Retiring Early Made This Possible

What essential lessons did Jason learn from the most impactful travel he’s done to date? In this episode, Eric and Jason catch up on a number of recent changes in their lives. Topics discussed include Eric and Laura’s recent big announcement, Jason’s Camino experience, the benefits and challenges of pre- and post-FI travel, and much more.

Be sure to check out the show notes below the video!


Show Notes

Essential Background:

Interested in learning more about Jason’s Camino de Santiago experience? You’ll want to see all of Jason’s blog posts leading up to and written during his recent walk on the Camino Portugués. There you’ll find information on his preparation as well as day by day accounts of his route, photos he took of the journey, as well as all his thoughts on the important lessons he took home from the Camino.

  • We talk a lot about travel given how important a part it plays in our retirement planning and we have two episodes wholly focused on the topic. “How We Travel: Pre + Post Financial Independence” is the first of these, and concerns just how different pre- and post-FI travel can be. More recently, we dug into the financial side of travel in “Did We Budget Enough for Travel in Early Retirement?“. Here we talked about the myriad financial elements of travel, disagreeing with your spouse, the value of planning by age range, and much more.
  • Did you see our episode where Laura talked with Eric about her plans to give notice to retire from her career in science? If you didn’t, “One Step Closer to FI/RE – Preparing to Give Notice” is a must-watch. A natural pairing to this is the earlier episode, Financially Independent, Recreationally Employed (FIRE). Here, Eric shares his thoughts on how he’s thinking about his business these days and what that might mean for the RE part of his FIRE plans.
  • Did you know we’ve had both our spouses on the show before? We’ve got a two part series from our conversation with Lorri and Laura, covering a wide range of topics. In part 1, we talk 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, we discuss how each couple shares financial responsibilities, the importance of finding friend networks, talking to our children about FIRE, and our hopes for their post-FI lives.
  • In this show we ended with some discussion of our kids’ college plans. We have two episodes wholly dedicated to our children, covering a broad range of subject areas – financial and otherwise. Be sure to check out both episodes – Teaching Our Teens About FI and Money (Part 1) and Financial Lessons We’re Passing On (Part 2).

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

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


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

One 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.

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

My Healthcare Costs in Early Retirement (Year 3)

What’s the true cost of healthcare in early retirement and can it break your budget? In this episode, Jason shares his experiences with Eric after three years on an ACA health insurance plan. Topics discussed include selecting and evaluating plans, how to estimate your income, premium tax credits, and why 2023 was Jason’s worst year for healthcare expenses to date.

Be sure to check out the show notes below the video!


Show Notes

Essential Background:

COBRA can be an important bridge strategy for health insurance for many people in the US, just as it was for Jason. The linked page is a great starting point and points to a variety of other sources that you will find helpful. Please note that some states have additional information available, and may even have further extension coverage offered beyond the federal requirements. As one tip – the best time to research COBRA is before leaving your employer. Your HR benefits partner or healthcare plan administrator is an ideal starting point to gather more information about your company’s plan and coverage options.

Healthcare.gov is the best starting point when it comes to information about Affordable care Act (ACA or “Obamacare”) plans. In many cases, you will be directed to a state-run plan with its own website, but this is not always the case. Presently, a number of states have federally-run, state-federal partnership, or federally-supported plans. Where there isn’t a state exchange, you’ll see options and apply for coverage directly from healthcare.gov.

Choosing a metal tier is an essential part of selecting an ACA plan. This chart from healthcare.gov explains the details of the Bronze, Silver, Gold, and Platinum options available. Importantly, the plan categories are based on how you and your plan split the costs of your health care; they have nothing to do with quality of care.

ACA plan subsidies (premium tax credits) are a topic we spent some time on in the episode. Many on a FIRE path plan on having incomes well within the limits where cost-reducing subsidies apply. Typically, as long as your household income is below 400% of the Federal Poverty Limit (FPL), these apply. When you investigate ACA coverage options, information will be provided on your eligibility for these based on the income information you supply.

Obamacare Optimization in Early Retirement is a great Go Curry Cracker article that goes into extensive details on ACA optimization, for those ready for a deeper dive. It’s worth noting that this is just one of a number of good ACA-related articles on GCC, which you can access via this tag.

Medicare.gov should be your starting point for researching healthcare coverage options for US retirees once they reach 65 years of age. It’s never too early to understand what this will look like for you even though it may seem far in the future. If you’re new to the topic, easy to digest summary information is available on this page. As you develop your retirement budget, this site will be a useful source of information to estimate those future costs.


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

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


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

Retired Early and Feeling Lost. What’s Next?

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


Show Notes

Essential Background:

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

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

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


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

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


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

The Health Risks of Early Retirement

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


Show Notes

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

Essential Background:

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

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


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

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


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

One More Year: My Decision to Postpone Early Retirement

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


Show Notes

Essential Background:

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

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

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


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

Will This Get Us Kicked Out of the FIRE Movement?

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

Show notes may be found below the video


Show Notes

Essential Background:

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

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

A photo of the menu from our French Laundry meal

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

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

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

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


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

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


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

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.