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Year 2 vs. Year 7: What Early Retirement is Really Like

Is early retirement everything you imagined or does the reality take years to settle into? In this honest check-in, Jason (year 2) and Eric (year 7) compare notes on what post-FIRE life actually feels like from two very different vantage points. They cover decision fatigue, the challenge of replacing work’s structure, and why the emotional side of retirement rarely gets the attention it deserves.

Show Notes

Essential Background:

Jason referenced his interest in options trading in this discussion. While not for everyone, it’s a topic of great interest among many in the FIRE community. In “How Options Trading Led this Engineer to Financial Independence in His 30s”, Jason spoke with David Sun, an engineer who stumbled into options trading . Only ten years later he launched his first hedge fund. Now in his mid-30s, David shared the keys to his success, as well as his thoughts on the role of options trading in a FIRE portfolio.

Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.

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Is This Goodbye?

Are we really ready to walk away from Two Sides of FI? In this candid conversation, Jason and Eric reflect on more than four years of recording together, what the project has meant, and whether it still fits into their lives. They talk openly about the rewards of community and connection, the challenges of generating new topics, and the weight of obligations in retirement. Is this the end, or just a pause?

Show Notes

Jason wrote a blog post to accompany this episode. This was written a few weeks after this episode was recorded and edited. It is meant to be read after viewing the video.

Essential Background:

Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.

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From Divorce to Financial Freedom: FI at 45

What happens when the plan was “we”… and now it’s just “me”? At 45, Kayla reached Financial Independence solo after divorce, living in the Bay Area without a tech salary. In this episode of Two Sides of FI, she shares how she rebuilt her finances, overcame her fear of investing, and designed a plan that works without a partner’s income or support. In this episode, Learn how a saving mentality and discovering the FIRE community in her 30s led her to the realization that early retirement was within her reach and how she achieved it.

Show Notes

Essential Background:

Kayla mentioned a book as a key part of her FIRE and investing eduction: The Simple Path to Wealth (JL Collins). It is widely regarded by many in the FIRE community as the most impactful book to their own journey. This fast and easily digestible read is chock-full of investment guidance that you will understand immediately and can readily apply. There is no better starting point to your FIRE journey than this book.

How do you find advice-only planners? Below you’ll find two resources. Please note that Two Sides of FI has no relationship nor do we receive any compensation from either:

1) XY Planning Network: As described on the site, their member advisors ascribe to fiduciary and CFP standards, earn no commissions, and require no minimum assets. They have convenient filters to allow searching by advisor specialities, including those with FIRE experience. Many work under multiple fee models, including advice-only, which can be a good source for one-time consults without any

2) Cody Garrett, CFP and advice-only planner from Measure Twice Financial, shared this list in the past on Twitter. As he described it, “these 11 advisors provide comprehensive financial planning without any expectation, obligation, or even the option to manage client investments. Options for project-based, hourly, or ongoing.” You’ll note there is overlap between these resources, which makes sense. But this is the list Cody has shared with prospective clients, so one can presume there’s been some personal vetting.

Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.

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Am 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

Essential Background:

Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.

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Are We Hiding Something? Our Real FIRE Portfolio + Expenses

Are 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

Essential Background:

Empower (formerly Personal Capital) is a commonly used free tool for tracking your various investment accounts, understanding your asset allocation + rebalancing opportunities, and monitoring your net worth. PC has simple to use account linking to make it a more automated experience. Give it a try risk-free!

Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.

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Life After FIRE: Your Toughest Questions, Answered

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.

Jason’s companion blog post on our 100-episode milestone:

Show Notes

Essential Background:

Empower (formerly Personal Capital) is a commonly used free tool for tracking your various investment accounts, understanding your asset allocation + rebalancing opportunities, and monitoring your net worth. PC has simple to use account linking to make it a more automated experience. Give it a try risk-free!

Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.

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How We’re Using ProjectionLab in (Early) Retirement

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 underneath the video for how you can try ProjectionLab for free!

Show notes may be found below the video

Show Notes

For a free trial of ProjectionLab, use this link: https://twosidesoffi.com/pl

Essential Background:

  • As mentioned in this episode, both Jason and Eric use Karsten “Big ERN” Jeske’s Safe Withdrawal Rate Toolbox. For all the details of this essential tool, please see our page dedicated to the Safe Withdrawal Rate Toolbox. It has all the information you need including all the videos in our series, including walkthroughs of the tool and the CAPE-based strategy that Jason referenced here.
  • Will you have enough to money to retire (early or otherwise)? Achieving financial independence requires many key elements to be in place and special consideration if you plan to retire early. In Have Enough to Retire (Early)? 10 Steps to Make Sure, we discussed a great post by Fritz Gilbert about how to ensure that you’re financially prepared.

Just getting started with ProjectionLab and in need of a quick start guide? This series of videos by the team at PL is a great place to start. This will ensure you avoid some of the mistakes we made along the way! There are a lot of other helpful videos on their YouTube channel, as well. Lastly, you can also find great content on many topics in their Help Center.

Don’t miss the ProjectionLab Discord server! As we discussed in today’s episode, there’s a wealth of information here to be found given the very active user community. As you’ll discover, the PL team also has a strong presence on the server, ensuring great access to feedback, questions, and feature requests from the community.

Eric and I both found Rob Berger’s recent review of ProjectionLab to be a good introduction to some of the powerful features in the tool.

Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason has a FIRE blog? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.

You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

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How 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

Here are the retirement personas that Eric shared in our conversation:

Essential Background:

  • Retirement Is Nothing Like I Thought It Would Be – We all daydream about what retirement will be like, but will reality live up to expectations? In this episode, Eric and Jason were joined by Fritz Gilbert, who blogs at The Retirement Manifesto. Our discussion went 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.
  • In We Each Hired a Flat Fee Financial Advisor. Was it Worth It? Eric and Jason each hired the same fee-only, advice-only advisor to evaluate their portfolios and answer 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.
  • 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 “Retiring Early – So Why Am I Worried?“, we discussed the first year of Jason’s early retirement and Eric shares his own concerns as he approaches FI.
  • Did you see our recent chat with Jordan “Doc G” Grumet, titled “Will You Run Out of Money or Time? FI Advice From a Hospice Doctor“. The topic of purpose can be found all over our conversation with him. In a related vein, Jason spoke with Doc G again in “Fulfillment Beyond FI: Life After Early Retirement with Jason”, on the Earn and Invest podcast.
  • How does it feel when you haven’t yet found your purpose after retiring early? In this episode, Retired Early and Feeling Lost. What’s Next?, Jason talks with Eric about the first three years years exploring his post-FIRE purpose. They discuss the phases of retirement, seeking out meaningful projects, lessons learned along the way, and much more. 
  • Did you see our recent episodes regarding Eric’s spouse, Laura’s, decision to retire from her career as a scientist? If not, you’ll definitely want to view:
    • The story begins with One Step Closer to FI/RE – Giving Notice. In this episode, 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 publication the week Laura submitted her resignation notice.
    • Next we published Unexpected Reactions to My Early Retirement, 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.
    • What’s it really like to be 5 days away from early retirement? The last chapter (so far) in this story is Retiring (Early) in 5 Days. Am I Ready? 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, Laura’s story offers inspiration and real-time insights about one of life’s biggest transitions.

Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.

Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.

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What No One Tells You About Purpose and Happiness in Retirement

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. See below for links to Doc G’s book as well as the show notes.

Show notes may be found below the video

Show Notes

To get your own copy of Jordan’s excellent book, “The Purpose Code: How to unlock meaning, maximize happiness, and leave a lasting legacy”, buy direct from his website or from Amazon. Here’s a book trailer for more information.

Essential Background:

  • As we mentioned in this episode, Jordan’s first appearance on Two Sides of FI was in 2022 in Will You Run Out of Money or Time? FI Advice From a Hospice Doctor. What can conversations with the dying teach us about the secret to financial independence? We talked about that and much more, as we dove into his book, The Purpose Code: How to unlock meaning, maximize happiness, and leave a lasting legacy.
  • How does it feel when you haven’t yet found your purpose after retiring early? In Retired Early and Feeling Lost. What’s Next?, Jason talked 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.
  • We’ve actually spoken to Doc G a few times! Our first chat was on Jordan’s own Earn and Invest podcast. Here’s a link to the episode, which was a really fun one for us and also represents the first time we were a guest on someone else’s show as Two Sides of FI! As you’ll find, Doc G is a very skilled interviewer. Did you ever think that everything will be okay once you are financially independent? In our conversation, we pushed back on this narrative.

Not familiar with hospice and want to learn more? This post from The Hospice Foundation of America is a great resource. Stated simply, hospice is medical care for people with an anticipated life expectancy of 6 months or less, when cure isn’t an option, and the focus shifts to symptom management and quality of life. The site is a wealth of information, including guidance on how to access hospice care and selecting hospice providers.

For links to all of Jordan’s content, including the Earn and Invest podcast and his DiverseFI blog, be sure to check out his website.

You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

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Retiring (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 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.

Don’t miss the show notes below for key background including other conversations featuring Laura!

Show Notes

Laura + I want to thank the Two Sides of FI community for all your comments, personal messages, and words of encouragement as we’ve been navigating this transition. Thank you for being a part of our journey!

Essential Background:

  • Have you seen our other recent episodes with Laura? If not, you’ll definitely want to view:
    • The story begins with One Step Closer to FI/RE – Giving Notice. In this episode, 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 publication the week Laura submitted her resignation notice.
    • Next we published Unexpected Reactions to My Early Retirement, 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.
    • Laura also took part in a very popular two-part series, Talking with our Spouses About FIRE: 2 x Two Sides of FI. In Part 1, Eric + Jason talk with Laura + Lorri 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. In Part 2, they discuss 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.
  • Did you know that Laura and Eric recently achieved their FI goal? In Financial Independence at 50 (Finally!), Jason and Eric discuss the challenges of moving goalposts, the decision to keep running Eric’s business, 30×40 Design Workshop (on their own terms), and their plans for the future.
  • For more on the rules and practices Eric and Laura followed in order to reach their financial goals, see Our 80/20 Rules for Early Retirement: How We Did It. 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.
  • A core element of Laura + Eric’s ability to achieve FI was Eric’s 30×40 Design Workshop business. If you haven’t seen our two-part series on the journey from zero to 90% income from passive sources, drop everything and check it out: Passive Income = A Path to Financial Independence (Part 1) and Lessons Learned in 7 Years Earning Passive Income – A Path to FI (Part 2). The link to Part 2 contains the show notes, which have a wealth of information provided by Eric. Don’t miss it!