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From Divorce to Financial Freedom: FI at 45

What happens when the plan was “we”… and now it’s just “me”? At 45, Kayla reached Financial Independence solo after divorce, living in the Bay Area without a tech salary. In this episode of Two Sides of FI, she shares how she rebuilt her finances, overcame her fear of investing, and designed a plan that works without a partner’s income or support. In this episode, Learn how a saving mentality and discovering the FIRE community in her 30s led her to the realization that early retirement was within her reach and how she achieved it.

Show Notes

Essential Background:

Kayla mentioned a book as a key part of her FIRE and investing eduction: The Simple Path to Wealth (JL Collins). It 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.

How do you find advice-only planners? Below you’ll find two resources. Please note that Two Sides of FI has no relationship nor do we receive any compensation from either:

1) XY Planning Network: As described on the site, their member advisors ascribe to fiduciary and CFP standards, earn no commissions, and require no minimum assets. They have convenient filters to allow searching by advisor specialities, including those with FIRE experience. Many work under multiple fee models, including advice-only, which can be a good source for one-time consults without any

2) Cody Garrett, CFP and advice-only planner from Measure Twice Financial, shared this list in the past on Twitter. As he described it, “these 11 advisors provide comprehensive financial planning without any expectation, obligation, or even the option to manage client investments. Options for project-based, hourly, or ongoing.” You’ll note there is overlap between these resources, which makes sense. But this is the list Cody has shared with prospective clients, so one can presume there’s been some personal vetting.

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, which started even before Two Sides of FI began. Get more information on those archived posts here.

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It’s Harder to Retire Than I Expected

Do some find it hard to retire because they don’t know how to stop working? In today’s episode, Eric talks with Jason about the challenges he’s experienced after achieving FI, finding it hard to ramp down his business. Are we just wired to work hard or is there more to it? We discuss why Eric can’t stop working, how it affects his spouse, and what Jason has learned in his five years of RE.

Show Notes

Essential Background:

  • How Do I Know When I’m Ready to Retire? Most on the FIRE path focus on the financial elements because in essence, they’re the easiest part of the equation. But many people struggle with the emotional elements of the decision. We tackle it head-on here.
  • Eric’s path to 90% passive income is truly impressive. To learn what his approach was like and to benefit from the many lessons he learned, check out Passive Income = A Path to Financial Independence (Part 1) and Lessons Learned in 7 Years Earning Passive Income – A Path to FI (Part 2). You won’t want to miss the show notes for these given all the valuable content Eric has linked here.
  • For more on Eric’s career journey as well as Jason’s path, you won’t want to miss Two Careers, Two Paths to Financial Independence.
  • 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 were joined by Fritz Gilbert, who blogs at The Retirement Manifesto. Our discussion went 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.
  • One of the ways many early retirees stay busy is to take on some time of part-time “fun job”. But have you truly retired if you continue to do any work for money? In Financially Independent, Recreationally Employed (FIRE), Eric and Jason talk about their respective journeys, why the latter has a part-time job after retiring, the internet retirement police, and much more.
  • How would you feel if you worked hard to retire early and later realized you hated being retired? In Does Retirement = Happiness?, we address the reality that some people who achieve FIRE are disappointed, bored, or otherwise unhappy in retirement.
  • Did you see our recent episodes regarding Eric’s spouse, Laura’s, decision to retire from her career as a scientist? If not, you’ll definitely want to view:
  • The story begins with One Step Closer to FI/RE – Giving Notice. In this episode, Eric and Laura discuss their preparations as they near their FI number and Laura prepares to notify her employer that she’s leaving. Recorded in the fall of 2023, this behind-the-scenes discussion was prepared for publication the week Laura submitted her resignation notice.
  • Next we published Unexpected Reactions to My Early Retirement, Contempt, concern, surprise, envy, admiration, and support; just a few of the reactions Laura received when she announced she was retiring early, closing her biomedical research laboratory, and beginning a new phase of life beyond work. Some reactions were expected and some surprised her. In this episode, Eric and Laura unpack these interactions and chart their next steps as they prepare to leave work and step into early retirement.
  • What’s it really like to be 5 days away from early retirement? The last chapter (so far) in this story is Retiring (Early) in 5 Days. Am I Ready? Whether you’re questioning if early retirement is worth leaving a dream job, wrestling with your professional identity, or wondering how it feels when that last paycheck stops, Laura’s story offers inspiration and real-time insights about one of life’s biggest transitions.

