
Jeremy challenges the notion that earning income after early retirement equals failure
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This is Optimal Finance Daily Failing at Early Retirement by Jeremy of Go Curry Cracker.com from the Inbox paraphrased Our portfolio is down and prices are up. This has caused some anxiety in our household and I've considered going back to work, even just part time. I think more income will help with cash flow and reduce worry, but I'm concerned that I'll feel like I failed at early retirement. What do you think about this? I don't know the best way to work through this decision and associated emotions, but a technique that I've used successfully in the past is to find others who have been through something similar and see if I can learn from their decisions and example. Let me be that example. I recently got a job Failing at early retirement. The idea that earning some income is equivalent to failure for an early retiree is common, but I think it's misplaced. One of the items in my foundation for long term success is be okay with going back to work for a while. 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. So if something doesn't feel right and you think work would help, than work. In my own recent experience, we moved back to the US about a year and a half ago and our cost of living has exploded. Our passive income is down. As expected. I have a lot of time on my hands. Both kids are in school at least part time. I don't enjoy biking in the rain. I can't snowboard during the week and still shuffle the kids to and from school. And after a decade of not having a job, I I was a little curious. The combination of this situation Time abundance, cash flow down, expenses up, years of hearing that I could never find a job again even if I wanted one and the email in the intro inspired me to look for some part time work. My job for the six weeks between the week before Thanksgiving and Christmas, I worked as a seasonal delivery driver for UPS using my own car, what they call a PVD or personal vehicle driver. I first learned about this position from a PVD dropping packages off on our porch last year. I understand that Amazon also has a similar position. This job paid $28 an hour or $42 an hour for overtime plus 68 cents a mile to compensate for wear and tear on my automobile. The job was fairly simple. I was paired up with one of those brown trucks and asked to deliver about 150 packages per day. I would fill my car with as many packages as possible and then meet the truck to fill again. Repeat as necessary at training or orientation. The boss man said they required I work 8 plus hours per day, 6 days per week through the holiday season. If I delivered all of the packages on my route, I was to call the UPS coordination office to get assigned to another route that was falling behind financials. Overall, I worked 90 hours with a gross pay of $3,151.75, about $34.25 an hour. I had some expenses. I charged my electric vehicle at home each night and had maybe $30 worth of fuel costs. Rough guess. Mostly I brought my own lunch, but I ate at Taco Bell a few times, always a risk, and bought a few Diet Cokes and coffees at McDonald's. The sweet safety vest was provided by UPS, but I was required to have work boots which cost me about $60. Although this was something I wanted for yard work anyway, so the job just provided some extra motivation. I also paid union dues and related fees of $53.65. Thoughts? The work itself was actually kind of enjoyable. I listened to music, got to explore some neighborhoods, and was paid to exercise a bit, about 15,000 steps per day. It was fairly relaxing and meditative, that is unless it was raining. Then it was not enjoyable at all. I only worked a few times after sunset, but that was not very enjoyable either, although some other PVD's loved it. Everything takes longer at night so the money per package goes up. Overall I would probably get a poor performance review. I delivered packages faster than requested, but I was unreliable time wise. At Most I worked 5 to 6 hours per day, only worked 2 Saturdays so minimal overtime and then only a few hours. And I missed three and a half weeks of work overall due to other plans and life circumstances including Disney and LA for a week, Tahoe for Thanksgiving so I couldn't help with Black Friday. The kids got sick for a few days, our toddler had the start of pneumonia and was put on antibiotics and I didn't work Christmas week because Junior was on holiday break. I'm glad I tried it, but was it worth it? Overall, I don't think it was worth it. I think the pay was reasonable or good for what the job entailed, but it had minimal impact on our finances. I was paid maybe 3% of our annual expenses, just enough to cover our Thanksgiving weekend in Tahoe, first snowboarding day of the season. Certainly I could have worked more and made 6%. The greatest financial benefit was that it reminded me of just how much time and energy is required to make a hundred dollars. The coffee machine we got ourselves for Christmas required almost 20 hours of life energy, but it seems worth it. But even though I contributed the bare minimum time wise, the impact to life was much larger and a good reminder of why retirement is so great in the first place. I still haven't caught up with the yard work and home projects that were put on hold during this time. I was tired when I got home and was a less attentive father and partner. Our household became more chaotic and Winnie bore a greater burden with taking care of two kids for more hours per day. I missed one or two days of good snowboarding and Junior missed an after school activity because we couldn't fit it into the tighter schedule. I also let the blog stagnate a little during this time and I'm sure income was lower as a result. 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 Summary should you feel like you failed at early retirement if you decide to do some paid work? No, I think my working part time was an interesting and worthwhile exercise because I learned that getting a reasonably paying job wasn't very difficult even after a decade of sloth. I was reminded the value of a hundred dollars And I got to be a bad example once again. 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. Either way, you get some extra money to pay for your next vacation. You just listened to the post titled Failing at Early Retirement by Jeremy of Go currycracker.com Imagine you're a business owner who has to rely on a dozen different software programs to run your company. 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Article made me think about what we like to call the retirement police in the fire community. There's this misconception that you're only really retired if you never again perform paid work or what looks like paid work. But financial independence and early retirement is not about never doing quote unquote work. It's about separating our finances from our work. It's about reaching a level of financial freedom where our financial needs aren't dictating the if, when where and how we decide to work. Early retirement requires that we be flexible because 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 in the future 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. 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. On another note, 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. Work in its many flavors and forms can be an important part of well being. If fear of failure is holding you back from an early retirement, remember that there's plenty of options and opportunity on the other side. And that'll do it for another edition of Optimal Finance Daily. Thanks so much for joining today and every day and for sharing the show that goes a long way to keep this podcast running. Have a great rest of your day and I'll see you back here tomorrow where your optimal life awaits.
Episode 3365 | November 25, 2025
Host: Diania Merriam
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.
"The idea that earning some income is equivalent to failure for an early retiree is common, but I think it's misplaced." (02:19)
"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)
"Should you feel like you failed at early retirement if you decide to do some paid work? No." (09:39)
"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)
“…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)
"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)
"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)
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)