PODCAST · business
Two Sides of FI
by Jason and Eric
Whether you are new to the financial independence / retire early (FIRE) movement, already on your FIRE journey, or have retired early, there’s something here for you. Go beyond the numbers and get the personal stories as experienced by Eric and Jason.
Episodes
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She Worked 25 Years for This? Year 2 Retirement Update.
What happens when you walk away from a career you've spent 25 years building? Nearly two years into early retirement, Laura's answers might surprise you. She retired at 51 after a career in biomedical research, including 13 years running her own laboratory. Before leaving, she had plenty of...
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REWIND: What’s Wrong with This Popular Retirement Strategy?
Do you worry about running out of money in retirement? How do you draw down your assets without tanking your portfolio? Eric + Jason talk with FIRE bloggers Karsten Jeske and Fritz Gilbert about the bucket strategy. Is it a reasonable withdrawal plan or nothing more than a gimmick? They discuss...
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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...
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REWIND: What I Learned in My First Year of ”Early Retirement”
Retiring at 47 is early by any definition. In this 2SFI Rewind episode, Jason reflects on his first year in early retirement. Not everything went smoothly as you might expect. Learn what's changed, what's been better, what's worse, and - importantly - has it lived up to his expectations? If…
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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...
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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...
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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...
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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...
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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…
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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...
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How Much Can You Really Spend in Retirement?
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....
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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…
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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...
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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…
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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…
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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...
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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…
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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 below for how…
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Are You on Track? Our 2024 Financial Review
What are the critical financial elements to track and review each year pre- and post-FI? In this episode, Eric and Jason share their processes and learnings from their 2024 annual review. Topics covered include tracking net worth and withdrawal rate, portfolio management, taxes, and much more.…
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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...
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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…
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BONUS: Retired Early and I Hated It - How NOT to FIRE, Part 2 (Post-FI/RE)
This is the second of two bonus episodes, pulled from the year one archives of Two Sides of FI. Imagine hitting your FI number, retiring early, and discovering you hate it? In this episode we discuss four examples of such an outcome: from quitting the perfect job and regretting it, to feelings of...
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BONUS: How NOT to FIRE - Part 1 (Pre-FI/RE)
This is the first of two bonus episodes, pulled from the year one archives of Two Sides of FI. On the path to financial independence, there are ample opportunities for mistakes and missteps. In this episode, we review stories from people who shared their FIRE experiences online in the hopes of...
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Retiring (Early) in 5 Days. Am I Ready?
What's it really like to be 5 days away from early retirement? Join Laura, a 51-year-old scientist, as she discusses her final days running her research lab. From wrestling with the "Am I really ready?" question to unexpected tears at faculty meetings to cleaning out decades of research, she…
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How Options Trading Led this Engineer to Financial Independence in His 30s
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.…
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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…
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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...
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Empty Nest, New Challenges: What’s Next After Early Retirement?
In this episode Eric and Jason share their experiences as new empty nesters and reflect on the emotional and identity shifts that come with this major life change, especially after retiring early. They dive into how life changes when the kids are gone and work is no longer a primary focus. From...
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Financial Independence at 50 (Finally!)
After years of planning, Eric and Laura have finally reached their FI number at 50! They discovered the FIRE movement 5 years ago and set their sights on achieving financial independence by 2024. Now, with both of their boys off to college, a paid-off home, and a 80/15/5 split between equities,...
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He Earned a Million Dollars Trading This Option Strategy
How would you like to earn $80,000 a year trading options against your existing portfolio? That's exactly what our guest, Karsten "Big ERN" Jeske, has achieved. In today's episode, Jason talks with Karsten about his simple SPX options trading strategy. Be sure to see the show notes linked below…
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Our 80/20 Rules for Early Retirement: How We Did It
If you are not aggressive, you are not going to make money, and if you are not defensive, you are not going to keep money (Ray Dalio). In this episode, Eric and Jason talk about their personal "80/20 Rules" for retiring early. That is, the decisions they made along the journey that served as key...
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Checking In: Year One of Early Retirement
A year later, Jason and Eric check in with their friend Erik, who retired early at 49 while his wife continues to work. In this follow-up episode, we find out how things are going and what important lessons he learned during his first year of early retirement. Show notes and our earlier chat with...
