9 (more) whimsical habits to keep you from spiraling into the darkness
Joy is resistance!
I wrote 11 whimsical habits to keep you from spiraling into the darkness in February when the new reality we were facing as a country started to settle in. I was desperate to make my own joy and be more intentional about adding whimsy to my life. 20K views later, it’s safe to say you felt the same!
For some reason (or actually, for all the obvious reasons), the article has started trending again. And while I’m thrilled it continues to resonate, there are a few more whimsical habits that deserve to be shared!
When coupled with action, I truly believe that joy is the resistance. So, with bows and ribbon and cake on Wednesdays… we fight on:
Wear slippers around the house. This was the biggest and most obvious miss from my first article. I’m a slipper loyalist. If I’m home, there are slippers on my feet. What’s more whimsical than sliding your feet into plush clouds and calling them house shoes? And I’m not talking about Uggs that you can wear running errands… Real, ridiculously fluffy slippers.
Compliment a stranger daily. The only thing better than getting an unexpected compliment is giving one. You have the power to positively change the trajectory of someone’s day in an instant — use it! I especially love to compliment older women I see in the city. Baddies are forever.
A friend I admire deeply for her gorgeous, oftentimes very whimsical, life journey, Jessica Harshman recently wrote on her Substack: “Not sharing a compliment is like wrapping a gift and never giving it.” It’s true. Free love is meant to be given away!


they deserve all the compliments Commit to a 10-minute daydream, every morning. I am ~always~ in my head. If my eyes are open, my brain is buzzing a million miles a minute and approx 99% of what’s going on up there is non-sense. I blame this on my Aquarius air-sign sun. To help calm the chaos, two of my best friends (both earth signs, worth noting) have continuously suggested I try meditation. After many failed attempts, I finally found a routine that works for me. And—can you believe!—the biggest adjustment is that it feels more whimsical. Before getting out of bed each morning, I put on a 10-minute guided meditation that asks me to envision “what’s the best that could happen?“. It feels more like dedicated daydream time. Some mornings I’m daydreaming about a love that feels like an ‘80s John Hughes movie. Others I’m walking around with Obama-era optimism and confidence in our country. One morning I spent 10 minutes thinking about my dream dog. But for the first 10 minutes of every day (for the last 15 days, my longest consecutive streak!), are spent imagining a life where everything goes right.
Adopt an “it’s the little things” mindset. My Pinterest has been serving me photos of at-home lattes made with ice cubes shaped like flowers, butterflies, hearts, etc. I fill my ice trays every night, whyyy on earth am I using square trays?! Naturally, I ordered some and daily drinks are exponentially happier. It really is the little things! Other little things you can do: name your plants and give them detailed background stories, subscribe to a print magazine for a monthly moment of screen-free delight, put old Disney movies on in the background (2D animation is soothing!), listen to a Nancy Meyers playlist when you’re cooking…



little things, big difference in seratonin Celebrate color!!! I fear we’re in the beige epidemic. Yes, in some instances a monochromatic look is chic and clean. But when your wardrobe, your home, and your desk are all 50 shades of grey, anything in color starts to feels out of place. And where’s the whimsy in that? Everyone’s tastes are different and I’m sure my dusty pink comforter would stress some of you out, but there’s always room to add more ~life~ back into your space. Choose the colorful flowers. Wear jewelry with some gem stones. Paint your toenails Got The Blues for Red instead of Bubble Bath. Wear a berry lipstick for fall. Buy a leopard blanket to cozy on the couch with…and hide it in the closet if you don’t want it out all day. More glad, less sad.
Create more immersive content experiences for yourself. My book club is currently obsessed with The Gilded Age on HBO (thanks to my BFF Alana Naber’s recommendation!). We all recently returned from Newport, RI where one of our book club members got married, so we were already enamored with the Gilded Age lore. We did the Cliff walk, toured the Breakers, and the bride’s welcome party was at the International Tennis Hall of Fame… all of which are featured in the show. But that wasn’t enough! A handful of us read/are reading books centered around this time period, too. It’s like our own Gilded Age history syllabus come to life! Everything about it felt richer. I have a trip to London coming up next month and will also be theming my content to align with my travels. Book & show recs welcome!
“Look for the hearts.” I listened to this Mel Robbins episode three years ago and it has always stuck with me. She talks about synchronicities and how to train your mind to spot magical moments. One of the exercises she suggests is to look for the hearts. When you’re walking around and going about your day, keep your eyes open for heart shapes. You will be shocked at how often you see them. On signs, logos, posters, graffiti, and on people’s clothes, in shadows on the sidewalk, in nature and clouds. They’re everywhere. And you could do this with anything ~ butterflies, your lucky number, a specific shade of a color, your favorite word. It’s just a practice in being aware and choosing to keep your eyes open for the good stuff.
Lean—the f*ck—in to the holidays. Whether you like it or not, festive season starts now! There’s no better way to connect to your inner child than to lean TF in. Wear the damn costume. Write in a gratitude journal every day in November. Drive around the fancy neighborhood and look at Christmas lights. Make a mulled potpourri pot for your stove. My personal favorite: make a seasonal craft! Be tacky, kitschy, and over-the-top simply because you can. The world feels so dark, so serious. Let this final season of the year be glittered with brevity and light. The holidays are easy and happy for some, tough and heavy for others. Wherever you sit on that spectrum, choosing to celebrate joy despite it all is an act of self-love you deserve.


My crafts of choice last year: felt ornaments and a village made from birdhouses Work from your local library. The greatest WFH hack of all time! Your local library has free WiFi, a quiet atmosphere, printer access, and overall beautiful, calming energy. Coffee shops can be so hit or miss when it comes to productivity. Libraries are much more consistent. My favorites in NYC are the Jefferson Market Library in Greenwich Village and, of course, the iconic New York Public Library next to Bryant Park.
Let’s end the year with an explosion of fun—dust off your glue gun, always take a look at the dessert menu, and don’t forget to tell your friends how much you love them.
What did I miss? Let me know your favorite whimsical habits <3
xx, Caylee





Yes to libraries! Etiquette is more strictly enforced there so it’s much more productive imo
Complimenting strangers to kick off this whimsical Friday thank you 💕