Shows
Two Sides of FIAm I Doing Retirement Wrong?Most don't stop to think about how much they might be missing by working "just one more year." It's impossible to put a price tag on some of the experiences Eric + Jason have had since leaving full time work behind. In today's episode, they talk about things they'd never have done before retiring early, the freedom that FIRE afford, and much more. Don't miss the show notes below for details on their work history and their journeys to financial independence.
Show notes: https://twosidesoffi.com/wrong
2025-07-1336 min
Two Sides of FIHow Much Can You Really Spend in Retirement?In Part 5 of our SWR Toolbox series, we answer your questions about our CAPE-based withdrawal strategy, how it compares to a fixed safe withdrawal rate approach, and much more. See the link below for all of our toolbox videos including tutorials and a host of supportive content in the show notes.
FREE SWR tool and show notes: https://twosidesoffi.com/toolbox
2025-06-2945 min
Two Sides of FIAre We Hiding Something? Our Real FIRE Portfolio + ExpensesAre FIRE content creators being honest about their numbers? YouTuber Duane isn't so sure. In this episode, Eric and Jason share detailed insights about their own FIRE numbers, portfolios, withdrawal rates, and what it actually means to be "retired." They also explain why context matters more than a single number, and get honest about how content creation fits into their financial picture. If you've ever wondered how real people make FIRE work, this one’s for you.
Show notes: https://twosidesoffi.com/numbers
2025-06-1530 min
Two Sides of FIOur Biggest Fears About Early RetirementWhat’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
2025-06-0150 min
Two Sides of FILife After FIRE: Your Toughest Questions, AnsweredAfter 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
2025-05-181h 17
Two Sides of FI2025 Market Chaos Blowing up our FIRE Plans?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
2025-05-0438 min
Two Sides of FIWhat Should We Do With Bonds and Cash in a Crazy Market?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
2025-04-2735 min
Two Sides of FIIt's Harder to Retire Than I ExpectedDo 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
2025-03-0932 min
Two Sides of FIHow We're Using ProjectionLab in (Early) RetirementWhy 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
2025-02-2350 minTwo Sides of FIAre You on Track? Our 2024 Financial ReviewWhat 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
2025-02-0951 min
Two Sides of FIHow Do I Know When I'm Ready to Retire?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
2025-01-1946 min
Two Sides of FIWhat No One Tells You About Purpose and Happiness in RetirementWorried 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
2025-01-0736 min
Two Sides of FIBONUS: Retired Early and I Hated It - How NOT to FIRE, Part 2 (Post-FI/RE)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...
2024-12-2926 min
Two Sides of FIBONUS: How NOT to FIRE - Part 1 (Pre-FI/RE)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...
2024-12-2936 min
Two Sides of FIRetiring (Early) in 5 Days. Am I Ready?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...
2024-12-1543 min
The Trade Busters141 - Guest Appearance - Two Sides of FI-Visit Two Sides of FI at https://twosidesoffi.com/-Follow Two Sides of FI on X @twosidesoffi-Watch the interview video at https://www.youtube.com/watch?v=Wxp-zT6UyWMThe Trade Busters provides actionable ideas to take your option trading to the next level. Through our educational podcast and instructional spreadsheets, we aim to empower the everyday retail trader. Discover unique ways of thinking through sizing, risk and leverage in your option strategies.-View strategy mechanics, tradelogs and more at the trading page: https://www.thetradebusters.com-The Trade Busters Discord server is no...
2024-12-0908 min
Two Sides of FIHow Options Trading Led this Engineer to Financial Independence in His 30sHow 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...
2024-12-0148 min
Two Sides of FIEarly Retirement + Group Travel: What Works, What Doesn’tAre 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
2024-11-1759 min
Two Sides of FIDoes Retirement = Happiness?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
2024-10-2746 min
Two Sides of FIEmpty Nest, New Challenges: What’s Next After Early Retirement?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
2024-09-2242 min
Two Sides of FIFinancial Independence at 50 (Finally!)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...
