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.

What’s Wrong with This Popular Retirement Strategy?

Do you worry about running out of money in retirement? How do you draw down your assets without tanking your portfolio? Eric + Jason talk with FIRE bloggers Karsten Jeske and Fritz Gilbert about the bucket strategy. Is it a reasonable withdrawal plan or nothing more than a gimmick? They discuss alternative approaches, how to generate a retirement paycheck, and the role of cash. Whether you’re interested in FIRE or on a traditional retirement path, you can’t afford to miss this episode!

Show notes may be found below the video


Show Notes

Essential Background

START HERE:

The 2023 bucket strategy showdown began with these two blog posts by Fritz and Karsten: “Is The Bucket Strategy a Cheap Gimmick?” (Retirement Manifesto), and “Discussing FIRE Bucket Strategies with Fritz Gilbert” (Early Retirement Now). These articles provide essential background to the debate about the utility and validity of the bucket strategy!

Fritz Gilbert’s Content

  • How To Build A Retirement Paycheck is the first of (currently) four great posts on Fritz’ implementation of the bucket strategy, which we discussed at length in this episode and also in prior videos. The other articles in the series are linked here too, including one he mentioned in this episode, “How to Build a Bond Ladder”.
  • A Strategy For Buying Into A Bear Market is a post which shares what Fritz learned from the 2008 financial crisis and how he’s managing today’s market volatility.
  • In this episode, Fritz mentioned his post “A Step-By-Step Guide for Your Annual Financial Update”. Within you’ll find his guide to an annual review, including a checklist he developed along with links to spreadsheets to help you implement your own process.  
  • In 2021, Fritz recently wrote a book called “Keys to a Successful Retirement” which captures the many lessons he has learned on his retirement journey so far. This is a great read for all current and future retirees. It goes far beyond the financial, and leans heavily into the social and emotional aspects of retirement, just like his blog. Highly recommended!
  • 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.” To learn more about this passion project, be sure to check out this link,

Karsten Jeske’s Content

  • Safe Withdrawal Rate series: This is the landing page for the 56-part SWR series (now; it will surely continue to grow) for which Karsten is best known. Be sure to start with the guidance he provides on how to navigate this great but expansive content. Many essential topics are covered and not all of them involve deep dives into math!
  • Has Karsten written about the bucket strategy before? Yep! In 2021 he posted Part 48 in the SWR series, “Retirement Bucket Strategies: Cheap Gimmick or the Solution to Sequence Risk? “. Be sure to check it out for all the details, including the financial modeling he referenced in today’s episode.
  • Portfolio rebalancing is an essential part of both strategies discussed in today’s video. This key topic is addressed in Part 39 of the SWR series. Rebalancing isn’t a panacea for sequence risk, but it’s certainly an important element to consider. As we’ve discussed previously, being consistent + avoiding market timing is essential.
  • A topic we didn’t hit on today but have talked about extensively in the past is Karsten’s Safe Withdrawal Rate Toolbox. We will be talking more about this powerful, free downloadable tool very soon. In the meantime, Part 28 is the post where the revisions to the original calculator are described and the latest tool is linked. To see the history of this tool, you’ll need to go back to Part 7 of the series.
  • You may have Karsten mention that Jason is using his CAPE-Adjusted Safe Withdrawal Rate strategy. Big ERN recently wrote several blog posts concerning a new “better” CAPE ratio. This article introduces the concept, while the next: “The 4% Rule Works Again! An Update on Dynamic Withdrawal Rates based on the Shiller CAPE – SWR Series Part 54” dives into details on how his SWR Toolbox can use this factor to model withdrawal rate in retirement. More on this topic soon!

Others Weigh In

Slides from this video:


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

Tax Strategies on FIRE: Financial Independence / Retire Early

Do you worry about taxes and how they impact your financial goals? Whether you’re on a FIRE path or retiring traditionally, there are many critical tax topics to consider. In this episode, Jason talks with financial planner and CPA Sean Mullaney, creator of the FI Tax Guy blog. We talk about common tax misunderstandings, the power of solo 401k accounts, Roth conversions, and tax loss harvesting.

Show notes may be found below the video

Note: The discussion is intended to be for general educational purposes and is not tax, legal, or investment advice for any individual. Eric, Jason, and Two Sides of FI do not endorse Sean Mullaney, Mullaney Financial & Tax, Inc. and their services.


