Take the Retirement Leap of Faith with Jordan Grumet

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

🗓️ 3 June 2026

⏱️ 59 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Roger Whitney explores the idea that retirement always involves both excitement and uncertainty. While people spend years gathering information, running projections, and refining plans, there comes a point when no amount of additional analysis can eliminate risk. Through a conversation with Dr. Jordan Grumet, Roger discusses why retirement ultimately requires a leap of faith, how fear of running out of money can overshadow the risk of missing life, and practical ways to build confidence in spending and living intentionally. The episode also features listener reflections on decluttering, strategies for letting go of physical and financial clutter, and a Rockin’ Retirement in the Wild story from Scott, who recently retired and embraced a long-awaited trip to Maui.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Roger reflects on the “sweet and sour” nature of retirement and introduces the concept of taking a leap of faith.
(01:56) Roger welcomes listeners, previews his conversation with Dr. Jordan Grumet, and invites listeners to the upcoming Noodle Live event.

ROCKIN’ RETIREMENT IN THE WILD

(04:01) Scott shares a retirement story from Maui, including a chance encounter with Roger’s realtor and reflections on taking the leap into retirement at age 57.

PRACTICAL PLANNING SEGMENT WITH DR. JORDON GRUMET

(05:47) Roger and Dr. Jordan Grumet discuss why confidence can be one of the biggest challenges in retirement, even for those who have prepared well financially.
(13:00) The conversation explores the tension between protecting financial security and fully embracing life’s opportunities.
(22:18) ) A discussion on longevity assumptions, retirement planning conservatism, and why many retirees may overestimate the likelihood of running out of money.
(27:04) Practical strategies for building spending confidence, including the “fun bucket” approach.
(35:24) Additional tactics for creating confidence, including prefunding near-term spending and focusing on purpose rather than optimization.
(42:12) How values-driven planning can help retirees intentionally use money to support the life they want to create.
(47:49) Key takeaways on abundance, mindset, and taking meaningful action despite uncertainty.

SMART SPRINT

(49:55) Identify one decision you've been researching, planning, or delaying. Ask yourself whether additional information will truly change the outcome, or if it's time to take a small leap of faith and move forward.

DECLUTTERING DEBRIEF

(51:06) Roger reflects on listener feedback from the decluttering series and shares a few practical insights and resources from the community.

REFERENCES

livewithroger.com — Register for Noodle Live on June 18!
Submit a Question for Roger
Sign up for The Noodle
Dr. Jordan Grumet / Earn & Invest Podcast

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	The other day during a writing session, I was reflecting on the last 30 or so years that I've worked on this idea of transitioning into and living in retirement.
0:11.9	And one thing that I discovered that is universal through all the countless people that I've talked to or walked that journey with is that there's a sweet and sour element to it.
0:22.5	The sweet part of it is all of that excitement about retiring and having time freedom. A lot of times just to breathe
0:29.0	and maybe to pursue passions that you haven't had time for or deepen relationships that you want to deepen.
0:36.6	Or perhaps it's travel or use your funds to help your children or charities, whatever.
0:43.2	That's all really exciting.
0:44.3	That's a lot of sweet stuff to figure out and have the opportunity to do.
0:48.3	But the sour side of it is if you leave your work, that means you're not going to earn a dollar that you might need
0:56.3	later in life. That's scary. Or if you are retired and you're spending a dollar on that trip
1:04.9	or that passion or whatever it is, how do you know you don't need that dollar 20, 30 years from now?
1:12.4	That lead you to go search for information and then use that information to plan and then
1:18.3	get some more information. And the honest truth is there's never enough information and there's
1:24.0	never enough planning to relieve that tension. That tension between all the sweet and the sour is always going to be there. It really is. It's always going to be there. It reminds me of a quote from Henry David Thoreau. He said, we must walk consciously only part of the way toward our goal and then leap into the dark to our success. That's what we're
1:47.6	going to talk about today on the show is taking that leap of faith in order to rock retirement.
1:56.3	Hey there. Welcome to the show dedicated to helping you not just survive retirement,
2:01.4	but to have the confidence so you can leap into rocking retirement.
2:07.0	My name is Roger Whitney.
2:08.2	I'm a practicing retirement planner, co-founder of Retire Agile.
2:12.9	And today on the show, we're going to have Dr. Jordan Grummet on to talk about a leap of faith into retirement.
2:21.5	Luckily for you and me, Jordan and I had this conversation before I got my sinus infection,
2:28.8	where my voice was much stronger than it is now.
2:31.2	So it won't be as painful to speak and hopefully not too painful to listen
	...

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