2024-08-2643 min
Two Sides of FIHe Earned a Million Dollars Trading This Option StrategyHow 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
2024-08-1851 min
Two Sides of FIOur 80/20 Rules for Early Retirement: How We Did ItIf 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
2024-08-0442 min
Two Sides of FIChecking In: Year One of Early RetirementA 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
2024-07-2146 minTwo Sides of FIFour Years Later: What I Wish I Knew Before Retiring EarlyFour 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
2024-06-3043 minTwo Sides of FIRetired Early? Here’s How to Pay YourselfHow 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
2024-05-2239 minTwo Sides of FIWhen is Enough, Enough? Working After Financial IndependenceWhy 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
2024-05-0545 minTwo Sides of FIUnexpected Reactions to My Early RetirementContempt, 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
2024-04-2137 minTwo Sides of FIRetiring Early Made This PossibleWhat 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
2024-04-1443 minTwo Sides of FIOne Step Closer to FI/RE - Preparing to Give NoticeEric 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
2024-03-1738 minTwo Sides of FIRetired Early to USVIs, Florida, and Spain: How They Did ItHave 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
2024-02-2654 minTwo Sides of FIMy Healthcare Costs in Early Retirement (Year 3)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
2024-02-0434 minTwo Sides of FIFI-nancial Checkup: New Year Routines + Goals for 2024What 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
2024-01-2142 minTwo Sides of FIFinancially Independent, Recreationally Employed (FIRE)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
2024-01-0743 minTwo Sides of FIDid We Budget Enough for Travel in Early Retirement?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
2023-12-0338 minTwo Sides of FIRetired Early and Feeling Lost. What’s Next?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
2023-11-1942 minTwo Sides of FIThe Health Risks of Early RetirementIf 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
2023-11-0538 minTwo Sides of FIOne More Year: My Decision to Postpone Early RetirementCan 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
2023-10-2239 minTwo Sides of FIWill This Get Us Kicked Out of the FIRE Movement?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
2023-10-0845 minTwo Sides of FIHe Retired Early, She Didn’t: A Coast FI Case StudyHow 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
2023-09-2447 min
Earn & InvestFulfillment Beyond FI: Life After Early Retirement with JasonJoin us in this insightful episode of Earn & Invest as we sit down with Jason from the Two Sides of FI podcast to explore the uncharted waters of life after early retirement. Together, we delve into the fascinating journey of financial independence and the vital question of how one fills their time, and whether boredom lurks in the shadows. Jason candidly shares his personal experiences, revealing the transformative impact of early retirement on his life.#FinancialIndependence#EarlyRetirement#LifeAfterFI#RetirementJourney#PersonalFinance
2023-09-181h 03Two Sides of FICan You Reach FI Faster? Advice From Someone Who Did.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
2023-08-2042 minTwo Sides of FIHalfway to FI? Surviving the Boring MiddleHow 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
2023-07-2344 minTwo Sides of FIAsk an Early Retiree Anything! Live Q&A with Jason from Two Sides of FIAre 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
2023-07-031h 27Two Sides of FIFI-ght Club: Friction Between Friends Pre and Post-FIQuestioning 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
2023-05-2133 minTwo Sides of FIOur Net Worth Is Up! Sharing Our Financial Review ProcessDo 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
2023-05-0735 minTwo Sides of FISecure Your Retirement with this Variable Withdrawal StrategyDo 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.
...
2023-04-2316 minTwo Sides of FIRetiring With $2M: Here’s How We’d Spend ItLove 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
2023-04-0946 minTwo Sides of FIAm I Failing at Early Retirement?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/
2023-03-2646 minTwo Sides of FIHaving Trouble Trusting the Math in 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
2023-03-1245 minTwo Sides of FINever Run Out of Money in Retirement - Use This Free FIRE Calculator!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
2023-02-2625 minTwo Sides of FIWhat’s Wrong with This Popular Retirement Strategy?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
2023-02-121h 09Two Sides of FIMy Next Phase of Early Retirement Won’t Include This…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...
2023-01-2934 minTwo Sides of FIMy FIRE Budget Didn’t Account for ThisAre 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 episode.
Show notes: https://twosidesoffi.com/iforgot
2023-01-1545 minTwo Sides of FIFinding My Way in Early Retirement: A 30 Month Check-InWhat 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 episode.
Show notes: https://twosidesoffi.com/30months
2023-01-0444 minTwo Sides of FIOur Most Impactful Tools and Purchases Under $250 (Part 2)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 epispode, as well as those on our under $50 list from part one.
Show notes: https://twosidesoffi.com/under50
2022-12-2130 minTwo Sides of FIBudget-Friendly Finds: Our Favorite Tools and Hacks Under $50 (Part 1)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 episode.