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, which started even before Two Sides of FI began. Get more information on those archived posts here.

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How Do I Know When I’m Ready to Retire?

How do you know when it’s the right time to retire? Most on the FIRE path focus on the financial elements because in essence, they’re the easiest part of the equation. But many people struggle with the emotional elements of the decision. In this episode, Jason and Eric talk about their own experiences and what they’ve found most challenging.

Show Notes

Here are the retirement personas that Eric shared in our conversation:

Essential Background:

  • 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 were joined by Fritz Gilbert, who blogs at The Retirement Manifesto. Our discussion went 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.
  • In We Each Hired a Flat Fee Financial Advisor. Was it Worth It? Eric and Jason each hired the same fee-only, advice-only advisor to evaluate their portfolios and answer questions. They share how they found this advisor, what the process was like, the specific questions + answers they had, and who they think could benefit from such a service.
  • Retiring early is a dream for many but the decision to leave the workplace early can impact us in ways we may not have predicted. In “Retiring Early – So Why Am I Worried?“, we discussed the first year of Jason’s early retirement and Eric shares his own concerns as he approaches FI.
  • Did you see our recent chat with Jordan “Doc G” Grumet, titled “Will You Run Out of Money or Time? FI Advice From a Hospice Doctor“. The topic of purpose can be found all over our conversation with him. In a related vein, Jason spoke with Doc G again in “Fulfillment Beyond FI: Life After Early Retirement with Jason”, on the Earn and Invest podcast.
  • How does it feel when you haven’t yet found your purpose after retiring early? In this episode, Retired Early and Feeling Lost. What’s Next?, Jason talks with Eric about the first three years years exploring his post-FIRE purpose. They discuss the phases of retirement, seeking out meaningful projects, lessons learned along the way, and much more. 
  • Did you see our recent episodes regarding Eric’s spouse, Laura’s, decision to retire from her career as a scientist? If not, you’ll definitely want to view:
    • The story begins with One Step Closer to FI/RE – Giving Notice. In this episode, Eric and Laura discuss their preparations as they near their FI number and Laura prepares to notify her employer that she’s leaving. Recorded in the fall of 2023, this behind-the-scenes discussion was prepared for publication the week Laura submitted her resignation notice.
    • Next we published Unexpected Reactions to My Early Retirement, Contempt, concern, surprise, envy, admiration, and support; just a few of the reactions Laura received when she announced she was retiring early, closing her biomedical research laboratory, and beginning a new phase of life beyond work. Some reactions were expected and some surprised her. In this episode, Eric and Laura unpack these interactions and chart their next steps as they prepare to leave work and step into early retirement.
    • What’s it really like to be 5 days away from early retirement? The last chapter (so far) in this story is Retiring (Early) in 5 Days. Am I Ready? Whether you’re questioning if early retirement is worth leaving a dream job, wrestling with your professional identity, or wondering how it feels when that last paycheck stops, Laura’s story offers inspiration and real-time insights about one of life’s biggest transitions.

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, which started even before Two Sides of FI began. Get more information on those archived posts here.

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Retiring (Early) in 5 Days. Am I Ready?

What’s it really like to be 5 days away from early retirement? Join Laura, a 51-year-old scientist, as she discusses her final days running her research lab. From wrestling with the “Am I really ready?” question to unexpected tears at faculty meetings to cleaning out decades of research, she opens up about the reality of choosing early retirement at the peak of her career. This isn’t just another FIRE success story – it’s a candid look at what it really feels like to step away from a meaningful career when you’re financially independent but emotionally invested.

Whether you’re questioning if early retirement is worth leaving a dream job, wrestling with your professional identity, or wondering how it feels when that last paycheck stops, her story offers inspiration and real-time insights about one of life’s biggest transitions.

Don’t miss the show notes below for key background including other conversations featuring Laura!

Show Notes

Laura + I want to thank the Two Sides of FI community for all your comments, personal messages, and words of encouragement as we’ve been navigating this transition. Thank you for being a part of our journey!

