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We Have Enough. So Why Is Spending Still Hard?

Your FIRE plan worked — so why is spending still so hard? In this episode, Jason (year 7) and Eric (year 2) share a candid early retirement update. Both portfolios have grown well above their FIRE numbers despite years of withdrawals, and a fee-only advisor delivered a surprising verdict: spend more. Learn why unwinding the accumulation mindset is harder than the math, how “life support” for adult kids reshapes the budget, and why unstructured time might be the truest form of wealth – and much more.

Show Notes

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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Year 2 vs. Year 7: What Early Retirement is Really Like

Is early retirement everything you imagined or does the reality take years to settle into? In this honest check-in, Jason (year 2) and Eric (year 7) compare notes on what post-FIRE life actually feels like from two very different vantage points. They cover decision fatigue, the challenge of replacing work’s structure, and why the emotional side of retirement rarely gets the attention it deserves.

Show Notes

Essential Background:

Jason referenced his interest in options trading in this discussion. While not for everyone, it’s a topic of great interest among many in the FIRE community. In “How Options Trading Led this Engineer to Financial Independence in His 30s”, Jason spoke with David Sun, an engineer who stumbled into options trading . Only ten years later he launched his first hedge fund. Now in his mid-30s, David shared the keys to his success, as well as his thoughts on the role of options trading in a FIRE portfolio.

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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Thinking About Slow Travel After FI? Watch This First

Is slow travel in retirement all that we hoped or is the dream far better than the reality? In this episode, Jason talks with Eric about his recent experiences during a month-long US road trip. Learn how the trip ended up way over budget, compare how Eric+Jason manage expenses, and whether they would do it again – and much more.

Show Notes

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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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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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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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.

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How Do I Know When I’m Ready to Retire?

How do you know when it’s the right time 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. In this episode, Jason and Eric talk about their own experiences and what they’ve found most challenging.

Show Notes

Here are the retirement personas that Eric shared in our conversation:

Essential Background:

  • 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.
  • In We Each Hired a Flat Fee Financial Advisor. Was it Worth It? Eric and Jason each hired the same fee-only, advice-only advisor to evaluate their portfolios and answer questions. They share how they found this advisor, what the process was like, the specific questions + answers they had, and who they think could benefit from such a service.
  • Retiring early is a dream for many but the decision to leave the workplace early can impact us in ways we may not have predicted. In “Retiring Early – So Why Am I Worried?“, we discussed the first year of Jason’s early retirement and Eric shares his own concerns as he approaches FI.
  • Did you see our recent chat with Jordan “Doc G” Grumet, titled “Will You Run Out of Money or Time? FI Advice From a Hospice Doctor“. The topic of purpose can be found all over our conversation with him. In a related vein, Jason spoke with Doc G again in “Fulfillment Beyond FI: Life After Early Retirement with Jason”, on the Earn and Invest podcast.
  • 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 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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What No One Tells You About Purpose and Happiness in Retirement

Worried about finding purpose in retirement? Most people are, but in reality it’s easy to address these fears head-on. In this episode, Eric + Jason are joined by Jordan “Doc G” Grumet, a hospice doctor, podcaster, blogger, and author. Topics discussed include how regret can be motivating, putting excuses behind us, the reality of purpose anxiety, and much more. Irrespective of your own retirement journey, you won’t want to miss our conversation. See below for links to Doc G’s book as well as the show notes.

Show notes may be found below the video

Show Notes

To get your own copy of Jordan’s excellent book, “The Purpose Code: How to unlock meaning, maximize happiness, and leave a lasting legacy”, buy direct from his website or from Amazon. Here’s a book trailer for more information.

Essential Background:

  • As we mentioned in this episode, Jordan’s first appearance on Two Sides of FI was in 2022 in Will You Run Out of Money or Time? FI Advice From a Hospice Doctor. What can conversations with the dying teach us about the secret to financial independence? We talked about that and much more, as we dove into his book, The Purpose Code: How to unlock meaning, maximize happiness, and leave a lasting legacy.
  • How does it feel when you haven’t yet found your purpose after retiring early? In Retired Early and Feeling Lost. What’s Next?, Jason talked with Eric about his three year journey exploring his post-FIRE purpose. In this episode, they discuss the phases of retirement, seeking out meaningful projects, lessons learned along the way, and much more.
  • We’ve actually spoken to Doc G a few times! Our first chat was on Jordan’s own Earn and Invest podcast. Here’s a link to the episode, which was a really fun one for us and also represents the first time we were a guest on someone else’s show as Two Sides of FI! As you’ll find, Doc G is a very skilled interviewer. Did you ever think that everything will be okay once you are financially independent? In our conversation, we pushed back on this narrative.

Not familiar with hospice and want to learn more? This post from The Hospice Foundation of America is a great resource. Stated simply, hospice is medical care for people with an anticipated life expectancy of 6 months or less, when cure isn’t an option, and the focus shifts to symptom management and quality of life. The site is a wealth of information, including guidance on how to access hospice care and selecting hospice providers.

For links to all of Jordan’s content, including the Earn and Invest podcast and his DiverseFI blog, be sure to check out his website.

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