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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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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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Early Retirement + Group Travel: What Works, What Doesn’t

Are group tours the ultimate hassle-free way to travel, or do they come with unexpected challenges? In this episode, Eric talks with Jason about his first experiences with group travel after a recent trip to Peru. They explore the pros, cons, and key lessons Jason learned—offering insights to help you plan your own adventure, whether you’re retired or just looking for your next great trip.

Jason’s blog post to accompany this episode: Empty nest, new adventures

Show Notes

Announcements

Don’t miss Eric’s appearance on Bigger Pockets Money! It’s a great interview with lots of details, some of which have never been shared publicly before. And if podcasts are more your thing, here’s the audio-only version.

Essential Background:

The tour company Jason and Lorri used for their trip to Peru was G Adventures. There are several Peru itineraries, and the one they selected was the 15-day National Geographic Journeys: Inca Explorer. You’ll find all the details at that link, including a full itinerary.

In this episode we spoke a little about travel insurance. Coverages vary among carriers as do the requirements for minimum coverage specified by tour operators. For this trip, Jason and Lorri opted against full trip cancellation protection, which kept the cost of their insurance to below $100 while meeting all requirements. They used Allianz Travel Insurance.

The slideshow below contains many of the pictures shared in this episode along with a few others from the trip:

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.

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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Does Retirement = Happiness?

How would you feel if you worked hard to retire early and later realized you hated being retired? Sadly, online forums make it clear that a number of people who achieve FIRE are disappointed, bored, or otherwise unhappy in retirement. In this episode, Eric and Jason discuss their feelings on this topic. Join us to hear Jason’s thoughts in his fifth year of early retirement, and Eric’s observations after a recent vacation with his family.

Show Notes

Lest Eric (and any viewers) be nervous about Jason and Lorri’s safety on their upcoming Peru trip, worry not. Jason misspoke about the price of the tour they’d booked. The cost was $3.6k per person, not $1.6k. Let’s chalk his error up to aging, shall we?

Essential Background:

  • Retired Early and I Hated It : How NOT to FIRE, Part 2 (Post-FI/RE) – As mentioned in this episode, we’ve tackled post-RE regret before. In this early 2SFI video, Eric and Jason discussed four examples of such an outcome: from quitting the perfect job and regretting it, to feelings of depression and lack of purpose. Some are unable to find motivation without financial incentives, while others realize they haven’t budgeted enough to do things they enjoy in life.
  • 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.
  • 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.
  • 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 goes 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 our most popular Two Sides of FI episodes of 2022 was our 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.
  • Retired Early and Feeling Lost. What’s Next? – How does it feel when you haven’t yet found your purpose after retiring early? In this episode, Jason talks with Eric about the first three years years 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. 
  • My Next Phase of Early Retirement Won’t Include This… – Year two in early retirement was very different for Jason than year one. It’s common that the honeymoon stage of retirement is followed by disappointment and a search for meaning. In this episode, Jason and Eric discuss a recent project Jason abandoned and what stage of retirement they think he’s in. You’ll hear his approach to guarding his free time, what Eric fears most about retiring early, and more.

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.

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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Retiring Early Made This Possible

What essential lessons did Jason learn from the most impactful travel he’s done to date? In this episode, Eric and Jason catch up on a number of recent changes in their lives. Topics discussed include Eric and Laura’s recent big announcement, Jason’s Camino experience, the benefits and challenges of pre- and post-FI travel, and much more.

Be sure to check out the show notes below the video!

Show Notes

Essential Background:

Interested in learning more about Jason’s Camino de Santiago experience? You’ll want to see all of Jason’s blog posts leading up to and written during his recent walk on the Camino Portugués. There you’ll find information on his preparation as well as day by day accounts of his route, photos he took of the journey, as well as all his thoughts on the important lessons he took home from the Camino.

  • We talk a lot about travel given how important a part it plays in our retirement planning and we have two episodes wholly focused on the topic. “How We Travel: Pre + Post Financial Independence” is the first of these, and concerns just how different pre- and post-FI travel can be. More recently, we dug into the financial side of travel in “Did We Budget Enough for Travel in Early Retirement?“. Here we talked about the myriad financial elements of travel, disagreeing with your spouse, the value of planning by age range, and much more.
  • Did you see our episode where Laura talked with Eric about her plans to give notice to retire from her career in science? If you didn’t, “One Step Closer to FI/RE – Preparing to Give Notice” is a must-watch. A natural pairing to this is the earlier episode, Financially Independent, Recreationally Employed (FIRE). Here, Eric shares his thoughts on how he’s thinking about his business these days and what that might mean for the RE part of his FIRE plans.
  • Did you know we’ve had both our spouses on the show before? We’ve got a two part series from our conversation with Lorri and Laura, covering a wide range of topics. In part 1, we talk about getting onboard with FIRE, financial topics including budgeting and setting the FI number, as well as the emotional aspects of choosing the FIRE path. In part 2, we discuss how each couple shares financial responsibilities, the importance of finding friend networks, talking to our children about FIRE, and our hopes for their post-FI lives.
  • In this show we ended with some discussion of our kids’ college plans. We have two episodes wholly dedicated to our children, covering a broad range of subject areas – financial and otherwise. Be sure to check out both episodes – Teaching Our Teens About FI and Money (Part 1) and Financial Lessons We’re Passing On (Part 2).

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, 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.

