Doug chats with Rusty about how to optimize the final year before (early) retirement, emphasizing the critical distinction between “one more year syndrome” vs. a calculated final year and how working a little longer can lower withdrawal rates & reduce sequence-of-returns worry.  They compare quitting to being fired or laid off and highlight some potential benefits such as severance, possible unemployment, and employer healthcare continuation.  Rusty also shares some personal negotiation tactics when leaving a job.

Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/

Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you!

Want to order MHFI stickers/temporary tattoos or create your own custom stickers?  Of course you do!  We ALL do!  Order them here using our affiliate link so that we might earn a commission: https://www.stickermule.com/dougcunnington

Links

—

Join the Mile High FI Club – It’s the email list!

Get MHFi Merch – It helps support the show. Get t-shirts & more

**Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.**

Brought To You By:

The Doug Show, aka Affiliate Marketing & Side Hustles

Email the show: [email protected]

0:00 Introduction

2:37 Working one more year

9:19 Stock market risk & flexibility

15:13 Quiet Quitting playbook

23:28 Quitting vs. getting fired or laid off

30:41 Real-world cautionary tales

35:38 Tips for quitting & identity issues

43:02 New baby update!

51:51 Tales of a jacked math major

59:52 Soundcheck – Food

Doug and co-host Kristen Knapp chat with Fritz Gilbert (The Retirement Manifesto) at the EconoMe Conference about various drawdown strategies and spending in early retirement.  Fritz describes how he personally implements a “bucket strategy” approach to withdrawing money by setting up a monthly “paycheck”, how decumulation differs from accumulation, and explains sequence-of-returns, inflation, & longevity risks.  The group also discusses annual financial reviews, dynamic spending guardrails, viability of DIY investors, and intentional living.

Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/

Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you!

Want to order MHFI stickers/temporary tattoos or create your own custom stickers?  Of course you do!  We ALL do!  Order them here using our affiliate link so that we might earn a commission: https://www.stickermule.com/dougcunnington

Links

—

Join the Mile High FI Club – It’s the email list!

Get MHFi Merch – It helps support the show. Get t-shirts & more

**Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.**

Brought To You By:

The Doug Show, aka Affiliate Marketing & Side Hustles

Email the show: [email protected]

0:00 Introduction

5:15 Why drawdown needs a plan

8:43 The Bucket Strategy

14:52 Balancing risks & retirement readiness

20:11 The 4% Rule vs. buckets

25:43 Creating a retirement paycheck

31:04 Dynamic spending & guardrails

36:17 Potentially increased spending

41:38 DIY vs. working with an advisor

48:27 Bond ladders

53:11 Tax location matters

Doug chats with Mark Trautman (Mark’s Money Mind) about the relevance of The 4% Rule in modern retirement planning.  They explore whether it remains a solid “north star” for those in the accumulation phase or if it has become an outdated guideline that potentially hinders retirees from living their best lives.  Mark also shares his personal transition from a high-saver to a strategic retiree focused on decumulation & creating memory dividends.

Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/

Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you!

Want to order MHFI stickers/temporary tattoos or create your own custom stickers?  Of course you do!  We ALL do!  Order them here using our affiliate link so that we might earn a commission: https://www.stickermule.com/dougcunnington

Links

—

Join the Mile High FI Club – It’s the email list!

Get MHFi Merch – It helps support the show. Get t-shirts & more

**Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.**

Brought To You By:

The Doug Show, aka Affiliate Marketing & Side Hustles

Email the show: [email protected]

0:00 Introduction

1:12 Discovering & defining the 4% Rule

6:32 Mark’s portfolio & retirement strategy

12:46 Why 4% misses reality

19:13 Die With Zero & spending

26:52 Stress testing projections

31:41 Guardrails

35:06 Agile retirement planning

41:24 Mark’s Money Mind

47:02 Soundcheck – Travel

Support the Pancreatic Cancer Action Network, PanCan, for the PurpleStride.

