Shows / Two Sides of FI
Two Sides of FI
You're listening to Two Sides of FI, a conversation between two lifelong friends about financial independence - what it takes to get there and what comes after. One of us reached FI in 2020, the other in 2024. We started this show to document our different paths, and now that we're both post-FI, we're still figuring out how to use the freedom we spent years working toward. I'm Eric and I'm joined by my friend Jason, and this is our story.
Episodes
Two Sides of FIShe 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…
Two Sides of FIREWIND: 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…
Two Sides of FIWe 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…
Two Sides of FIREWIND: 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…
Two Sides of FIYear 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…
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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…
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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…
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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…
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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…
Two Sides of FIAm 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…
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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…
Two Sides of FIAre 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…
Two Sides of FIOur 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…
Two Sides of FILife 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…
Two Sides of FI2025 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…
Two Sides of FIWhat 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…
Two Sides of FIIt'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…
Two Sides of FIHow 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…
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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…
Two Sides of FIHow 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…
Two Sides of FIWhat 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…
Two Sides of FIBONUS: 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…
Two Sides of FIBONUS: 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…
Two Sides of FIRetiring (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…
Two Sides of FIHow 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…
Two Sides of FIEarly 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…
Two Sides of FIDoes 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…
Two Sides of FIEmpty 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…
Two Sides of FIFinancial 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…
Two Sides of FIHe 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…
Two Sides of FIOur 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…
Two Sides of FIChecking 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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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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…
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Ask an Early Retiree Anything! Live Q&A with Jason from Two Sides of FI
Are you on the FIRE path or interested in learning more about early retirement? Three years ago I retired from my career at age 47 after reaching financial…
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FI-ght Club: Friction Between Friends Pre and Post-FI
Questioning their roles, priorities, and the uncertain future of Two Sides of FI, Jason and Eric unveil hidden tensions arising from the pursuit and…
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Our Net Worth Is Up! Sharing Our Financial Review Process
Do you have a process for regular financial reviews? If not, you aren't alone - many people are unsure about how to calculate their net worth and keep their…
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Secure Your Retirement with this Variable Withdrawal Strategy
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)…
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Retiring With $2M: Here’s How We’d Spend It
Love it or hate it, budgeting is an essential part of financial success. In this episode, Eric and Jason share their own financial details using a simple…
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Am I Failing at Early Retirement?
Has your shrinking retirement portfolio left you considering part-time work to ease your anxiety? Inspired by a blog post from Go Curry Cracker, we discuss…
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Having Trouble Trusting the Math 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…
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Never Run Out of Money in Retirement - Use This Free FIRE Calculator!
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…
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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…
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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…