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.

• Eric’s business: 30X40 Design Workshop
• Jason’s blog: the next phase is now
• Eric’s YouTube Channel
• Our podcast