Welcome back to Don’t Retire… Graduate! I’m excited to kick off our seventh season with a powerful conversation about redefining retirement—and how to do it with confidence, purpose, and a solid financial plan. For our season premiere, I had the pleasure of hosting Jeremy Keil, author of the highly acclaimed book Retire Today. Jeremy is not only an experienced financial advisor with over two decades of expertise, but he’s also a passionate advocate for helping people move from confusion to clarity with retirement planning. Together, we delved deep into the “battle of the books”—comparing his vision of retiring today with my philosophy of graduating into your next chapter.

In our discussion, Jeremy and I explored the five-step framework from his book designed to help you maximize income, minimize taxes, and sidestep costly retirement mistakes. We tackled the critical concept of “retirement longevity” and why getting your timeline right is as important, if not more so, than knowing how much you’ll spend. Jeremy shared actionable insights on planning for spending spikes in the early go-go years of retirement and preparing for potential healthcare costs in the later stages. We broke down one-time decisions like Social Security, pensions, and annuities and talked candidly about the importance of optimizing these choices—especially when they’re irreversible.

We also discussed the often-overlooked art of tax planning in retirement, how to make the most of your investment accounts, and why wise estate planning means leaving behind a legacy, not a mess. Throughout, Jeremy emphasized process, preparation, and having a thoughtful plan for everything from cash flow and investments to healthcare and long-term care. Finally, we sparred a bit on the qualitative side of retirement, discussing whether full retirement is the ultimate goal or if “graduating” to financial independence is the best way to live a meaningful, high-impact life.

5 Key Takeaways:

1. Retirement Longevity Matters Most: Jeremy introduced the concept of the “retirement longevity number”—the importance of planning not only when you’ll retire but how long you’ll need your money to last, factoring in early retirements and underestimated life expectancies.
2. Spending Is Not One-Dimensional: Expect higher spending in your first decade of retirement. Do detailed cash flow planning that accounts for one-time costs like travel or home renovations and prepare for possible healthcare spikes in your later years.
3. One-Shot Decisions Require Strategy: Social Security, pension choices, and annuities are often irrevocable. Plan ahead using net present value calculations and seek advice that considers math—not just gut feeling or sales incentives.
4. Tax Planning Is a Game Changer: Post-retirement offers tremendous flexibility for tax strategies. Learn how different account types are taxed, and consider timing and sizing Roth conversions to optimize your lifetime tax outlay.
5. Invest After You Plan—Not Before: Good financial planning puts investments near the end, not the beginning. Build your foundation first by aligning investments with your spending, income, and risk tolerance. Join us for this enlightening episode and discover why retirement isn’t just a final destination—it’s the start of your next, most purposeful chapter. Subscribe, rate, and share our show so others can join you in reimagining—and graduating into—a life of financial freedom and fulfillment!

Welcome back to Don’t Retire… Graduate! Today’s episode offers a behind-the-scenes look at the journey of a financial advisor, featuring a special guest from our own team: Joey Mills, who recently became a Certified Financial Planner™ and is on the path to becoming an associate advisor at BFG Financial Advisors.

I’m excited to introduce Joey, who joined us in 2022 after graduating from Towson University with a degree in Business Administration and a concentration in Financial Planning. Beyond his financial expertise, he’s also a baseball enthusiast who recently checked off a major personal goal: visiting every major league baseball stadium in the country—even though we still haven’t converted him from being a Yankees fan!

5 Key Takeaways:

1. The Value of Specialized Education: Joey Mills shared how Towson University’s financial planning concentration gave him both a solid foundation and the flexibility to shift from corporate finance to a more people-focused career.
2. Lifelong Learning Is Essential: Success as a financial advisor requires constant learning—both through formal education and by keeping up with ever-changing financial rules and best practices.
3. Mentorship and Community Matter: Having peers and mentors who’ve followed a similar career trajectory provides invaluable support, insight, and motivation for professional growth.
4. Behavioral Finance Is the Game-Changer: Understanding not just the numbers, but also the psychology behind money decisions—both in clients and oneself—is critical to effective advising.
5. Start Early, Communicate Often: Open family conversations about money and starting good financial habits early—like saving and living below your means—are powerful tools for long-term success.

Join us for this candid conversation as we demystify the career path of a financial advisor and share lessons that can help anyone on their own journey to financial freedom. Don’t forget to subscribe, rate, and share this episode with anyone who’s passionate about meaningful work, lifelong learning, and living with purpose!

1. Creatives Need Tailored Tax Help:Hannah Cole identified a huge gap for artists and freelancers, who are often stereotyped as being "bad at money," and built resources to help them thrive, including her book and visual guides.
2. Tax Planning, Not Just Tax Paying:Tax planning is about making the system work for you—not just paying what you owe. It’s about grabbing “the coins in the couch cushions” and using the tax code’s incentives to your advantage, which is very different from the pain of cutting a check.
3. Choosing the Right Tax Pro Matters:Not all CPAs are created equal. Hannah recommends prioritizing respect in your tax adviser relationships and being wary of anyone who’s aggressive to the point of danger. A good adviser makes you part of the decision-making process.
4. Myths About the IRS and Enforcement:The societal fear of the IRS is often fueled by those who benefit from weakened tax enforcement. Hannah contends that, in practice, IRS agents are often kinder and easier to deal with than their reputations suggest—and that real “tax terror” often serves the interests of high-net-worth rule breakers.
5. Calls for a Fairer, Simpler System:We debate estate taxes, sales tax, VAT, and even the promise of a flat tax. Regardless of where you stand politically, we agree: a fair, equitable tax code—one that doesn’t require an army of CPAs and endless stress—would benefit everyone.