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:

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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.

Don’t Let the Cost of Healthcare Break Your Early Retirement Plan

Calculating the cost of health insurance is a complicated and stressful exercise when you’re retiring early. Hear Jason’s experience with his first full year using the California ACA Exchange and learn how Eric arrived at his budget of $350K, his worst case scenario. We discuss how to choose a plan, ACA subsidies, differences by state, and other alternative options. If you missed our earlier healthcare episode, be sure to see the link below in the Show Notes.

Show notes may be found below the video


Show Notes

Essential Background:
If you missed our earlier healthcare insurance episode, “Healthcare is my Second Highest Cost in Early Retirement”, it’s a great one to review. In that video, we were joined by a career HR benefits expert, and covered a huge diversity of topics – unlike the ACA focus here. We talked about Medicare, COBRA, Long Term Care, prescription drug coverage, among others.

In this episode we mentioned a number of useful resources primarily for US residents seeking healthcare that we’d like to share with you. Note that many apply whether you are on a FIRE path or traditional retirement age.

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. As Eric mentioned, they have nothing to do with quality of care.

ACA plan subsidies 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. Importantly, in 2021 and 2022, provisions of the American Rescue Plan (ARP) legislation made further improvements to eligibility, eliminating so-called “subsidy cliffs”.

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.

States where Obamacare plans cost the most in 2021 is an interesting post from Policygenius that digs into the diversity of plan costs across US states. Some states have much higher average costs by plan, so this is a key factor worth investigating when considering where to live if you will rely on ACA plans.

Healthcare Sharing Ministries (HSMs) are an option of interest to many. We’ve decided they weren’t for us, as they’re not bound by the same requirements as true insurance plans. That said, this page seems to be a reasonable starting point for high level information on a number of options available. If you have interest in these plans, be sure to dig deeper. Many user stories are available online via Reddit and other sources. For information on the potential downsides of HSMs, we found this recent John Oliver segment very eye-opening. Caveat emptor, friends.


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

Healthcare is my Second Highest Cost in Early Retirement

Health insurance may not be top of mind in early retirement when you’re young and healthy, but it should be. In the US, healthcare costs are a significant line item in our budget. To help us decode what you need to know, we’ve invited a retirement benefits expert to answer our questions through the lens of those seeking financial independence and early retirement.

To protect against astronomical expenses resulting from unexpected medical issues it’s prudent to carry insurance and if you’re retiring before 65 (when Medicare kicks in) you’ll be responsible for covering those costs. What do you need to consider? What ARE the costs involved? What insurance shouldn’t you purchase? Are there other options for coverage? What about long term care insurance? These are just a few of the topics we cover in this hour-long episode.

Our sincere thanks to Amy Manning for sharing her time, knowledge and expertise with us!


Show Notes

In this episode we mentioned a number of useful resources primarily for US residents seeking healthcare that we’d like to share with you. Note that many apply whether you are on a FIRE path or traditional retirement age.

COBRA is 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.

ACA plan subsidies are a topic worth a deeper dive than our time allowed in this 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. Importantly, in 2021 and 2022, provisions of the American Rescue Plan (ARP) legislation made further improvements to eligibility, eliminating so-called “subsidy cliffs”.

Healthcare Sharing Ministries (HSMs) are an option of interest to many. However, neither of us are experts on the topic. We’ve looked into HSMs and decided they weren’t for us, as they’re not bound by the same requirements as true insurance plans. That said, this page seems to be a reasonable starting point for high level information on a number of options available. If you have interest in these plans, be sure to dig deeper. Many user stories are available online via Reddit and other sources. For information on the potential downsides of HSMs, we found this recent John Oliver segment very eye-opening. Caveat emptor, friends.

GoodRx and RxSaver are convenient tools to find out where you can get your prescriptions filled for the lowest cost via coupon discounts. A related tip for diagnostic testing + labwork is that for many insurance companies, it’s easy to use their website to confirm your options for in-network testing. Don’t be surprised by higher bills that come from using labs that are out-of-network! A few minutes of work is well worth it to ensure you’re getting the lowest cost options available to you.

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.


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