Retire Today: Five Steps to Avoid Costly Retirement Mistakes with Jeremy Keil

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!