Top 5 Mistakes Pilots Make with Their Money and How to Avoid Them

1. Measuring Your Financial Success on Cockpit Talk
It’s inevitable that while on a trip, you’ll end up discussing stocks, investments, or retirement plans with your co-pilot. Topics often include mega-backdoor Roth strategies, how much is “enough” to retire, or multiple vacation homes. But using your co-pilot’s finances as a benchmark for your own is a mistake. What works for them may not align with your goals, risk tolerance, or family situation. Blindly following others can cause more harm than good.
2. Ignoring Disability and Life Insurance Needs
Many pilots overlook the importance of proper disability and life insurance. With major airline pilots earning around $200,000 annually and often being the primary provider, a sudden loss of income can be devastating. While employer-provided coverage has improved, it’s often not sufficient. It’s essential to assess your needs independently and review term life insurance options to ensure your family’s future is protected.
3. Focusing on Stuff Instead of Building Wealth
Flashy material possessions, such as cars, boats, or vacation homes, can distort what financial success really looks like. When your co-pilot talks about their new luxury car or weekend lakehouse, remember they might also be managing significant debt to fund that lifestyle. True wealth comes from building assets, not collecting liabilities. Growing your 401(k) may not seem glamorous, but it’s a far better long-term investment.
4. Thinking You Can Outsmart the Market
Despite overwhelming evidence to the contrary, many investors still believe they can beat the market. In fact, 94% of the time, the S&P 500 outperforms active asset managers. Rather than picking individual stocks or timing the market, focus on a diversified portfolio with long-term strategies. Let the numbers speak for themselves and don’t let cockpit chatter derail your investment plan.
5. Forgetting Your Individuality
It’s tempting to compare your financial progress to others, but your plan should reflect your unique goals, values, and circumstances. Financial planning is like medical treatment: what works for one person could be harmful to another. A personalized plan tailored to your needs will always be more effective than following a one-size-fits-all strategy based on someone else’s situation. If you’re ready to build a personalized, comprehensive financial plan, schedule a consultation with one of our fiduciary financial advisors.
Michaela Dowdy
Financial Advisor, Wiser Wealth Management
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