Why “Brief, Fly, Debrief” Should Guide Your Investments (& Your Life)
On a recent episode of the "My Worst Investment Ever" podcast, I shared a personal story that’s all-too-relatable for many newer investors: trusting in rumor, chasing hype, and feeling invincible—until you’re not. Early in my career, I bought a hot tech stock based purely on peer recommendations and market trends, ignoring essential financial planning advice and skipping my research. The portfolio became lopsided, lacking diversification, and ultimately, my 10s of thousands turned into just a few hundred dollars. Painful? Absolutely. But also educational.
Here’s the big lesson I shared with host Andrew Stotz: Don’t walk into an investment seeking "an investment"—seek a specific outcome. That means overestimating your risks, underestimating your gains, and always asking yourself: what’s the real purpose behind this decision? Forget what your friends (or your favorite social feeds) are doing; personal finances are personal for a reason. As a fiduciary financial advisor, I now help clients focus not on the hottest tip, but on building a solid foundation: diversifying portfolios, understanding the power of compounding, and making sure every choice lines up with their unique goals for retirement, gifting, or wealth creation.
The podcast explored the value of “Brief, Fly, Debrief”—borrowed from my Navy experience—when it comes to managing money. Before any move, pause and assess your objectives. Take action with discipline. Then step back to review, learn, and adjust your course. That single framework, applied to investing, can prevent emotional missteps and help every investor (from rookies to seasoned pros) develop habits that stand the test of time.
My parting advice for listeners (and anyone seeking independent financial advice): Get clear about your risk tolerance, educate yourself before hitting “buy,” and remember—success in investing is less about outsmarting the market and more about learning from your own history.
If you want to avoid repeating your own “worst investment ever,” or need a certified financial planner to help you design an investment strategy you’ll feel good about through every cycle, let’s talk. Sometimes the best win is simply not making the same mistake twice.