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).

Getting close to retirement? This episode gives a real, operational checklist for each milestone &mdash; 7&ndash;10 years, 5&ndash;7 years, 3&ndash;5 years &mdash; 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&rsquo;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 <a data-start="1149" data-end="1174">https://askthecaptain.com</a> or call 833-DREW-CAP (833-373-9227).

The Money Captain — Host Chris Drew of BayTrust cuts through the noise and makes smart money simple. Each episode peels back the curtain on real financial decisions — from retirement and investments to taxes, family planning, and the everyday tradeoffs few advisors talk about. Expect clear frameworks, practical moves you can use this week, and interviews with entrepreneurs, planners, and people who’ve learned the hard way.

This is not finance theater. Chris steers with curiosity and candor, asking the questions professionals and do-it-yourselfers wish they’d asked sooner. Whether you’re building wealth, protecting it, or just trying not to make avoidable mistakes, The Money Captain gives you honest, usable guidance and a plan for your next step. Subscribe now and get a new roadmap every two weeks.

Call to action: Subscribe on Apple Podcasts/Spotify, visit baytrust.com/the-money-captain for show notes, and follow @BayTrust on LinkedIn for episode updates.

The Money Captain &mdash; Host Chris Drew of BayTrust cuts through the noise and makes smart money simple. Each episode peels back the curtain on real financial decisions &mdash; from retirement and investments to taxes, family planning, and the everyday tradeoffs few advisors talk about. Expect clear frameworks, practical moves you can use this week, and interviews with entrepreneurs, planners, and people who&rsquo;ve learned the hard way.
This is not finance theater. Chris steers with curiosity and candor, asking the questions professionals and do-it-yourselfers wish they&rsquo;d asked sooner. Whether you&rsquo;re building wealth, protecting it, or just trying not to make avoidable mistakes, The Money Captain gives you honest, usable guidance and a plan for your next step. Subscribe now and get a new roadmap every two weeks.
Call to action: Subscribe on Apple Podcasts/Spotify, visit baytrust.com/the-money-captain for show notes, and follow @BayTrust on LinkedIn for episode updates.