Show Notes

Essential Background
If you’re not familiar with Sean’s great blog, “The FI Tax Guy: The Tax Efficient Path to Financial Independence“, you’ll definitely want to check it out. He’s been posting there for over four years, so there’s a wealth of information available. We’ll link to some essential content below, including a few articles we referenced in this episode. In addition, Sean also has a YouTube channel.

Sean’s book: “Solo 401(k): The Solopreneur’s Retirement Account” – Navigating retirement for solopreneurs is not easy—strategically save with the Solo 401(k). If you’re self-employed, saving enough money to retire can feel complicated when you wear both the employer and employee hats. Get educated and empower your retirement with Solo 401(k). In this book, Sean Mullaney, a financial planner and licensed CPA, cuts through the complexity and boils down what solopreneurs need to know about saving for the future. The Solo 401(k) plan allows self-employed entrepreneurs to reduce taxes and strategically save for retirement. This guide will give you the valuable insight you need to create, navigate, and optimize your own Solo 401(k) plan with tax planning you may not have considered.

Key Posts From The FI Tax Guy Blog:

  • FIRE Tax Strategies for Beginners – Are you new to financial independence (FI or FIRE)? Are you steeped in financial independence, but confused about tax optimization? If so, this is the post for you. This post works on the 80/20 principle: sure, there’s a ton of knowledge, expertise, and hacks out there, but often times 80 percent of the benefit can come from 20 percent of the knowledge. 
  • The Special Tax Loss Harvesting Opportunity for 2022 – There is a tax loss harvesting opportunity in 2022 that has not existed in recent years to the scope and scale it exists today: tax loss harvesting with bonds and bond funds. In most recent years, many bonds and bond funds have not had significant built-in-losses. 2022 is different: now there are plenty of bonds and bond funds in taxable accounts with significant built-in-losses. 
  • The Advantages of Living On Taxable Assets First in Early Retirement – The FIRE community loves the accumulation phase. Build up assets towards the goal of financial independence. Questions increasingly creep in when it comes to the distribution phase. Members of the FIRE community wonder: what do I live on when I get to retirement? This is particularly true when one reaches early retirement prior to age 59 ½. In this post, Sean discusses the options and the reasons he believes that for many, the best assets to live off of first in early retirement are taxable assets.
  • 2022 Year-End Tax Planning – In this post, Sean shares the primary tax planning items for the year 2022 as he sees them. Topics covered include tax loss harvesting, Roth conversions, tax gain harvesting, HSA contributions, RMDs, and more.
  • The Four Backstops to the Four Percent Rule – We’ve talked plenty on 2SFI about the 4% Rule (of thumb) and what our own strategies are with respect to withdrawal rate. This post adds a wrinkle to the discussion: the four backstops to the 4% Rule for early retirees. What if worries about the adequacy of the 4% Rule for early retirees can be addressed by factors outside of the 4% Rule safe withdrawal rate? And what if those factors quite naturally occur for early retirees?  Read on to get Sean’s thoughts on why this may be the case.

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

Will You Run Out of Money or Time? FI Advice From a Hospice Doctor

What can conversations with the dying teach us about the secret to financial independence? In this episode, Eric + Jason are joined by Jordan “Doc G” Grumet, a hospice doctor, podcaster, blogger, and author. Topics discussed include the mirage of wealth, living meaningfully, and Jordan’s experiences eight years post-FI. Irrespective of your own retirement journey, you won’t want to miss our conversation. See below for links to Doc G’s book as well as the show notes.

Show notes may be found below the video


Show Notes

Essential Background:

  • Did you know we’ve spoken to Jordan in the past? It wasn’t on Two Sides of FI, but rather on Jordan’s own Earn and Invest podcast. Here’s a link to the episode, which was a really fun one for us and also represents the first time we were a guest on someone else’s show as Two Sides of FI! As you’ll find, Doc G is a very skilled interviewer. In our conversation, we talk finances and how they relate to purpose. We also explore whether it is money that solves our problems. Did you ever think that everything will be okay once you are financially independent? In our conversation, we push back on this narrative.