Show notes: https://twosidesoffi.com/under50
2022-12-1835 minTwo Sides of FITax Strategies on FIRE: Financial Independence / Retire EarlyDo you worry about taxes and how they impact your financial goals? Whether you're on a FIRE path or retiring traditionally, there are many critical tax topics to consider. In this episode, Jason talks with financial planner and CPA Sean Mullaney, creator of The FI Tax Guy blog. We talk about common tax misunderstandings, the power of solo 401(k) accounts, Roth conversions, and tax loss harvesting. Check out the link below for the show notes including all the content we mentioned in the episode.
Show notes: https://twosidesoffi.com/fitaxguy
Sean's book: "Solo 401(k): The...
2022-12-0444 minTwo Sides of FIYou Asked, We Answered. FIRE Q&AAnswering your financial independence, retire early (FIRE) questions, including the one we're asked most often. This special Ask Us Anything format commemorates the 50th episode of Two Sides of FI. THANK YOU to all who submitted questions and for your continued support of the show!
Show notes: https://twosidesoffi.com/ep50
2022-11-201h 06Two Sides of FIMy Plan to Retire Early is ON HOLDThe bear market has forced many to revise their FI goals and retirement plans. In this episode, Eric talks with Jason about pushing back his FI date, options he's considering, whether BaristaFIRE could be the answer, the possibility of redefining work, and advice for others in a similar position. See the link below for the show notes.
Show notes: https://twosidesoffi.com/delayed
2022-11-0643 minTwo Sides of FIReacting to YOUR Ideas for Holding CashAre you worried about holding cash in this high inflation environment? In a recent video, we talked about the role of cash pre- and post-retirement. In this episode, Eric + Jason review and react to YOUR ideas that you shared with us. Topics covered include bond ladders, high yield savings, real estate, gold and other cash alternatives, and emergency funds. Check out the link below for the show notes, including all the content referenced in this episode.
Show notes: https://twosidesoffi.com/cash
2022-10-2345 minTwo Sides of FIIs This a Part of Your FIRE Plan?Chasing short term market conditions adds a lot of risk to reaching your long term investing goals. An investment policy statement (IPS) can help ensure you stick to your strategy, and avoid market timing and other investing pitfalls. In this episode, Eric talks with Jason about his IPS, and why he finds it such a useful tool. Topics covered include defining portfolio makeup + objectives, the mechanics of cash generation + rebalancing, and why you might consider implementing an IPS yourself. See the link below for the show notes, where we link to Jason's IPS and other content we referenced in...
2022-10-0943 min
Two Sides of FIBONUS - Submit a question and be a part of our 50th episode!Do you have any questions you'd like to ask Eric and Jason? Be a part of our upcoming 50th full-length episode by sharing any questions addressed to either or both of us. In just over a week, we'll be recording an Ask Me Anything (AMA) episode to celebrate our Two Sides of FI milestone. THANK YOU for your support of the show!
Leave us a message: http://twosidesoffi.com/speakpipe
2022-10-0201 minTwo Sides of FIWill You Run Out of Money or Time? FI Advice From a Hospice DoctorWhat can conversations with the dying teach us about the secret to financial independence? In this episode, Eric + Jason are joined by Jordan "Doc G" Grumet, a hospice doctor, podcaster, blogger, and author. Topics discussed include the mirage of wealth, living meaningfully, and Jordan's experiences eight years post-FI. Irrespective of your own retirement journey, you won't want to miss our conversation. See below for links to Doc G's book as well as the show notes.
Show notes: https://twosidesoffi.com/DocG
Doc G's book: "Taking Stock: A Hospice Doctor's Advice on Financial Independence, Building Wealth...
2022-09-2546 minTwo Sides of FIFIRE and Holding Cash - What We’re DoingHow much cash in your portfolio is enough - or too much? In this episode, Eric + Jason discuss the idea of holding cash allocations pre- and post-retirement. Topics covered include emergency funds, the temptation to invest in a down market, bonds, and building cash reserves. Join us as we discuss this essential retirement topic. Check out the link below for the show notes, including all the content referenced in this episode.
Show notes: https://twosidesoffi.com/cash
2022-09-1149 minTwo Sides of FIDo I Wish I’d Worked One More Year?With all of the volatility in the market, should you delay retirement by a year? A viewer asked Jason if he would feel more secure had he worked another year or two before retiring early. In today's episode, Eric + Jason discuss that question and the merits of considering "one more year". Join us as we discuss this idea and the reasons you might consider that option, what Jason would have missed out on if he had worked longer, and the value he found in retiring when he did. Check out the link below for the show notes, including all...