Essential Background:

  • Have you seen our other recent episodes with Laura? If not, you’ll definitely want to view:
    • The story begins with One Step Closer to FI/RE – Giving Notice. In this episode, Eric and Laura discuss their preparations as they near their FI number and Laura prepares to notify her employer that she’s leaving. Recorded in the fall of 2023, this behind-the-scenes discussion was prepared for publication the week Laura submitted her resignation notice.
    • Next we published Unexpected Reactions to My Early Retirement, Contempt, concern, surprise, envy, admiration, and support; just a few of the reactions Laura received when she announced she was retiring early, closing her biomedical research laboratory, and beginning a new phase of life beyond work. Some reactions were expected and some surprised her. In this episode, Eric and Laura unpack these interactions and chart their next steps as they prepare to leave work and step into early retirement.
    • Laura also took part in a very popular two-part series, Talking with our Spouses About FIRE: 2 x Two Sides of FI. In Part 1, Eric + Jason talk with Laura + Lorri about getting onboard with FIRE, financial topics including budgeting and setting the FI number, as well as the emotional aspects of choosing the FIRE path. In Part 2, they discuss how they share financial responsibilities, the importance of finding friend networks, talking to their children about FIRE, and their hopes for their post-FI lives.
  • Did you know that Laura and Eric recently achieved their FI goal? In Financial Independence at 50 (Finally!), Jason and Eric discuss the challenges of moving goalposts, the decision to keep running Eric’s business, 30×40 Design Workshop (on their own terms), and their plans for the future.
  • For more on the rules and practices Eric and Laura followed in order to reach their financial goals, see Our 80/20 Rules for Early Retirement: How We Did It. In this episode, Eric and Jason talk about their personal “80/20 Rules” for retiring early. That is, the decisions they made along the journey that served as key pivot points towards ensuring their achievement of financial independence.
  • A core element of Laura + Eric’s ability to achieve FI was Eric’s 30×40 Design Workshop business. If you haven’t seen our two-part series on the journey from zero to 90% income from passive sources, drop everything and check it out: Passive Income = A Path to Financial Independence (Part 1) and Lessons Learned in 7 Years Earning Passive Income – A Path to FI (Part 2). The link to Part 2 contains the show notes, which have a wealth of information provided by Eric. Don’t miss it!

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How Options Trading Led this Engineer to Financial Independence in His 30s

How can a hobby turn into a second career and lead to financial independence before 40? In this episode, Jason talks with David Sun, an electrical engineer who stumbled into options trading after hearing about it from a fellow grad student. Only ten years later he launched his first hedge fund. Now in his mid-30s, David shares the keys to his success, as well as his thoughts on the role of options trading in a FIRE portfolio. Be sure to check out the show notes linked below for all the key resources shared in this conversation.

Show Notes

Are you completely new to options trading? The seemingly endless vocabulary can be a big barrier to entry for newcomers. Don’t miss our options glossary which you can find on the show notes page for Jason’s chat with Karsten. There’s a ton of useful information linked on that page so be sure to check it out.

A reminder that neither we at Two Sides or FI, nor David Sun, are providing individual investment advice. Each of us has our own circumstances, risk tolerance, and risk capacity. Options trading, while potentially lucrative, is also potentially risky given the regular use of leverage, and is therefore best suited for experienced investors. We strongly recommend the use of simulated or “paper trading” accounts (you can create one free at Interactive Brokers and Charles Schwab, among others) to learn and test strategies. You may also benefit from consultation with financial professionals.

Essential Background:

  • David and Jason talked about the latter’s earlier chat with Karsten Jeske regarding his SPX strategy. For more on this, you won’t want to miss “He Earned a Million Dollars Trading This Option Strategy”.
  • Among our most popular episodes to date were our chat with Karsten about his Safe Withdrawal Toolbox, and our own four-part series on how we use this essential retirement planning tool. You can find all of these and much more at our SWR landing page, including a link to Big ERN’s options posts.
  • David has also spoken with Karsten. Jason enjoyed this Trade Busters episode, titled “From FIRE to PCR w/Karsten Jeske aka Big ERN”. It’s an important element of understanding how Karsten’s own options trading strategy has evolved over time.

David Sun’s Trade Busters landing page is a great starting point to dive into all the valuable content he has produced. To contact him or request access to his Discord, you’ll want to head here. The Trade Busters podcast is also an excellent resource. Be sure to check out Episode 48, “Where do I Start?”. You can also follow David on Twitter.

In our conversation, David mentioned several good resources for getting started with an education in options trading. The Options Alpha courses, and Options Playbook are one he found particularly useful in his own path to success.

