What My Career Change From Olympian to Financial Planner Taught Me About Money

When people hear that I went from earning more than $200,000 a year as a professional athlete to making $12 an hour as a financial planning intern, they usually focus on the pay cut.I understand why. It’s a dramatic contrast.But I’ve never seen that part of my story as a fall from success or a cautionary tale about what happens when an athlete’s career ends. To me, the more important story is what happened in between.I was competing at the highest level — including in four Olympic Games — and making six figures as a professional athlete with a Nike contract. From the outside, it looked like I had made it.But internally, I was still trying to understand my money.About Adviser IntelThe author of this article is a participant in Kiplinger’s Adviser Intel program, a curated network of trusted financial professionals who share expert insights on wealth building and preservation. Contributors, including fiduciary financial planners, wealth managers, CEOs and attorneys, provide actionable advice about retirement planning, estate planning, tax strategies and more. Experts are invited to contribute and do not pay to be included, so you can trust their advice is honest and valuable.Organizing and understanding my financesI knew there were responsible things people were supposed to do with money, but I didn’t know what they were. I didn’t know how to organize my finances or fully understand what was coming in, what was going out, what I was invested in or how my financial decisions would affect me after sports.It’s uncomfortable to admit when you look successful from the outside, but earning money and understanding money are two different skills.Early in my career, I looked for help, but most of the advice I received started with investing instead of financial literacy. Investing matters, but it should come after you understand your expenses, cash flow, goals, taxes and long-term income reality. At that point, I didn’t need someone to simply take over. I needed someone to help me become financially literate.Figuring out what was going onWhen my adviser told me, “We lost a lot of money today. Don’t panic,” I realized the problem wasn’t just the loss. It was that I didn’t know what the loss meant. I didn’t know what I was invested in or how the market worked. I didn’t know whether the loss was normal, serious or connected to the plan I supposedly had. I was trusting someone else to make sure my money was growing, but I didn’t have enough knowledge to participate in the conversation myself.That experience taught me something I still believe: You cannot fully outsource your understanding.Learning the hard wayThere were other lessons along the way. I bought too much house, more than once. The first time, I was listening to advice from friends and family. The second time, an adviser encouraged me to buy a second home.How was I going to pay for two homes for 30 years? How long would my athletic income last? No athlete has a 30-year playing career. I was doing well, but how long would that window stay open?That lesson doesn’t only apply to athletes. Many people make major decisions based on what they can afford now, without asking if the choice still works when income, health, career or priorities change.Can future me live with this decision?That’s why the first question should not always be, “Can I afford this today?” but rather, “Can future me live with this decision?”When I began transitioning out of professional sports, I was 30 and trying to choose a career path for the first time. I had a finance degree, an MBA and a real estate license, but I still didn’t fully understand what kind of work fit the life I wanted to build. Taking the internship was part of that adjustment.From the outside, it may have looked like a step backward. But I had savings, which gave me options. I could pay my bills while earning less in the short term so I could invest in myself for the long term.That’s the part people often miss. The internship was a deliberate move, not desperation. It gave me structure, responsibility and a chance to become a beginner again. I was earning much less, but what I was learning felt invaluable.It was an investment in becoming the kind of professional I wished I had found when I was younger.Not an easy transitionThat doesn’t mean the transition was easy. Starting over professionally was humbling. The internship was part of the process of earning my CFP® certification, which was key to entering the financial planning profession. I also needed to take the CFP® certification exam. I failed the exam twice before passing on the third try, which reminded me that being smart wasn’t enough. I had to prepare differently, stay persistent and keep going. Sports helped me with that. Athletics taught me how to come back after disappointment and keep going when something is hard.When I began working with clients, financial planning stopped feeling like a backup plan almost immediately. Many of the people coming to me had basic questions, but those questions mattered. They wanted to understand their money and feel more confident. They wanted someone to explain things without judgment.The kind of adviser I amThose early experiences shaped the kind of adviser I wanted to become. I didn’t want people to feel talked down to, confused by jargon or left out of conversations about their own money. I wanted to help clients understand their whole financial picture, not just their investments.That became the foundation for my firm, Worth Winning. I expected to follow a traditional one-on-one planning model, but I saw many people needed education, accountability and a safe place to ask questions. That led me into classes, speaking, corporate financial wellness programs and retreats.If there’s one thing my career transition taught me, it’s that financial confidence comes from staying engaged.Looking for expert tips to grow and preserve your wealth? Sign up for Adviser Intel, our free, twice-weekly newsletter.Making decisions with more confidenceYou don’t need to become an expert in every investment strategy, tax rule or planning tool. But you do need to understand enough to know when something doesn’t make sense, when a decision feels rushed or when the advice you’re getting doesn’t match the life you’re trying to build.That starts with paying attention to your own numbers and being willing to stay in the conversation. Know what you earn, what you spend, what you owe, what you own and what trade-offs you’re making. Those details may not feel exciting, but they are what give you the ability to make decisions with more confidence.The $12-an-hour internship may be the surprising part of the story, but it’s not the most important part. For me, the shift from athlete to financial planner was never really about starting over. It was about learning to take ownership of my financial life and then building a career helping other people do the same. Related ContentHigh-Income But Low Confidence? This 5-Point Plan From a Financial Planner Can Fix ThatFinancial Confidence? It’s Just Good Planning, Boomers SayThe $200,000 Olympic ‘Pension’ is a Retirement Game-Changer for Team USAFinancial Pros Provide a Beginner’s Guide to Building Wealth in 10 YearsA Crisis That’s Too Big to Ignore: Financial Illiteracy Puts Our Nation at RiskThis article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.