
Have you ever said “yes” to an event, regretted it immediately, spent the next week trying to come up with an excuse to cancel … and then had a blast once you actually went? Yeah. Me, too. Almost. Every. Single. Time.
So why do we resist fun like it’s a tax audit? Fun should be the easiest thing in the world. It’s literally called fun. But somehow it ends up feeling like another item on the to-do list, right between “buy lightbulbs” and “question all my life choices.”
Here’s why:
First, our brains are survival machines. They prioritize “important” things like working, grocery shopping, and Googling, “Why is my eye twitching? Am I dying or just dehydrated?” “Fun” doesn’t get flagged as urgent, even though it’s arguably as essential as water. And coffee.
Then there’s my personal nemesis: the productivity trap. Americans have been brainwashed into believing that unless something produces measurable results, it doesn’t count. No deliverables, no justification. We can’t just relax; we need a PowerPoint and a business plan. You can almost hear your inner boss saying, “You spent an afternoon making friendship bracelets?” Yes, actually. And they’re adorable. Here’s yours.
Then there’s the logistics of fun. Which are exhausting. You have to choose the activity, find a place, maybe spend money, coordinate schedules, and then summon the energy to actually leave the house. By the time you finish planning your “spontaneous” night out, you’re ready for a nap.
And don’t forget the expectations. The voice in your head that says, “I changed out of my sweatpants for this so it had better be amazing.” What if you’re terrible at axe throwing? What if the otter bites? What if the book really is better than the movie? (Psst, it probably is.) Sometimes it feels easier to avoid fun altogether than risk being disappointed by it.
But before you give FUN the big FU, hear me out. When you do carve out time for real, unapologetic, useless fun, you come back more creative, energized, and human. Fun is not a waste of time. Fun is how you remember you’re alive.
Here’s how to make it easier:
Shrink your expectations
Fun doesn’t have to mean an all-day adventure or even a two-hour drive. Think bite-sized joy. Ten minutes with a book you love (I’m currently devouring Get Me Through the Next 5 Minutes by James Parker. Thanks, Jim, for the recommendation!) Blast your favorite song and dance like no one can see you. They probably can’t. Or own it and video yourself dancing to The Cure like my friend Leo recently did.
Schedule it
Look at your calendar. Where’s the fun? Nowhere? Fix that. Block out 30 minutes and literally title it “FUN THING.” You don’t even have to know what it is yet (see next tip). Your brain just needs to see it’s officially on the schedule. Consider it a dentist cleaning for your soul.
Make a “fun list”
Thinking of fun things on the spot is impossible. It’s like trying to name a single song when someone asks, “What’s your favorite Beatles tune?” So, make a list in your phone. You can even start with lame things like watch a funny video or eat a fun-sized candy bar (or all the fun-sized candy bars, I won’t judge). Add to the list whenever inspiration strikes. That way, when your brain says, “I’m too tired,” your Notes app can say, “I got you.”
Pair fun with habits
Productivity experts love a good “habit stack.” So, steal their trick by pairing fun with something you already do. Sip your morning coffee while playing a word game. Listen to a murder mystery podcast on your commute. Fold laundry while watching a stand-up special. Instant mood lift with zero extra effort.
Phone a friend
Fun is like exercise; it’s easier with company and a lot harder to bail on. Find your fun buddy. Go on a walk, hit a concert, sign up for ukulele lessons, or just grab dinner somewhere that serves drinks with umbrellas. Bonus: telling someone “I’m doing this fun thing” makes you 82% more likely to actually do it. (I made that stat up, but it feels about right.)
Here’s the secret they don’t tell you: fun isn’t the opposite of productivity. It’s the fuel for it. The more fun you have, the more you want to show up for your life.
So yes, we can do fun things. Even when they feel hard. Especially when they feel hard. Life’s too short to skip the otter encounter.

Great one, Stephanie! ❤️
Spot on, as always.
I’m sharing this with a Meetup Organizer friend of mine who is constantly in motion planning and participating in, you guessed it…fun!
Thanks! And I hope you get to have lots of fun in the process.