New to Rolling in Doh? 🤗 Start Here: A Mad Lib (+ Template!)
📝 Copy the Google doc to join the "Less Than Ideal Day" fill-in-the-blanks fun :)
If you are new here, welcome! I’m delighted to have you, and deeply grateful to Substack Writers for featuring Doh this week :)1
The Ideal Day Mad Lib is one of my favorite templates to share with readers of Pivot and Free Time. But sometimes our ideal day doesn’t go as planned . . . for days that stretch into weeks and months and even years. 😭
No matter how short we fall of rolling in actual dough, let’s at least have a laugh: How did your last year go? Write your story using the same prompts as the ones in this post by saving a copy of the Google Doc template and filling in the blanks.
❤️ In lieu of rolling out an actual red carpet for you, my version is below! Each link points to a post from the Doh archives, in chronological(ish) order. You can also check out the full Rolling in Doh podcast playlist on Spotify here »
I
After losing 80% of my projected income during the first two weeks of pandemic lock-downs, two years later in the summer of 2023, I hit a major dip when I got “The Ax” from my favorite licensing client—the Big One after 2020’s losses.
I didn’t know what else to do. It was the last straw after years of stressors. So I started Writing My Way Out.
I had a hunch it could be my Getaway Car 🚘.
Despite the Starting Friction,
II
My husband celebrated the move by saying 🏴☠️ “Burn the Boats,”
As I lurched into Full Catastrophe Business-Building.
I took some deep breaths, reminding myself to: 🎬 BELIEVE, Ignore the Odds, aim for 51/49, and Survive til ‘25.
. . . and that it would okay if I browse /careers after 12 years of self-employment.
III
I wished someone would Save Me while 🧱Rebuilding from Rubble.
Still, despite the low moments I remember thinking, 🚧 This is a Wonderful Day!
And then immediately growing afraid that soon the other shoe would drop.
IV
Although I had major issues with Critters and Cash Flow,
I tried to be grateful for BBQ & BBB.
After all, ✨“Good Vibes, Good Life.”
While embracing the fact that my life was a Hot Mess 🍔, I returned to a mantra that served me well: There Is Only One Wish.
V
Things started to shift as I released The Self-Imposed Pressure to Be an Expert,
Especially when I admitted Revenue Goals Don’t Work (For Me).
I took stock of all that happened since 2020 by conducting An Honest Accounting, replete with an emoji balance sheet.
VI
I had a lot of ambiguous grief around 👻 Saying No to the Ghost of a Former Self, as evidenced by a podcast host interviewing my fossilized self, and the feeling that my pre-pandemic 👖 closet belongs to someone else.
A wave of insecurities rush in, as I wondered:
Is my Favorite (Former) Client thinking, Why are you so obsessed with me?
Am I an 🥸 Unreliable CEO?
At the same time, I felt a Weight Lifted.
VII
I had an aha moment when I realized The Suspense is Terrible . . . and yet I hoped it would last.
Plus 🌊 This is Like That, after confronting my fears of fish and drowning.
Serendipity kicked in one 👟 Strange and Wonderful Morning.
At the peak of my overwhelm, I made a small business owner ✔️ To Do List.
I shook off the temptation to Sail the Sea of Shiny Shoulds; reminding myself 🚬 Smoking is Essential for Your Success, They Said 🙄.
VIII
I laughed when I realized that just like my angel-in-fur-coat Ryder, I too was 🚿 Fooled by Joyful Randomness.
Before I knew it, I found myself 🪜 Climbing Down the Entrepreneurial Ladder;
It was time to 🏆 Put the Podcast Trophies Away.
Still, there was 🎤 one thing I forgot to say to my career these last four years.
IX
As last year came to a close, I reflected on a few of the strange lessons it brought 🧐 Do What You Love and the Money Will Follow...only IF you meet certain criteria, and that 🪶 the abyss does not always become a feather bed.
There might not be a big breakthrough, it seemed I was on a path toward 🌱 Ten Years to Middle-of-the-Pack Success.
So to ring in the new year, I wrote ✉️ Dear 2024: A Letter, with a response 📩 From 2024.
In my most uncertain moments, I Asked for a Sign (and another, and another).
Sometimes they were unmistakable, like the 🚨 Four-Alarm Fire on my block.
X
Even though I gave up trying to lap the 🚓 Ghost Car,
I knew that I wouldn’t stop Chasing the Taste of Creative Freedom.
After all, as the kids say 🤸🏻♀️ Delulu is the Solulu!
It’s normal to experience a 🚏 Creative Crossroads After Achieving Success.
XI
Sure, my fear of failure bubbled up when I contemplated 📘 The Free Time Afterword I Never Wrote and 🌟 My Favorite One-Star Review.
But I surrendered to the 🧺 Crumpled Laundry Piles All Over My House, and later, to Chekhov’s law of crème clothing.
