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.

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.

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.

Ask an Early Retiree Anything! Live Q&A with Jason from Two Sides of FI

Are you on the FIRE path or interested in learning more about early retirement? Three years ago I retired from my career at age 47 after reaching financial independence the prior year. This video is from a livestream where community members had the opportunity to ask me questions about what my experience has been like. Thanks to all who joined!

Don’t miss the extensive show notes below, which list all the episodes and resources discussed in the episode.

Show notes may be found below the video


Show Notes

Essential Background:

Here are links to the episodes Jason talked about in the show. In many cases these point to show notes, which contain not only the episode video itself, but also a variety of associated content meant to help support the content. Check them out!


Resources Mentioned:

Still haven’t subscribed to our YouTube channel or want to share an easy link with people you know? Here it is! Click it, say yes, and you’re in! Easy, peasy.

In this episode we talked about the new Two Sides of FI Discord server. If you’re not familiar, this is an instant messaging social network. 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!

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.

In this episode, Jason mentioned Empower (formerly Personal Capital) for summarizing his portfolio performance as a part of rebalancing. Both him and Eric 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 )

Do you have a copy of our free Rebalancing Calculator? This simple tool can help you make your own decisions about buying and selling in order to rebalance your portfolio. If you’d like something more DIY, this is a calculator you should consider.

In case you missed the link above, our popular three-part tutorial series on the Safe Withdrawal Rate (SWR) Toolbox can be found here.

The Retirement Income Style Awareness (RISA) is a tool by Wade Pfau (mentioned today) and the team at Retirement Researcher. It came from research performed on individual styles, risk tolerance, and other factors, and is aimed at deriving a personal retirement income strategy. Fritz Gilbert at Retirement Manifesto posted a nice write up on this last year, which we’d recommend. If you’re interested in learning more about this assessment, check out Wade’s book: “Retirement Planning Guidebook: Navigating the Important Decisions for Retirement Success”.

Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins, is discussed often in the FIRE community – so no surprise it came up in this episode. 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.


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

FI-ght Club: Friction Between Friends Pre and Post-FI

Questioning their roles, priorities, and the uncertain future of Two Sides of FI, Jason and Eric unveil hidden tensions arising from the pursuit and realization of financial independence. Will they find common ground and keep the project alive?

Show notes may be found below the video


Show Notes

Essential Background:

  • Eric and Jason have been friends for a long time – nearly 37 years as this episode was recorded. For more background on their upbringing, their relationship, and their FI paths, you’ll definitely want to watch these two early episodes: Our Financial Past and Our FIRE Present and Two Careers, Two Paths to Financial Independence.
  • To date we haven’t talked much “inside baseball” about how the show comes together. One exception is this outtake footage which we released two years ago: How Do We Feel About Making Two Sides of FI? Find out how much (or little) has changed since this video!
  • Lastly, we think our two-part series where we discuss our FIRE paths with our spouses is essential content: Part 1 and Part 2.

In this episode we talked about the new 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? One recent post came after filming this episode. For more on this thoughts about this conversation and related topics, don’t miss The Flipside of Time Freedom. To be notified of future posts, please consider subscribing here.


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

You Asked, We Answered. FIRE Q&A

Answering your financial independence, retire early (FIRE) questions, including the one we’re asked most often. This special Ask Us Anything format commemorates the 50th episode of Two Sides of FI. THANK YOU to all who submitted questions and for your continued support of the show!

Show notes may be found below the video


Show Notes

First, THANK YOU so much again for all your support of Two Sides of FI. We’d never have achieved this 50 episode milestone without all the engagement and encouragement we receive from you, our community. We truly appreciate you and are thankful for your constant support.

We are often asked how to support + promote the show. Here are three simple ideas which we humbly suggest: 1) Share a link to our channel with people who you think can benefit – via social media, 1:1, or however works for you. 2) Use the ‘like’ feature on videos and subscribe (click here!) to the channel. The YouTube algorithm sees these signals as indications of merit, and they play a vital role in helping to promote our content. 3) Consider rating + reviewing the podcast – even if you always watch it on YouTube. Apple Podcasts is the most important tool out there to drive visibility on the audio format. We get thousands of podcast downloads each month yet have <80 total reviews at the time this episode went live. Thank you!

Essential Background:

  • Our first episode, “Our Financial Past and our FIRE Present – Two Sides of FI is where it all began for the show. 50 episodes later, there certainly have been plenty of changes – and improvements (particularly on Jason’s side of the screen, as he likes to point out). This episode is the best place to learn about our financial backgrounds a bit better.
  • So, What’s Your Financial Independence (FI) Number? was one of our early popular – and controversial videos. We’ve got a long history with this question, and you won’t want to miss the end of today’s episode to hear our current thoughts on it. But this earlier installment sets the stage for this essential question + many FIRE fundamentals.
  • We’ve actually done another Q&A episode: “Answering Your Financial Independence Questions”. In this video, we tackled topics including changing withdrawal rates, our FI numbers, redefining identity in early retirement, rental real estate, and more.
  • In today’s episode we referenced a fun experiment, captured in “We Each Hired a Flat Fee Financial Advisor. Was it Worth It?”. Prior to this video, we each hired the same fee-only, advice-only advisor to evaluate our portfolios and answer our questions. We then shared how we found this advisor, what the process was like, the specific questions + answers we had, and who we believe could benefit from such a service.
  • Safe Withdrawal Rate has been an ongoing topic for us on 2SFI, and naturally it came up here as well. Did you know we spoke with SWR expert, Karsten Jeske? To see that episode, our follow-up conversation, and get the best collection of all the resources we have on this topic (including the free SWR Toolbox), you’ll want to see this show notes page.