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

Not familiar with hospice and want to learn more? This post from The Hospice Foundation of America is a great resource. Stated simply, hospice is medical care for people with an anticipated life expectancy of 6 months or less, when cure isn’t an option, and the focus shifts to symptom management and quality of life. The site is a wealth of information, including guidance on how to access hospice care and selecting hospice providers.

For links to all of Jordan’s content, including the Earn and Invest podcast and his DiverseFI blog, be sure to check out his website.


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

How I Plan to Retire Early on a $50K Salary

Can you retire early without a high-paying tech industry salary? In this episode, we talk with Stephen about how he plans to do just that. At 30 years old, he’s earning $50k as a higher education administrator, yet he plans to retire with at least a million dollars by his early 50s. How will he do that? Join us as we discuss his plans, the role of financial discipline, why he doesn’t feel he’s overly frugal, and the challenges of his FIRE path.

Show notes may be found below the video


Show Notes

Essential Background:
Are you newer to the show? If so, you may not have seen our first two episodes, which include a lot of background on Jason + Eric’s lives. Check out Our Financial Past and our FIRE Present and Two Careers, Two Paths to Financial Independence, to learn how we got our own start in life and in the workplace.

Stephen’s Budget: Are you interested in more details on Stephen’s financial picture? He graciously shared the Sankey diagram below, which captures his Jan-Jul 2022 income and expenses. This visualization makes it easy to see both sides of the balance sheet, and provides a lot more detail on Stephen’s finances than we were able to achieve in our conversation.

The Shockingly Simple Math Behind Early Retirement is an article by blogger Mister Money Mustache, which many cite among their most important inspirations for getting on the FIRE path. As you heard from Stephen, MMM was one of his early sources as well.

Still doubting whether FIRE is achievable on a more traditional salary? See The Millionaire Next Door (Thomas Stanley), a profoundly insightful book for a very easy read. Dr. Stanley studied wealth and the habits of the wealthy for many years, capturing his observations in this work and others. Learn how frugality, living below one’s means, and investing, truly powers the path to financial independence.

The Simple Path to Wealth (JL Collins) is widely regarded by many in the FIRE community as the most impactful book to their own journey. This fast and easily digestible read is chock-full of investment guidance that you will understand immediately and can readily apply. There is no better starting point to your FIRE journey than this book.

We didn’t dig into it, but you may have heard Stephen refer to feeling “YNAB poor” in this episode. 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.

What the FIRE Community Gets Wrong – Talking with Karsten Jeske (and our follow-up conversation!)

Note: This post has been updated to include our episode with our follow-up conversation, in which we we review our take-homes from that conversation, and react to comments and feedback we received about the episode with Karsten.

What would you do if you ran out of money in retirement? It’s hard to imagine a scarier outcome, and yet many on the FIRE path may be at risk for this if they get their portfolio withdrawal rate wrong. In this episode, Eric + Jason talk with Karsten Jeske, the creator of the Early Retirement Now blog. Known by many as “Big ERN”, he is an economist who is well known to the FIRE community for his extensive work in characterizing safe withdrawal rates (SWR). In this episode, we dig into Karsten’s free, powerful SWR Toolbox, and discuss topics including the downsides of FIRE calculators, 100% stock portfolios, the bucket strategy, why dividend investors are wrong, and his own post-FIRE life. If you’re interested in FIRE, you can’t afford to miss this information-packed episode!

Show notes may be found below the videos

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

Conversation with Karsten:

Follow-up episode:


Show Notes

Essential Background
One of the key dangers underpinning the importance of safe withdrawal is Sequence Risk (sometimes called Sequence of Returns Risk). Sequence risk is “the danger that the timing of withdrawals from a retirement account will have a negative impact on the overall rate of return available to the investor” – for example, starting withdrawals in a period with several years of severe market underperformance. This is a topic we’ve discussed before but for those new to the topic, check out this post from Investopedia.

Key Early Retirement Now Content
We referenced a number of Karsten’s blog posts from Early Retirement Now in this episode. Below you’ll find links to that content, along with the main landing page for his SWR series. You’ve got enough reading to keep you busy!

But first a little guidance: given Karsten’s extensive knowledge and expertise on these topic areas, his approach employs analysis which some may find unwieldy or even a little overwhelming. Don’t panic! Skim the math and stick with the text, and you’ll find that it’s not essential to fully comprehend all the analyses to understand the messages being delivered.

