Podcast Summary: Optimal Finance Daily – "Failing at Early Retirement" by Jeremy of Go Curry Cracker

Episode 3365 | November 25, 2025
Host: Diania Merriam

Episode Overview

This episode centers on the emotional and practical complexities of "early retirement," specifically addressing feelings of failure when returning to work after retiring early. The featured reading is a post by Jeremy of Go Curry Cracker, chronicling his personal experience with part-time work after financial independence. Diania Merriam follows up with reflections on how flexible mindsets and redefining "retirement" are essential to a healthy relationship with work and money.

Key Discussion Points and Insights

1. Listener Question: Anxiety Over Returning to Work (01:17)

• A listener expresses worry about their declining portfolio and rising prices, considering a return to work but feeling it would be a failure in the context of early retirement.
• Jeremy responds by sharing his own story, aiming to destigmatize working after early retirement.

2. Reframing Work as Part of Early Retirement

• Jeremy emphasizes that returning to work should not be seen as a moral failure:

  "The idea that earning some income is equivalent to failure for an early retiree is common, but I think it's misplaced." (02:19)

• He suggests being open to work as one foundation for long-term success:

  "Be okay with going back to work for a while....There's no right or wrong or moral weight to the decision to add or subtract dollars from a retirement portfolio." (02:37)

3. Jeremy’s Return to Work: UPS Delivery Driver

• Details of the job:
  • Seasonal UPS personal vehicle driver (PVD) for the 6 weeks before Christmas.
  • Pay: $28/hr standard; $42/hr overtime; $0.68/mile for car use.
  • 90 hours over several weeks, with a gross pay of $3,151.75 (~$34.25/hr).
• Realities of the job:
  • Mostly enjoyable (“listened to music, got to explore some neighborhoods, and was paid to exercise a bit”—06:41).
  • Dislike for certain conditions: "unless it was raining. Then it was not enjoyable at all." (07:08)
  • Only worked part-time, not meeting all company requirements; missed several weeks for personal travel and family needs.

4. Lessons and Reflections from Part-Time Work

• Financial Impact:
  • Earnings were around 3% of annual expenses: "just enough to cover our Thanksgiving weekend in Tahoe, first snowboarding day of the season." (08:15)
  • "The greatest financial benefit was that it reminded me of just how much time and energy is required to make a hundred dollars." (08:35)
• Impact on Life:
  • Increased household stress and less time for family and personal projects.
  • "I was tired... a less attentive father and partner. Our household became more chaotic and Winnie bore a greater burden with taking care of two kids..." (09:01)
  • Missed out on family activities and personal passions (snowboarding, blog writing).

5. Jeremy’s Conclusion on Working After Early Retirement

• "Overall, I don't plan to do this again next season and I'm not looking for any other income opportunities at this time, but I could." (09:32)
• Key message:

  "Should you feel like you failed at early retirement if you decide to do some paid work? No." (09:39)

• Encourages experimentation: "Try some things. No big deal. Maybe you'll enjoy some work and find it brings value to your life. Maybe you'll find that overall, it isn't worth it." (09:57)

6. Diania Merriam’s Commentary: The 'Retirement Police' and Redefining Retirement (10:31)

• Discusses the misconception prevalent in the FIRE community ("retirement police")—that any paid work undoes early retirement.
• Redefines financial independence and early retirement:

  "Financial independence and early retirement is not about never doing 'work.' It's about separating our finances from our work... where our financial needs aren't dictating if, when, where, and how we decide to work." (10:42)

• Stresses that flexibility is key:

  “…we can't possibly anticipate what circumstances we need to navigate in the future. It is absolutely possible that you'll need or want to make some money for a variety of reasons, but I don't think that's failing at early retirement. I think that's simply an appropriate response to the uncertainty of life." (11:05)

• Notes existential challenges:

  "They say the reward for financial independence is an existential crisis. Losing that 9-to-5 job may result in a lack of identity. Working, even part time can help provide identity and purpose along with some welcome income." (11:35)

• Encouragement for listeners:

  "If fear of failure is holding you back from early retirement, remember that there's plenty of options and opportunity on the other side." (12:03)

Notable Quotes & Memorable Moments

• Jeremy, on the stigma of returning to work:
  "Only death and taxes are guaranteed... Although I beg to differ somewhat on that point. Also, there's no right or wrong or moral weight to the decision to add or subtract dollars from a retirement portfolio." (02:37-02:48)

• Jeremy, reflecting on the value of time:
  "The coffee machine we got ourselves for Christmas required almost 20 hours of life energy, but it seems worth it." (08:45)

• Diania, on flexibility and self-permission:
  "Retirement at any age is an optimistic act, and no one can be 100% sure at any one point in time that they have all the money they will ever need." (11:19)

• Diania, addressing identity post-retirement:
  "Work in its many flavors and forms can be an important part of well being." (11:52)

Timestamps for Key Segments

• 01:17 – Listener question paraphrased and Jeremy's introductory thoughts
• 02:19 – Jeremy: Is working after early retirement a failure? Foundational attitudes
• 03:30 – Jeremy's story: why he sought part-time work
• 04:46 – Working at UPS: pay, expectations, routine
• 06:41 – Jeremy: Enjoyable aspects of the job
• 08:15 – Was it worth it? Financial and personal reflections
• 09:32 – Final summary and Jeremy's personal decision
• 10:31 – Diania Merriam's commentary: Retirement Police, redefining retirement, and flexibility
• 11:35 – Importance of purpose and identity after leaving full-time work
• 12:03 – Final encouragement to listeners

Episode Takeaways

• Early retirement isn’t a rigid, one-way street: Dipping back into work doesn’t erase your progress or invalidate your journey toward financial independence.
• Personal experiments are valuable: Trying out part-time or seasonal work can provide perspective on the value of money, work, and time.
• Flexibility is a core skill of early retirees: Shifting plans or working again is simply adapting to life’s uncertainties.
• Self-compassion is essential: Letting go of strict definitions and societal expectations allows for a healthier, happier relationship with money and work.