Two Sides of FI

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

In this episode Eric and Jason share their experiences as new empty nesters and reflect on the emotional and identity shifts that come with this major life change, especially after retiring early. They dive into how life changes when the kids are gone and work is no longer a primary focus. From adjusting to the quiet at home to rethinking purpose and identity, they discuss the highs and lows of this new phase. Join them as they explore what comes next in this post-parenting, post-career chapter of life.

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

After years of planning, Eric and Laura have finally reached their FI number at 50! They discovered the FIRE movement 5 years ago and set their sights on achieving financial independence by 2024. Now, with both of their boys off to college, a paid-off home, and a 80/15/5 split between equities, fixed income and cash, they’ve officially hit their financial independence (FI) goal and plan to retire early.

In this episode, they discuss the challenges of moving goalposts, their decision to keep running Eric's business, 30X40 Design Workshop (on their own terms), and their plans for the future. Laura will be leaving her job as a research scientist in January 2025 to operate 30X40 remotely, with a goal of maintaining a flexible, time-limited schedule. They also cover practical topics like their pretax/taxable split, health insurance considerations, and their withdrawal strategy. Learn what reaching FI looks like for them, the steps they’re taking next, and what their plans are moving forward!

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

How would you like to earn $80,000 a year trading options against your existing portfolio? That's exactly what our guest, Karsten "Big ERN" Jeske, has achieved. In today's episode, Jason talks with Karsten about his simple SPX options trading strategy. Be sure to see the show notes linked below for definitions, associated blog posts, and more.

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

If you are not aggressive, you are not going to make money, and if you are not defensive, you are not going to keep money (Ray Dalio). In this episode, Eric and Jason talk about their personal "80/20 Rules" for retiring early. That is, the decisions they made along the journey that served as key pivot points towards ensuring their achievement of financial independence.

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

A year later, Jason and Eric check in with their friend Erik, who retired early at 49 while his wife continues to work. In this follow-up episode, we find out how things are going and what important lessons he learned during his first year of early retirement.

Show notes and our earlier chat with Erik - https://twosidesoffi.com/erik

Four years after retiring early at 47, Jason reflects on the key lessons he wishes he knew beforehand. He discusses his portfolio, spending habits, healthcare, mental health, relationships, and more.

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

How do you plan to set up your retirement paycheck to avoid running out of money? In this episode, Jason talks with Eric about how he uses a free online tool to manage his finances in early retirement. Topics covered include his variable withdrawal strategy, managing cash, portfolio rebalancing, and much more.

FREE SWR tool and show notes: https://twosidesoffi.com/toolbox