2022-08-2825 minTwo Sides of FIHow I Plan to Retire Early on a $50K SalaryCan you retire early without a high-paying tech industry salary? In this episode, we talk with Stephen about how he plans to do just that. At 30 years old, he's earning $50k as a higher education administrator, yet he plans to retire with at least a million dollars by his early 50s. How will he do that? Join us as we discuss his plans, the role of financial discipline, why he doesn't feel he's overly frugal, and the challenges of his FIRE path.
**Show notes: https://twosidesoffi.com/50k
2022-08-1435 minTwo Sides of FIKarsten Spoke, We Listened. Here’s What We Learned.We're making changes. Here's what we learned and how our FIRE strategies are changing after talking to "Big ERN" Karsten Jeske, an economist, CFA, and safe withdrawal rate expert. In this episode, we review our take-homes from that conversation, and react to comments and feedback we received about the episode. If you missed the original episode, be sure to listen to Episode 40 first.
Show notes: https://twosidesoffi.com/swr
2022-07-3138 minTwo Sides of FIDon’t Let the Cost of Healthcare Break Your Early Retirement PlanCalculating the cost of health insurance is a complicated and stressful exercise when you're retiring early. Hear Jason's experience with his first full year using the California ACA Exchange and learn how Eric arrived at his budget of $350K, his worst case scenario. We discuss how to choose a plan, ACA subsidies, differences by state, and other alternative options. If you missed our earlier healthcare episode, be sure to see the link below.
Show notes: https://twosidesoffi.com/aca
2022-07-1647 minTwo Sides of FIWhat the FIRE Community Gets Wrong - Talking with Karsten JeskeWhat would you do if you ran out of money in retirement? It's hard to imagine a scarier outcome, and yet many on the FIRE path may be at risk for this if they get their portfolio withdrawal rate wrong. In this episode, Eric + Jason talk with Karsten Jeske, the creator of the Early Retirement Now blog. Known by many as "Big ERN", he is an economist who is well known to the FIRE community for his extensive work in characterizing safe withdrawal rates (SWR). In this episode, we dig into Karsten's free, powerful SWR Toolbox, and discuss topics...
2022-07-031h 04Two Sides of FIWe Each Hired a Flat Fee Financial Advisor. Was it Worth It?Here's what we learned by hiring a financial advisor for a fixed fee of $1,000. Rather than pay a costly ongoing assets under management (AUM) fee, we wanted to test out this increasingly popular fee-for-service advisement model. Eric and Jason discuss each hired the same fee-only, advice-only advisor for $1,000 to evaluate their portfolios and answer a variety of key questions. They share how they found this advisor, what the process was like, the specific questions + answers they had, and who they think could benefit from such a service. Is this the right option for you? Maybe.
Show notes: ht...
2022-06-191h 07Two Sides of FIStock Market on FIRE: What We’re Doing in a DownturnYou're on a FIRE path and the markets keep falling - what do you do? In this episode, Jason + Eric revisit the topic of market downturn and candidly discuss their pre- and post-FI moods in this turbulent time. Join us to learn what they're doing and thinking about right now as Jason nears the two-year post-FI mark and Eric contemplates pushing his 2024 FI date back. Topics discussed include rebalancing, how to monitor portfolio performance, moves we are making now, and feeling down about FIRE.
Show notes: https://twosidesoffi.com/downmarket
2022-06-0556 minTwo Sides of FIMy New Life: Two Years After Early RetirementWondering what a day in the life in early retirement is like? Eric travels to California to shadow Jason and find out what his FIRE life is like nearly two years into early retirement. We learn how Jason fills his days, hear his concerns pre- and post-FI, discuss the merits of part-time "fun" jobs, and the reality of finances.
Show notes: https://twosidesoffi.com/tryingonFI
2022-05-2237 minTwo Sides of FIWe Avoided Estate Planning. Here’s Why You Can’t Afford To (Part 2)Don't make a common mistake that could cost your family dearly. If you don't have an estate plan, many essential decisions will be left to others, including the government. In this second installment in a two-part series, Eric + Jason continue their conversation about what they did to get their respective plans in place. Topics discussed in this episode include end of life decisions, powers of attorney, insurance, and how to get started. Don't delay further - join us now for the second episode of this two-part series.