Donate here

PurpleStride is an inspiring event for anyone who has been affected by pancreatic cancer. We are raising funds to ensure vital research continues and free resources are made available to all who need them.

We’ll be at the Dallas event (PurpleStride) DFW. If the this episode is up, then donations are still open. Thank you.

Doug and Mark Trautman (Mark’s Money Mind) answer questions from the listener mailbag.  They discuss how to prepare for retirement, building social connections beyond work, psychological shifts of leaving a career, strategies for “manufacturing” a retirement paycheck, how to navigate the changing landscape of car ownership (buying vs. leasing), and the mindset shift of decumulation & spending.

Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/

Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you!

Want to order MHFI stickers/temporary tattoos or create your own custom stickers?  Of course you do!  We ALL do!  Order them here using our affiliate link so that we might earn a commission: https://www.stickermule.com/dougcunnington

Links

—

Join the Mile High FI Club – It’s the email list!

Get MHFi Merch – It helps support the show. Get t-shirts & more

**Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.**

Brought To You By:

The Doug Show, aka Affiliate Marketing & Side Hustles

Email the show: [email protected]

0:00 Introduction

0:56 Recent travels

5:53 Question – Preparing to retire

11:13 Social connections, hobbies, & identity

18:50 Retirement paycheck strategy

23:35 Question – Leasing vs. buying cars

29:16 Longevity & when leasing makes sense

34:17 Question – Decumulation & spending

40:47 Calculating downside risk & seeking advice

49:24 Soundcheck – Casa Bonita

Doug chats with his wife Elizabeth about her 2-year anniversary in early retirement.  Elizabeth describes why she loves not working, challenges with balancing routine vs. flexibility, and how reduced stress has improved relationships and communication.  Doug & Elizabeth also discuss budgeting with a financial advisor, differences in “fun fund” spending, the impact of market returns on retirement confidence, perceived social pressure within the FI community to retire, and not necessarily retiring “to something”.

Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/

Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you!

Want to order MHFI stickers/temporary tattoos or create your own custom stickers?  Of course you do!  We ALL do!  Order them here using our affiliate link so that we might earn a commission: https://www.stickermule.com/dougcunnington

Links

—

Join the Mile High FI Club – It’s the email list!

Get MHFi Merch – It helps support the show. Get t-shirts & more

**Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.**

Brought To You By:

The Doug Show, aka Affiliate Marketing & Side Hustles

Email the show: [email protected]

0:00 Introduction

2:08 Leaving a full-time career

8:07 Part-time work experiment

18:36 Retirement surprises

23:03 Finding a routine

29:46 Relationship improvements

36:28 Pressure to retire

43:31 Spending & budgeting

50:30 Influence of the stock market

55:24 Retirement tips & readiness

1:00:05 What do you do?

1:08:10 Soundcheck – Caffeine cutback

Doug and Kristen Knapp (FI Friends Travel) dive into a listener-submitted topic from Dell regarding the potential benefits of oversaving.  Doug & Kristen discuss the pros & cons of oversaving, the necessity of having a plan for “retiring to something” after work, and explore the psychological shifts that occur when you no longer need a paycheck.  They also tackle common traps in the FI community such as “One More Year Syndrome”, golden handcuffs, and identity issues tied to a career.

Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/

Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you!

Want to order MHFI stickers/temporary tattoos or create your own custom stickers?  Of course you do!  We ALL do!  Order them here using our affiliate link so that we might earn a commission: https://www.stickermule.com/dougcunnington

Links

—

Join the Mile High FI Club – It’s the email list!

Get MHFi Merch – It helps support the show. Get t-shirts & more

**Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.**

Brought To You By:

The Doug Show, aka Affiliate Marketing & Side Hustles

Email the show: [email protected]

0:00 Introduction

4:17 Dell’s voicemail

9:20 Pros of oversaving

17:14 Legacy vs. Die With Zero

20:59 Cons of oversaving

27:55 Golden handcuffs & “enough”

34:36 Retiring to something… or not

40:16 Identity struggles & FI

49:43 Staying busy vs. intentional boredom

56:50 Early retirement pitfalls

1:01:16 Only boring people are bored

1:05:47 The nuances of FI

1:12:02 Longest soundcheck ever

Please support the show if you like it! I play highlights about Die With Zero, specifically about Time Bucketing.

