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

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 and Jason sit down for an honest, wide-ranging AMA based on questions from our community. We cover everything from money and mindset shifts to healthcare, travel, and even music choices. Whether you're already on your FIRE path or just curious what life really looks like on the other side, this conversation is for you.

Show notes: https://twosidesoffi.com/episode100

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 it’s impacted our early retirement finances, and whether our original FIRE strategy can still hold up. We also catch up post-Liberation Day and share how our thinking has evolved after real-world stress testing our withdrawal plan. If you're navigating FIRE in 2025—or just wondering what a 20% portfolio loss feels like—this one's for you.

Show notes: https://twosidesoffi.com/chaos

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 in the mouth". In this episode, Eric talks with Jason about an unexpected opportunity to update his early retirement portfolio. Topics discussed include bond and cash allocations, asset location, and what they're doing to manage extreme market volatility.

Show notes: https://twosidesoffi.com/bonds

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

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

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

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

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

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