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Our Biggest Fears About Early Retirement

What’s the scariest part of retiring early? For many, it’s not just about money—it’s the unknowns that come after leaving work behind. In this candid conversation, Eric and Jason unpack the biggest fears they and others faced on the path to FIRE, from financial worries and healthcare to identity shifts and societal judgment. Whether you’re planning your own early retirement or already there, this episode will help you feel less alone and more prepared.

Show Notes

As Eric and Jason discussed, times like there are good opportunities for stress testing your plan and modeling alternate scenarios. We find ProjectionLab an essential and easy-to-use software package to support this practice. You can get your own free trial here. Want more info? Here’s our episode, How We’re Using ProjectionLab in (Early) Retirement.

Essential Background:

  • Once again, the idea of safe withdrawal rates and Big ERN’s Safe Withdrawal Rate Toolbox came up in this conversation. For practical help with modeling your own safe withdrawal rate plan, don’t miss our very popular multi-part tutorial series on the SWR Toolbox. You can find them all here.
  • How Do I Know When I’m Ready to Retire? This episode was referenced a few times, and for good reason. Most on the FIRE path focus on the financial elements because in essence, they’re the easiest part of the equation. But many people struggle with the emotional elements of the decision. For more on the retirement personas we highlighted via the slides shown in the current video, check out the episode!
  • Jason mentioned how his concerns have changed a good deal over time. We’ve done a number of milestones-related episodes, charting our FIRE journeys, a number of which are among our most popular content. Here’s the list of all of them. Additionally, Jason hosted a solo AMA in 2023 called Ask an Early Retiree Anything! Live Q&A with Jason from Two Sides of FI.
  • Underspending is a very common stumbling block for those transitioning from saving to drawing down from their portfolio i.e. spending. In “How much money can you safely spend in retirement?“ we tackle this head-on.
  • Certainly in the US, one of the most common fears about retirement is healthcare. Did you know we’ve tackled this topic at least three times before? Check out these show notes for links to all of them. There, you’ll find the episodes and a host of associated content on the topic.
  • Many, if not most early retirees will eventually struggle with the question of working “just one more year”. We’ve tackled that essential topic a few times, most recently in Do I Wish I’d Worked One More Year? In this episode, we discuss the reasons you might consider that option, what Jason would have missed out on if he had worked longer, and the value he found in retiring when he did.

Empower (formerly Personal Capital) is a commonly used free tool for tracking your various investment accounts, understanding your asset allocation + rebalancing opportunities, and monitoring your net worth. PC has simple to use account linking to make it a more automated experience. Give it a try risk-free!

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, which started even before Two Sides of FI began. Get more information on those archived posts here.

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Are You on Track? Our 2024 Financial Review

What are the critical financial elements to track and review each year pre- and post-FI? In this episode, Eric and Jason share their processes and learnings from their 2024 annual review. Topics covered include tracking net worth and withdrawal rate, portfolio management, taxes, and much more.

Show Notes

Essential Background:

In this video, we talked about how much we’re enjoying using Projection Lab for financial modeling including What-If scenarios. Stay tuned for an upcoming episode with lots more details! In the meantime, you can try out Projection Lab for yourself, free.

Jason mentioned that he still 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. 

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, which started even before Two Sides of FI began. Get more information on those archived posts here.

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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.

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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.

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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.

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Comparing our FIRE Portfolios + Asset Allocations (Part 2)

Choosing how to divide your assets among stocks, bonds, and other investment vehicles is a good first step, but asset allocation also impacts your tax rate, portfolio performance, and long-term ease of maintaining it all. In part two, Eric and Jason dig further into their own portfolios from their respective sides of FI and discuss the role of bonds, risk, tools you can use to assess your portfolio and model performance, rebalancing, and an interesting – not often discussed – case for financial advisors.

Did you miss Part 1? Check it out here.

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

Show Notes

Portfolio Charts offers a wealth of different portfolio visualization tools and calculators for deeper analysis of your asset allocation, and other personal finance elements. As Eric mentioned in the episode, you’re not likely to find another resource with so many different visualizations available.

Morningstar is perhaps best known as a resource for analysis + ratings for mutual funds. However, the site also has a variety of tools for portfolio analysis and exploration. Some functionality is provided free of charge, while others come with a premium subscription. Importantly, the latter is offered as a 14-day free trial so you can readily use these tools to analyze your asset allocation and then cancel without risk prior to billing.

Big ERN’s SWR Spreadsheet (Early Retirement Now) is a comprehensive planning tool largely aimed at investigating safe withdrawal rate. In line with Big ERN’s standard approach, this is a resource aimed at those desiring detailed, quantitative analysis, and is a bit more “in the weeds”. But having the ability to input your asset allocation along and projected rates of return, is vital to do truly informed modeling. Other tools may be easier starting points, but this one has lots of power when you’re ready to dig deeper.

M1 Pies (M1 Finance) are one of the visualizations Eric discussed to reference the investment approaches of others in the personal finance community, like JL Collins and Paula Pant, which we talked about in Part 1. These are M1 Finance’s flagship portfolio tool, allowing you to see the asset allocations of others and potentially invest in the same approaches.

cFIREsim – This popular tool is the “Crowdsourced Financial Independence and Retire Early Simulator”. cFIREsim is among our favorite sites for performing Monte Carlo analysis of a given FIRE strategy. While you can get started with just a handful of simple parameters, this site is extremely flexible and will allow you to do more complex modeling if that is of interest.

Portfolio Visualizer is a site containing a variety of modeling tools, including the one linked here which allows one to backtest different portfolio asset allocations. While past results are not necessarily predictive of future returns, this approach does allow one to understand the merit + drawbacks of various asset allocations. One useful approach this enables is to compare the performance of your current portfolio vs. a variety of others of your construction.

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

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Discussing our FI Numbers : Changing our minds, talking to family

Things have changed: attitudes, spending habits, withdrawal rates, what we’ve chosen to reveal to family and friends. In this episode, we discuss how our early FI goals and calculations underestimated today’s needs and move beyond the math of financial independence to discuss the psychological aspects, including important conversations with family and friends. These discussions can be challenging and touch on deep-seated ideas about money, entitlement, and often guilt. It’s common to overlook the importance of these conversations and this side of FIRE when you’re focused on the financial side. Join us as we explore these areas and more in this second episode focused on the math of financial independence.

Show Notes

A few months after posting this episode, Jason wrote a blog post on one aspect of this show – talking about the “RE” part of FIRE and what retirement actually means. The inspiration for the article was a chance encounter at a winery tasting room. What was discussed there and how did it inform his thinking? Read on to find out why we at Two Sides of FI think “retirement” is a word that is perhaps overdue to be redefined!

You can find information on the tools we mention in the 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.