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Four Years Later: What I Wish I Knew Before Retiring Early
Four years after retiring early at 47, Jason reflects on the key lessons he wishes he knew beforehand. He discusses his portfolio, spending habits, healthcare, mental health, relationships, and more. Show notes: https://twosidesoffi.com/fouryears
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Retired Early? Here’s How to Pay Yourself
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,...
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When is Enough, Enough? Working After Financial Independence
Why would anyone continue to work for money once they've achieved financial independence? In this episode, Eric and Jason discuss this common practice, including why Jason and Lorri currently have part-time jobs post-FI. Topics covered include de-risking retirement, charitable giving,...
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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...
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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...
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One Step Closer to FI/RE - Preparing to Give Notice
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 release on the week that Laura submits her resignation letter (which she did on...
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Retired Early to USVIs, Florida, and Spain: How They Did It
Have you considered living a life outside of your home country in retirement? Jeff went from broke at 38 to financially independent at 45 with six rental properties supporting them. He and his wife relocated to St Thomas, USVI for a few years, bought a rental property in Puerto Rico and now…
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My Healthcare Costs in Early Retirement (Year 3)
What's the true cost of healthcare in early retirement and can it break your budget? In this episode, Jason shares his experiences with Eric after three years on an ACA health insurance plan. Topics discussed include selecting and evaluating plans, how to estimate your income, premium tax…
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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. Show notes: https://twosidesoffi.com/newyear
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Financially Independent, Recreationally Employed (FIRE)
Have you truly retired if you continue to do any work for money? In this episode, Eric and Jason talk about their own FIRE goals and how they've changed over time. Topics discussed include their respective journeys, why Jason has a part-time job after retiring, the internet retirement police, and...
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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,...
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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 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…
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The Health Risks of Early Retirement
If you're not giving mental and physical health the same level of attention as your financial health, you're playing with fire. In this episode, Jason talks with Eric about what steps he's taking to prioritize his own wellness in early retirement, including a frank conversation about mental…
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One More Year: My Decision to Postpone Early Retirement
Can you imagine changing your mind about retiring early just as the finish line comes into view? What factors could cause someone to consider working one more year? In this episode, Eric talks with Jason about the idea to delay his retirement. Topics covered include why he's considering it…
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Will This Get Us Kicked Out of the FIRE Movement?
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,...
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He Retired Early, She Didn’t: A Coast FI Case Study
How would your spouse feel if you retired early while they kept working? In this episode, Eric + Jason talk with our friend Erik, who recently left the workplace while his wife continues to work. How does this arrangement work for them, and why is a coastFIRE path their choice? Topics discussed...
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Can You Reach FI Faster? Advice From Someone Who Did.
Can you shorten the time to achieve financial independence (FI)? In this episode, Eric talks with Jason about his journey to FI and the steps he took to reach FI faster and retire before 50. Topics discussed include risks taken + sacrifices made, how Eric's path differed, why early retirement is…
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Halfway to FI? Surviving the Boring Middle
How can you accelerate the boring middle on the path to reaching your financial independence goals? Online FIRE communities are full of posts talking about the challenges of "the messy middle" and, "the long boring middle." Eric and Jason discuss the topic from their pre- and post-FI viewpoints,...
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ABOUT THIS SHOW
Whether you are new to the financial independence / retire early (FIRE) movement, already on your FIRE journey, or have retired early, there’s something here for you. Go beyond the numbers and get the personal stories as experienced by Eric and Jason.
HOSTED BY
Jason and Eric
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Frequently Asked Questions
How many episodes does Two Sides of FI have?
Two Sides of FI currently has 115 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Two Sides of FI about?
Whether you are new to the financial independence / retire early (FIRE) movement, already on your FIRE journey, or have retired early, there’s something here for you. Go beyond the numbers and get the personal stories as experienced by Eric and Jason.
How often does Two Sides of FI release new episodes?
Two Sides of FI publishes regularly with 115 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Two Sides of FI?
You can listen to Two Sides of FI on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Two Sides of FI?
Two Sides of FI is created and hosted by Jason and Eric.
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