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.

Ask an Early Retiree Anything! Live Q&A with Jason from Two Sides of FI

Are you on the FIRE path or interested in learning more about early retirement? Three years ago I retired from my career at age 47 after reaching financial independence the prior year. This video is from a livestream where community members had the opportunity to ask me questions about what my experience has been like. Thanks to all who joined!

Don’t miss the extensive show notes below, which list all the episodes and resources discussed in the episode.

Show notes may be found below the video


Show Notes

Essential Background:

Here are links to the episodes Jason talked about in the show. In many cases these point to show notes, which contain not only the episode video itself, but also a variety of associated content meant to help support the content. Check them out!


Resources Mentioned:

Still haven’t subscribed to our YouTube channel or want to share an easy link with people you know? Here it is! Click it, say yes, and you’re in! Easy, peasy.

In this episode we talked about the new Two Sides of FI Discord server. If you’re not familiar, this is an instant messaging social network. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests!

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first 1.5 years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.

In this episode, Jason mentioned Empower (formerly Personal Capital) for summarizing his portfolio performance as a part of rebalancing. Both him and Eric really like this free tool for tracking investment accounts, understanding asset allocation + rebalancing opportunities, and monitoring net worth. Empower employs a simple account linking process to make it a more automated experience. Give it a try risk-free! (affiliate link; free program )

Do you have a copy of our free Rebalancing Calculator? This simple tool can help you make your own decisions about buying and selling in order to rebalance your portfolio. If you’d like something more DIY, this is a calculator you should consider.

In case you missed the link above, our popular three-part tutorial series on the Safe Withdrawal Rate (SWR) Toolbox can be found here.

The Retirement Income Style Awareness (RISA) is a tool by Wade Pfau (mentioned today) and the team at Retirement Researcher. It came from research performed on individual styles, risk tolerance, and other factors, and is aimed at deriving a personal retirement income strategy. Fritz Gilbert at Retirement Manifesto posted a nice write up on this last year, which we’d recommend. If you’re interested in learning more about this assessment, check out Wade’s book: “Retirement Planning Guidebook: Navigating the Important Decisions for Retirement Success”.

Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins, is discussed often in the FIRE community – so no surprise it came up in this episode. It’s intended as a “practical guide on how to get the most out of your money—and out of your life”. If you like the aim of prioritizing memorable experiences far ahead of simply accumulating money for later in life, you’ll definitely want to check it out.


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

FI-ght Club: Friction Between Friends Pre and Post-FI

Questioning their roles, priorities, and the uncertain future of Two Sides of FI, Jason and Eric unveil hidden tensions arising from the pursuit and realization of financial independence. Will they find common ground and keep the project alive?

Show notes may be found below the video


Show Notes

Essential Background:

  • Eric and Jason have been friends for a long time – nearly 37 years as this episode was recorded. For more background on their upbringing, their relationship, and their FI paths, you’ll definitely want to watch these two early episodes: Our Financial Past and Our FIRE Present and Two Careers, Two Paths to Financial Independence.
  • To date we haven’t talked much “inside baseball” about how the show comes together. One exception is this outtake footage which we released two years ago: How Do We Feel About Making Two Sides of FI? Find out how much (or little) has changed since this video!
  • Lastly, we think our two-part series where we discuss our FIRE paths with our spouses is essential content: Part 1 and Part 2.

In this episode we talked about the new Two Sides of FI Discord server. If you’re not familiar, this is an instant messaging social network. 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? One recent post came after filming this episode. For more on this thoughts about this conversation and related topics, don’t miss The Flipside of Time Freedom. To be notified of future posts, please consider subscribing here.


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

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.

Financial Independence, Retire Early…Go Back to Work?

Discussing the concerns, worries, and interests occupying our thoughts right now. A temporal look from their respective sides of FI, Eric and Jason discuss a new job prospect, while Eric is a little too focused on saving to achieve FI. They probe ideas about how “vacation time” is different post-RE, as well as their current favorite podcasts and books. 

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


Show Notes

Eric’s “NOW” page @ 30X40 Design Workshop is where you’ll find links to some of the things that are inspiring Eric right now in his studio: tools, books, YouTube channels, podcasts and more. This includes links to the content he referenced in this episode.

Jason’s reading list – Here’s a list of all the books he’s read recently, is currently reading, or are up next. This is an example of a simple Notion page where you’ll find links out to learn more about these titles. Simply click on the triangles to the left of each section header to expand the respective lists.

Tenet was one of Jason’s favorite movies of 2021 and the link will take you to the film’s website. This movie can be a little challenging to wrap your brain around at times, so be forewarned. But once you get comfortable with “how the world works” in Tenet, it’s a really wild ride. It’s also visually stunning, so watch it on the largest screen you can. At the above linked you’ll find paths to digital copies and other purchase options. Depending on your region, you may also find it streaming on HBO or HBOMax, and potentially other services.


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

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.

Getting Your FIRE Asset Allocation Right. Here’s Ours (Part 1)

What is the best way to divide up your investments among stocks, bonds, and other vehicles? Asset allocation is an essential yet confusing topic. That said, it is an area of critical importance when thinking about early retirement. This is because decisions made about asset allocation can have huge implications on portfolio performance, taxation, and ease of maintenance. Join us for this first episode in a two-part series, as Eric and Jason talk about their portfolios, the merits of simple vs. more complex strategies, the role of bonds, and the risks they considered along the way.

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


Show Notes

Our asset allocations:

I do have a very small crypto stake but it’s well below 1% – Jason

The Bogleheads Wiki is an excellent place to begin one’s research on the potentially complicated topic of asset allocation. Named after and inspired by Vanguard founder, Jack Bogle, the Boglehead philosophy is focused on a “small number of simple investment principles that have been shown over time to produce risk-adjusted returns far greater than those achieved by the average investor”. Most commonly these employ so-called “lazy portfolios” of only a few diverse funds that are low cost, easily managed, and capture the performance of the entire market. The site also has an excellent discussion forum.

An Investment Policy Statement (IPS) is an important starting point for any portfolio. The IPS is a document that – according to the Bogleheads wiki: “defines general investment goals and objectives. It describes the strategies that will be used to meet these objectives and contains specific information on subjects such as asset allocation, risk tolerance, and liquidity requirements.” See the link for more information and a template you can use for your own portfolio.

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. These are M1 Finance’s flagship portfolio tool, allowing you to see the asset allocations of others and potentially invest in the same approaches.

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.

“Our Retirement Investment Drawdown Strategy” (Retirement Manifesto) is a great article describing how Fritz employs the bucket strategy to build a retirement paycheck and manage his investment portfolio post-FIRE. This is just one element of our last episode – be sure to watch for helpful background – but is a great example of how one’s asset allocation very much informs how assets are drawn down in the de-cumulation phase of FIRE.

Preferred Stocks (Early Retirement Now) and associated funds, are one of the “hybrid” investment vehicles one could consider in a portfolio. In the linked article, Big ERN talks about how he invests in an ETF made up of preferred stock elements, which have features of both stocks and bonds.


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: