Two Sides of FI

Jason and Eric
  • 4.9 (453)
  • Investing
  • Biweekly

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.

  1. Oct 11

    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 questions. Would she miss the work? Her colleagues? The sense of purpose and identity that came with being a scientist? And what would happen when the structure she'd known for decades dropped away? Now that she's had some time to experience life after work, we're revisiting those questions. We talk about what Laura misses (and what she doesn't), the unexpected emotional side of giving up a paycheck, finding purpose without a job title, and what it's been like spending more time together than at any other point in our relationship. We also dig into a piece of conventional retirement advice that Laura chose to ignore: the idea that you need to retire to something. Was that a mistake? Has the retirement honeymoon worn off? And would she ever consider going back to work? Along the way, we answer questions from our audience about friendships, daily routines, staying healthy, intellectual curiosity, and what a fulfilling retirement actually looks like when you're living it. If you're approaching financial independence, particularly after a career you've invested decades in building, you'll find plenty to consider in this conversation. Show notes: https://twosidesoffi.com/laurayear2/

    She Worked 25 Years for This? Year 2 Retirement Update.

  2. Aug 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

  3. Apr 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/

    Year 2 vs. Year 7: What Early Retirement is Really Like

  4. 12/14/2025

    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

  5. 09/21/2025

    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

  6. 09/07/2025

    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

  7. 08/17/2025

    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

  8. 07/13/2025

    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

    Am I Doing Retirement Wrong?
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4.9
out of 5
453 Ratings

About

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.

Information

  • Creator
    Jason and Eric
  • Years Active
    2021 - 2026
  • Episodes
    111
  • Rating
    Clean
  • Copyright
    © Copyright 2024 All rights reserved.
  • Show Website
    Two Sides of FI

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