I’m listening to Tim Ferriss’ Four Hour Work Week, and something he says aligns with what I’ve been thinking about… a lot. If not now, then when? And at what cost?
So, as I’m going through my mid-life crisis (here’s looking at you, fifty), I’m thinking a lot about my dreams from when I was young, like in middle school. Maybe that has to do with living with a middle schooler, but I think it’s more than that. I think that as I get older, I cling to the memories of my youth a bit tighter. Which, frankly, has me concerned for when I’m really old and have zero filter, that I’ll just start talking about life in my twenties (that was one of the best times of my life).
But for now, I’m thinking back to when I was in elementary and middle school (grades 2-8) and my passion was writing and telling stories.
I remember the first time I told a story. The four of us were sitting around the dinner table, Mom at one end, Daddy at the other. Jenny was across from me and Sammy was at my feet—my feet were resting on him. And I told a story.
I don’t remember the context of the story—I remember that it was fiction.
We had just been served chocolate ice cream for dessert, and as the bowl was placed before me, my story started. When I finished the story, the scoop of ice cream had melted. I remember looking down at the chocolate soup and wondering what happened.
I suppose the word for it now would be flow. But back then, all I knew was that while telling the story, I had completely removed myself from the kitchen table and started to walk within the scene as the narrator. I lost touch with my family and what was happening around me and mentally disappeared. When I returned, I remember feeling so light—my heart was light. My mind felt light—I felt as if I had just released something powerful that had been bottled up in me.
The second story I remember telling was through words and pictures on the page. I was in second grade and I wrote a story called “The Big Blob and the Little Blob.” They went on an adventure in the forest. I don’t remember the whole story, but I remember the title, the yellow folder I put it in to make it look official with a semi-hard cover. I remember having the same feeling when I wrote that story—I escaped from my surroundings. One minute I was sitting on the maple hardwood floor of my room, and the next I was in the forest with the blobs. And I participated in their adventure.
Again, when I returned, I felt a lightness, a sense of freedom and release—maybe it was euphoria (that seems like such a big word for a second grader, but I felt like I had magically disappeared and reappeared).
As I cross into this mid-life—and think back to my dreams from when I was little—my dream of being a writer, I wonder what happened to all that time? More bluntly, what do I have to show for it? And if I had started back then, maybe it wouldn’t be so hard to start today?
The Search for Permission
Here’s what’s wild: I wanted to be a writer. I still want to be a writer. But somewhere between second grade and fifty, I convinced myself I’d lost the right to call myself one.
Over the past year, I’ve listened to and read over 26 books. Young adult. Fantasy. Memoir. Biography. Business. Self-help. Some have won Pulitzer Prizes, been on the New York Times bestseller list, been chosen by Reese Witherspoon and Oprah for their book clubs. Some I’ve just found on a random search of Kindle Unlimited or Amazon Originals. Some have been self-published, some are from large publishing groups.
I think I was searching for something. Permission, maybe?
Then I found it in the most unexpected place.
I loved The Wedding People by Alison Espach—the unlikely circumstance the lead characters find themselves in, the way the author strung together the words, everything. When I finished, I immediately searched for another book she’d written and started it on Audible. I didn’t make it far, maybe 30% of the way, and I had to stop. It was as if the author had a lobotomy because nothing about the two books resembled the other.
And that taught me something incredible: It’s possible, as a writer, to change your voice and tone. The same author can sound completely different across books.
That permission—that’s what I’d been looking for.
Because here’s the truth: My voice has changed so dramatically since my high school days. Now, instead of wanting to be canonized, I’d love to write a carefree YA book (well, as carefree as a YA book can be when you’re talking about love, social power, crushes, pimples, and testing parental boundaries).
I’d been holding myself hostage to a version of myself that doesn’t exist anymore. And instead of that being a problem, it’s liberation.
If Not Now, Then When?
The desire to write, to live creatively, is alive and well. It’s pushing me to grab hold and see where I go.
There are two areas where I want to grow and explore—written word and spoken word. Writing and podcasting.
But to do that, I need to make some rules. I like rules. I can be very black and white, and so I need these to help guide me into unknown territory:
1. I’m writing to get lost.
Lost in my thoughts, in my words, in the story, in making sense of things, in exploration.
2. I’m creating to find a story, to write a story, to be part of a story, and to share my story.
3. I won’t be right all the time. I won’t be wrong all the time.
I’m writing to explore, not because I’m the expert. I’m not.
4. It’s okay to change my mind.
What I write isn’t written in stone. I can re-evaluate my writing, my ideas, my questions, and my answers. This is how I see it now. Sure, someone may screenshot what I write today and compare it with what I write in the future and then do a line-by-line comparison, or ask Claude or ChatGPT to do it—and if they do, well, quite frankly, that’s a win. It means that someone out there cares enough.
5. Commit to this fully, until I decide that it’s not what I want.
6. I can come back and change these rules.
See #3, #4.
What Comes Next
These rules aren’t just for my writing journey—they’re how I want to show up in the world. They’re how I want to show up for other women who are standing at their own crossroads, wondering “if not now, then when?”
Women who are ready to commit to their dreams, create something meaningful, and celebrate every step forward—even the messy, imperfect ones.
Because here’s what melted ice cream taught me: When you’re fully present in your creative flow, you lose track of everything else. Time disappears. Doubt quiets. And when you come back, you feel lighter.
That’s what I’m chasing. And if you’re reading this and something resonates—if you’re fifty, or forty-five, or sixty, and wondering what happened to that dreamer you used to be—maybe you’re chasing it too.
Welcome. Let’s get lost together.
This is the first post in my journey back to writing. I’ll be exploring stories, sharing book insights, connecting ideas from podcasts and business books, and documenting what it looks like to commit to a creative life in midlife. Subscribe to follow along.