When is Enough, Enough? Working After Financial Independence

Why would anyone continue to work for money after they’ve achieved financial independence? In this episode, Eric and Jason discuss this common practice, including why Jason and Lorri currently have part-time jobs post-FI. Topics covered include de-risking retirement, charitable giving, skill-building, and more.


Show Notes

Essential Background:


Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

FI-nancial Checkup: New Year Routines + Goals for 2024

What financial lessons did we learn last year and what will we do differently in 2024? In today’s episode, Eric and Jason discuss their end of year review processes. Topics include investing goals, their net worth reviews, lessons learned, and much more. Be sure to check out the show notes below the video!


Show Notes

Essential Background:

  • We’ve talked about our review processes before, and for the full details check out Our Net Worth Is Up! Sharing Our Financial Review Process. If you don’t have a process for regular financial reviews, you aren’t alone. Many people are unsure about how to calculate their net worth and keep their personal finances on track. In this episode, Eric and Jason share their simple pre- and post-FI review processes for net worth tracking, portfolio review, setting savings and budget goals, and more.
  • Jason mentioned staying below his safe withdrawal rate ceiling in this episode. For all the details (and more), you’ll want to see our page dedicated to the Safe Withdrawal Rate Toolbox. If you’re familiar with Karsten Jeske, you’ll definitely want to check this out. It has all the information you need including all three videos in our series, including walkthroughs of the tool and the CAPE-based strategy that Jason referenced here.
  • If you’re not familiar with Eric’s 30×40 Design Workshop business and his FI journey, you’ll want to see our two-part series: Passive Income = A Path to Financial Independence (Part 1) and Lessons Learned in 7 Years Earning Passive Income – A Path to FI (Part 2). Those links are to the show notes pages, which link both the episodes themselves and a host of related content that you’ll want to check out – particularly Part 2. In that post he shares lots of information on his various passive income streams
  • We talk about travel often on the show – it’s a clear priority for us both. Did We Budget Enough for Travel in Early Retirement? is our most recent episode on the topic. What happens if all the travel you want to do after retiring would break the budget? In this episode, Eric and Jason talk about the importance of travel to their early retirement plans. Topics discussed include financial concerns, disagreeing with your spouse, the value of planning by age range, and much more.
  • Want to learn more about that budget-busting 50th birthday celebration? Will This Get Us Kicked Out of the FIRE Movement? has all the details. Would you spend $1000 on dinner for a special occasion – or more? Eric and Jason recently enjoyed a milestone birthday celebration with their spouses + friends at a world famous restaurant. The total cost may shock you. In this episode, they talk about the experience, spending decisions pre- vs, post-financial independence, and whether it was actually worth it.

We talked about New Retirement in this episode. Jason really likes this platform and plenty of people on Reddit are discussing this comprehensive retirement planning tool as well. They have a full-featured free offering  as well as a reasonably priced paid “PlannerPlus” version with a host of really nice features, as well as consulting services. Huge benefits of PlannerPlus include a solid Roth conversion modeler and Monte Carlo analysis. Be sure to check out their 14-day free trial and see if you’re as convinced as Jason was! There’s a very active Facebook community around the tool as well.

Jason referenced a very popular Wait But Why post in this episode. The Tail End is the material in question. We wholeheartedly recommend it as a must-read for anyone – but be prepared for some thought provoking stuff!


Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Financially Independent, Recreationally Employed (FIRE)

Have you truly retired if you continue to do any work for money? In this episode, Eric and Jason talk about their own FIRE goals and how they’ve changed over time. Topics discussed include their respective journeys, why Jason has a part-time job after retiring, the internet retirement police, and much more. Be sure to check out the show notes below.


