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Is This Goodbye?

Are we really ready to walk away from Two Sides of FI? In this candid conversation, Jason and Eric reflect on more than four years of recording together, what the project has meant, and whether it still fits into their lives. They talk openly about the rewards of community and connection, the challenges of generating new topics, and the weight of obligations in retirement. Is this the end, or just a pause?

Show Notes

Jason wrote a blog post to accompany this episode. This was written a few weeks after this episode was recorded and edited. It is meant to be read after viewing the video.

Essential Background:

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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Early Retirement: How Things Have Changed for Us

Retirement doesn’t follow a script – it rewrites itself in real time. In this episode, Jason and Eric unpack why the classic “phases” of retirement actually overlap and how that feels day to day. They dig into the challenges of switching from super-saver to intentional spender, using side income (like options trading or creative work) to fund experiences without derailing the plan, and how travel has changed for them. No matter where you are on the FIRE path, there’s something here for you.

Show Notes

Essential Background:

  • Are you new to the show? To find out where our FIRE paths began along with more on our backgrounds, you’ll want to watch our first three episodes: “Our Financial Past and our FIRE Present – Two Sides of FI“, “Two Careers, Two Paths to Financial Independence“, and “Financially Independent. Retire Early? Let’s Discuss!“
  • How does it feel when you haven’t yet found your purpose after retiring early? In this episode, Retired Early and Feeling Lost. What’s Next?, Jason talks with Eric about the first three years years exploring his post-FIRE purpose. They discuss the phases of retirement, seeking out meaningful projects, lessons learned along the way, and much more. 
  • Did you miss our recent chat with Kayla? In From Divorce to Financial Freedom: FI at 45, you’ll learn about someone on the solo FI path and how she achieved her goals.
  • Drawdown is a favorite topic of ours and one we’ve come back to time and time again. 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 can a hobby turn into a second career and lead to financial independence before 40? In this episode, Jason talks with David Sun, an electrical engineer who stumbled into options trading after hearing about it from a fellow grad student. Only ten years later he launched his first hedge fund. 
  • The topic of cash positions and how we manage them has been a regularly occurring topic on 2SFI. Get all the details here, including episodes devoted to the topic.
  • In this episode, Jason mentions his “IPS” or Investment Policy Statement. Chasing short term market conditions adds a lot of risk to reaching your long term investing goals. In “Is This a Part of Your FIRE Plan?”, we talk about how an IPS can help ensure you stick to your strategy, and avoid market timing and other investing pitfalls.
  • Why has ProjectionLab quickly become one of the most popular early retirement planning tools? In this episode, learn why PL is an essential software package for both Eric and Jason. Topics covered include how to get started, best practices, and powerful new features. 

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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From Divorce to Financial Freedom: FI at 45

What happens when the plan was “we”… and now it’s just “me”? At 45, Kayla reached Financial Independence solo after divorce, living in the Bay Area without a tech salary. In this episode of Two Sides of FI, she shares how she rebuilt her finances, overcame her fear of investing, and designed a plan that works without a partner’s income or support. In this episode, Learn how a saving mentality and discovering the FIRE community in her 30s led her to the realization that early retirement was within her reach and how she achieved it.

Show Notes

Essential Background:

Kayla mentioned a book as a key part of her FIRE and investing eduction: The Simple Path to Wealth (JL Collins). It 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.

How do you find advice-only planners? Below you’ll find two resources. Please note that Two Sides of FI has no relationship nor do we receive any compensation from either:

1) XY Planning Network: As described on the site, their member advisors ascribe to fiduciary and CFP standards, earn no commissions, and require no minimum assets. They have convenient filters to allow searching by advisor specialities, including those with FIRE experience. Many work under multiple fee models, including advice-only, which can be a good source for one-time consults without any

2) Cody Garrett, CFP and advice-only planner from Measure Twice Financial, shared this list in the past on Twitter. As he described it, “these 11 advisors provide comprehensive financial planning without any expectation, obligation, or even the option to manage client investments. Options for project-based, hourly, or ongoing.” You’ll note there is overlap between these resources, which makes sense. But this is the list Cody has shared with prospective clients, so one can presume there’s been some personal vetting.

