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.

Halfway to FI? Surviving the Boring Middle

How can you accelerate the boring middle on the path to reaching your financial independence goals? Online FIRE communities are full of posts talking about the challenges of “the messy middle” and, “the long boring middle.” Eric and Jason discuss the topic from their pre- and post-FI viewpoints, sharing their own experiences.

Show notes may be found below the video


Show Notes

Essential Background:

We referenced several Reddit posts in this episode. For more on that, check out these links – and don’t forget to see the comments, where you’ll often find good value in the many different viewpoints in our community:

If you DO like tracking FI milestones, free resources like Empower (formerly Personal Capital) can make that 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 )

The Tail End is the great Wait But Why post that we discussed in this episode. We wholeheartedly recommend it as a must-read for anyone – but be prepared for some thought provoking stuff!

Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins – which Jason did end up reading! – 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.


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.

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.

This is part 2 of our How NOT to FI/RE series. For part 1 and the PRE FI/RE examples, be sure to check out that video here: https://youtu.be/Jb438jvebd0


Show Notes

For Jason’s own thoughts, observations, and lessons learned in his first year of early retirement, check out this Two Sides of FI episode, as well as his blog post.

Are you on Reddit? Join us in the Two Sides of FI subreddit if you’d like to continue the conversation.

Full text of Reddit posts from the episode:

You can find information on the tools we mention in the episode along with additional information in the Resources section of this site! To navigate to this material at any time, just click the menu button at the top of any page on the site.

How NOT to FIRE – Part 1 (Pre-FI/RE)

How much do you really need to achieve financial independence? We decode the math On the path to financial independence, there are ample opportunities for mistakes and missteps. In today’s episode, we review stories from people who shared their FIRE experiences online in the hopes of educating others. Here we review five of these tales: incurring tragic losses due to trying to beat the market, losing 75% of your portfolio value due to sector investing, regretting aggressively saving at the expense of living your life, and resenting your partner who doesn’t have the same degree of FIRE ambitions as you do.


Show Notes

You can find information on the tools we mention in the episode along with additional information in the Resources section of this site! To navigate to this material at any time, just click the menu button at the top of any page on the site.

Full text of Reddit posts from the episode: