My New Life: Two Years After Early Retirement

Wondering what a day in the life in early retirement is like? Eric travels to California to shadow Jason and find out what his FIRE life is like nearly two years into early retirement. We learn how Jason fills his days, hear his concerns pre- and post-FI, discuss the merits of part-time “fun” jobs, and the reality of finances.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Essential Background:

  • Did you see our earlier episode called “What I Learned in My First Year of ‘Early Retirement'”? Our most popular video to date, this installment captures Eric + Jason’s discussion about the latter’s lessons learned in year one of RE.
  • How did Jason + Lorri decide where to relocate post-FIRE, and what are Eric + Laura considering for their own next steps? If you missed our two-part series on “Where to Live”, be sure to check it out here: (part 1 and part 2).
  • Talking With Our Spouses about FIRE” is the first part of our conversation with our partners on the show (part 2 here). To get the full picture of what Eric + Jason’s FIRE paths have been like, it’s essential to hear from Laura + Lorri as well.

Jason has been blogging since he left his career nearly two years ago. Part of that has included a series of milestones posts, in which he captures how he’s feeling at various points in time post-RE. At this link, you’ll learn more about what that journey has been like over the past two years.

What I’ve Learned From Two Years of Retirement is a great post by Fritz Gilbert @ The Retirement Manifesto, on his own experience in RE. No two FIRE journeys are the same, so we think it’s highly informative to learn from others’ paths too.


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

If You Want Financial Freedom You Can’t Ignore This (Parts 1 and 2)

We avoided estate planning for a long time; here’s why you shouldn’t. Without an estate plan, you’re giving over the control of what happens to all your assets to others. In part one of this two-part series, Eric + Jason talk about what they did to – finally – get their respective plans in place. Topics discussed in this episode include the elements of estate planning, why people delay + how to get started, living trusts, and taking care of your heirs. Don’t be like those who put this off “until they’re older”: join us now for the first episode of this two-part series.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.

Part 1

Part 2


Show Notes

Essential Background: If you’re not familiar with our family situations, check out our earlier videos where we’re joined by our spouses (part 1 and part 2), and the recent episodes about our kids (part 1 and part 2). Note that each is a two-part series, and separate links are provided for all videos.

Estate planning FAQs: After viewing these videos, you’ll be better equipped to ask deeper questions about your own estate planning needs. We found this resource from the American College of Trust and Estate Counsel (ACTEC) to be really helpful. All of the high level topics discussed in our series are covered here.

What is a trust? This Investopedia article is a good starting point for clarification on the different types of trusts and other pertinent details. This is a subject where it’s easy to fall down a very deep rabbit hole, and having a good foundation first is always helpful. Be sure to research the particulars of your state or country as well, as things differ substantially.

Advanced care planning is an essential element of estate planning, and one we touched on in part 1 and expand upon in part 2 of this series. Thinking through your own preferences can be difficulty, but planning for them is vitally important.

Umbrella Insurance is among the most important (and least expensive) tools available to protect your assets. These policies sit on top of your existing liability coverage (auto, home, etc) and extend it. To learn more about umbrella policies, check out this Investopedia post.


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

Breaking Up With My Financial Advisor?

Did you know that financial advisor fees can eat up HALF of your portfolio’s value over time? While happy with the good support and great relationship he had with them, Jason was thinking about leaving his financial planners late last year. In this episode, we capture a conversation Eric + Jason had on this topic, as they discussed the merits and downsides of paying assets under management (AUM) fees. Topics covered in this episode include why he stuck with them over the years, the value advisors can bring, more cost-effective options for financial advice, and how Jason is making his decision. Get the facts and make the right choice for yourself!

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Essential Background:

  • Have you seen our two-part series (part 1 and part 2) on asset allocation? These episodes provide context from Jason on his portfolio and work to date with advisors.
  • The Bogleheads wiki contains some great content about investment advisors and financial planners, helping to clarify the differences between them. In these two articles you can learn some important definitions and information that provide key background to this topic.

10 Questions to Ask Your Financial Advisor was put out by the Certified Financial Planner Board of Standards, Inc. (CFP Board), which is a “non-profit organization that serves the public by fostering professional standards in personal financial planning”. This document is a must-read for anyone even considering financial planning services, and helps to arm you with the information you need to have any conversations.

Interested in researching financial advisors? This link will take you to one of the better resources we’ve seen for investigating potential options. As described on the site, XY Planning Network’s member advisors ascribe to fiduciary and CFP standards, earn no commissions, and require no minimum assets. They have convenient filters to allow searching by advisor specialities, including those with FIRE experience. Many work under multiple fee models, including advice-only, which can be a good source for one-time consults without any ongoing feels. [Two Sides of FI has no relationship with XY Planning nor do we receive any compensation from them.]

BrokerCheck is a resource by FINRA (Financial Industry Regulatory Authority), which allows you to research individual financial planners and brokers, as well as firms. This is a key site for looking into the details of a potential financial advisor or perhaps one with whom you are already working.


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

Our FIRE Portfolios Are Down 20%, What Now?

How has the recent market downturn changed our plans? Jason + Eric candidly discuss their pre- and post-FI moods in this volatile time. Learn what they’re doing and thinking about right now as Jason nears the two-year post-FI mark and Eric contemplates pushing his 2024 FI date back.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Essential Background: Let’s start out with some definitions. Terms like correction, market crash, and bear market are thrown around casually at times and knowing their meaning is important. This Fortune article is a brief and effective summary.

Buying Stock in a Down Market is a part of show guest, Fritz Gilbert’s, post-FIRE strategy, which he discussed in a recent conversation with us. In this episode highlight, we discuss how he felt during the 2020 market decline and learn about his approach to continue buying in order to take advantage of low equity prices.

The Psychology of Money (Morgan Housel), is the book Eric discussed in this episode. Subtitled “Timeless lessons on wealth, greed, and happiness”, it recounts 19 short stories “exploring the strange ways people think about money and teaches you how to make better sense of one of life’s most important topics”.

Fixed Income has an essential role to play in any portfolio, particularly as you approach your retirement date. Did you miss our two-part series on Eric’s recent efforts to change their asset allocation from 100% stock? As he referenced in the current episode, that was an important part of increasing his confidence in this down market. Be sure to check out part one and part 2 of our conversation, as well as the behind the scenes conversation Eric and his wife Laura shared on this essential topic.

Tax Loss Harvesting is a concept we’ve discussed on the show before, but haven’t dug into deeply. This Investopedia article is a good summary. In brief, TLH is an approach by which investors can sell an asset at a loss, reducing the total amount of capital gains taxes due from the sale of profitable investments. You can then use the sale proceeds to purchase a similar asset or security, maintaining your asset allocation.


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

Teaching Our Teens About FI and Money (Parts 1 and 2)

Having children comes along with many necessary expenses, but also provides a key opportunity to provide them with a solid financial education. In part one of a two part series, we tackle a topic that’s been requested many times by viewers: all things relating to kids. Topics discussed in this episode include our own financial upbringing, early attempts to teach our kids about saving + investing, the value of teens having jobs, and talking with them about FIRE. Join us for the first episode of this two-part series.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.

Part 1


Part 2

Show Notes

Essential Background: If you haven’t watched our very first episode of Two Sides of FI which contains much of our own financial backstory, this is definitely material relevant to our discussion here.

UTMA custodial accounts may be useful investment vehicles for you to consider for your children, particularly when they don’t yet have earned income and are not eligible for a Roth IRA. These accounts are very flexible by design, and unlike with a 529 plan, the funds in a custodial account do not have to be used solely for higher-education expenses. 

529 Plans are tax-advantaged savings plans designed to encourage saving for future education costs. There are many different places that can host these accounts including but not limited to the same brokerages you may use for your own investments. Be sure to look into whether there are (tax or other) advantages in your state of residence before deciding where to invest.

Roth IRAs are well known by most viewers of our channel, but did you know there are compelling reasons to consider them for your kids? For minors, these will need to be custodial accounts just like a UTMA and most brokerages offer them.


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

Buying Bonds. Still Not Convinced I’m Doing the Right Thing! (Part 2)

I reallocated my investment portfolio, sold out of my 100% equity position and I’m not happy about it. Part two of a two-part series, you’ll learn why and how I’m making peace with it. Ensuring that your investment portfolio can fund your lifestyle for the duration of your lifespan is essential to success in FIRE. One of the most impactful elements of that is how your portfolio is constructed, or your asset allocation. In this episode, Eric discusses his desire to reduce the risk of his portfolio with Jason, and ensure he + Laura are set up for success. Topics discussed include the role of bonds + fixed income, the types of investment risk, seeking feedback from internet forums, and tax considerations. Join us for the second episode of this two-part series on Eric’s reallocation experience.

If you missed Part 1, which includes a link to a behind the scenes conversation with Eric + Laura, be sure to check it out first!

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Essential Background: If you haven’t watched our previous episodes on asset allocation (part 1 and part 2), this is highly relevant material to our discussion here.

Series I Savings Bonds (I Bonds): These assets are rightfully getting a lot of interest in the moment given their unusually high returns (for now). Get all the details via Treasury Direct. For more details, check out this recent Money Guy Show episode as well.

Investment Policy Statements (IPS) are key guiding documents for your investment portfolio. Don’t have one? Have a look at this Bogleheads wiki article for all the details that you’ll need to help put one in place.

How To Build A Retirement Paycheck:  This is the first of three great Retirement Manifesto posts on author Fritz Gilbert’s implementation of the Bucket Strategy, which we have touched on in several episodes to date. Here you’ll find guidance on how to determine the asset allocation you’ll want to have in place by the time you retire early. The other two articles in the series are linked here as well.

