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

Retirement Answer Man

Roger Whitney, CFP®, CIMA®, RMA, CPWA®

Education, Investmentmanagement, Saving, Self-improvement, Careerplanning, Retirement, Business, Lifeplanning, Investing, Retirementplanning, Financialplanning, Retirementpodcast

4.6 • 1.2K Ratings

🗓️ 15 April 2026

⏱️ 48 minutes

🔗️ Recording | iTunes | RSS

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Summary

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

ON THE BOOKSHELF

Note: The opinions expressed are for informational purposes only and should not replace personalized advice from licensed professionals.

Transcript

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0:00.0	Mike emailed in and said he's retiring in two years and wanted to know what he should be doing
0:06.0	different between now and retirement. And his questions were framed, well, I'll read them to you.
0:12.0	Should I do something different with our money during these last two years? What should we do with
0:16.7	our 457 or 401k when we retire? Should we leave them there? Should we draw on them or something else?
0:22.6	All very good questions that are actually putting the cart before the horse in terms of how they're framed.
0:29.5	And we're going to try to answer Mike's question and so much more today on the show.
0:35.3	Well, welcome to the show dedicated to helping you not just survive retirement, but to have the
0:40.1	confidence to lean in and rock it because you're asking the right questions and doing the work
0:47.3	to create a great life. My name is Roger Whitney. I'm a practicing retirement planner with over 35
0:52.9	years experience, co-founder of Retire Agile, which I'm a practicing retirement planner with over 35 years experience, co-founder of
0:55.8	Retire Agile, which I'm excited to say because we just changed the name of our firm after
1:01.0	our merger with Tanya. And our new website is up today. Retireagile.com took a lot of work to
1:07.9	bring our brands together. We're excited about the focus and the team that we have. And check it out at retireagile.com. We're actually accepting clients. It hasn't been that way in a long time, which is going to be great. So today we're going to talk about Mike's question and try to answer that. We're also going to have a retirement toolkit and talk about inflation and get to a number of your questions.
1:28.4	So without further ado, let's get this party started.
1:35.3	Recently, Jamie Diamond was interviewed and he mentioned the five risks that he is thinking about
1:42.3	for the economy and for his firm, J.P. Morgan. And one of them was
1:48.1	inflation. Inflation risk was one that he highlighted because we've had a big rise in oil
1:53.6	prices because of what's going on in Iran. And oil prices can lead to inflation and that could
1:59.0	lead to higher interest rates and that could hurt the economy. So for today's retirement toolkit, I want to revisit and do some basics of
2:06.8	what is inflation and what is inflation risk when it comes to your retirement planning? Because
2:14.5	this is a key risk. If we think of financial risks, there are two big ones. One is sequence of return risks, which I believe we talked about
2:22.2	before, and the other one is inflation risk. So what is inflation and what is inflation risk?
	...

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