Two Sides of FI

By Jason and EricBusiness Education Investing How To

Two Sides of FI episodes

September 20 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 alternative approaches, how to generate a retirement paycheck, and the role of cash. Whether you’re interested in FIRE or on a traditional retirement path, you can’t afford to miss this episode!
show notes: https://twosidesoffi.com/bucketstrategy/
1 hr 9 min
August 30 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: https://twosidesoffi.com/spendmore
53 min
August 04 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 you're excited to reach this milestone but still harbor some reservations about crossing into "retirement", Jason offers a grounded, thoughtful perspective on what to expect and how to prepare for such a life-altering transition.
Read more about his journey on his blog, starting with the post that originally accompanied this episode: https://www.thenextphaseisnow.com/p/yearone
31 min
April 12 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: https://twosidesoffi.com/year2/
48 min
December 14, 2025 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: https://twosidesoffi.com/slowtravel
43 min
September 21, 2025 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: https://twosidesoffi.com/goodbye
Jason's blog post: https://www.thenextphaseisnow.com/p/goodbye
41 min
September 07, 2025 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: https://twosidesoffi.com/phases
41 min
August 17, 2025 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: https://twosidesoffi.com/kayla
49 min
July 13, 2025 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: https://twosidesoffi.com/wrong
37 min
June 29, 2025 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.
FREE SWR tool and show notes: https://twosidesoffi.com/toolbox
46 min

About Two Sides of FI

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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…