A Bond Tent strategy is one of the common approaches used by the FIRE community to mitigate both Retirement Date + Sequence of Returns Risks (RD and SRR in the images below). As is often the case, Michael Kitces has a great article on the topic. We couldn’t cover sufficient depth on this important topic in our episode, but this post has all the details you need. See the graphics below:


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

I Rebalanced My FI/RE Portfolio and I Hate It! (Part 1)

Eric reallocated his investment portfolio, sold out of his 100% equity position and he’s not happy about it. In this two-part episode, you’ll learn why and how he’s making peace with it. Ensuring that your investment portfolio can fund your lifestyle for the duration of your lifespan is essential to success in FIRE. One of the most impactful elements of that is how your portfolio is constructed, or your asset allocation. In part one, Eric discusses his desire to reduce the risk of his portfolio with Jason, and ensure he + Laura are set up for success. Topics discussed include the role of bonds + fixed income, the types of investment risk, seeking feedback from internet forums, and tax considerations.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.

Pick up where part 1 leaves off with a bonus, behind-the-scenes look at Eric and Laura’s decision-making process (video below).


Eric + Laura Discuss Their Reallocation

Show Notes

Essential Background: If you haven’t watched our previous episodes on asset allocation (part 1 and part 2), this is highly relevant material to our discussion here.

Vanguard’s Principles of Investing Success is a really great read. It’s chock-full of information, including the chart showing average returns by asset mix (pp. 10) that Eric referenced in this episode. Whether you’re just getting started with investing or are very experienced, we suspect you’ll find something of value in this easy read.

How To Build A Retirement Paycheck:  This is the first of three great Retirement Manifesto posts on author Fritz Gilbert’s implementation of the Bucket Strategy, which we have touched on several episodes to date. Here you’ll find guidance on how to determine the asset allocation you’ll want to have in place by the time you retire early. The other two articles in the series are linked here as well.

Financial Independence: How Long Will It Take? We showed visuals from this Go Curry Cracker post, which highlights the dramatic impact that your overall savings rate has on determining your FI timeline. This concept is also covered in the “Principles of Investing Success” article linked above.


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

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. Now nearly four years after retiring early, Fritz brings valuable experience + perspectives to this question. 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.

Note: This content does not constitute investment advice and is being presented for informational and educational purposes only.


Show Notes

Retirement Is Nothing Like I Thought It Would Be – This is Fritz’ post that inspired us to make an episode of Two Sides of FI together. As you may have gathered from our earlier episodes, Jason completely agrees with Fritz that it’s impossible to really know what retirement is going to be like until you experience it. Now in his fourth year of early retirement, Fritz has a lot of experience to reflect upon and we’re grateful that he’s chosen to share it with us.

Keys to a Successful Retirement – As we discussed in this episode, Fritz recently wrote a book capturing lessons he learned on his retirement journey so far. His own description of the book is a really apt summary: “Covering topics like finances, embracing your passions, and dealing with feelings of aimlessness, grief, and depression that may crop up, this in-depth guide to retired living answers all the burning questions you want to ask—as well as those you’re afraid to. Take a complete look at your newfound freedom and explore what it really means to have a successful retirement.” We highly recommend it!

In this episode, we referenced a number of different blog posts Fritz wrote that we found useful, inspiring, and impactful. Please be sure to check them out:

Freedom for Fido is the charity that the Gilberts started, whose stated purpose is to:
“Free the dogs who live on chains in the North Georgia Mountains. We are a charity which provides free fencing and dog houses for low-income residents of the Blue Ridge area.” This project is clearly an important part of their lives and we’d recommend you check out the great and impactful work they’re doing together with their volunteer community.


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.

How We Travel: Pre + Post Financial Independence

A seven day vacation or 5 weeks of travel – which would you prefer? When you’re working towards financial independence, vacations are a time to set aside work and everyday chores. But they’re constrained by things you don’t often control: accrued vacation time, work and school schedules, business obligations, and holidays, to name a few. In this episode, Eric and Jason compare notes from their two respective sides of FI and their recent vacations: 7 days for Pre-FI Eric and 5 weeks for Post-FI Jason. See just how different is travel once you reach FI and the constraints have been removed.

For more information on Jason’s five-week trip, including the valuable lessons he and his family learned on their longest trip ever, check out his blog post: https://thenextphaseisnow.com/longest-vacation-of-my-life/


Show Notes

As we mentioned in the episode, one leg of Jason’s travels brought the Two Sides of FI together in the same place for the first time in several years, as he and Lorri visited Eric and Laura in Maine. Along with all the fun times we’d planned (and carried out!) for our few days together, we’d intended to film episodes with our spouses – which we did. Unfortunately, a few technical issues meant that we decided not to use that footage after all. However, we believe the two episodes we recorded later with our spouses (Part 1 and Part 2) turned out even better in terms of the quality of our conversations. If you haven’t seen these shows yet, please check them out. Two times Two Sides of FI is the only way to get the full picture!

Two times Two Sides of FI: Jason, Lorri, Eric and Laura
Dinner time in Maine: (back) Eric + Laura, (front) Lorri + Jason

For a closer look at some of our trip photos, check out these galleries:

Eric’s photos:


Jason’s photos:


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