3 Lessons From Business That Have Changed My Creative Life
On people-pleasing, self-advocacy, and learning to make the ask.
In 2023, I left my job as a public school teacher to pursue writing full-time. And then a funny thing happened: I became a businesswoman.
I couldn’t have predicted how that mindset shift would change everything I thought I knew about success — including my creative life.
Let me start at the beginning.
For years, I’d tried to manage it all: a full-time job, writing on the side, and raising two young kids. But any educator will tell you that classroom teaching is really more like 5 full-time jobs. The summers are amazing, but the nine months during which every ounce of cellular energy is zapped from your body before 4:30pm are grueling.
Most nights, I came home too overstimulated to even chat with my own kids, let alone to sit down and create art. It triggered a cycle that would trap me for years: stuck in the false narrative that I should be able to do it all — write, teach, parent — and failing every day to meet my own expectations.
Something had to give. And naturally, it had to be the thing that demanded the most of my energy, creativity, affection, and executive functioning.
My job.
Before we go any further, let me be clear: I do not recommend quitting one’s day job to support their art (we’ll talk about my new full-time job in just a minute). Leaving behind a generous pension and a secure position was no flip-of-the-coin decision. In this day and age, with AI, inflation, and so much general uncertainty, a job is a blessing.
(So, please don’t go telling your boss tomorrow that I told you to quit and focus on your knitting.)
What I do recommend is trying on a different hat.
A month after leaving the classroom, I was approached by a local business owner about joining the team at her small education company. The invitation surprised me.
Sure, I knew about teaching and kids. But I didn’t know anything about business, let alone how differently a company operates from a school.
I quickly discovered that while the nuts and bolts of business are easy enough to learn, it’s the mindset that requires the most growth — and has taught me the most along the way.
Three years later, I am now the COO of that company. The lessons below are among those that have helped me get out of my own way and start claiming my creative dreams.
Lesson #1: Learn to be your own best cheerleader.
Many women excel at teaching because it’s closely aligned with the other roles we fill in life: daughters, caregivers, mothers, women.
As someone who checks every one of those boxes, I learned early on that the more I pleased others and the fewer boundaries I claimed, the more praise I received. Every “good job” or “thanks for accommodating me” reinforced the belief that the strongest tool in my toolbox was making others happy.
It wasn’t until I left the classroom that I could see how that belief upheld a system that exploits unpaid female labor. Or, that by masking my desires, I was self-sabotaging my sacred work: writing.
I discovered this the hard way after my memoir was released. Throughout the 18-month publishing process, I was so pinch-me ecstatic to have the opportunity that I followed my tried-and-true playbook of going with the flow and not asking questions along the way.
I didn’t understand just how much self-advocacy would be required until it was time to promote the damn thing. And then it was like stepping onto a stage for a role I’d never prepared for: my own best cheerleader.
Buy. My. Book. Three words I’d rather eat live worms than utter.
The audacity! I thought. You can’t just say nice things about your own work! It wasn’t humble. Or demure. It was what loud-mouthed, disagreeable women did — the kind of women we’re taught to fear like the plague.
But anyone who knows anything about publishing or business in general knows that you don’t get anywhere if you’re not willing to push your own product.
In business, excess humility is a roadblock, not a virtue. When you put your name on something, you should be proud enough to scream about it from the rooftops. You can’t just wait for the universe to recognize how “nice” you’ve been along the way and do you a solid by spreading the word.
After all, if you won’t be the head cheerleader of your own life, who will?
Lesson #2: Make the ask.
I have learned so much from my colleague, friend, and Amore Learning founder, Chloe Kaplan. Chiefly, that no one will send you to the gulag simply for asking! In my previous life (the one where I’d rather eat worms than talk up my own book), I couldn’t think of anything more fear-inducing than asking for what I actually wanted.
And then I watched a miraculous thing happen. And happen again.
In conversations with clients, potential partners, and collaborators, I watched Chloe unapologetically make the ask. Then (with shocking frequency), as it was granted.
In the writing world, there are a lot of asks to be made. Will you read my pages? Will you blurb my book? Will you please mentor me?
For a solitary practice, it’s a community-based career, one in which you won’t get far unless you find your tribe. Which means, you must get comfortable with the vulnerable practice of asking for what you want.
(Of course, there are polite and authentic ways to go about this, as well as cringe-inducing, inappropriate ways, but that’s a conversation best saved for another day.)
Only now, in my reformed people-pleasing era, can I embrace the familiar saying, “The worst someone can say is no.” And that’s because in my business experience, I’ve been on the side of “no” enough times to discover that I actually will survive it.
Rarely are “nos” personal (rarely is anything in business personal!). And the more practice you get hearing it, the more skilled you become at learning how to turn the “no” into a “yes," or even a “yes, please!”
Lesson #3: Enthusiasm begets creativity.
When you love what you do, it’s easy to make others fall in love with it too. I love serving children — I mean this with every fiber of my being — so to continue that work on my own terms has been a great gift. Our business has grown exponentially over the past few years, largely due to the enthusiasm of our leadership team. We love our clients. We love our team of teachers. Yes, there are headaches (there are headaches in every job!), but I feel lucky to have found a job that fuels my energy instead of depleting it. And this has impacted every part of my life, including my writing.
Oftentimes, energy for one feeds the other (which is another reason I don’t recommend quitting!). Two summers ago, I was struck by inspiration while sitting by the lake. As I began working on what would become a middle-grade mystery, I had an “OOH OOH” moment. Maybe I could take my newfound interest in detective work and get real kids on board. When I got home, I developed an afterschool class called Mystery Solvers, one of our company’s most popular offerings.
Your hobby doesn’t have to become your job. Nor does your job need to feel like a hobby. Think of them instead as a marriage of two kick-ass individuals, two complementary outputs of your energy. Whatever excites you will likely excite others. Follow that enthusiasm — it will grow in directions you never expected.
For those (like me) who can do hard things but can’t get dressed in the morning.
Next month, we are launching our first Lifelong Learner series at Amore Learning. In you’re in D.C., consider joining us for The Style Edit: an evening with the wise and wonderful Vanja Amodeo, beloved image and fitness coach (not to mention, Dr. Jill Biden’s beloved barre teacher!).
For Vanja, image isn’t about luxury brands or optimizing the body. It’s about identifying a personal style that’s authentic to the chapter you’re living, and resisting the pressures and habits that keep us stuck. This intimate conversation promises confidence, clarity, and intention for every woman.
Join us at Amore HQ on Tuesday, June 2nd from 7-8pm
I’d love to see you there.