The Hardest Year of Retirement: What No One Warned Me About | Retirement Reality
Ready For Retirement
James Conole, CFP®
4.8 • 793 Ratings
🗓️ 17 December 2025
⏱️ 40 minutes
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| 0:00.0 | You know, if I was just to arbitrarily chop up your retirement into four chapters, your one, |
| 0:05.1 | your two, your three, your four, which of those was the most difficult and which has been |
| 0:10.5 | the best so far? |
| 0:11.7 | The first year was the hardest. |
| 0:13.3 | It was the most difficult just as a psychological component, like we talked about before. |
| 0:17.9 | This last year has to be the best. |
| 0:20.7 | And so it's kind of been a |
| 0:22.0 | evolution, finding out what I'm going to do. And I'm kind of locking into that now. And so now I |
| 0:29.9 | can make some progress. Retirement is not a death sentence. I mean, we all are going to die, |
| 0:34.8 | but it's not like I'm going home to die kind of thing. |
| 0:38.8 | And retirement, if you look over the history, is a relatively unique thing. |
| 0:44.0 | A hundred years ago, our great grandparents didn't retire per se. |
| 0:47.6 | They still had to still had to work on their farm. |
| 0:50.2 | So we have to figure out how to survive this retirement, and more survive, how do we thrive |
| 0:56.2 | in a new environment? |
| 0:57.9 | Jim retired at 59, but his retirement was challenging. |
| 1:01.4 | Listening as he talks about his loss of identity and purpose, and in many cases, didn't |
| 1:05.7 | even feel like getting out of bed in the morning. |
| 1:07.8 | What turned that around was a move to a new environment pursuing his creative |
| 1:11.5 | interests and some serendipitous interactions. All this and more on today's episode of retirement |
| 1:17.0 | reality. My guest today is Jim. Jim, thank you for joining me. How long have you now been |
| 1:21.8 | retired for? At the beginning of October, it was four years. Four years. |
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