Show notes: https://twosidesoffi.com/houseinorder
2022-05-0833 minTwo Sides of FIIf You Want Financial Freedom You Can’t Ignore This (Part 1)We avoided estate planning for a long time; here's why you shouldn't. Without an estate plan, you're giving over the control of what happens to all your assets to others. In part one of this two-part series, Eric + Jason talk about what they did to - finally - get their respective plans in place. Topics discussed in this episode include the elements of estate planning, why people delay + how to get started, living trusts, and taking care of your heirs. Don't be like those who put this off "until they're older": join us now for the first episode of...
2022-04-2433 minTwo Sides of FIBreaking Up With My Financial Advisor?Did you know that financial advisor fees can eat up HALF of your portfolio's value over time? While happy with the good support and great relationship he had with them, Jason was thinking about leaving his financial planners late last year. In this episode, we capture a conversation Eric + Jason had on this topic, as they discussed the merits and downsides of paying assets under management (AUM) fees. Topics covered in this episode include why he stuck with them over the years, the value advisors can bring, more cost-effective options for financial advice, and how Jason is making his...
2022-04-1038 minTwo Sides of FIFinancial Lessons We’re Passing On (Part 2)Kids are incredibly impressionable and as parents, we have a responsibility to educate them in all ways, including in financial matters. In this second installment of a two part series, we continue our discussion on a topic that's been requested many times by viewers: all things relating to kids. Concepts discussed in this episode include saving for college and the roles of parents vs children in that, budgeting, investing, and sharing life lessons by example.
Show notes: https://twosidesoffi.com/kids
2022-03-2731 minTwo Sides of FIOur FIRE Portfolios Are Down 20%, What Now?How has the recent market downturn changed our plans? Jason + Eric candidly discuss their pre- and post-FI moods in this volatile time. Learn what they're doing and thinking about right now as Jason nears the two-year post-FI mark and Eric contemplates pushing his 2024 FI date back.
show notes: https://twosidesoffi.com/crash
2022-03-1351 minTwo Sides of FITeaching Our Teens About FI and Money (Part 1)Having children comes along with many necessary expenses, but also provides a key opportunity to provide them with a solid financial education. In part one of a two part series, we tackle a topic that's been requested many times by viewers: all things relating to kids. Topics discussed in this episode include our own financial upbringing, early attempts to teach our kids about saving + investing, the value of teens having jobs, and talking with them about FIRE. Join us for the first episode of this two-part series.
**Show notes: https://twosidesoffi.com/kids
2022-02-2726 minTwo Sides of FIBuying Bonds. Still Not Convinced I’m Doing the Right Thing! (Part 2)I reallocated my investment portfolio, sold out of my 100% equity position and I'm not happy about it. Part two of a two-part series, you'll learn why and how I'm making peace with it. Ensuring that your investment portfolio can fund your lifestyle for the duration of your lifespan is essential to success in FIRE. One of the most impactful elements of that is how your portfolio is constructed, or your asset allocation. In this episode, Eric discusses his desire to reduce the risk of his portfolio with Jason, and ensure he + Laura are set up for success. Topics discussed...
2022-02-1334 minTwo Sides of FII Rebalanced My FI/RE Portfolio and I Hate It! (Part 1)I reallocated my investment portfolio, sold out of my 100% equity position and I'm not happy about it. In this two-part episode, you'll learn why and how I'm making peace with it. Ensuring that your investment portfolio can fund your lifestyle for the duration of your lifespan is essential to success in FIRE. One of the most impactful elements of that is how your portfolio is constructed, or your asset allocation. In this episode, Eric discusses his desire to reduce the risk of his portfolio with Jason, and ensure he + Laura are set up for success. Topics discussed include the...
2022-01-3129 minTwo Sides of FIRetirement Is Nothing Like I Thought It Would BeWe all daydream about what retirement will be like, but will reality live up to expectations? In this episode, Eric and Jason are joined by Fritz Gilbert, who blogs at The Retirement Manifesto (https://theretirementmanifesto.com). Now nearly four years after retiring early, Fritz brings valuable experience + perspectives to this question. Our discussion goes well beyond the numbers, covering topics including finding your purpose, working "one more year", determining your FIRE timing, and the keys to success in retirement.
*Be sure to check out the show notes for links to all the blog posts we referenced in...
2022-01-1657 minTwo Sides of FIHealthcare is my Second Highest Cost in Early RetirementHealth insurance may not be top of mind in early retirement when you're young and healthy, but it should be. In the US, healthcare costs are a significant line item in our budget. To help us decode what you need to know, we've invited a retirement benefits expert to answer our questions through the lens of those seeking financial independence and early retirement.
To protect against astronomical expenses resulting from unexpected medical issues, it's prudent to carry insurance. If you're retiring before 65 (when Medicare kicks in), you'll be responsible for covering those costs. What do you need...
2021-11-1558 minTwo Sides of FIRetired Early and I Hated It: How NOT to FIRE, Part 2 (Post-FI/RE)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.
This is part 2 of our How NOT to FI/RE series for part 1 and the PRE FI/RE examples, be sure to check out that video here: https://youtu.be/Jb438jvebd0
The...
2021-10-1726 minTwo Sides of FIHow NOT to FIRE - Part 1 (Pre-FI/RE)On the path to financial independence, there are ample opportunities for mistakes and missteps. In today's 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...
2021-10-0436 minTwo Sides of FIAnswering Your Financial Independence QuestionsYou asked, we answered. Bringing the Two Sides of FI together to discuss changing withdrawal rates, Jason and Eric's own FI numbers, redefining identity in early retirement, rental real estate, and more. Want your question featured on an upcoming show?
Leave us a comment on YouTube - https://youtube.com/c/TwoSidesOfFI
or reach out on our contact page - https://twosidesoffi.com/
2021-09-2036 minTwo Sides of FIDiscussing FIRE with our Spouses: 2 x Two Sides of FI (Part 2)Talking about FIRE with your partner involves so much more than finances: from friend groups and career aspirations, to personal goals and family dynamics. In part two, Eric + Jason continue the conversation with their spouses, Laura + Lorri, discussing how they share financial responsibilities, the importance of finding friend networks, talking to their children about FIRE, and their hopes for their post-FI lives.
For show notes and resources please check out our website - https://twosidesoffi.com/
2021-08-2331 minTwo Sides of FITalking with our Spouses About FIRE: 2 x Two Sides of FI (Part 1)Talking with a spouse or partner about FIRE isn't always easy. In this episode, Eric + Jason bring their wives, Laura + Lorri, into the conversation to share their personal experiences. In part 1 of our two-part conversation, they talk about getting onboard with FIRE, financial topics including budgeting and setting the FI number, as well as the emotional aspects of choosing the FIRE path.
For show notes and resources please check out our website: https://twosidesoffi.com/
2021-08-0930 minTwo Sides of FIRetiring Early - So Why Am I Worried?Retiring early is a dream for many but the decision to leave the workplace early can impact us in ways we may not have predicted. In this episode, we discuss the first year of Jason's early retirement and Eric shares his own concerns as he approaches FI. For many, work provides a sense of purpose and identity, as well as validation, utility, not to mention financial security. What happens when that no longer exists? What takes its place? How does it impact your personal relationships and your personal sense of accomplishment? Much of the discussion about financial independence, retire...
2021-07-2638 minTwo Sides of FIFinancially Independent, Live Anywhere? How to Choose (Part 2)Choosing a new area to call home once you've reached financial independence can be an overwhelming task given just how large the problem space is. In part two of this series, Eric and Jason continue their conversation about how to narrow the options of where to live post-FIRE. There's a lot to consider beyond the finances, and the "Where to Live" process they used is again highlighted as a useful tool to support that. Irrespective of your own retirement path, this approach can help you make decisions about relocating to a new area.
Check out the show...
2021-07-1230 minTwo Sides of FICan't Decide Where to Live? Here's How We Chose (Part 1)As Eric nears his Financial Independence number he asks Jason for help and advice on how to narrow the range of options of where to live. Choosing a place to call home once you've reached financial independence can be an overwhelming task, given just how large the problem space is. Jason shares how he and Lorri approached where to live in "retirement" before taking the plunge to move their family. Irrespective of your own retirement path, the process they used will apply universally to making decisions about relocating to a new area.
Check out the show notes a...
