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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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Does 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

Lest Eric (and any viewers) be nervous about Jason and Lorri’s safety on their upcoming Peru trip, worry not. Jason misspoke about the price of the tour they’d booked. The cost was $3.6k per person, not $1.6k. Let’s chalk his error up to aging, shall we?

Essential Background:

  • Retired Early and I Hated It : How NOT to FIRE, Part 2 (Post-FI/RE) – As mentioned in this episode, we’ve tackled post-RE regret before. In this early 2SFI video, Eric and Jason discussed 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.
  • 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.
  • One of the ways many early retirees stay busy is to take on some time of part-time “fun job”. But have you truly retired if you continue to do any work for money? In Financially Independent, Recreationally Employed (FIRE), Eric and Jason talk about their respective journeys, why the latter has a part-time job after retiring, the internet retirement police, and much more.
  • 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 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.
  • One of our most popular Two Sides of FI episodes of 2022 was our 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.
  • Retired 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 the first three years years 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. 
  • My 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.

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.

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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Unexpected Reactions to My Early Retirement

Contempt, concern, derision, surprise, envy, admiration, and support; these are 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 took us by surprise.

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. If you didn’t see Part 1 of this conversation, you’ll want to check out One Step Closer to FI/RE – Giving Notice.

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!

Links + Resources

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One Step Closer to FI/RE – Preparing to Give Notice

Eric here checking in with a quick update and preface to our new video. Sorry for the gap in our publishing schedule, Jason has been off walking the Camino de Santiago from Portugal to Spain (you can follow along on his blog here) and I’ve been traveling to warm places to escape winter in Maine.

In this episode I asked my wife, Laura, to join me to discuss next steps as we near our FI number. Our discussion was recorded in the fall of 2023, as a behind-the-scenes episode. Just this past week (mid-March 2024) she gave her notice to her employer of 23 years and now we can finally share it publicly. We discuss our hesitations, how Laura’s thoughts have changed since first learning about the FI/RE movement, and ready ourselves for what’s ahead.

Watch the Video on YouTube

The reactions to her departure from her long-time job have been interesting. Most express surprise and offer enthusiastic support. Some respond with envy, “Must be nice…” and even concern, “Is everything okay?” And still others immediately reframe the conversation around their own plans for retirement either near or far in the future. There’s much to unpack here and I think it’ll make for a great episode when Jason and I reconvene.

Nevertheless, sharing this experience with the Two Sides of FI community feels incredibly rewarding. We’re thrilled to openly discuss our ‘secret’ here on our Maine island and your support has been invaluable to us!

Thank you for being a part of our journey.

Links + Resources

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Retired Early to USVIs, Florida, and Spain: How They Did It

This is a conversation Eric had with Jeff, a self-described: financially independent, recreationally employed realtor. He and Eric crossed paths as Eric was researching his dream of retiring to the US Virgin Islands. Jeff and his wife, a Spanish teacher, lived in St Thomas for two years making content about their life there on two YouTube channels: How2Beach and TheRetirementality offering an honest review of the pros and cons of living on a tropical island. It helped change Eric’s mind about living there too!

Jeff went from broke at 38 to financially independent at 45. He and his wife have six rental properties in total and the income from those have enabled them to move around the world as they choose. As of early 2024, they’re preparing to relocate to Spain. 

Even though Jeff took risks many aren’t willing to take, we think his story is interesting because it proves there’s no one way to reach FIRE. Not only were they able to reach FI in a few short years, they did it on modest income (a teacher’s and a realtor’s salary). So, if you’ve considered what a life outside the mainland US might look like, we know you’ll find his story interesting.

Show Notes:

Be sure to check out Jeff’s two YouTube channels:

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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First Year of “Early Retirement” Lessons Learned

Retiring at 47 is early by any definition. In this episode, Jason reflects on his first year in early retirement after reaching his FI goal in 2020. Not everything went smoothly as you might expect. Learn what’s changed, what’s been better, what’s worse, and – importantly – has it lived up to his expectations? If you’re excited to reach this milestone but still harbor some reservations about crossing into “retirement”, Jason offers a grounded, thoughtful perspective on what to expect and how to prepare for such a life-altering transition.

Be sure to read Jason’s milestone post for additional thoughts and details not covered in the video.

Show Notes

Eric here, checking in with a little behind-the-scenes detail. If you’re a long-time viewer, you’ll have noticed we switched sides in the edit. The reason? I joked with Jason after we finished recording the original episode that his next “skill development task” was to learn Final Cut ProX and cut the episode together. He agreed, not knowing the depth and form my critical feedback would take nor the time and effort making changes would entail! The editing switch was a subtle “tell” that we switched roles. And, although I don’t think this marks a permanent shift in our roles for this project, it did give each of us a better perspective on the skills we bring to the collaboration.

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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Financially 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.

Show Notes

You can find information on the tools we mention in the episode along with additional information in the Resources section of this site! To navigate to this material at any time, just click the menu button at the top of any page on the site.

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Two Careers, Two Paths to Financial Independence

Our 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!

Show Notes:

Given the length of our episodes, it’s impossible to cover all of the depth we’d like on any topic. As a follow up to this installment, Jason wrote a blog article diving into his “career leveling up” strategy. The piece concerns how he approached advancement in the workplace. Irrespective of your own FIRE status or chosen career, we believe you will find information you can use!

You can find information on the tools we mention in the episode along with additional information in the Resources section of this site! To navigate to this material at any time, just click the menu button at the top of any page on the site.