Listener Questions: What Should I Be Doing When I'm Two Years from Retirement?

In this episode, Roger Whitney breaks down essential elements you need to consider before and during retirement. From understanding inflation risks to strategic asset reallocation, this episode offers practical advice to help you make informed decisions and craft a retirement that aligns with your values. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PODCAST (00:00) Introduction and overview of upcoming topics RETIREMENT TOOLKIT (01:49) Why inflation poses a significant risk to retirees (02:32) What is inflation and how is it measured (03:33) Causes of inflation: demand, supply constraints, and rising costs (05:20) Historical inflation rates and what they mean for your planning (06:48) How to choose a realistic inflation assumption in your plan (08:40) Strategies to hedge against inflation ROCKIN RETIREMENT IN THE WILD (12:47) Jim’s story: diversity in retirement activities and the importance of adaptability PRACTICAL PLANNING SEGMENT (16:07) Mike’s question reframed: focus on designing your retirement life first, not account tactics (17:50) Roger reviews Mike’s facts (18:56) The importance of building a feasible plan of record, estimating expenses, and creating a realistic monthly budget for retirement (23:13) Clarifying values and how they shape your retirement goals (25:20) Income side of the plan: social security, pensions, and tax considerations (30:15) Once the plan is feasible, start testing versions of the plan and planning paycheck (31:52) 401(k) and 457 decisions can wait—focus on positioning assets for income first (33:12) Consider building after-tax savings now to increase future optionality LISTENER QUESTIONS (35:50) Listener shares story about roadside cafe (36:20) Michael asks a question about ROTH conversions in a down market (38:50) Steve asks how to better time Roth conversions to avoid triggering IRMAA Medicare surcharges? SMART SPRINT (45:14) Smart Sprint: Before acting, ask yourself “what problem am I actually solving?” ON THE BOOKSHELF (46:25) Roger talks about his love of notebooks and shares book recommendations REFERENCES Submit a Question for Roger Sign up for The Noodle ON THE BOOKSHELF Ugmonk Notebooks Theo of Golden by Allen Levi The Three Musketeers by Alexandre Dumas Note: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.

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Listener Questions: What Should I Be Doing When I'm Two Years from Retirement? is an episode from Retirement Answer Man by Roger Whitney.

This episode is 47:56 long.

This episode was published on Apr 15, 2026.

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