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FI-nancial Checkup: New Year Routines + Goals for 2024

What financial lessons did we learn last year and what will we do differently in 2024? In today’s episode, Eric and Jason discuss their end of year review processes. Topics include investing goals, their net worth reviews, lessons learned, and much more. Be sure to check out the show notes below the video!

Show Notes

Essential Background:

  • We’ve talked about our review processes before, and for the full details check out Our Net Worth Is Up! Sharing Our Financial Review Process. If you don’t have a process for regular financial reviews, you aren’t alone. Many people are unsure about how to calculate their net worth and keep their personal finances on track. In this episode, Eric and Jason share their simple pre- and post-FI review processes for net worth tracking, portfolio review, setting savings and budget goals, and more.
  • Jason mentioned staying below his safe withdrawal rate ceiling in this episode. For all the details (and more), you’ll want to see our page dedicated to the Safe Withdrawal Rate Toolbox. If you’re familiar with Karsten Jeske, you’ll definitely want to check this out. It has all the information you need including all three videos in our series, including walkthroughs of the tool and the CAPE-based strategy that Jason referenced here.
  • If you’re not familiar with Eric’s 30×40 Design Workshop business and his FI journey, you’ll want to see our two-part series: Passive Income = A Path to Financial Independence (Part 1) and Lessons Learned in 7 Years Earning Passive Income – A Path to FI (Part 2). Those links are to the show notes pages, which link both the episodes themselves and a host of related content that you’ll want to check out – particularly Part 2. In that post he shares lots of information on his various passive income streams
  • We talk about travel often on the show – it’s a clear priority for us both. Did We Budget Enough for Travel in Early Retirement? is our most recent episode on the topic. What happens if all the travel you want to do after retiring would break the budget? In this episode, Eric and Jason talk about the importance of travel to their early retirement plans. Topics discussed include financial concerns, disagreeing with your spouse, the value of planning by age range, and much more.
  • Want to learn more about that budget-busting 50th birthday celebration? Will This Get Us Kicked Out of the FIRE Movement? has all the details. Would you spend $1000 on dinner for a special occasion – or more? Eric and Jason recently enjoyed a milestone birthday celebration with their spouses + friends at a world famous restaurant. The total cost may shock you. In this episode, they talk about the experience, spending decisions pre- vs, post-financial independence, and whether it was actually worth it.

We talked about New Retirement (now called Boldin) in this episode. Jason really likes this platform and plenty of people on Reddit are discussing this comprehensive retirement planning tool as well. They have a full-featured free offering  as well as a reasonably priced paid “PlannerPlus” version with a host of really nice features, as well as consulting services. Huge benefits of PlannerPlus include a solid Roth conversion modeler and Monte Carlo analysis. Be sure to check out their 14-day free trial and see if you’re as convinced as Jason was! There’s a very active Facebook community around the tool as well.

Jason referenced a very popular Wait But Why post in this episode. The Tail End is the material in question. We wholeheartedly recommend it as a must-read for anyone – but be prepared for some thought provoking stuff!

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, 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.

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Did We Budget Enough for Travel in Early Retirement?

What happens if all the travel you want to do after retiring would break the budget? In this episode, Eric and Jason talk about the importance of travel to their early retirement plans. Topics discussed include financial concerns, disagreeing with your spouse, the value of planning by age range, and much more. Be sure to check out the show notes below.

Show Notes

Essential Background:

Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins – was mentioned by Eric here, and is a much-discussed book in the FIRE community. 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.

Are you familiar with the Camino de Santiago? Jason talked a little about this including his plans to walk the most famous of the Camino routes, the Camino Francés (the French Way), in 2025. There is a wealth of information available online, including on YouTube. If you’re US-based, consider checking out the American Pilgrims site.

Wondering what that word was we were trying to pronounce when talking about traveling to Croatia? Hvar is a Croatian island in the Adriatic Sea, located off the Dalmatian coast, lying among several other islands. It’s consistently ranked in the top of many lists concerned with the best of island travel, and Hvar promotes itself as “the sunniest spot in Europe”.

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, 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.

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How We Travel: Pre + Post Financial Independence

A seven day vacation or 5 weeks of travel – which would you prefer? When you’re working towards financial independence, vacations are a time to set aside work and everyday chores. But they’re constrained by things you don’t often control: accrued vacation time, work and school schedules, business obligations, and holidays, to name a few. In this episode, Eric and Jason compare notes from their two respective sides of FI and their recent vacations: 7 days for Pre-FI Eric and 5 weeks for Post-FI Jason. See just how different is travel once you reach FI and the constraints have been removed.

For more information on Jason’s five-week trip, including the valuable lessons he and his family learned on their longest trip ever, check out his blog post: https://thenextphaseisnow.com/longest-vacation-of-my-life/

Show Notes

As we mentioned in the episode, one leg of Jason’s travels brought the Two Sides of FI together in the same place for the first time in several years, as he and Lorri visited Eric and Laura in Maine. Along with all the fun times we’d planned (and carried out!) for our few days together, we’d intended to film episodes with our spouses – which we did. Unfortunately, a few technical issues meant that we decided not to use that footage after all. However, we believe the two episodes we recorded later with our spouses (Part 1 and Part 2) turned out even better in terms of the quality of our conversations. If you haven’t seen these shows yet, please check them out. Two times Two Sides of FI is the only way to get the full picture!

Two times Two Sides of FI: Jason, Lorri, Eric and Laura
Dinner time in Maine: (back) Eric + Laura, (front) Lorri + Jason

For a closer look at some of our trip photos, check out these galleries:

Eric’s photos:

Jason’s photos:

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