Getting close to retirement? This episode gives a real, operational checklist for each milestone — 7–10 years, 5–7 years, 3–5 years — so you stop guessing and start executing. Chris Drew covers the high-impact moves: max your catch-up contributions, build a tax plan (Roth timing, partial rollovers, and conversion pacing), map realistic retirement expenses and a cashflow model, set up SSA.gov and run Social Security timing scenarios, finalize Medicare options, and design a Medicare/healthcare bridge for the years before you’re eligible. He also walks through practical start-now items (beneficiaries, PODs, emergency fund, overlap/cost-and-risk review) and near-term operational tasks (Monte Carlo stress tests, withdrawal sequencing, and when to add guaranteed lifetime-income building blocks). Tactical, calendarable, and focused on turning uncertainty into a step-by-step retirement roadmap.

Want help converting the checklist into a personalized timeline? Book a free consultation at https://askthecaptain.com or call 833-DREW-CAP (833-373-9227).