The SWR Toolbox: This is the free, downloadable tool that Karsten developed and which we discussed in this episode. Part 28 is the post where the revisions to the original calculator are described and the latest tool is linked. To see the history of this tool, you’ll need to go back to Part 7 of the series.

  • Safe Withdrawal Rate series: This is the landing page for the SWR series for which Karsten is best known. However, it’s also a 53-part series (now; it will surely grow). So we recommend following the guidance he provides about how to get started. You might begin with a topic of interest found below or listed at this landing page rather than diving into the whole series – though it’s a great read if you have interest in going through the whole thing!
  • Equity Glidepaths are a type of dynamic asset allocation plan often discussed in retirement planning. In Karsten’s words, “if we start with a relatively low equity weight and then move up the equity allocation over time we effectively take our withdrawals mostly out of the bond portion of the portfolio during the first few years. If the equity market were to go down during this time, we’d avoid selling our equities at rock bottom prices. That should help with Sequence of Return Risk!”. He covers glidepaths in Part 19 and Part 20.
  • Dividend stock strategies are commonly touted in the investment community, yet are seemingly poorly understood. We talked about this idea in our episode, and Karsten has written several great articles on the topic: Part 29, Part 30, and Part 31.
  • How often should we rebalance our portfolio? This key topic is addressed in Part 39 of the SWR series. Rebalancing isn’t a panacea for sequence risk, but it’s certainly an important element to consider. As we’ve discussed previously, being consistent + avoiding market timing is essential.
  • Is it crazy to hold 100% equities until retirement? Eric asked this question in response to his portfolio moves earlier this year to change his allocation to include 30% fixed income (Two Sides of FI episodes: Part 1 and Part 2). See Part 43 of Karsten’s series for further detail on his position, expanding on what he said in this episode.
  • Bucket Strategies is a topic we’ve addressed before on the show, including our conversation with Fritz Gilbert (The Retirement Manifesto). In Part 48, Karsten tackles this topic as well. In the episode, Jason also mentioned an article by Michael Kitces on this.
  • Inflation is certainly a topic on everyone’s mind at the time this episode was recorded. In one of his more recent posts (Part 51) Karsten digs deep on this topic. Is what’s currently predicted for the inflation path within historical norms – and is our withdrawal rate modeling at risk? Read on to find out…
  • The Retirement Income Style Awareness (RISA) assessment was discussed in our follow-up episode. This tool, by Wade Pfau and the team at Retirement Researcher, 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”.
  • Bonus: If you haven’t had enough yet, we’d recommend Part 26: “Ten things the ‘Makers’ of the 4% Rule Don’t Want You to Know”. It’s written rather tongue-in-cheek, while still being packed with the insight we’ve grown to expect from Karsten’s style of writing. We touched on some of these points in the episode but there are a bunch more not covered that are very much worth reading.

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.

Talking with our Spouses About FIRE: 2 x Two Sides of FI (Parts 1 and 2)

Part 1:


Part 2:

Talking with a spouse or partner about FIRE isn’t always easy. In this two-part series, Eric + Jason bring their wives Laura + Lorri into the conversation to share their personal experiences. In part 1, they 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, they discuss how they share financial responsibilities, the importance of finding friend networks, talking to their children about FIRE, and their hopes for their post-FI lives.


Show Notes

After recording this episode, Jason realized just how right Lorri was regarding his (non-)efforts to make friends in their new town. That got him thinking about some of the events of the past year, leading him to write a blog post on the topic. We think it’s a good accompaniment to the conversation in these episodes and hope you enjoy it. Do you have any thoughts on making friends in a new town? Please share them in the comments!

A fun story for you (not so much fun for us!) – you may have seen the earlier picture of all four of us together, in one place. That, along with this episode’s thumbnail, was a real photo from Jason + Lorri’s visit to Eric + Laura’s house in Maine – not photoshopped! Naturally you’re wondering why this episode was recorded in our usual remote format vs. in person. Well…we did record two hours of content when we were all together in Maine. However, a few technical issues meant that we decided not to use that footage. It still exists and perhaps will take on a new life someday as outtakes or otherwise. We’re really happy with how this two-part series turned out despite it being in our usual remote format, and hope you enjoy it too!

You can find information on the tools we mention in each episode along with additional information in the Resources section of this site. To navigate to this material at any time, just click the menu button at the top of any page on the site.