Podcast Summary: The Long View

Episode: Dana Anspach and Fritz Gilbert: ‘This Is What a Joyful Retirement Could Feel Like’

Date: September 23, 2025
Hosts: Christine Benz, Amy C. Arnott (Morningstar)
Guests: Dana Anspach (Sensible Money), Fritz Gilbert (Retirement Manifesto)

Overview

This episode explores the practical and emotional journey into and through retirement. Hosts Christine Benz and Amy Arnott engage returning guests Dana Anspach and Fritz Gilbert in a candid discussion about planning for a satisfying retirement beyond the numbers—focusing on decisions around spending, the phases of retirement, non-financial fulfillment, and the realities of transitioning out of work life. The guests draw on their professional work and personal experiences, including Dana's pre-retirement reflections and Fritz's early retirement journey, offering advice and anecdotes for those contemplating or living through retirement.

1. Guest Introductions and Collaborative Blogging

• Fritz Gilbert describes his blog, The Retirement Manifesto, which he started as a personal experiment three years before his retirement. It became a long-term project and a key outlet for sharing thoughts and interacting with fellow retirees.

  "I've been writing for 10 years now. It's turned into kind of a thing and I'm just really enjoying the interaction with the readers and having a forum where I can just share my thoughts as I live this life in retirement." [02:24]

• Dana Anspach, founder of Sensible Money, focuses her financial planning firm on clients 55+ in the decumulation (retirement income) phase. She announced she'll now contribute personal reflections to Fritz’s blog, aiming to explore and document her pre-retirement journey.

  "We see hundreds of examples and we see this bell curve of how it usually plays out...As I was thinking about my own retirement, I've been thinking, like, I really miss that expression [of blogging]." [05:43]

2. Phasing Into Retirement: Approaches and Reflections

Dana's Gradual Path

• Dana shares her "pre go" phase—the period where one transitions from work into contemplating and experimenting with retirement before fully committing.

  "For me, the prego phase starts when you really start contemplating retirement. Not just the number side...How do I take some more time off?" [10:21]

• She emphasizes exploring actual experiences (e.g., a 14-day hiking vacation) to envision what joyful retirement could be, especially for those whose careers bring fulfillment or who lack typical retirement family activities (like grandchildren).

  "But on that particular vacation...I actually enjoyed it. I never got bored. By the time it was over, I was like, wow, this is what a joyful retirement could feel like. And it was the first time I ever really felt that." [07:40]

Fritz’s Perspective: All-In vs. Gradual

• Fritz retired "hard stop" at 55 from a corporate career, after mental and logistical prep, including a "mini retirement" to test the waters.

  "I took a mini retirement...We came up to our cabin in the mountains...and we said, let's just think about retirement...What do we want our life to be?" [15:04]

• He notes that thinking ahead about identity, relationships, and purpose is crucial to avoid the often-cited disorientation or depression many retirees face.

  "60% of people struggle with the transition. And the way to avoid that is to do exactly what Dana is talking about." [15:04]

• Recommends running retirement models assuming no additional income so work post-retirement is purely optional, not a default for structure or meaning.

  "Even if you think that's going to be the path you want to take, run your numbers as if you don't take that path and give yourself the freedom." [18:02]

3. Spending in Retirement: Permission and Mindset

The Struggle to Spend

• Many retirees, especially savers, have difficulty "giving themselves permission" to spend even when plans and numbers say they can.

  • Dana’s practical hacks: gifting meaningful books (like "Die with Zero"), or setting up direct deposits. Results are mixed:

    "We've tried just setting up a direct deposit...and a client...three months later said, no, stop that. I don't need that. So we've tried all kinds of things." [21:04]

  • Stories highlight the joy of meaningful spending—both on oneself and on others.

• Fritz's gradual adaptation included setting up “retirement paychecks” from his portfolio to create a spending permission system:

  "I set up automatic paychecks...based on my safe withdrawal rate. I know I'm good to spend it...At the end of the year, if there's $10,000 in there that we haven't spent, okay, let's give it to charity, right?" [24:12]

• Both stress that planned, intentional spending in the “go-go” years (active, healthy early retirement) increases joy and gives flexibility later.

  "The thing you don't want to do is have safety over, safety over safety and not live this life you can enjoy now in your go go years." – Fritz [27:09]

4. Planning for Market Ups and Downs

• Market Volatility Preparation: Dana recounts the 2008 financial crisis as a pivotal reminder to have action plans ready for bear markets.

  "Going through the great financial crisis with retired clients was terrifying...We were able to keep almost all of our clients...They needed to stick with their plan." [29:38]

  • The lesson: Build a “crash plan” in advance, acknowledge bear markets will happen, and resist recency bias.

• Use of Annuities: Dana utilizes low-fee, straightforward annuities in some client cases to provide guaranteed income and mitigate longevity and cognitive risk.

