We’ve always played by the rules.
Done the work.
Did the “responsible things.”
And it sucks.
#Ibetso
We are both very much first-born ruler followers, me more so than my wife. I’m a ruler follower to a fault. Much of it goes back to my childhood, and not wanting to disappoint ANYONE: parents, teachers, peers, family, or whoever had an expectation about me. It’s not hard to imagine, but it gets exhausting when I come across non-rule following people.
However, as I’ve gotten older, I’ve asked myself this question and not liked my answer: Where has following the rules gotten me?
#whereindeedyoubigdope
Hush.
But where? It’s gotten me more work. It’s gotten me less time with my family. It’s filled my list with things to do because it’s hard to say no. Sure, it’s gotten me appreciation and thank yous, but at what cost?
We typically don’t vacation in the school year. We’ve watched as teacher after teacher takes off for a week here or a week there. We’ve been the steady ones. The ones who cover or keep down the fort.
Again, for what?
So this year, we took the trip. It was a short one, a Thursday through Sunday trip to Key West with my college roommate and his wife. We used personal days. We felt like we were breaking the rules.
And it was freaking amazing.
We went to Hemingway’s House in Key West, saw his main area for writing, and of course, petted the polydactyl (six-toed) cats! We did the pose next to the southernmast point sign! We took a walking ghost tour and learned some creepy things about Key West (don’t go see the doll!). We ate Key Lime pie! The Saturday we were there was Valentine’s Day, so we took a sunset dinner cruise (which was awesome!!). And we drank too much and stayed out too late. One of the best things we did there was sneak out! We’d seen three different bands on Friday night, and we were kind of tired, so we started walking back to the Air B&B. My wife leans over and says, “Do you want to quit yet?” I look back at her and shake my head, so we get back, we say good night, then, we slip back out.
#whatyourebels
I know!!
We scooted down to the Hard Rock Cafe where they were having Latin Night. Oh My Goodess. As I’ve said before, we teach in a highly diverse school, so it didn’t feel any different other than we were in the middle of a dance floor where we could feel the bass in bone marrow. We danced and laughed and people watched and danced for at least an hour when my wife FINALLY said she was tired. Sunday was tough, but oh it was worth it.
And this was exactly what we needed. Time away, with dear friends, in a place where no one knows your name. We did everything by the book, it felt like we were breaking the rules! 🙂
We talked with a friend yesterday about ruling following and asked again, where has it gotten us?
So, take the trip. Use the vacation days. Take the mental health day. Do what you need to do to take care of you. And don’t feel guilty about it.
Businesses, even schools, have made it painfully obvious that we are replaceable. Use that PTO for what YOU need.
Because you can’t take it with you when you are gone!


March 2, 2026 at 8:33 pm
On my gosh, Yes! take the trip. find the time! So sweet. I went with my 2 sisters and their husbands in September. I love it so much. I went even though I sometimes feel like an extra. My husband of 51 years passed almost 4 years ago. We often used long weekends to make quick jaunts. I miss those
March 2, 2026 at 9:01 pm
Darin, I am delighted to read your slice, just like the old days when we followed each other at the end of the TWT’s long line of slicers. I think slipping in just before the midnight hour was actually fun. I used to laugh at which one of us would come in last. We followed the rules and made long-lasting friends but now is the time to get into the self-help routine, as you say…
March 2, 2026 at 10:12 pm
Darin, this sounds like such a great trip! One of my friends, also an educator, visited Key West in December and enjoyed Hemingway’s house along with the cats. I agree with taking those vacation days. I took my own off-season vacation in October and have no regrets.
March 2, 2026 at 10:15 pm
Love this post! Both the sentiment, and the descriptions of your time away. The Latin night sounds like so much fun — that’s what it’s all about! I’ve only been to Key West once — it’s just magical.