Two Sides of FI

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

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

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

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 work and step into early retirement. Show notes: https://twosidesoffi.com/unexpected

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 notes + resources: https://twosidesoffi.com/one-step-closer-to-fi

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 look like, I think you'll find his story interesting. Show notes: https://twosidesoffi.com/retirementality

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.com/ouch

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. Don't miss the show notes as they include a link to Jason's latest blog post on the topic of mental health. Show notes: https://twosidesoffi.com/wellness

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://twosidesoffi.com/OMY

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/frenchlaundry

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: https://twosidesoffi.com/erik

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 the episodes and resources discussed in the episode: Show notes: https://twosidesoffi.com/AMA

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/networth

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 sure to see the show notes below to get your free copy, to see the two prior episodes, and for all the links we discuss in the video. Show notes: https://twosidesoffi.com/toolbox

Love it or hate it, budgeting is an essential part of financial success. In this episode, Eric and Jason share their own financial details using a simple, model budget and offer tips for making budgeting a less daunting task. See the link below for the show notes, which includes the full details of our budgets. Show notes: https://twosidesoffi.com/fire-budget

Has your shrinking retirement portfolio left you considering part-time work to ease your anxiety? Inspired by a blog post from Go Curry Cracker, we discuss BaristaFIRE, time freedom, what it means to be "unemployable", and what work we might consider post-retirement. Be sure to see the links below for the show notes and to the blog post referenced in the video.   Show notes: https://twosidesoffi.com/failing GCC post: https://www.gocurrycracker.com/failing-at-early-retirement/

How much money can you safely spend in retirement? In part two of this series on safe withdrawal rates, we discuss the #1 tool we've found to help you answer that question. Topics covered include the SWR Toolbox, our thoughts on Social Security, the challenges of spending in retirement, and how to get comfortable with increasing your withdrawal rate. Be sure to see the links below for the show notes and to Part 1 which walks through this FREE retirement tool. Show notes: https://twosidesoffi.com/toolbox

Do you want to avoid the biggest retirement risk? This simple to use tool will let you model your safe withdrawal rate and help ensure you don't run out of money. In this walkthrough video, we teach you how to use this powerful, flexible, and FREE tool created by Karsten Jeske. Using the SWR Toolbox, you can ensure that you have a personalized plan that works with your own financial situation.  Show notes: https://twosidesoffi.com/toolbox

Do you worry about running out of money in retirement? How do you draw down your assets without tanking your portfolio? Eric + Jason talk with FIRE bloggers Karsten Jeske and Fritz Gilbert about the bucket strategy. Is it a reasonable withdrawal plan or nothing more than a gimmick? They discuss alternative approaches, how to generate a retirement paycheck, and the role of cash. Whether you're interested in FIRE or on a traditional retirement path, you can't afford to miss this episode! Show notes: https://twosidesoffi.com/bucketstrategy

Year two in early retirement was very different for Jason than year one. It's common that the honeymoon stage of retirement is followed by disappointment and a search for meaning. In this episode, Jason and Eric discuss a recent project Jason abandoned and what stage of retirement they think he's in. You'll hear his approach to guarding his free time, what Eric fears most about retiring early, and more. Check out the link below for the show notes, including all the content referenced in this video. Show notes: https://twosidesoffi.com/noblog Jason's blog archive: https://www.thenextphaseisnow.com/

Are you worried about neglecting to budget for key expenses in early retirement? Even if you put good effort into creating your FIRE budget, it's easy to miss some very important items. In this episode, Jason and Eric discuss these commonly forgotten or underestimated expenses, including healthcare costs, taxes, dealing with inflation, and more. Check out the link below for the show notes, including all the content referenced in this video. Show notes: https://twosidesoffi.com/iforgot

What is early retirement really like? In this episode, Eric checks in with Jason two and a half years after he left his career behind. They discuss his recent financial moves, the impact of inflation, how Jason spends his time, and what's truly important to him. Check out the link below for the show notes, including all the content we referenced in this video. Show notes: https://twosidesoffi.com/30months

How big of an impact can a single purchase under $250 make on your life? In part two of this series, Eric and Jason talk about some of the best things they've bought in recent years. Topics discussed include travel, outdoor gear, concert tips, kitchen aids, and more. Be sure to see the link below for the show notes, which includes info on all the items we discussed in the video, as well as those on our under $50 list from part one. Show notes: https://twosidesoffi.com/under50

Can low cost items - or even free things - truly impact your quality of life positively? In this episode, Eric and Jason talk about some of their favorite purchases under $50, as well as some tools and life hacks that have done just that. Topics discussed in part one of this series include apps, books, games, outdoors essentials, and organizational tools. Be sure to see the link below for the show notes, which includes info on all the items we discussed in the video. Show notes: https://twosidesoffi.com/under50