
Two lifelong friends document and share their personal journey as they seek to become financially independent and retire early (FIRE). One achieves his FIRE goal in 2020 during a global pandemic, inspiring the other to play catch-up. Whether you are new to the 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

Sunday Mar 09, 2025
It's Harder to Retire Than I Expected
Sunday Mar 09, 2025
Sunday Mar 09, 2025
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 can't stop working, how it affects his spouse, and what Jason has learned in his five years of RE.
Show notes: https://twosidesoffi.com/crisis

Sunday Feb 23, 2025
How We're Using ProjectionLab in (Early) Retirement
Sunday Feb 23, 2025
Sunday Feb 23, 2025
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 you can try ProjectionLab for free!
Check out ProjectionLab for free: https://twosidesoffi.com/pl
Show notes: https://twosidesoffi.com/projectionlab

Sunday Feb 09, 2025
Are You on Track? Our 2024 Financial Review
Sunday Feb 09, 2025
Sunday Feb 09, 2025
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.
Show notes: https://twosidesoffi.com/2024review

Sunday Jan 19, 2025
How Do I Know When I'm Ready to Retire?
Sunday Jan 19, 2025
Sunday Jan 19, 2025
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 experiences and what they've found most challenging.
Show notes: https://twosidesoffi.com/whentoretire

Tuesday Jan 07, 2025
What No One Tells You About Purpose and Happiness in Retirement
Tuesday Jan 07, 2025
Tuesday Jan 07, 2025
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, putting excuses behind us, the reality of purpose anxiety, and much more. Irrespective of your own retirement journey, you won't want to miss our conversation.
Show notes: https://twosidesoffi.com/purposecode
Doc G's book, "The Purpose Code": https://amzn.to/3DIcNnk

Sunday Dec 29, 2024
BONUS: Retired Early and I Hated It - How NOT to FIRE, Part 2 (Post-FI/RE)
Sunday Dec 29, 2024
Sunday Dec 29, 2024
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 depression and lack of purpose. Some are unable to find motivation without financial incentives, while others realize they haven't budgeted enough to do things they enjoy in life.
The full text of each of the Reddit posts we discussed is posted in the show notes at: https://twosidesoffi.com/how-not-to-fire-2

Sunday Dec 29, 2024
BONUS: How NOT to FIRE - Part 1 (Pre-FI/RE)
Sunday Dec 29, 2024
Sunday Dec 29, 2024
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 educating others. Here we review five of these tales: incurring tragic losses due to trying to beat the market, losing 75% of your portfolio value due to sector investing, regretting aggressively saving at the expense of living your life, and resenting your partner who doesn't have the same degree of FIRE ambitions as you do.
Show notes, including the full text of Reddit posts from this episode:
https://twosidesoffi.com/how-not-to-fire-1/

Sunday Dec 15, 2024
Retiring (Early) in 5 Days. Am I Ready?
Sunday Dec 15, 2024
Sunday Dec 15, 2024
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 opens up about the reality of choosing early retirement at the peak of her career. This isn't just another FIRE success story – it's a candid look at what it really feels like to step away from a meaningful career when you're financially independent but emotionally invested.
Whether you're questioning if early retirement is worth leaving a dream job, wrestling with your professional identity, or wondering how it feels when that last paycheck stops, her story offers inspiration and real-time insights about one of life's biggest transitions.
Show notes: https://twosidesoffi.com/retiring-early-in-five-days

Sunday Dec 01, 2024
How Options Trading Led this Engineer to Financial Independence in His 30s
Sunday Dec 01, 2024
Sunday Dec 01, 2024
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. Now in his mid-30s, David shares the keys to his success, as well as his thoughts on the role of options trading in a FIRE portfolio. Be sure to check out the show notes linked below for all the key resources shared in this conversation.
Show notes: https://twosidesoffi.com/davidsun

Sunday Nov 17, 2024
Early Retirement + Group Travel: What Works, What Doesn’t
Sunday Nov 17, 2024
Sunday Nov 17, 2024
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 help you plan your own adventure, whether you’re retired or just looking for your next great trip.
Show notes: https://twosidesoffi.com/tours