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.

When is Enough, Enough? Working After Financial Independence

Why would anyone continue to work for money after they’ve achieved financial independence? In this episode, 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.


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, 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.

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

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

Retired Early to USVIs, Florida, and Spain: How They Did It

This is a conversation Eric had with Jeff, a self-described: financially independent, recreationally employed realtor. He and Eric crossed paths as Eric was researching his dream of retiring to the US Virgin Islands. Jeff and his wife, a Spanish teacher, lived in St Thomas for two years making content about their life there on two YouTube channels: How2Beach and TheRetirementality offering an honest review of the pros and cons of living on a tropical island. It helped change Eric’s mind about living there too!

Jeff went from broke at 38 to financially independent at 45. He and his wife have six rental properties in total and the income from those have enabled them to move around the world as they choose. As of early 2024, they’re preparing to relocate to Spain. 


Even though Jeff took risks many aren’t willing to take, we think his story is interesting because it proves there’s no one way to reach FIRE. Not only were they able to reach FI in a few short years, they did it on modest income (a teacher’s and a realtor’s salary). So, if you’ve considered what a life outside the mainland US might look like, we know you’ll find his story interesting.

Show Notes:

Be sure to check out Jeff’s two YouTube channels:


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

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.

FI-nancial Checkup: New Year Routines + Goals for 2024

What financial lessons did we learn last year and what will we do differently in 2024? In today’s episode, Eric and Jason discuss their end of year review processes. Topics include investing goals, their net worth reviews, lessons learned, and much more. Be sure to check out the show notes below the video!


Show Notes

Essential Background:

  • We’ve talked about our review processes before, and for the full details check out Our Net Worth Is Up! Sharing Our Financial Review Process. If you don’t have a process for regular financial reviews, you aren’t alone. Many people are unsure about how to calculate their net worth and keep their personal finances on track. In this episode, Eric and Jason share their simple pre- and post-FI review processes for net worth tracking, portfolio review, setting savings and budget goals, and more.
  • Jason mentioned staying below his safe withdrawal rate ceiling in this episode. For all the details (and more), you’ll want to see our page dedicated to the Safe Withdrawal Rate Toolbox. If you’re familiar with Karsten Jeske, you’ll definitely want to check this out. It has all the information you need including all three videos in our series, including walkthroughs of the tool and the CAPE-based strategy that Jason referenced here.
  • 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 lots of information on his various passive income streams
  • We talk about travel often on the show – it’s a clear priority for us both. Did We Budget Enough for Travel in Early Retirement? is our most recent episode on the topic. What happens if all the travel you want to do after retiring would break the budget? In this episode, Eric and Jason talk about the importance of travel to their early retirement plans. Topics discussed include financial concerns, disagreeing with your spouse, the value of planning by age range, and much more.
  • Want to learn more about that budget-busting 50th birthday celebration? Will This Get Us Kicked Out of the FIRE Movement? has all the details. 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.

We talked about New Retirement in this episode. Jason really likes this platform and plenty of people on Reddit are discussing this comprehensive retirement planning tool as well. They have a full-featured free offering  as well as a reasonably priced paid “PlannerPlus” version with a host of really nice features, as well as consulting services. Huge benefits of PlannerPlus include a solid Roth conversion modeler and Monte Carlo analysis. Be sure to check out their 14-day free trial and see if you’re as convinced as Jason was! There’s a very active Facebook community around the tool as well.

Jason referenced a very popular Wait But Why post in this episode. The Tail End is the material in question. We wholeheartedly recommend it as a must-read for anyone – but be prepared for some thought provoking stuff!


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.

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.

Did We Budget Enough for Travel in Early Retirement?

What happens if all the travel you want to do after retiring would break the budget? In this episode, Eric and Jason talk about the importance of travel to their early retirement plans. Topics discussed include financial concerns, disagreeing with your spouse, the value of planning by age range, and much more. Be sure to check out the show notes below.


Show Notes

Essential Background:

Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins – was mentioned by Eric here, and is a much-discussed book in the FIRE community. 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.

Are you familiar with the Camino de Santiago? Jason talked a little about this including his plans to walk the most famous of the Camino routes, the Camino Francés (the French Way), in 2025. There is a wealth of information available online, including on YouTube. If you’re US-based, consider checking out the American Pilgrims site.

Wondering what that word was we were trying to pronounce when talking about traveling to Croatia? Hvar is a Croatian island in the Adriatic Sea, located off the Dalmatian coast, lying among several other islands. It’s consistently ranked in the top of many lists concerned with the best of island travel, and Hvar promotes itself as “the sunniest spot in Europe”.


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.