Sun Mar 30 2025, by Tyler Gardner

Retirement RegretsLife LessonsPersonal GrowthRelationshipsFinancial Planning

3 Biggest Regrets of Retirees You Should Know

What are the three biggest regrets that retirees have that nobody warns you about? And if any of this resonates with you, tune into my new podcast, Your Money Guide on the Side, by clicking the link in my bio.

1. Waiting Too Long to Enjoy Life

The first regret is waiting too long to enjoy life. Many of us spend decades thinking, once I retire, then I’ll be happy. The problem is akin to when you were a kid and said, once this exam is over, then I'll be happy. You just ended up having another exam the following week. It’s not the exam, and it’s not your current work; it’s about finding a way to build joy into every phase of your life.

2. Losing Purpose After Leaving Work

The second regret is losing purpose after leaving work. Your career provides you with structure, identity, and purpose. Honestly, that’s one of the reasons I started creating content; I hope to keep taking this walk well into my 60s. Always have something to retire to.

3. Not Investing in Relationships

Lastly, not investing in relationships while there's still time. One of the saddest things I ever read was from British essayist Samuel Johnson. After he finally published the first English dictionary, after about nine years of hard work, he offered it to the world with complete apathy because everyone he wanted to impress had died. At life's end, nobody wishes they had worked more for an extra buck; they regret not spending more time with family, friends, and beloved pets. Retirement is the perfect time to deepen relationships and focus on what actually matters.

And again, if this resonates, see you over on the podcast!

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