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.

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.

Am I Failing at Early Retirement?

Has your shrinking retirement portfolio left you considering part-time work to ease your anxiety? Inspired by a blog post from Go Curry Cracker, we discuss BaristaFIRE, time freedom, what it means to be “unemployable”, and what work we might consider post-retirement. Be sure to see the links below for the show notes and to the blog post referenced in the video.

Show notes may be found below the video


Show Notes

Essential Background:

Failing at Early Retirement, a Go Curry Cracker blog post, was the inspiration for this episode. As we discussed in the video, in the article you’ll learn how author Jeremy took on some seasonal part-time work as a UPS driver, and what he learned from the experience.

We talked a lot about BaristaFIRE in today’s episode. The linked post from Financial Samurai is a comprehensive look at this path, and is a good 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.

Volunteer Income Tax Assistance (VITA) is a great IRS program for US taxpayers who qualify for free federal tax preparation. If you’d like information on VITA including how you can volunteer like Jason is doing, be sure to see the IRS Tax Volunteers page.


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.

Have Enough to Retire (Early)? 10 Steps to Make Sure

Will you have enough to money to retire (early or otherwise)? Achieving financial independence requires many key elements to be in place and special consideration if you plan to retire early. You need a plan: what will you do? What will you spend? Where will it come from?

In this episode, Eric and Jason discuss a recent blog post by Fritz @ The Retirement Manifesto where he discusses the “10 Steps to Make Sure You Have Enough Money to Retire”. We cover how we’ve been designing our “dream retirement”, how we track current expenses and project future spend, how Jason is drawing down assets and Eric’s evolving plan to use “the bucket strategy”, and much more.


Show Notes

10 Steps to Make Sure You Have Enough Money to Retire – This is The Retirement Manifesto blog post that inspired our episode. Be sure to visit Fritz’ website for this article, as well as all the associated tools we mentioned in the show. We also highly recommend his three-part series on The Bucket Strategy, which we referred to in the episode.

Social Security is an important aspect to consider in most US retirement income plans. This link will take you to calculators that you can use to estimate your retirement benefits. SSA Tools is another useful site, one in which where you can copy/paste your SSA.gov data and use “…clear interactive visuals that let the user investigate how different choices might affect their overall benefit.” It’s a really good tool for modeling different scenarios. Lastly, Open Social Security runs the math for each possible claiming age and reports which strategy is expected to provide the most total spendable dollars over your lifetime.

New Retirement.com – More and more people on Reddit seem to be discussing this comprehensive retirement planning suite. They have a very full-featured free offering as well as a modestly priced paid version with a host of really nice features, plus consulting services. There’s a very active Facebook community as well.

Financial Order of Operations (Money Guy Show) – is a really great resource that “outlines the 9 steps anyone can take to build wealth and reach financial abundance.” We recommend downloading a copy and having a look at the associated episodes on their YouTube channel too. This is an essential tool to ensure your personal financial habits are supporting your FIRE goals.

You Need a Budget (YNAB) – By our observation, there is no budgeting tool more widely discussed, nor with a user base so passionate than YNAB. If manual spreadsheets aren’t your thing, or you’ve struggled with budgeting, look no further. YNAB has a free 34-day trial and the subsequent annual fee readily pays for itself. (affiliate link – a free month for each of us if you sign up!)


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

Retired Early and I Hated It : How NOT to FIRE, Part 2 (Post-FI/RE)

Imagine hitting your FI number, retiring early, and discovering you hate it? In this episode we discuss four examples of such an outcome: from quitting the perfect job and regretting it, to feelings of depression and lack of purpose. Some are unable to find motivation without financial incentives, while others realize they haven’t budgeted enough to do things they enjoy in life.

This is part 2 of our How NOT to FI/RE series. For part 1 and the PRE FI/RE examples, be sure to check out that video here: https://youtu.be/Jb438jvebd0


Show Notes

For Jason’s own thoughts, observations, and lessons learned in his first year of early retirement, check out this Two Sides of FI episode, as well as his blog post.

Are you on Reddit? Join us in the Two Sides of FI subreddit if you’d like to continue the conversation.

Full text of Reddit posts from the episode:

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.

How NOT to FIRE – Part 1 (Pre-FI/RE)

How much do you really need to achieve financial independence? We decode the math On the path to financial independence, there are ample opportunities for mistakes and missteps. In today’s episode, we review stories from people who shared their FIRE experiences online in the hopes of educating others. Here we review five of these tales: incurring tragic losses due to trying to beat the market, losing 75% of your portfolio value due to sector investing, regretting aggressively saving at the expense of living your life, and resenting your partner who doesn’t have the same degree of FIRE ambitions as you do.


Show Notes

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.

Full text of Reddit posts from the episode: