Two Sides of FI

Jason and Eric
  • 4.9 (438)
  • INVESTING
  • UPDATED 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. DEC 14

    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

    42 min

  2. SEP 21

    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

  3. SEP 7

    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

  4. AUG 17

    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

    48 min
  5. Am I Doing Retirement Wrong?

    JUL 13

    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

    36 min

  6. JUN 29

    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

    45 min
  7. Are We Hiding Something? Our Real FIRE Portfolio + Expenses

    JUN 15

    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 a single number, and get honest about how content creation fits into their financial picture. If you've ever wondered how real people make FIRE work, this one’s for you. Show notes: https://twosidesoffi.com/numbers

    31 min

  8. JUN 1

    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 shifts and societal judgment. Whether you're planning your own early retirement or already there, this episode will help you feel less alone and more prepared. Show notes: https://twosidesoffi.com/fears

    51 min
See All (108)

4.9
out of 5
438 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 - 2025
  • Episodes
    108
  • Rating
    Clean
  • Copyright
    © Copyright 2024 All rights reserved.
  • Show Website
    Two Sides of FI

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