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.