2021-06-2834 minTwo Sides of FILessons Learned in 7 Years Earning Passive Income - A Path to FI (Part 2)Diversifying your sources of income is an important step on the path to financial independence. On average, millionaires have seven streams of income. In part 2 of our series on passive income, Eric shares the lessons learned and mistakes made as he created passive income streams for his architecture practice. In 2020, 90% of his small business revenues came from passive sources, bringing him closer to reaching financial independence. Join us as we explore these topics and more in this second episode in our series about passive income.
For show notes and resources please check out our website: https://twosidesoffi...
2021-06-1324 minTwo Sides of FIPassive Income = A Path to Financial Independence (Part 1)Earning money while you sleep is the dream of passive income that few realize. In part, that's because it requires a significant upfront investment of active work and time to build the assets necessary. For those seeking financial independence, passive income can be both an accelerator and a plentiful source of cash once you reach FI, and leave your primary career. In this show, we discuss Eric's experience gained over the past eight years intentionally creating a diverse array of passive income streams. Today, 90% of his small business revenues come from passive sources, bringing him closer to reaching FI...
2021-05-3025 minTwo Sides of FIFinancial Mistakes We Won't Make Again (Part 2)We all make mistakes on the path to financial independence. Learn from ours as we chronicle the poor choices, bad habits, and missteps we’ve made on the road to FI. In this episode we talk about big ticket items like cars, student loans, and mortgages. Mistakes made in these areas can certainly have a large impact on your FI journey! Join us as we explore these topics and more in this second episode in a series documenting our financial mistakes and missteps on the path to FIRE.
For show notes and resources please check out our we...
2021-05-1630 minTwo Sides of FISharing Our Financial Mistakes and Missteps (Part 1)We all make mistakes on the path to financial independence. Learn from ours as we chronicle the poor choices, bad habits and missteps we’ve made on the road to FI. In this episode, we share our own experiences from our teens through our 30s, reflecting on what we've learned in hopes of helping our children avoid repeating them. Join us as we explore these topics and more in this first episode in a series documenting our financial mistakes and missteps on the path to FIRE.
For show notes and resources please check out our website: https://tw...
2021-05-0638 minTwo Sides of FIDiscussing our FI Numbers : Changing Our Minds, Talking to FamilyThings have changed: attitudes, spending habits, withdrawal rates, what we’ve chosen to reveal to family and friends. In this episode, we discuss how our early FI goals and calculations underestimated today’s needs and move beyond the math of financial independence to discuss the psychological aspects, including important conversations with family and friends. These discussions can be challenging and touch on deep-seated ideas about money, entitlement, and often guilt. It's common to overlook the importance of these conversations and this side of FIRE when you're focused on the financial side. Join us as we explore these areas and more...
2021-04-1534 minTwo Sides of FISo, What's Your FI Number? Sharing Ours HereHow much do you really need to achieve financial independence? We decode the math used to calculate our FI numbers, talk about the different flavors of FIRE and you'll learn where our FI numbers fall on the FIRE spectrum. All finance is personal but it's difficult not to compare your financial situation to those around you. The pragmatics of calculating your FI number are easier to comprehend and address than the psychological ones and this episode touches on those too. And, the closer you get to financial independence the more these conversations impact your day-to-day life. Be sure to...
2021-04-0832 minTwo Sides of FIFinancially Independent. Retire Early? Let's Discuss!You’ve reached financial independence, but are you really ready to retire? Join us as we discuss what FIRE means to us, why traditional retirement isn't very interesting, and the challenges of speaking to friends and family about it. Whether you're already on the FIRE path or simply interested in learning more about it, Eric and Jason bring perspectives from the two sides of financial independence.
For show notes and resources please check out our website: https://twosidesoffi.com/
2021-03-3033 minTwo Sides of FITwo Careers, Two Paths to Financial IndependenceOur path through life is heavily influenced by the career choices we make early in adulthood. Learn how we leveraged our chosen professions in science and architecture to chart our respective paths to achieving financial independence. One of us employed a job "leveling up" strategy to accumulate wealth, while the other started their own business and became a successful content creator. There's a lot to learn from our journeys and we walk you through how we did it!
For show notes and resources please check out our website: https://twosidesoffi.com/
2021-03-1631 minTwo Sides of FIOur Financial Past and our FIRE PresentSo much of who we are and how we think is informed by our early experiences. Learn how we got started on our financial independence journey as we unpack our financial pasts. We'll walk you through what we learned from our parents, our early careers, and how that set us on the FIRE path.
For show notes and resources please check out our website: https://twosidesoffi.com/
2021-03-0127 min