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We Have Enough. So Why Is Spending Still Hard?

Your FIRE plan worked — so why is spending still so hard? In this episode, Jason (year 7) and Eric (year 2) share a candid early retirement update. Both portfolios have grown well above their FIRE numbers despite years of withdrawals, and a fee-only advisor delivered a surprising verdict: spend more. Learn why unwinding the accumulation mindset is harder than the math, how “life support” for adult kids reshapes the budget, and why unstructured time might be the truest form of wealth – and much 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, which started even before Two Sides of FI began. Get more information on those archived posts here.

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Year 2 vs. Year 7: What Early Retirement is Really Like

Is early retirement everything you imagined or does the reality take years to settle into? In this honest check-in, Jason (year 2) and Eric (year 7) compare notes on what post-FIRE life actually feels like from two very different vantage points. They cover decision fatigue, the challenge of replacing work’s structure, and why the emotional side of retirement rarely gets the attention it deserves.

Show Notes

Essential Background:

Jason referenced his interest in options trading in this discussion. While not for everyone, it’s a topic of great interest among many in the FIRE community. In “How Options Trading Led this Engineer to Financial Independence in His 30s”, Jason spoke with David Sun, an engineer who stumbled into options trading . Only ten years later he launched his first hedge fund. Now in his mid-30s, David shared the keys to his success, as well as his thoughts on the role of options trading in a FIRE portfolio.

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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Is This Goodbye?

Are we really ready to walk away from Two Sides of FI? In this candid conversation, Jason and Eric reflect on more than four years of recording together, what the project has meant, and whether it still fits into their lives. They talk openly about the rewards of community and connection, the challenges of generating new topics, and the weight of obligations in retirement. Is this the end, or just a pause?

Show Notes

Jason wrote a blog post to accompany this episode. This was written a few weeks after this episode was recorded and edited. It is meant to be read after viewing the video.

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

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Life After FIRE: Your Toughest Questions, Answered

After five years of early retirement and 100 episodes of Two Sides of FI, what have we learned? A lot—and we’re sharing it all. To mark this milestone, Eric and Jason sit down for an honest, wide-ranging AMA based on questions from our community. We cover everything from money and mindset shifts to healthcare, travel, and even music choices. Whether you’re already on your FIRE path or just curious what life really looks like on the other side, this conversation is for you.

Jason’s companion blog post on our 100-episode milestone:

Show Notes

Essential Background:

Empower (formerly Personal Capital) is a commonly used free tool for tracking your various investment accounts, understanding your asset allocation + rebalancing opportunities, and monitoring your net worth. PC has simple to use account linking to make it a more automated experience. Give it a try risk-free!

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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Financial Independence at 50 (Finally!)

After years of planning, Eric and Laura have finally reached their FI number at 50! They discovered the FIRE movement 5 years ago and set their sights on achieving financial independence by 2024. Now, with both of their boys off to college, a paid-off home, and a 80/15/5 split between equities, fixed income and cash, they’ve officially hit their financial independence (FI) goal and plan to retire early.

In this video, they discuss the challenges of moving goalposts, their decision to keep running Eric’s business, 30X40 Design Workshop (on their own terms), and their plans for the future. Laura will be leaving her job as a research scientist in January 2025 to operate 30X40 remotely, with a goal of maintaining a flexible, time-limited schedule. They also cover practical topics like their pretax/taxable split, health insurance considerations, and their withdrawal strategy. Learn what reaching FI looks like for them, the steps they’re taking next, and what their plans are moving forward!

Show Notes

Essential Background:

We touched on a number of 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 Eric and Laura’s FI path:

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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Four Years Later: What I Wish I Knew Before Retiring Early

Four years after retiring early at 47, Jason reflects on the key lessons he wishes he knew beforehand. He discusses his portfolio, spending habits, healthcare, mental health, relationships, and more.

Show Notes

Essential Background:

Robert Atchley’s Six Phases of Retirement was discussed at the end of our conversation in this episode. While not the original 1976 manuscript, the article linked here is a good summary of the concepts Atchley wrote about. If you are interested in the original text, “The Sociology of Retirement” is available from Amazon. On a related point, this blog post from Can I Retire Yet by Chris Mamula is a good deep dive into the six phases. It’s a worthwhile read.

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