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 We Hiding Something? Our Real FIRE Portfolio + Expenses

Are FIRE content creators being honest about their numbers? YouTuber Duane isn’t so sure. In this episode, Eric and Jason share detailed insights about their own FIRE numbers, portfolios, withdrawal rates, and what it actually means to be “retired.” They also explain why context matters more than a single number, and get honest about how content creation fits into their financial picture. If you’ve ever wondered how real people make FIRE work, this one’s for you.

Show Notes

Essential Background:

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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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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Life After FIRE: Your Toughest Questions, Answered

After five years of early retirement and 100 episodes of Two Sides of FI, what have we learned? A lot—and we’re sharing it all. To mark this milestone, Eric and Jason sit down for an honest, wide-ranging AMA based on questions from our community. We cover everything from money and mindset shifts to healthcare, travel, and even music choices. Whether you’re already on your FIRE path or just curious what life really looks like on the other side, this conversation is for you.

Jason’s companion blog post on our 100-episode milestone:

Show Notes

Essential Background:

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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2025 Market Chaos Blowing up our FIRE Plans?

With markets down at one point nearly 20% in 2025, is this the sequence risk moment we feared? In this episode, we reflect on recent market volatility, how it’s impacted our early retirement finances, and whether our original FIRE strategy can still hold up. We also catch up post-Liberation Day and share how our thinking has evolved after real-world stress testing our withdrawal plan. If you’re navigating FIRE in 2025—or just wondering what a 20% portfolio loss feels like—this one’s for you.

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:

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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What Should We Do With Bonds and Cash in a Crazy Market?

How should you respond to market conditions to ensure financial stability? Like the famous Mike Tyson quote says, “Everyone has a plan until they get punched in the mouth”. In this episode, Eric talks with Jason about an unexpected opportunity to update his early retirement portfolio. Topics discussed include bond and cash allocations, asset location, and what they’re doing to manage extreme market volatility.

Show Notes

Essential Background:

A Bond Tent strategy is one of the common approaches used by the FIRE community to mitigate both Retirement Date + Sequence of Returns Risks. As is often the case, Michael Kitces has a great article on the topic. We couldn’t cover sufficient depth on this important topic in our episode, but this post has all the details you need.

Despite there being several good rules of thumb, the “right” asset location for bonds can be a controversial subject, and one that involves many factors to consider. Jason mentioned The White Coat Investor podcast and blog as having covered this topic before. Here are three articles worth your time, particularly for high income earners: Asset Location – Bonds Go In Taxable!, My 2 Asset Location Pet Peeves, and What Is Asset Location? Tax-Efficient Fund Placement.

How To Build A Retirement Paycheck:  This is the first of three great Retirement Manifesto posts on author Fritz Gilbert’s implementation of the Bucket Strategy, which we have touched on in several episodes to date. Here you’ll find guidance on how to determine the asset allocation you’ll want to have in place by the time you retire early. The other two articles in the series are linked here as well.

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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It’s Harder to Retire Than I Expected

Do some find it hard to retire because they don’t know how to stop working? In today’s episode, Eric talks with Jason about the challenges he’s experienced after achieving FI, finding it hard to ramp down his business. Are we just wired to work hard or is there more to it? We discuss why Eric can’t stop working, how it affects his spouse, and what Jason has learned in his five years of RE.