Show Notes

  • Needless to say, as a FIRE-themed show we’ve talked a lot about our thoughts on early retirement. We won’t try to capture all that content here, but rather will highlight a handful of key episodes. Be sure to review the show notes for each as they’ll point you to additional relevant content!
    • Retired Early and Feeling Lost. What’s Next? – How does it feel when you haven’t yet found your purpose after retiring early? In this episode, Jason talks with Eric about his three year journey exploring his post-FIRE purpose. In this episode, they discuss the phases of retirement, seeking out meaningful projects, lessons learned along the way, and much more. 
    • Retiring Early – So Why Am I Worried? – For many, work provides a sense of purpose and identity, as well as validation, utility, not to mention financial security. What happens when that no longer exists? What takes its place? How does it impact your personal relationships and your personal sense of accomplishment? Much of the discussion about financial independence, retire early (FIRE) focuses on saving and investing, in this conversation we unpack what it means to leave work behind and fully embrace this life-changing transition.
    • One More Year: My Decision to Postpone Early Retirement – Imagine changing your mind about retiring early just as the finish line comes into view? What factors might cause you to consider working one more year? In this episode, Eric talks with Jason about the idea to delay his retirement. They discuss why he’s considering it, finding alignment with his spouse, how others reacted to the idea, and much more.
    • Retirement Is Nothing Like I Thought It Would Be – We all daydream about what retirement will be like, but will reality live up to expectations? In this episode, Eric and Jason are joined by Fritz Gilbert, who blogs at The Retirement Manifesto. Our discussion goes well beyond the numbers, covering topics including finding your purpose, working “one more year”, determining your FIRE timing, and the keys to success in retirement.
    • My Next Phase of Early Retirement Won’t Include This… – Year two in early retirement was very different for Jason than year one. It’s common that the honeymoon stage of retirement is followed by disappointment and a search for meaning. In this episode, Jason and Eric discuss a recent project Jason abandoned and what stage of retirement they think he’s in. You’ll hear his approach to guarding his free time, what Eric fears most about retiring early, and more.
    • Am I Failing at Early Retirement? – Has your shrinking retirement portfolio left you considering part-time work to ease your anxiety? Inspired by a blog post from Go Curry Cracker, we discuss BaristaFIRE, time freedom, what it means to be “unemployable”, and what work we might consider post-retirement.
    • Retired Early and I Hated It : How NOT to FIRE, Part 2 (Post-FI/RE) – Imagine hitting your FI number, retiring early, and discovering you hate it? In this episode we discuss four examples of such an outcome: from quitting the perfect job and regretting it, to feelings of depression and lack of purpose. Some are unable to find motivation without financial incentives, while others realize they haven’t budgeted enough to do things they enjoy in life.
  • For more on Jason’s FI journey, check out these episodes centered on his retirement milestones to date: What I Learned in My First Year of “Early Retirement (1 year), My New Life: Two Years After Early Retirement (2 years), and Finding My Way in Early Retirement: A 30 Month Check-In (2.5 years).

Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Did We Budget Enough for Travel in Early Retirement?

What happens if all the travel you want to do after retiring would break the budget? In this episode, Eric and Jason talk about the importance of travel to their early retirement plans. Topics discussed include financial concerns, disagreeing with your spouse, the value of planning by age range, and much more. Be sure to check out the show notes below.


Show Notes

Essential Background:

Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins – was mentioned by Eric here, and is a much-discussed book in the FIRE community. It’s intended as a “practical guide on how to get the most out of your money—and out of your life”. If you like the aim of prioritizing memorable experiences far ahead of simply accumulating money for later in life, you’ll definitely want to check it out.

Are you familiar with the Camino de Santiago? Jason talked a little about this including his plans to walk the most famous of the Camino routes, the Camino Francés (the French Way), in 2025. There is a wealth of information available online, including on YouTube. If you’re US-based, consider checking out the American Pilgrims site.

Wondering what that word was we were trying to pronounce when talking about traveling to Croatia? Hvar is a Croatian island in the Adriatic Sea, located off the Dalmatian coast, lying among several other islands. It’s consistently ranked in the top of many lists concerned with the best of island travel, and Hvar promotes itself as “the sunniest spot in Europe”.


Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Retired Early and Feeling Lost. What’s Next?

How does it feel when you haven’t yet found your purpose after retiring early? In this episode, Jason talks with Eric about his three year journey exploring his post-FIRE purpose. In this episode, they discuss the phases of retirement, seeking out meaningful projects, lessons learned along the way, and much more. Be sure to check out the show notes below.


Show Notes

Essential Background:

Interested in more information about Jason’s decision not to pursue his private pilot’s certification? Check out his recent blog post, Catching up on life, in which he shares the details of why he recently put that long-held dream to rest.

Did you know Jason blogged regularly for the first 2+ years of his post-RE life? This included documenting his feelings on purpose and navigating his new post-career world. While he decided to archive that original blog, you can still access those old posts. Check out this post on his new blog for all the details on how you can get a free copy.

