July 31, 2026
Hi Reader
Have you ever been really looking forward to something — a trip, a dinner, a get-together with friends — and then had it just... fall apart? That happened to me this week. I had a little getaway planned, and then Chicago got hit with crazy weather that grounded 900 flights, mine included. By the time I could rebook, it was already time to be back home. So we just cancelled the whole trip. I've been walking around in a fog and a bad mood ever since.
When Plans Fall Apart in Retirement
Here's the thing I've been sitting with: a cancelled trip probably wouldn't have wrecked my week like this a few years ago. Back when I was working, disappointments like this got absorbed into the noise of a busy schedule — there was always a next thing pulling my attention forward. But now, the trip wasn't a break from something. It was the something. When it disappeared, there wasn't much else standing behind it to catch the fall.
I think this is actually a retirement moment, and I'd guess a lot of you know exactly what I mean. The things we plan now carry more weight, because we've made more room for them. So when they get cancelled, it hits harder — and that's not us being overly sensitive. It's just math: less on the calendar means each thing on it matters more.
Getting Out of the Fog
I don't have a magic fix, but here's how I worked through this:
- Let the disappointment be real for a bit. I kept telling myself "it's just a trip," and that never actually made me feel better — it just made me feel like I wasn't allowed to be annoyed. By sitting with the disappointment for awhile, I realized that I just needed to get away from the everyday stuff. I needed a little excitement.
- Plan something small and immediate. Not a replacement for the trip — just something to look forward to before the weekend. I actually did this: we booked a trip (one night) to Milwaukee - nice and close - to see my cousin and his wife over dinner. It's not the getaway we'd planned, but it gave the week a little excitement and change of scenery. I kept calling it my micro-party. And on the way home we stopped at the Mars Cheese Castle to get a Kringle and Spotted Cow Beer!
- Treat flexibility like a skill, not a personality trait. My cousin reminded me of the time we were stuck at a port for three days due to an engine failure on our riverboat. Some of the passengers complained and were very upset. But Mike and I decided to make an adventure of it and found a cool wine bar, a nearby city tour and made it exciting even though it wasn't what we really wanted.
A Question for You This Week
Has something fallen through on you recently — big or small? How did you find your way out of the funk? Hit reply and tell me — I'd really love to hear it.
Warmly, Wendy
Quote of the Week
"It's not what happens to you, but how you react to it that matters." — Epictetus
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Have a wonderful week.
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