  "The more guaranteed income you have later in life, the more you're protecting a certain minimum lifestyle." [33:17]

5. Withdrawal Rates and Adjustment Strategies

• Safe Withdrawal Rate Approaches

  • Fritz: Advocates a conservative, flexible rate (3.25%–4.25%), recalculated annually using a “guardrail” approach based on portfolio performance and upcoming Social Security income.

    "Every year end I update our net worth...Multiply that times three and a quarter. Three and a half. Four and a half...and create this guardrail approach." [38:53]

  • Dana: Takes a “lifetime safe withdrawal rate” using a fundedness model (akin to pension funding), sometimes allowing high one-off withdrawals if the long-term plan sustains it.

    "We don't look at any kind of annual safe withdrawal rate. We look at what I would call a lifetime safe withdrawal rate...There's adjustments that can be made." [40:03]

• Market Valuations and Diversification

  • Both recommend broad diversification, systematic rebalancing, and adhering to a disciplined investment process rather than reacting to headlines or valuations.

    "I'm a big fan of pretty very deliberate diversification...I can look at whatever asset class has outperformed in the prior year and sell a little bit of those holdings to restock the cash bucket." – Fritz [42:48] "We use a different kind of equity model...based on what's called a Mini Max principle...maximizing the outcome of a minimum return scenario." – Dana [45:07]

6. Roth Conversions and Tax Planning

• Fritz discusses his experience with aggressive Roth IRA conversions and notes the surprising “stickiness” of traditional IRA balances due to market gains, a common experience echoed by his readers.

  "It hasn't paid off...It's really hard to get it [IRA balance] to come down...Combine good market with a healthy IRA balance and it's surprising how large those Roth conversions have to be to materially bring down the IRA balance." [48:08]

7. Social Security and Guaranteed Income

• Fritz's Plan: Wife, as the lower earner, claimed at 62; Fritz will defer to 70 to maximize longevity and spousal benefits, with long-term scenarios modeled on a potential 25% benefit cut for conservatism.

  "We ran a cash flow out to age 95 and I looked at scenarios where I took a 25% cut on Social Security..." [35:10]

8. Non-Financial Fulfillment

• Fritz: The biggest surprise was how well the non-financial transition went, crediting thorough pre-retirement curiosity and experimentation (“childlike mentality”).

  "The biggest takeaway that I have learned from that is how important it is to really foster your curiosity...When you were a kid, you just go out and do stuff and play, right?...[It] worked really, really well." [50:03]

  • He warns of the high risk of depression/disorientation post-retirement and emphasizes the need to intentionally address these risks in advance.

• Dana: Despite expertise, she expects to struggle with the same mindset and spending issues as her clients but finds value in awareness, intentionality, and giving oneself grace during the journey.

  "I think I'm going to struggle with the same things my clients are going to struggle with...I'll probably be kinder and have more grace for myself as I navigate these phases." [52:40]

9. Memorable Quotes & Moments

• “You need to have something that you're retiring to, not just retiring from.” – Amy Arnott [11:46]
• “[Retirement] doesn't have to be that way, but you've got to be aware of the importance of thinking about it. And more importantly, start listening to that curiosity and taking that first step...” – Fritz Gilbert [51:45]
• “Here's what this is like, let's all get better at it together.” – Dana Anspach [56:17]
• “If we get good markets, we're all going to be fine. That is really not what we're concerned about. We're always concerned about the worst case scenario.” – Dana Anspach [45:07]

10. Recommended Resources

• Retirement Manifesto Blog – for firsthand journey, community, and practical advice.
• Die With Zero by Bill Perkins – for reframing spending in retirement.
• Dana’s upcoming book: Living Off Your Acorns: Your Guide to the Four Phases of Retirement (Pre-go, Go-go, Slow-go, No-go).

11. Selected Timestamps

• Intro, guest intros, Fritz’s blog origin: [01:07]–[02:53]
• Dana on pre-go phase and vacation epiphany: [07:40]
• On gradual vs. hard-stop retirement: [15:04]–[18:02]
• Permission to spend, spending hacks: [21:04]–[24:12]
• Managing downturns and crash planning: [29:38]
• Annuities and Social Security discussion: [33:17]; [35:10]
• Withdrawal rates and spending guardrails: [38:04]–[40:03]
• Asset allocation, process discipline: [42:48]–[47:31]
• Roth conversion realities: [48:08]

Conclusion

This episode offers a realistic, empathetic, and data-driven roadmap for those planning retirement or already retired. Key themes include the value of phased, personalized transitions, intentional spending, pre-emptive planning for both market downturns and psychological shifts, and the enduring importance of reflection, experimentation, and community support.

Learn more:

• retirementmanifesto.com
• sensiblemoney.com
• Morningstar: Financial planning, articles, and tools

Note: This summary omits advertisements, episode introductions, and disclaimers to focus on core content.