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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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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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Am I Doing Retirement Wrong?

Most don’t stop to think about how much they might be missing by working “just one more year.” It’s impossible to put a price tag on some of the experiences Eric + Jason have had since leaving full time work behind. In today’s episode, they talk about things they’d never have done before retiring early, the freedom that FIRE afford, and much more. Don’t miss the show notes below for details on their work history and their journeys to financial independence.

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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Never Run Out of Money in Retirement – Use This Free FIRE Calculator!

Show notes may be found below the videos, all of which are also available on our Safe Withdrawal Rate series playlist.

Scroll down for the newest video!

Part 1: Walkthrough of the SWR Toolbox

Do you want to avoid the biggest retirement risk? This simple to use tool will let you model your safe withdrawal rate and help ensure you don’t run out of money. In this walkthrough video, we teach you how to use this powerful, flexible, and FREE tool created by Karsten Jeske. Using the SWR Toolbox, you can ensure that you have a personalized plan that works with your own financial situation.

Part 2: Eric + Jason discuss how they’re using the SWR Toolbox and how Jason is struggling to spend as much as he can safely do in early retirement

How much money can you safely spend in retirement? In part two of this series on safe withdrawal rates, we discuss the #1 tool we’ve found to help you answer that question. Topics covered include the SWR Toolbox, our thoughts on Social Security, the challenges of spending in retirement, and how to get comfortable with increasing your withdrawal rate.

Part 3: Walkthrough of the CAPE-Based Rule tab in the SWR Toolbox

Do you like the idea of a portfolio withdrawal strategy that can’t run out of money? This walkthrough video is the third part in our Safe Withdrawal Rate (SWR) series, and teaches you how to model a variable withdrawal strategy based on the CAPE ratio. Using this powerful and FREE tool created by Karsten Jeske, you can design a personalized plan that works with your own financial situation.

Part 4: How Jason builds his retirement paycheck using the SWR Toolbox

How do you plan to set up your retirement paycheck to avoid running out of money? In this episode, Jason talks with Eric about how he uses a free online tool to manage his finances in early retirement. Topics covered include his variable withdrawal strategy, managing cash, portfolio rebalancing, and much more.

Part 5: Answering your questions about using CAPE-adjusted strategies

In Part 5 of our SWR Toolbox series, we answer your questions about our CAPE-based withdrawal strategy, how it compares to a fixed safe withdrawal rate approach, and much more. See the link below for all of our toolbox videos including tutorials and a host of supportive content in the show notes.

Show Notes

Download the Safe Withdrawal Rate (SWR) Toolbox

  • The Safe Withdrawal Rate Toolbox is available via Karsten Jeske’s Early Retirement Now blog. The current version can be downloaded via Part 28 of the SWR series. This is also the post where the revisions to the calculator are described. To see the history of this tool, you’ll need to go back to Part 7. We found reading both posts to be essential to really understand how the tool works. Please ensure you follow the directions in the video to make your own copy of the tool. There’s no need to email Karsten to request edit rights!

Essential Blog Posts

Safe Withdrawal Rate series: This is the landing page for the 61-part SWR series (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 in the series and not all of them involve deep dives into math! While we think all of his posts are interesting, you’ll find guidance below about the specific articles we think are most important to the topic of this video – in addition to Parts 28 and 7 listed above.

In Part 3 of this series, we covered the CAPE-Adjusted Safe Withdrawal Rate tab in the Toolbox, and described what the Shiller CAPE is. For those who want further details, there’s ample material available on Karsten’s blog for you to review. In addition to the introduction to the feature provided in Part 28, Big ERN recently wrote several posts concerning a new “better” CAPE ratio – i.e. CAPE model 2 in the SWR Toolbox. 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 the SWR Toolbox employs this factor to model a variable withdrawal strategy. To go a level deeper on the foundations of this approach, including how to evaluate these types of strategies, you’ll definitely want to read Part 18: Flexibility and the Mechanics of CAPE-Based Rules.

Sequence Risk is more important than your average return rate. Surprised? Be sure to check out Part 15: More Thoughts on Sequence of Return Risk. As mentioned in the video, SWR is overwhelmingly determined by the first 10-15 years of portfolio drawdown.

Are you the kind of person who wants all the gory details about the math underlying the SWR Toolbox? If so, you won’t want to miss Part 8: Technical Appendix. It’s got all the information you need to fully understand how Karsten’s approach works. There are also some good references at the bottom of the post on related material found elsewhere.

Did you know we’ve spoken to Karsten twice before? “What the FIRE Community Gets Wrong” was the first time he came on Two Sides of FI. We covered a lot of ground in this episode about safe withdrawal strategies – so much so that we also released a follow-up video called “Karsten Spoke, We Listened. Here’s What We Learned”. These two episodes are popular with our audience for a good reason and are definitely worth viewing for anyone interested in SWR strategies.

Our second conversation with Karsten also featured Fritz Gilbert (from The Retirement Manifesto), in a continuation of their debate about the merits of bucket strategies. In “What’s Wrong with This Popular Retirement Strategy?” we covered a lot of ground that you won’t want to miss!

Other Show Notes

We get a lot of questions about portfolio rebalancing. Would you like a free tool to help you rebalance your portfolio using the same approach we do? This calculator provides a convenient mechanism to enter and track your asset allocation, flag when any assets exceed your allocation targets, and model any rebalancing that may be needed. It’s really easy to use as you’ll see in our introductory video.

Eric mentioned Rob Berger’s “Ultimate Investment Tracking Spreadsheet” in part 5 of the series. If you’d like another tool to track asset allocation, you’ll want to check this out.

In Part 4, 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. Topics covered include defining portfolio makeup + objectives, the mechanics of cash generation + rebalancing, and why you might consider implementing an IPS yourself

cFIREsim (or  Crowdsourced Financial Independence and Retire Early Simulator) is a very popular and powerful FIRE calculator created by Lauren. We found a lot of value in this tool throughout our FIRE journey, and clearly many others do as well. In the developer’s words, “What can cFIREsim do? At its core, you can enter information in the a few simple inputs and return the basic simulation. At its most complicated, it can determine your portfolio success based on 80 individual portfolio adjustments, multiple types of inflation, multiple types of market returns, and graphically show you the results. There are many options to choose from outside of the ‘Basic Inputs’ “, including a number of variable withdrawal strategies under “Spending Plan”.

Variable Percentage Withdrawal (VPW) is another method besides CAPE-adjusted WR for allowing market conditions to influence the amount you take out of your portfolio in drawdown. As mentioned in parts 2 and 4, VPW is popular among some adherents the Bogleheads approach to investing. As you’ll read at this link, this method “adapts adjustments to portfolio withdrawal amounts to the retiree’s retirement horizon, asset allocation, and portfolio returns during retirement… to allow the retiree to spend most of the portfolio using return-adjusted withdrawals. By adapting withdrawals to market returns, VPW will never prematurely deplete the portfolio.”

stickK is the app Eric mentioned in Part 2 to help track adherence to a goal – like keeping to spending your planned withdrawal rate. Created from a behavioral economics framework, stickK allows you to create “Commitment Contracts, [which are] a binding agreement you sign with yourself to ensure that you follow through with your intentions—and it does this by utilizing the psychological power of loss aversion and accountability to drive behavior change.” We’ve not tried this yet but this is a pretty appealing (an a little scary) idea!

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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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.