The Retirement Caddie

Best Of: Estate Planning Isn’t Just for the Rich—Here’s Why

More than half of Americans don’t have their estate planning basics in place—and many don’t realize why that matters until it’s too late. In this episode, Matt Eilers breaks down why wills, powers of attorney, and healthcare directives often get delayed and what can happen when important decisions are left to the courts. He explains common misconceptions around estate planning, why it’s not just for the wealthy, and how clear documentation can reduce confusion and stress for loved ones when it matters most. Ready to get out of the rough and get your retirement plan in place? Contact [https://medalistwealth.com/#contact] Matt today! Facebook [https://www.facebook.com/medalistwealth/] | Instagram [https://www.instagram.com/medalistwealth/] | LinkedIn [https://www.linkedin.com/company/medalist-wealth-management/] | YouTube [https://www.youtube.com/@medalistwealth] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Best Of: Can You Really Retire Early—or Just Hope You Can?

Retiring early sounds simple—until you start asking the right questions. In this episode, Matt Eilers breaks down why popular retirement checklists don’t tell the full story when it comes to deciding when you can actually retire. The conversation explores needs versus wants, emergency funds, mortgages, taxes, healthcare, Social Security timing, and why income planning—not just asset totals—drives retirement readiness. Matt also explains why retirement decisions aren’t one‑size‑fits‑all and how overlooked details can quietly change the outcome if they’re not addressed as part of a coordinated plan. Ready to get out of the rough and get your retirement plan in place? Contact [https://medalistwealth.com/#contact] Matt today! Facebook [https://www.facebook.com/medalistwealth/] | Instagram [https://www.instagram.com/medalistwealth/] | LinkedIn [https://www.linkedin.com/company/medalist-wealth-management/] | YouTube [https://www.youtube.com/@medalistwealth] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

The “What If” Scenario That Can Change Everything

Ignoring long-term care planning can leave families facing difficult emotional and financial decisions when it matters most. In this episode, Matt Eilers discusses the real impact of unexpected health events, from caregiving burdens to the high cost of professional care. He explains why having a clear plan in place—before a crisis—can help guide decisions around assets, family roles, and care options. The conversation highlights common blind spots in retirement planning and why thinking through “what if” scenarios is an important part of building a more complete financial picture. Ready to get out of the rough and get your retirement plan in place? Contact [https://medalistwealth.com/#contact] Matt today! Facebook [https://www.facebook.com/medalistwealth/] | Instagram [https://www.instagram.com/medalistwealth/] | LinkedIn [https://www.linkedin.com/company/medalist-wealth-management/] | YouTube [https://www.youtube.com/@medalistwealth] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Best Of: The Retirement Spending Smile Most People Don’t Plan For

Retirement spending doesn’t move in a straight line—and that can catch a lot of people off guard. In this episode, Matt Eilers breaks down the “retirement spending smile,” explaining why expenses often rise early in retirement, dip in later years, and increase again as healthcare needs grow. He explores the shift from asset allocation to asset designation, why retirement requires a different planning mindset, and how income, risk, and healthcare planning all change once paychecks stop. The conversation focuses on preparing for each phase of retirement so surprises don’t dictate decisions later on. Ready to get out of the rough and get your retirement plan in place? Contact [https://medalistwealth.com/#contact] Matt today! Facebook [https://www.facebook.com/medalistwealth/] | Instagram [https://www.instagram.com/medalistwealth/] | LinkedIn [https://www.linkedin.com/company/medalist-wealth-management/] | YouTube [https://www.youtube.com/@medalistwealth] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

The Small Mistakes That Can Become Big Retirement Problems

The biggest retirement mistakes often come from the small financial details people overlook today. In this episode, Matt Eilers explains how “hidden risks” like required minimum distributions, tax planning gaps, and excess market exposure can create bigger challenges later in retirement. The conversation highlights why avoiding major missteps—rather than chasing perfect outcomes—can shape long-term financial stability. Matt also discusses how proactive planning, from managing taxes to adjusting risk, can help reduce surprises and keep retirement strategies aligned with changing conditions. Ready to get out of the rough and get your retirement plan in place? Contact [https://medalistwealth.com/#contact] Matt today! Facebook [https://www.facebook.com/medalistwealth/] | Instagram [https://www.instagram.com/medalistwealth/] | LinkedIn [https://www.linkedin.com/company/medalist-wealth-management/] | YouTube [https://www.youtube.com/@medalistwealth] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.