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

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/

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

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

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

How would you feel if you worked hard to retire early and later realized you hated being retired? Sadly, online forums make it clear that a number of people who achieve FIRE are disappointed, bored, or otherwise unhappy in retirement. In this episode, Eric and Jason discuss their feelings on this topic. Join us to hear Jason's thoughts in his fifth year of early retirement, and Eric's observations after a recent vacation with his family.

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