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Could Retire, Doesn’t: The Psychology of Staying at Work

Phil’s Tax Hacks · August 13, 2026

Here’s some of what we discuss in this episode:

🤝 Social Connection: Work can provide relationships, routine, and identity

🏠 Retirement Adjustment: Suddenly spending more time at home can require some adjustment

🦠 COVID Perspective: The pandemic gave many couples a preview of retirement life

💵 Financial Necessity: Some retirees work because they need the additional income

🎯 Retire to Something: Hobbies, volunteering, and interests can help fill the work void

🤝 Advisor Guidance: Professional planning can replace uncertainty with informed decisions

Today’s Hack

More people in their 60s and 70s are staying on the job than ever before, and it’s not always about the money. Today, Phil digs into the real reasons retirees keep showing up to work. Working longer isn’t automatically the wrong call. Sometimes it’s exactly right. The real question is whether it’s a choice or a fallback. That’s worth figuring out before you assume the answer.

Go Inside the Episode:

0:00 – Intro

1:06 – Social Connection

2:43 – With Your Spouse 24/7

3:58 – The COVID Preview

5:54 – Financial Necessity

8:38 – When You Doubt Your Plan (Or Don’t Have One)

10:36 – Advisor Guidance

If you have any questions about what we discussed in this episode, reach out and we’ll be happy to set up a time to talk.

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