Taking Stock: A Hospice Doctor’s Advice on Financial Independence, Building Wealth, and Living a Regret-Free Life (also available as an audiobook) is Doc G’s recently published book. As you will readily glean from our conversation in the episode linked above, this text contains pure gold. It’s not at all a traditional FIRE book – and this is precisely why we found so much value in it. As a hospice doctor, Jordan Grumet has had a unique front-row seat to the regrets of his dying patients. And the stories he relates in this book will remind you to take stock of life now, before it is too late. Please do check it out and recommend it to those in your life!


Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

The Health Risks of Early Retirement

If you’re not giving mental and physical health the same level of attention as your financial health, you’re playing with fire. In this episode, Jason talks with Eric about what steps he’s taking to prioritize his own wellness in early retirement, including a frank conversation about mental health. Here they discuss steps to promote wellness, the distinct challenges of retirement, and much more. Be sure to check out the show notes below, which include a link to a blog post Jason wrote to go along with this episode.


Show Notes

Subsequent to recording this episode, Jason wrote a blog post called “Let’s talk about mental health“. Check it out for additional insight beyond the conversation in this video.

Essential Background:

As we discussed in the episode, both Eric and Jason read physician Peter Attia’s book Outlive: The Science and Art of Longevity”. In the latter’s opinion, this is among the most important books retirees (or those anywhere on a FIRE path!) should read. To obtain a copy of this book in paperback, Kindle ebook, or Audible audiobook (read by the author), check out this link.

Unbeknownst to us at the time, we recorded this conversation on World Mental Health Day. For more on the essential topic of mental health and wellbeing, be sure to check out the WHO’s webpage on this subject.


Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

One More Year: My Decision to Postpone Early Retirement

Imagine changing your mind about retiring early just as the finish line comes into view? What factors might cause you to consider working one more year? In this episode, Eric talks with Jason about the idea to delay his retirement. They discuss why he’s considering it, finding alignment with his spouse, how others reacted to the idea, and much more.


Show Notes

Essential Background:

  • If you’re not familiar with Eric’s 30×40 Design Workshop business and his FI journey, you’ll want to see our two-part series: Passive Income = A Path to Financial Independence (Part 1) and Lessons Learned in 7 Years Earning Passive Income – A Path to FI (Part 2). Those links are to the show notes pages, which link both the episodes themselves and a host of related content that you’ll want to check out – particularly Part 2. In that post he shares tons of information on his various passive income streams
  • This isn’t the first time we’ve talked about the concept of “One More Year”? Given last year’s market volatility, a viewer asked Jason if he would feel more secure had he worked another year or two before retiring early. We talked about his thoughts on that in an episode called Do I Wish I’d Worked One More Year?
  • Alignment with our spouses is a topic that’s come up multiple times on the show, including in this episode. Particularly for critical financial decisions, it’s essential to be on the same page. Many seem to agree that our two-part series where we discuss our FIRE paths with our spouses, Lorri and Laura, is must-see Two Sides of FI content. Check it out here: Part 1 and Part 2!
  • In this video we mentioned Jason’s recent conversation with Jordan, “Doc G” Grumet. Check out “Fulfillment Beyond FI: Life After Early Retirement with Jason” for the Earn and Invest podcast episode in question. But that actually wasn’t the first time we talked with Doc G. In fact, one of our most popular Two Sides of FI episodes of 2022 was our conversation with him titled “Will You Run Out of Money or Time? FI Advice From a Hospice Doctor“. In those show notes, you’ll also find a link to our earlier joint appearance on E&I as well as to Doc G’s impactful book.

Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Will This Get Us Kicked Out of the FIRE Movement?

Would you spend $1000 on dinner for a special occasion – or more? Eric and Jason recently enjoyed a milestone birthday celebration with their spouses + friends at a world famous restaurant. The total cost may shock you. In this episode, they talk about the experience, spending decisions pre- vs, post-financial independence, and whether it was actually worth it.

Show notes may be found below the video


Show Notes

Essential Background:

Interested in learning more about The French Laundry? Their website is a great source for further details about the restaurant, their current menus, as well as Chef Thomas Keller. At the site you’ll also find links to his other restaurants; helpful if you’re based in places like New York, Las Vegas, or Florida!

The image below is a photo of the menu from our meal at the restaurant.

A photo of the menu from our French Laundry meal

Perhaps like us, you’ve enjoyed episodes of A Chef’s Tour, and may remember Anthony Bourdain once visited The French Laundry on that show for a very special dinner. While the menu served to him and the other chefs was even more expansive than the normal, it provides a ready example of the artistry of Chef Keller and his team at the restaurant.

