Optimal Finance Daily - Financial Independence and Money Advice 3365: Failing at Early Retirement by Jeremy of Go Curry Cracker on Retirement Planning
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Nov 25, 2025 Jeremy challenges the idea that working after early retirement equals failure. He shares his experience as a seasonal UPS driver, emphasizing flexibility and self-awareness in redefining retirement. Reflecting on the demanding nature of deliveries, he finds joy in work but acknowledges its impact on family and personal hobbies. Ultimately, the conversation highlights that earning post-retirement can enrich life, not diminish it, prompting listeners to rethink their own definitions of success and fulfillment.
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Seasonal UPS Driving Experience
- Jeremy took a seasonal job as a UPS personal vehicle driver for six weeks over the holidays.
- He delivered about 150 packages a day using his own car and worked roughly 90 hours total.
Work Without Moral Judgment
- If work would ease worry or improve cash flow, do it without attaching moral failure to the choice.
- There is no moral weight to adding or subtracting dollars from a retirement portfolio.
Earnings Versus Impact
- Jeremy earned about $3,151 gross for 90 hours, roughly $34.25 per hour after expenses.
- He found the pay reasonable but the net financial impact on annual expenses was minimal.