Show Notes

Essential Background:

  • How Do I Know When I’m Ready to Retire? 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. We tackle it head-on here.
  • Eric’s path to 90% passive income is truly impressive. To learn what his approach was like and to benefit from the many lessons he learned, check out Passive Income = A Path to Financial Independence (Part 1) and Lessons Learned in 7 Years Earning Passive Income – A Path to FI (Part 2). You won’t want to miss the show notes for these given all the valuable content Eric has linked here.
  • For more on Eric’s career journey as well as Jason’s path, you won’t want to miss Two Careers, Two Paths to Financial Independence.
  • Retirement Is Nothing Like I Thought It Would Be – We all daydream about what retirement will be like, but will reality live up to expectations? In this episode, Eric and Jason were joined by Fritz Gilbert, who blogs at The Retirement Manifesto. Our discussion went well beyond the numbers, covering topics including finding your purpose, working “one more year”, determining your FIRE timing, and the keys to success in retirement.
  • One of the ways many early retirees stay busy is to take on some time of part-time “fun job”. But have you truly retired if you continue to do any work for money? In Financially Independent, Recreationally Employed (FIRE), Eric and Jason talk about their respective journeys, why the latter has a part-time job after retiring, the internet retirement police, and much more.
  • How would you feel if you worked hard to retire early and later realized you hated being retired? In Does Retirement = Happiness?, we address the reality that some people who achieve FIRE are disappointed, bored, or otherwise unhappy in retirement.
  • Did you see our recent episodes regarding Eric’s spouse, Laura’s, decision to retire from her career as a scientist? If not, you’ll definitely want to view:
  • The story begins with One Step Closer to FI/RE – Giving Notice. In this episode, Eric and Laura discuss their preparations as they near their FI number and Laura prepares to notify her employer that she’s leaving. Recorded in the fall of 2023, this behind-the-scenes discussion was prepared for publication the week Laura submitted her resignation notice.
  • Next we published Unexpected Reactions to My Early Retirement, Contempt, concern, surprise, envy, admiration, and support; just a few of the reactions Laura received when she announced she was retiring early, closing her biomedical research laboratory, and beginning a new phase of life beyond work. Some reactions were expected and some surprised her. In this episode, Eric and Laura unpack these interactions and chart their next steps as they prepare to leave work and step into early retirement.
  • What’s it really like to be 5 days away from early retirement? The last chapter (so far) in this story is Retiring (Early) in 5 Days. Am I Ready? Whether you’re questioning if early retirement is worth leaving a dream job, wrestling with your professional identity, or wondering how it feels when that last paycheck stops, Laura’s story offers inspiration and real-time insights about one of life’s biggest transitions.

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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How We’re Using ProjectionLab in (Early) Retirement

Why has ProjectionLab quickly become one of the most popular early retirement planning tools? In this episode, learn why PL is an essential software package for both Eric and Jason. Topics covered include how to get started, best practices, and powerful new features. See the link underneath the video for how you can try ProjectionLab for free!

Show notes may be found below the video

Show Notes

For a free trial of ProjectionLab, use this link: https://twosidesoffi.com/pl

Essential Background:

  • As mentioned in this episode, both Jason and Eric use Karsten “Big ERN” Jeske’s Safe Withdrawal Rate Toolbox. For all the details of this essential tool, please see our page dedicated to the Safe Withdrawal Rate Toolbox. It has all the information you need including all the videos in our series, including walkthroughs of the tool and the CAPE-based strategy that Jason referenced here.
  • 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. In Have Enough to Retire (Early)? 10 Steps to Make Sure, we discussed a great post by Fritz Gilbert about how to ensure that you’re financially prepared.

Just getting started with ProjectionLab and in need of a quick start guide? This series of videos by the team at PL is a great place to start. This will ensure you avoid some of the mistakes we made along the way! There are a lot of other helpful videos on their YouTube channel, as well. Lastly, you can also find great content on many topics in their Help Center.

Don’t miss the ProjectionLab Discord server! As we discussed in today’s episode, there’s a wealth of information here to be found given the very active user community. As you’ll discover, the PL team also has a strong presence on the server, ensuring great access to feedback, questions, and feature requests from the community.

Eric and I both found Rob Berger’s recent review of ProjectionLab to be a good introduction to some of the powerful features in the tool.

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 has a FIRE blog? 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.

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