Building a Roadmap for the Last Five Years Before Retiring

Retirement can seem straightforward when it's decades away—you split your paycheck between living expenses and 401(k) contributions and throw money at the problem. But once you're five years out, you need to plan more intentionally. If you want to retire early and smoothly, your mindset and action list have to shift. In this episode, Sam Benson and Linwood Fraher break down exactly what to solve for in the critical retirement “red zone”, the five years before and after you quit working. They explain why the biggest expense shock isn’t world travel, but health insurance, with premiums that can feel like a new mortgage payment for early retirees. They share strategies that let you road-test your budget and lifestyle before you pull the plug, plus the identity shifts many people miss. Episode Outline: 03:08: How to bridge your income gap when your paycheck ends but Social Security or pensions haven’t started 05:13: The surprisingly high costs of healthcare before Medicare kicks in—and all the real options to cover them 09:49: Why a 12–24 month “retirement rehearsal” is critical for both your finances and sense of purpose 13:06: How tax planning in your 50s and 60s (like Roth conversions and multi-year projections) creates more freedom, family experiences, and even inheritance 16:47: The non-financial essentials—estate documents, conversations with loved ones, and property/casualty insurance—that protect your hard-earned security With tested advice grounded in hundreds of pre-retirement conversations, this is your playbook for turning the last five working years into a confident transition (not a cliff dive) into retirement. Contact Us Learn more about working with Sam Benson and Linwood Fraher at www.martinwealth.com