Two Sides of FI

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://twosides...

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

Why would anyone continue to work for money once they've achieved financial independence? In this episode, Eric and Jason discuss this common practice, including why Jason and Lorri currently have part-time jobs post-FI. Topics covered include de-risking retirement, charitable giving, skill-building, and more. Show notes: https://twosidesoffi.com/enough

Contempt, concern, surprise, envy, admiration, and support; just a few of the reactions Laura received when she announced she was retiring early, closing her biomedical research laboratory, and beginning a new phase of life beyond work. Some reactions were expected and some surprised her. In this episode, Eric and Laura unpack these interactions and chart their next steps as they prepare to leave...

What essential lessons did Jason learn from the most impactful travel he's done to date? In this episode, Eric and Jason catch up on a number of recent changes in their lives. Topics discussed include Eric and Laura's recent big announcement, Jason's Camino experience, the benefits and challenges of pre- and post-FI travel, and much more. Show notes: https://twosidesoffi.com/catchingup

Eric and Laura discuss their preparations as they near their FI number and Laura prepares to notify her employer that she's leaving. Recorded in the fall of 2023, this behind-the-scenes discussion was prepared for release on the week that Laura submits her resignation letter (which she did on Thursday!) They discuss their hesitations, changes of heart, and ready themselves for what's ahead. Show n...

Have you considered living a life outside of your home country in retirement? Jeff went from broke at 38 to financially independent at 45 with six rental properties supporting them. He and his wife relocated to St Thomas, USVI for a few years, bought a rental property in Puerto Rico and now they’re preparing to relocate to Spain. So, if you’ve considered what a life outside the mainland US might l...

What's the true cost of healthcare in early retirement and can it break your budget? In this episode, Jason shares his experiences with Eric after three years on an ACA health insurance plan. Topics discussed include selecting and evaluating plans, how to estimate your income, premium tax credits, and why 2023 was Jason's worst year for healthcare expenses to date. Show notes: https://twosidesoffi...

What financial lessons did we learn last year and what will we do differently in 2024? In today's episode, Eric and Jason discuss their end of year review processes. Topics include investing goals, their net worth reviews, lessons learned, and much more. Show notes: https://twosidesoffi.com/newyear

Have you truly retired if you continue to do any work for money? In this episode, Eric and Jason talk about their own FIRE goals and how they've changed over time. Topics discussed include their respective journeys, why Jason has a part-time job after retiring, the internet retirement police, and much more. Show notes: https://twosidesoffi.com/busted

What happens if all the travel you want to do after retiring would break the budget? In this episode, Eric and Jason talk about the importance of travel to their early retirement plans. Topics discussed include financial concerns, disagreeing with your spouse, the value of planning by age range, and much more. Show notes: https://twosidesoffi.com/travel

How does it feel when you haven't yet found your purpose after retiring early? In this episode, Jason talks with Eric about his three year journey exploring his post-FIRE purpose. In this episode, they discuss the phases of retirement, seeking out meaningful projects, lessons learned along the way, and much more. Show notes: https://twosidesoffi.com/purpose

If you're not giving mental and physical health the same level of attention as your financial health, you're playing with fire. In this episode, Jason talks with Eric about what steps he's taking to prioritize his own wellness in early retirement, including a frank conversation about mental health. Here they discuss steps to promote wellness, the distinct challenges of retirement, and much more. D...

Can you imagine changing your mind about retiring early just as the finish line comes into view? What factors could cause someone to consider working one more year? In this episode, Eric talks with Jason about the idea to delay his retirement. Topics covered include why he's considering it, getting agreement with your spouse, how others reacted to the idea, and much more. Show notes: https://twosi...

Would you spend $1000 on dinner for a special occasion - or more? Eric and Jason recently enjoyed a milestone birthday celebration with their spouses + friends at a world famous restaurant. The total cost may shock you. In this episode, they talk about the experience, spending decisions pre- vs, post-financial independence, and whether it was actually worth it. Show notes: https://twosidesoffi.com...

How would your spouse feel if you retired early while they kept working? In this episode, Eric + Jason talk with our friend Erik, who recently left the workplace while his wife continues to work. How does this arrangement work for them, and why is a coastFIRE path their choice? Topics discussed include being thrown into retirement, finding purpose, talking about FIRE, and much more. Show notes: ht...

Can you shorten the time to achieve financial independence (FI)? In this episode, Eric talks with Jason about his journey to FI and the steps he took to reach FI faster and retire before 50. Topics discussed include risks taken + sacrifices made, how Eric's path differed, why early retirement is so attractive, and much more. Show notes: https://twosidesoffi.com/fasterFI

How can you accelerate the boring middle on the path to reaching your financial independence goals? Online FIRE communities are full of posts talking about the challenges of "the messy middle" and, "the long boring middle." Eric and Jason discuss the topic from their pre- and post-FI viewpoints, sharing their own experiences. Show notes: https://twosidesoffi.com/messymiddle

Are you on the FIRE path or interested in learning more about early retirement? Three years ago I retired from my career at age 47 after reaching financial independence the prior year. This video is from a livestream where community members had the opportunity to ask me questions about what my experience has been like. Thanks to all who joined! Don't miss the extensive show notes, which list all t...

Questioning their roles, priorities, and the uncertain future of Two Sides of FI, Jason and Eric unveil hidden tensions arising from the pursuit and realization of financial independence. Will they find common ground and keep the project alive? Show notes: https://twosidesoffi.com/fightclub

Do you have a process for regular financial reviews? If not, you aren't alone - many people are unsure about how to calculate their net worth and keep their personal finances on track. In this episode, Eric and Jason share their simple pre- and post-FI review processes for net worth tracking, portfolio review, setting savings and budget goals, and more. Show notes: https://twosidesoffi.com/networt...

Do you like the idea of a portfolio withdrawal strategy that can't run out of money? This walkthrough video is the third part in our Safe Withdrawal Rate (SWR) series, and teaches you how to model a variable withdrawal strategy based on the CAPE ratio. Using this powerful and FREE tool created by Karsten Jeske, you can design a personalized plan that works with your own financial situation. Be sur...