Marathon finish line is incredible beyond words, but true success occurs during unseen moments. I found it on cold, dark mornings, layered in clothing when no one else was around.

• Similarly, investing success also happens when no one‘s watching – the decision to save more than you spend, live within your means, and not keep up with the Joneses. It’s these decisions, invisible to social media, that make us the “millionaires next door.”
  

10. Keep the Right Score – I’ve run eight marathons and my “score” has always been my time. But knowing this would be my last Boston for a while, I changed my scoreboard. Last year, it was about thanking dozens of volunteers and police, hugging my dad at mile 10, getting a famous good luck kiss from a Wellesley student at mile 12, and a beer from a Boston College student at mile 20. Finally, it was about high-fiving hundreds of kids in the crowd over 26 miles and telling them “This could be you!” – giving them the belief that I lacked for so many years. After I finished the race, several friends asked my time and I couldn’t tell them – for once, it wasn’t on my scoreboard. But I know without a shadow of a doubt that I won MY race.

• At times, we all struggle to keep the right score and play by our scoreboard. Pursuing and achieving financial success can be a wonderful blessing but remember it’s what we do with that success that truly matters in winning our own races.

The journey of qualifying for and running the Boston Marathon was difficult and arduous. It will also always be one of the highlights of my life. The same can be said for the path towards achieving our financial dreams. Hopefully these investing lessons make that journey a little smoother.

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Castle Quote: “Planning is important, but the most important part of every plan is to plan on the plan not going according to plan. A plan is only useful if it can survive reality. And a future filled with unknowns is everyone’s reality.”

– Morgan Housel