Listener Questions: Should I Take Social Security Early and Invest It?

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

🗓️ 8 April 2026

⏱️ 42 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

In this episode of the Retirement Answer Man, Roger Whitney explores the critical decision of when to claim Social Security benefits, weighing the pros and cons of taking them early versus delaying. Through listener questions, he delves into the impact of investment returns, health considerations, and income needs on retirement strategies. Roger also shares inspiring retirement stories and offers practical advice on managing retirement accounts and planning for the future. With insights into the psychological and financial aspects of retirement, this episode equips listeners with the knowledge to make informed decisions about their financial well-being.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Introduction: Navigating retirement decisions with confidence

ROCKIN’ RETIREMENT IN THE WILD

(00:42) Highlighting stories of unique retirement adventures
(01:08) The non-financial benefits of enjoying freedom day-by-day
(04:25) Cultural pressure to plan and set goals in retirement
(06:19) Retirement dreams: taking the world's longest flight

PRACTICAL PLANNING SEGMENT

(07:32) Addressing the dilemma: take Social Security early and invest it?
(09:22) Key facts impacting Social Security claiming strategy
(12:23) Investment return scenarios
(14:17) Benefits of not taking SS early: market risk, guaranteed income, simplicity
(19:00) Managing uncertainty and balancing investment returns
(21:23) Strategies for inherited Roth IRAs and mega backdoor Roth approaches
(24:40) Inheritance, aspirational goals, and resilient plans
(32:03) How to avoid fees moving 401k

SMART SPRINT

(36:00) Smart Sprint: Download your most recent Social Security statement

ON THE BOOKSHELF

(37:19) Book recommendations from the team

REFERENCES

Social Security Statement – Create or access your account to view benefits
Unforgettable: The Art and Science of Creating Memorable Experiences by Phil Marshon
How the Word is Passed by Clint Smith
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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	Hey there. Welcome to the show dedicated to helping you not just survive retirement, but you have the
0:07.9	confidence because you're doing the work to lean in and rock it. My name is Roger Whitney. I'm excited to
0:15.2	hang out with you today. Today on the show, we're going to have two rocking retirement in the wild stories, and then we're going to answer a number of your questions to help you take a baby step towards rocking retirement and perhaps share a book or two that are on our bookshelf.
0:33.5	So without further ado, let's get this party started.
0:46.8	All right, it's time to highlight those rocking retirement in the wild. I love these stories of people just like you doing all sorts of things to create a great life in retirement.
0:52.9	Our first one comes from Steve, and I really love this perspective because it's one that can
0:58.5	get lost in this rah-rah-ra-go mindset that permeates maybe too much on this show, but
1:06.8	in other shows as well.
1:08.8	Steve says, I've enjoyed learning from your perspective on retirement planning.
1:13.1	I tend to be highly analytical,
1:15.1	love spreadsheets,
1:16.3	and perhaps attuned to optimizing my financial plan.
1:20.3	I'm 67 and have been retired for a year and a half
1:23.1	and in pretty good shape financially right now.
1:25.4	I'd like to share my thoughts on some of the non-financial
1:29.7	aspects of retirement. I listen or read many of your podcasts and I also studied advice from many
1:37.1	other sources for several years prior to retiring. Every piece of non-financial advice I got about retirement was oriented towards
1:47.4	planning meaningful activities. But what I have enjoyed the most is having the freedom to not do
1:54.9	anything. Allowing my mind to wander, explore, whatever happens to interest me day by day is a privilege that brings
2:04.0	me joy. I love this, Steve. Steve goes on to say, I spent my whole career planning and driving
2:10.3	towards accomplishing goals with most of those goals being directed by others. My desire to explore and express my own creativity
2:20.2	was partially fulfilled in working within their direction, but my highest ambitions were severely
	...

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