I realized that although I might be 🃏 Decorating My House of Cards and 🪂 Building a Parachute on the Way Down,
it was time to 🛋️ Pull up a Seat
and embrace Rolling in Doh.2
❤️
XII — Postscript, Part One: 2024
The story continues even after this post went live . . .
Sometimes it felt like even my best efforts fell short. I AM DOING THE BEST THAT I CAN! I wanted to scream into the void.
When friends asked, “How are you doing?” flashes of Apple’s cruel iPad commercial flickered across my mind. Crushing it! I’d say with a 😂
A blue jay looking for a mate (or rival) by slamming into sliding glass doors seemed an apt metaphor for the down days in my business.
As my friend Jamie put it, 🪩 “I am no longer allowing praise to be my currency.”
As I reflected on One Year of Rolling in Doh in the summer of 2024, I imagined what my business would say if it could talk. How about yours?
Bob the Neck Throb demanded attention, too, by sending me to the E.R. with a must-heed health memo. Yes, giving up your favorite vice is good for business.
I became an unlikely Hilderbabe, inspired by prolific author Elin Hilderbrand’s daily routines.
This led to an exploration of my Flop Era, where I became a self-appointed flopologist, as an old identity floated away and the new one hadn’t fully yet arrived.
I studied audacious creative bets by movie directors Kevin Costner and Francis Ford Coppola, unpacked my own publishing pivots, and examined the relationship between risk and regret after several people asked if I missed podcasting a year after pausing my two shows after nine years and 750+ episodes.
Did I set myself up to fail? Is there even such a thing as failure?
If money weren’t an issue, I’d ring a psychic for reassurance, so they could tell me what I want to hear. Sometimes, it just took a friend sending a “truly tiny something,” a talisman, to lead the way into my new identity as a writer.
Other friends spotted hope, a stranger blessed me on the subway, I encountered reclining liberty, and three serendipity signs kept me from losing faith. I’m always listening to the magic of New York City.
That’s the truth about how I run my business: on serendipity and surrender, for better or for worse, while leaning into the terroir of transformation.
As Donna Tartt poignantly wrote in her Pulitzer-prize-winning novel, The Goldfinch, “We don’t get to choose our own hearts.”
Sometimes you need to put down the donkey and bake your own cake.
Together with fellow Dohnuts, we explored monthly(ish) community prompts like, is “just be yourself” good career advice?
My friend MBS shared his thoughts on being a One Hit! Wonder with a mantra, “I’ve already won.” I was worried my biggest publishing success was behind me (it very well might be).
Why aren’t you enlightened yet?! My inner critic demands, cringing at my questions.
You know what? Sometimes, it’s okay to cry over spilled donuts.
XII — Postscript, Part Two: 2025
Rolling in Doh alchemizes faith and doubt; but there’s a third missing ingredient.
Dwindling confidence can be hard-to-stomach when mid-Crumbling, and the old chestnut about stockpiling marshmallows doesn’t help.
Sometimes, a soul-stirring daily ritual is all you have to hang onto—although even those could be misinterpreted when in a flop era—at least until a lucky seedling sprouts.
I still feel like an alien in much of my work, scavenging for signs on the subway (and even the mouse in my house), while my most toxic trait still holds me back more than I’d like.
Still, I keep writing my way through. I’m not here to give advice; as Saul Bellow said, “I’m not an ornithologist, I’m a bird.” A harpist reminded me that not all feedback is created equal.
Suddenly, after over a decade of resistance, I caved and purchased the book I had been avoiding for twelve years—based on a big decision at the NYC crossroads.
Time to make “Enormous Changes at the Last Minute,” then hurry up and wait.
In the meantime, realize Adulting is Easy! But only if you follow a very particular 100-step daily checklist. Still, sometimes even The Responsible Route™ fails.
While waiting, I worked on slowly moving from Fawning to Flopping to Phoenixing. I tried to keep the faith in Perfect Flow.
“Keep your head in the clouds, and your feet on the ground” a friend said.
Thank you for reading! If you enjoyed this post, tap the heart or restack buttons below, share it with a friend, or leave a comment—I’d love to hear from you! If you’re feeling brave, share one of your mad lib sections in the comments :)
The blurb knocked my socks off! Big thanks again to Substack Writers for the kind words :)
If you’re new here, this is a (mostly) paid publication about my travails as a breadwinner and small business owner living in New York City, with lots of embedded links for your perusing pleasure. I hope it brings you as much catharsis as it has for me—you are not alone if you, too, are Rolling in D🤦🏻♀️h!
If you enjoyed this post, don’t forget to take a crack at the Less Than Ideal Day Mad Lib template yourself, with the same prompts as above.
And here’s the Rolling in Doh podcast playlist on Spotify, with stories from others, too, on how they navigate what Luvvie Ajayi Jones calls “The Crumbling.”









Congrats on getting featured, Jenny! I really enjoy your newsletters 💕
I absolutely love ❤️ Doh!!