As a complement to Two Sides of FI, Jason’s milestones blog posts are perhaps the easiest way to understand what his journey has been like since retiring early. In these articles, he discusses candidly what he’s felt, experienced, and achieved in the 2+ years since he left his career behind. If there’s a specific topic you’re seeking, don’t miss this list of all his blog posts to date.

Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing is a book by Bronnie Ware that we mentioned in this episode. It originally started as a blog post, outlining the most common regrets that the people she had supported through palliative care had expressed. The post quickly blew up and was viewed by more than three million readers worldwide in its first year. Bronnie subsequently wrote this fascinating and meaningful book capturing all that she learned.

CoastFI came up in a question we addressed in this video. 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 last year? If you missed it then, you’ll definitely want to check out A CoastFI Path to Financial Security: An Interview with Catherine.

Eric has talked about his “Possible Futures” Notion page in several episodes to date. Here is a screenshot of the kind of information he and Laura track here

In today’s episode, we shared footage of what Eric’s filming setup looks like. For the full details on the equipment he uses, check out this page.

By his own description, Jason’s filming setup is more “bespoke”. They say a picture is worth a thousand words:


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

How I Plan to Retire Early on a $50K Salary

Can you retire early without a high-paying tech industry salary? In this episode, we talk with Stephen about how he plans to do just that. At 30 years old, he’s earning $50k as a higher education administrator, yet he plans to retire with at least a million dollars by his early 50s. How will he do that? Join us as we discuss his plans, the role of financial discipline, why he doesn’t feel he’s overly frugal, and the challenges of his FIRE path.

Show notes may be found below the video


Show Notes

Essential Background:
Are you newer to the show? If so, you may not have seen our first two episodes, which include a lot of background on Jason + Eric’s lives. Check out Our Financial Past and our FIRE Present and Two Careers, Two Paths to Financial Independence, to learn how we got our own start in life and in the workplace.

Stephen’s Budget: Are you interested in more details on Stephen’s financial picture? He graciously shared the Sankey diagram below, which captures his Jan-Jul 2022 income and expenses. This visualization makes it easy to see both sides of the balance sheet, and provides a lot more detail on Stephen’s finances than we were able to achieve in our conversation.

The Shockingly Simple Math Behind Early Retirement is an article by blogger Mister Money Mustache, which many cite among their most important inspirations for getting on the FIRE path. As you heard from Stephen, MMM was one of his early sources as well.

Still doubting whether FIRE is achievable on a more traditional salary? See The Millionaire Next Door (Thomas Stanley), a profoundly insightful book for a very easy read. Dr. Stanley studied wealth and the habits of the wealthy for many years, capturing his observations in this work and others. Learn how frugality, living below one’s means, and investing, truly powers the path to financial independence.

The Simple Path to Wealth (JL Collins) is widely regarded by many in the FIRE community as the most impactful book to their own journey. This fast and easily digestible read is chock-full of investment guidance that you will understand immediately and can readily apply. There is no better starting point to your FIRE journey than this book.

We didn’t dig into it, but you may have heard Stephen refer to feeling “YNAB poor” in this episode. What is YNAB? You Need a Budget is a popular budgeting tool for many in the FIRE community. If manual spreadsheets aren’t your thing or you’ve struggled with budgeting in the past, this may be a good solution. YNAB has a generous, free 34-day trial so you can see how well it works to help you understand and control spending. (affiliate link; no credit card needed )


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

If You Want Financial Freedom You Can’t Ignore This (Parts 1 and 2)

We avoided estate planning for a long time; here’s why you shouldn’t. Without an estate plan, you’re giving over the control of what happens to all your assets to others. In part one of this two-part series, Eric + Jason talk about what they did to – finally – get their respective plans in place. Topics discussed in this episode include the elements of estate planning, why people delay + how to get started, living trusts, and taking care of your heirs. Don’t be like those who put this off “until they’re older”: join us now for the first episode of this two-part series.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.

Part 1

Part 2


Show Notes

Essential Background: If you’re not familiar with our family situations, check out our earlier videos where we’re joined by our spouses (part 1 and part 2), and the recent episodes about our kids (part 1 and part 2). Note that each is a two-part series, and separate links are provided for all videos.

Estate planning FAQs: After viewing these videos, you’ll be better equipped to ask deeper questions about your own estate planning needs. We found this resource from the American College of Trust and Estate Counsel (ACTEC) to be really helpful. All of the high level topics discussed in our series are covered here.

What is a trust? This Investopedia article is a good starting point for clarification on the different types of trusts and other pertinent details. This is a subject where it’s easy to fall down a very deep rabbit hole, and having a good foundation first is always helpful. Be sure to research the particulars of your state or country as well, as things differ substantially.

Advanced care planning is an essential element of estate planning, and one we touched on in part 1 and expand upon in part 2 of this series. Thinking through your own preferences can be difficulty, but planning for them is vitally important.

Umbrella Insurance is among the most important (and least expensive) tools available to protect your assets. These policies sit on top of your existing liability coverage (auto, home, etc) and extend it. To learn more about umbrella policies, check out this Investopedia post.


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