For more on Chef Keller, we recommend checking out his MasterClass episodes. Far from highly technical haute cuisine guidance, these videos are simple to understand for cooks at any level, and provide excellent foundational instruction on kitchen technique.

Speaking of milestones, free resources like Empower (formerly Personal Capital) can make tracking FI milestones, a lot easier. We both use and really like this free tool for tracking investment accounts, understanding asset allocation + rebalancing opportunities, and monitoring net worth. Empower employs a simple account linking process to make it a more automated experience. Give it a try risk-free! (affiliate link; free program )

A note from Jason – Every episode of Two Sides of FI provides an opportunity for reflection, and this episode provokes a lot of emotions for me. On one hand, it feels really good to recall memories of a truly special and wonderful experience, sharing a key lifetime milestone with Eric, Lorri, Laura, and our friends. However, openly talking about spending a lot of money on something as luxurious as fine dining admittedly feels more than a little weird. I don’t think it’s unusual to feel emotions like guilt or embarrassment in this situation, is it? In any case, I truly enjoyed our conversation about this wonderful occasion we spent together, and I earnestly hope that you will too.


Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first 1.5 years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

He Retired Early, She Didn’t: A Coast FI Case Study

How would your spouse feel if you retired early while they kept working? In this episode, Eric + Jason talk with our friend Erik, who recently left the workplace while his wife continues to work. How does this arrangement work for them, and why is a coastFIRE path their choice? Topics discussed include being thrown into retirement, finding purpose, talking about FIRE, and much more.

Show notes may be found below the video


Show Notes

Essential Background:

The FI journey is far from a solo one for most people, particularly those with long term partners or spouses. Particularly for the kinds of weighty decisions that we discussed in this episode, it’s essential to be on the same page regarding one’s FI path. Many seem to agree that our two-part series where we discuss our FIRE paths with our spouses, Lorri and Laura, is essential Two Sides of FI content. Check it out here: Part 1 and Part 2!

Want even more candid conversation among spouses? As a bonus, check out the conversation with Eric + his wife Laura, “FI-nancial Decisions – Transitioning to FI with Laura + Eric”, for a behind the scenes look at how they decided to revise their revised asset allocation.

Erik and Deb have termed their path as one following CoastFIRE principles. This is a term used to describe someone who isn’t yet FI but has already put in the necessary effort to mathematically achieve that goal without further contributions. Did you hear our earlier conversation on this topic in an podcast-only episode two years ago? If you missed it then, you’ll definitely want to check out A CoastFI Path to Financial Security: An Interview with Catherine.


Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first 1.5 years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Can You Reach FI Faster? Advice From Someone Who Did.

Can you shorten the time to achieve financial independence (FI)? In this episode, Eric talks with Jason about his journey to FI and the steps he took to reach FI faster and retire before 50. Topics discussed include risks taken + sacrifices made, how Eric’s path differed, why early retirement is so attractive, and much more.

Show notes may be found below the video


Show Notes

Essential Background:

The FI journey is far from a solo one for most people, particularly those with long term partners or spouses. As we discussed in this video, it’s essential to be on the same page regarding FI path decisions. Many seem to agree that our two-part series where we discuss our FIRE paths with our spouses, Lorri and Laura, is essential Two Sides of FI content. Check it out here: Part 1 and Part 2!

Want even more candid conversation among spouses? As a bonus, check out the conversation with Eric + his wife Laura, “FI-nancial Decisions – Transitioning to FI with Laura + Eric”, for a behind the scenes look at how they decided on their revised asset allocation last year.

We mentioned BaristaFIRE in today’s episode. In the linked post from Financial Samurai, he describes it as “being able to retire before the conventional age of 60+, but taking on a part-time job (e.g. like at a coffee shop) for supplemental income and potentially subsidized health insurance.” This article provides a good look at this path, and is an effective primer for those seeking more information. In addition to the financial calculations provided in the article, there are numerous supporting tools available online including this BaristaFIRE calculator from Walletburst.

Another common FI path is called CoastFIRE. This is a term used to describe someone who isn’t yet FI but has already put in the necessary effort to mathematically achieve that goal without further contributions. Did you know we talked with someone on this topic in an podcast-only episode two years ago? If you missed it then, you’ll definitely want to check out A CoastFI Path to Financial Security: An Interview with Catherine.


Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first 1.5 years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.