Two Sides of FI

Retiring at 47 is early by any definition. In this 2SFI Rewind episode, Jason reflects on his first year in early retirement. 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. 

Read more about his journey on his blog, starting with the post that originally accompanied this episode: https://www.thenextphaseisnow.com/p/yearone

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: https://twosidesoffi.com/year2/

Is slow travel in retirement all that we hoped or is the dream far better than the reality? In this episode, Jason talks with Eric about his recent experiences during a month-long US road trip. Learn how the trip ended up way over budget, compare how Eric+Jason manage expenses, and whether they would do it again - and much more.

Show notes: https://twosidesoffi.com/slowtravel

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: https://twosidesoffi.com/goodbye
Jason's blog post: https://www.thenextphaseisnow.com/p/goodbye

Retirement doesn’t follow a script - it rewrites itself in real time. In this episode, Jason and Eric unpack why the classic “phases” of retirement actually overlap and how that feels day to day. They dig into the challenges of switching from super-saver to intentional spender, using side income (like options trading or creative work) to fund experiences without derailing the plan, and how travel has changed for them. No matter where you are on the FIRE path, there's something here for you.

Show notes: https://twosidesoffi.com/phases