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.

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.

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.

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.

Show notes may be found below the video


Show Notes

Essential Background:

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? As a bonus, 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.

Can You Reach FI Faster? Advice From Someone Who Did.

Can you shorten the time to achieve financial independence (FI)? In this episode, Eric talks with Jason about his journey to FI and the steps he took to reach FI faster and retire before 50. Topics discussed include risks taken + sacrifices made, how Eric’s path differed, why early retirement is so attractive, and much more.

Show notes may be found below the video


Show Notes

Essential Background:

The FI journey is far from a solo one for most people, particularly those with long term partners or spouses. As we discussed in this video, it’s essential to be on the same page regarding FI path decisions. 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? As a bonus, 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 on their revised asset allocation last year.

We mentioned BaristaFIRE in today’s episode. In the linked post from Financial Samurai, he describes it as “being able to retire before the conventional age of 60+, but taking on a part-time job (e.g. like at a coffee shop) for supplemental income and potentially subsidized health insurance.” This article provides a good look at this path, and is an effective primer for those seeking more information. In addition to the financial calculations provided in the article, there are numerous supporting tools available online including this BaristaFIRE calculator from Walletburst.

Another common FI path is called CoastFIRE. 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 know we talked with someone 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.

Halfway to FI? Surviving the Boring Middle

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

Show notes may be found below the video


Show Notes

Essential Background:

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

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

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

Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins – which Jason did end up reading! – is discussed often in the FIRE community, so no surprise it came up in this episode. It’s intended as a “practical guide on how to get the most out of your money—and out of your life”. If you like the aim of prioritizing memorable experiences far ahead of simply accumulating money for later in life, you’ll definitely want to check it out.


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

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


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

Our Net Worth Is Up! Sharing Our Financial Review Process

Do you have a process for regular financial reviews? If not, 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. Check the show notes for all the details.

Show notes may be found below the video


Show Notes

Essential Background:


In this episode, Eric mentioned Empower (formerly Personal Capital) for summarizing his portfolio performance as a part of rebalancing. 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 )

In this episode, Jason mentioned that he uses the software called YNAB to budget. What is YNAB? You Need a Budget is a popular budgeting tool for many in the FIRE community. If manual spreadsheets aren’t your thing or you’ve struggled with budgeting in the past, this may be a good solution. YNAB has a generous, free 34-day trial so you can see how well it works to help you understand and control spending. (affiliate link; no credit card needed for trial )

Are you interested in tracking net worth, income, FIRE progress, and your budget all in one convenient tool? This popular Reddit post by Redditor u/BloomingFinances outlines a free and powerful way that you can do just that.


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

Retiring With $2M: Here’s How We’d Spend It

Love it or hate it, budgeting is an essential part of financial success. In this episode, Eric and Jason share their own financial details using a simple, model budget and offer tips for making budgeting a less daunting task. See the show notes below, which include the full details of our budgets.

Show notes may be found below the video


Show Notes

This is a copy of Eric and Laura's budget fitted to the model described in the episode.

Eric + Laura’s Budget (click to enlarge)

This is a copy of Jason and Lorri's budget fitted to the model described in the episode.

Jason + Lorri’s Budget (click to enlarge)

Essential Background:

Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins, is discussed often in the FIRE community. As Eric shared 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.

Lumpy spending in retirement is another commonly discussed budget issue. Sinking funds are only one way to think about these occasional – and sometimes very large expenses. In the Reddit post “Budgeting for ‘one time expenses’ in retirement” and the comments, you’ll find some thoughts on this topic.

Eric mentioned Empower (formerly Personal Capital ) for summarizing his portfolio performance. 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 )

In this episode, Jason mentioned that he uses the software called YNAB to budget. What is YNAB? You Need a Budget is a popular budgeting tool for many in the FIRE community. If manual spreadsheets aren’t your thing or you’ve struggled with budgeting in the past, this may be a good solution. YNAB has a generous, free 34-day trial so you can see how well it works to help you understand and control spending. (affiliate link; no credit card needed )


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