Experience NOT Necessary: Failing at Retirement

Two Days Out, Nothing Wrapped

It's almost Christmas Eve and Chris, my fiancé (yes that just happened - another blog), asked delicately, "Babe, what are you planning on doing with all of these gifts in the guest room bathtub?"

I stared at him. Then at the bathtub. Then at the calendar.

Christmas Eve. Twelve people are coming to our apartment. Gifts still in shopping bags. Nothing wrapped. Tree up, but that's about it.

When I was working 50-60 hours a week, living in airports, back-to-back meetings all day - by Black Friday, gifts were wrapped, under the tree, perfect.

Now I'm "retired." No deadlines, no Zoom calls, no one waiting for my approval on anything.

And somehow I'm so busy that my bathtub looks like the end of the day at a sample sale!

Is It Just Me, Or Is "Free Time" a Scam?

Every day, I wake up at 8:30 — the same time I used to get ready for work. Chris brings me coffee with a little drawing on the napkin (yes, every morning — that's love).

I sit down at my computer.
Then 6:30 rolls around.
Chris walks in from work.
The whole day is fuzzy.
Suddenly, it's time for dinner.

I don't know how anybody gets shit done when they retire!

When I was working, there was a deadline for everything. Revenue targets. Quarterly objectives. Deliverables. You knew what you were doing because there was a direction, an end goal.

Now? No deadlines. No deliverables.
No one's waiting.
And somehow I'm getting LESS done.
Not more.

Can you actually fail at retirement?

Everyone Has an Explanation

"It's Parkinson's Law! You find things to fill the time available."
It's apparently physics? Not helpful.

"You lost your structure!"
Yes, I noticed.

"Track your time! Journal what you do each day!"
Sure, let me add that to the list of things I'm not getting done.

"You should be grateful! You're lucky to have this time!"
I AM grateful. I'm also confused.
Both things are true.

My one sister tells me,
"You should go back to work,"
while the other says, "You just need a hobby."

WTF does that even mean?
Should I start crocheting?

Here's what the gurus love to say:
Retirement is about organizing your time around your values instead of your employer's schedule.

Great. Who sets the values? What's the KPI for achieving retirement?

Not Optimizing Christmas

So am I failing at retirement, the concept I envisioned whenever someone says the word?

Because in the last three months? I'm just filling the wide-open space with "doing things," hoping that something, anything, will give me an adrenaline rush of accomplishment as it did with work.

Corporate muscle memory without the demand.

My logical brain wants a definition.
My corporate self wants a scoreboard.
And "retirement" doesn't come with either.

Perhaps I need to think of it as a Sabbatical instead.

A 12-month sabbatical to figure out who I am now. What I actually like. What I enjoy doing — not what I'm used to doing.

But how do you retrain a brain that's been obsessed with the trophy for 2/3 of my life?

No clue. That's the experiment.

No rushing back to the Hunger Games. No forcing an answer. No pretending I've got it figured out.

Just space. Yes, this is a bit pseudo-corporate. Sue me.

And this week — the week between Christmas and New Year's (when our, I mean my ex-company, would shut down) - I'm actually taking the time.

Just... being with my family and enjoying Christmas without optimization.

Ask me in January if I pulled it off.

Your Move?

Maybe your move is figuring out what you'd do with free time if you stopped filling it with "responsibilities."

Maybe it's one intentional thing that sparks you — not just a spa day (although I could use one), but something you'd do again tomorrow.

Or maybe it's just admitting: I don't know what this chapter looks like yet. And that's okay.

Whatever you choose, make it unapologetically yours.

P.S. Thank you for your private messages and encouragement each week - nice to know I am not writing into the void.

P.P.S. For women in the Unscripted Middle — between who they were, who they are today, and who they'll be — if a friend sent this to you and you thought "that's me," pull up a chair every Sunday by subscribing.

P.P.P.S. Wondering how I got here? I got restructured by AI, spent three weeks planning instead of doing, watched my face stage a hostile takeover, realized I'd weaponized my hobbies, got called out for my high expectations, and had an epiphany that friendships have expiration dates. Standard stuff.