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.

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Empty Nest, New Challenges: What’s Next After Early Retirement?

In this episode Eric and Jason share their experiences as new empty nesters and reflect on the emotional and identity shifts that come with this major life change, especially after retiring early. They dive into how life changes when the kids are gone and work is no longer a primary focus. From adjusting to the quiet at home to rethinking purpose and identity, they discuss the highs and lows of this new phase. Join them as they explore what comes next in this post-parenting, post-career chapter of life.

Show Notes

Essential Background:

In this episode, we touched on a number of topics that we’ve explored greater depth in earlier conversations. Check these out for all the details:

  • Retiring early is a dream for many but the decision to leave the workplace early can impact us in ways we may not have predicted. In “Retiring Early – So Why Am I Worried?“, we discussed the first year of Jason’s early retirement and Eric shares his own concerns as he approaches FI.
  • 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. 
  • 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 were 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.
  • One of our most popular Two Sides of FI episodes of 2022 was our chat with Jordan “Doc G” Grumet, titled “Will You Run Out of Money or Time? FI Advice From a Hospice Doctor“. The topic of purpose can be found all over our conversation with him. In a related vein, Jason spoke with Doc G again in “Fulfillment Beyond FI: Life After Early Retirement with Jason”, on the Earn and Invest podcast.
  • 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.
  • 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.

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.

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Our 80/20 Rules for Early Retirement: How We Did It


“If you are not aggressive, you are not going to make money, and if you are not defensive, you are not going to keep money” (Ray Dalio). In this episode, Eric and Jason talk about their personal “80/20 Rules” for retiring early. That is, the decisions they made along the journey that served as key pivot points towards ensuring their achievement of financial independence.

Show Notes

Essential Background:

We touched on quite a few topics that we explored in much greater depth in earlier episodes. For the full details, you won’t want to miss these shows which paint a fuller picture of our FI paths:

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.

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Unexpected Reactions to My Early Retirement

Contempt, concern, derision, surprise, envy, admiration, and support; these are just a few of the reactions Laura received when she announced she was retiring early, closing her biomedical research laboratory, and beginning a new phase of life beyond work. Some reactions were expected and some took us by surprise.

In this episode, Eric and Laura unpack these interactions and chart their next steps as they prepare to leave work and step into early retirement. If you didn’t see Part 1 of this conversation, you’ll want to check out One Step Closer to FI/RE – Giving Notice.

Laura + I want to thank the Two Sides of FI community for all your comments, personal messages, and words of encouragement as we’ve been navigating this transition. Thank you for being a part of our journey!

Links + Resources

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One Step Closer to FI/RE – Preparing to Give Notice

Eric here checking in with a quick update and preface to our new video. Sorry for the gap in our publishing schedule, Jason has been off walking the Camino de Santiago from Portugal to Spain (you can follow along on his blog here) and I’ve been traveling to warm places to escape winter in Maine.

In this episode I asked my wife, Laura, to join me to discuss next steps as we near our FI number. Our discussion was recorded in the fall of 2023, as a behind-the-scenes episode. Just this past week (mid-March 2024) she gave her notice to her employer of 23 years and now we can finally share it publicly. We discuss our hesitations, how Laura’s thoughts have changed since first learning about the FI/RE movement, and ready ourselves for what’s ahead.

Watch the Video on YouTube

The reactions to her departure from her long-time job have been interesting. Most express surprise and offer enthusiastic support. Some respond with envy, “Must be nice…” and even concern, “Is everything okay?” And still others immediately reframe the conversation around their own plans for retirement either near or far in the future. There’s much to unpack here and I think it’ll make for a great episode when Jason and I reconvene.

Nevertheless, sharing this experience with the Two Sides of FI community feels incredibly rewarding. We’re thrilled to openly discuss our ‘secret’ here on our Maine island and your support has been invaluable to us!

Thank you for being a part of our journey.

Links + Resources

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

Show notes may be found below the two videos

Part 1: 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.

Part 2: Checking In: Year One of Early Retirement

A year later, Jason and Eric check in with their friend Erik, who retired early at 49 while his wife continues to work. In this follow-up episode, we find out how things are going and what important lessons he learned during his first year of early retirement.

Show Notes

Essential Background:

So far, Erik has had zero interest in doing any kind of paid work. In “When is Enough, Enough? Working After Financial Independence”, 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.

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? 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.