You can donate via Buy Me a Coffee. You get extra content and know that you’re making the show possible.

Mile High FI is listed as one of the TOP Podcast on Careers in Apple Podcasts!

Spotify is 28% of the audience, so that’s grown in 2025 and higher than I said in this episode.

If you extrapolate the Spotify year end review data to the total downloads, here is what you get…

Mile High FI is a:

I don’t have ads anymore so I want to cover production costs. Most of the costs are related to software and tools and hosting. Many other podcasts have sucky ads every 15 minutes. I don’t want to do that.

Producer Chris volunteers to edit and produce the show. We’re not trying to get rich doing the show, but it takes a lot of time, effort, and planning.

You can also check out the affiliate offers here, which are products that I recommend. Mile High FI usually gets a small percentage, say 1% to 15%, depending on the arrangement. It helps, but direct donations are the best.

Doug chats with Pete Adeney (Mr. Money Mustache) about various fears that some people have about early retirement.  They explore why some people may be reluctant to retire, despite being financially ready, and specifically how fear of boredom can hold people back.  They discuss “One More Year Syndrome” and the irrational fear of running out of money despite what the math says.

Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/

Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you!

Want to order MHFI stickers/temporary tattoos or create your own custom stickers?  Of course you do!  We ALL do!  Order them here using our affiliate link so that we might earn a commission: https://www.stickermule.com/dougcunnington

Links

—

Join the Mile High FI Club – It’s the email list!

Get MHFi Merch – It helps support the show. Get t-shirts & more

**Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.**

Brought To You By:

The Doug Show, aka Affiliate Marketing & Side Hustles

Email the show: [email protected]

0:00 Introduction

1:51 One More Year Syndrome

5:50 Scared of boredom

10:18 Building social skills

17:22 Boring people are bored

22:03 FI Collective

25:51 Soundcheck – New house

Doug chats with Pete Adeney (Mr. Money Mustache) about evolving perspectives within the FIRE movement.  Moving beyond external critiques, they dive into a confessional-style discussion about genuine problems within the community – from the pitfalls of ultra-frugality, over-saving, over-optimizing, and “One More Year Syndrome” to the identity crisis retirees face.  They explore why FIRE isn’t a “gospel” but instead a set of ideas that should be modified in real-time based on what actually works for each individual.

Do you like the podcast and want to support the show?  Follow the link to find out how: https://milehighfi.com/support/

Curious to know exactly what products Doug uses?  Check out his Amazon lists below. *Affiliate links below, so if you buy something or spend money, we might earn a commission. That helps the show and doesn’t cost you anything extra. Thank you!

Want to order MHFI stickers/temporary tattoos or create your own custom stickers?  Of course you do!  We ALL do!  Order them here using our affiliate link so that we might earn a commission: https://www.stickermule.com/dougcunnington

Links

—

Join the Mile High FI Club – It’s the email list!

Get MHFi Merch – It helps support the show. Get t-shirts & more

**Disclaimer: The podcast is for informational purposes. Maybe entertainment but we won’t even make such a claim. You shouldn’t take the info as financial, legal, or tax advice. We aren’t certified financial planners or advisors. We’re not qualified for much. So get advice from professionals.**

Brought To You By:

The Doug Show, aka Affiliate Marketing & Side Hustles

Email the show: [email protected]

0:00 Introduction

1:16 MMM persona & early FIRE ideas

8:50 Ultra-frugality

18:00 Over-saving & One More Year Syndrome

24:23 Over-optimizing in the FIRE community

29:30 DoorDash spectrum

34:24 Paying for convenience

42:21 Balancing the future & the present

48:09 MMM’s retirement spending strategies

53:49 Retiring to something meaningful

1:02:18 Soundcheck – Casa Bonita