We recently connected with Jennie O’Connor and have shared our conversation below.

Alright, Jennie thanks for taking the time to share your stories and insights with us today. Has your work ever been misunderstood or mischaracterized?

I’ve spent most of my life being misunderstood.

To the outside world, I was flaky. Distractable. A woman with so much potential, if I’d just settle on one thing.

At age three, I announced that I wanted to be an actor/singer/dancer. At 15, a veterinarian. I entered college thinking I’d fight biohazard level 4 diseases at the CDC and came out with a degree in theatrical costume design.

Over the years, I’ve been a bartender, CEO for an Upper East Side couturier, a food blogger, a wedding planner, a private chef specializing in food allergies, a travel writer and a brand strategist—just to name a few.

Society looked at that resume and saw someone who lacked direction. Jack of all trades, master of none, they said. And back then, I let “them” be louder than my own knowing.

They said I had to pick one thing to be successful. Then I had to devote my life to it, because how else would I become the very best? They drove home the belief that passion was frivolous unless it turned a profit.

And I bought it.

“You need to niche down.”
“You’re not a real artist unless you’ve sold your work.”
“Multihyphenates are confusing, and a confused mind doesn’t buy.”

Despite being willing to learn and obsessed with each career, I felt my newness was shameful. I’d need more experience, more credentials, more pro bono work under my belt before I could be taken seriously. I let businesses die because I didn’t feel “legit” enough to show up and ask for the sale. And all the while, it felt like I had been born into a world that had no place for me.

What I know now is that, for multipassionates, choosing just one thing is a recipe for dying on the vine.

We don’t fit neatly into boxes—and that’s not a liability, it’s a superpower. We are endlessly adaptable. We find patterns others miss. We bring nuance and curiosity to everything we do. And we’d be useful AF in a zombie apocalypse.

No wonder the actual quote is:
“A Jack of all trades is a master of none, but oftentimes better than a master of one.”

It took me almost 40 years to see that my patchwork career was actually a treasure map. That every rabbit hole and odd job was equipping me to be better able to help others find joy, clarity and permission to be fully themselves.

So yes, I’ve been misunderstood. But it brought me to the realization that I’d rather be an outcast than do anything that doesn’t light me up for any length of time.

And if it helped develop that internal compass?

It was worth it.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’m Jennie O’Connor—and I’m in constant search of evidence that you can defy conventional wisdom and still be a roaring success.

I’m a writer, storyteller, branding strategist and all-around curiosity chaser who helps multipassionate creatives choose a direction (without sacrificing their loves), build magnetic brands and get paid to be themselves. I work with the wildly talented folks who’ve been told their whole lives they need to “pick one thing,” and I help them turn their too-muchness into their secret weapon.

Because being multihyphenate isn’t a flaw. It’s a competitive edge.

What I Offer

I work with creatives, coaches, solopreneurs and multipotentialite unicorns in a few different ways:

VIP & Mini VIP Days: You hand me the words you’re struggling with (sales page, website copy, email welcome sequence, etc.), and by day’s end, I hand you back a version of yourself that sounds so good, you’ll want to get a room.

Brand Strategy & AI-Enhanced Imagery: From your visual identity to the story your brand tells, we dial in the vibe that makes you unforgettable—and use AI tools to bring your vision to life in technicolor.

Dream Job Academy: My signature course for multipassionates who don’t know which of their passions to monetize—but do know that they’re ready to quit spinning and start building something of their own.

Whether it’s done-for-you or done-with-you, all of my work is about helping you create a brand and business so aligned with your soul, it feels like play.

The Problems I Solve

I work with people who are:

Drowning in ideas but unsure which one to pursue
Struggling to talk about what they do in a way that makes sense
Tired of being overlooked because their brand is bland or inconsistent
Ready to break up with hustle culture but still want to make bank
Seeking more fun, freedom and self-expression in the work they do

I use clarity clues, creative direction and sexy wordsmithing to make your brand leap off the page and tap dance.

What Sets Me Apart

I don’t do subtle. I’m allergic to high-falutin’ jargon. And I will not let you leave the house with “Helping change makers step into their power” as a tagline.

What I do is help you put your best foot forward—debut you as the wildly compelling human you are. Through a combo of storytelling, psychology and strategy, I help you build a brand that turns heads and earns dollars, without selling pieces of your soul or pretending to be someone you’re not.

Freedom comes from giving yourself permission. To chase the squirrels, to take up space, to set the destination on your GPS to “joy.”

I’ll show you how it’s done.

I’m Most Proud Of…

The fact that my work gives people the courage to be themselves, warts and all. (We call them quirks, and we turn them into your trademark.) I’m proud I’ve been the cheerleader who’s nudged aspiring authors scared to hit publish to *do the thing.*

Nothing brings me more joy than watching a client finally step out of the shadows with a brand they’re so excited by, they can’t NOT share.

I’m confident that my clients leave our time together feeling like their personal definition of success–once we’ve stripped away the one society says they should want–is actually attainable. And that feels amazing.

Just like knowing I’ve created a corner of the internet where success looks like more naps and abundance spotting is #trending.

Above all, I’m proud that my life—and the way I walk my talk—has helped other people fall in love with their lives.

What I’d Most Like You to Know

You don’t need to pick one thing. You just need a throughline that ties all your loves in a bow.

You don’t need another certificate to prove you’re worthy. You just need to start.

You don’t need a legacy. You simply need to delight or inspire a handful of people in your time.

My newsletter, Down the Rabbit Hole, is about redefining success on your terms. It’s about the absurdity of the hustle culture narrative—and how to stage your own personal rebellion. It’s about the sheer delight that comes from embracing all your shiny objects without guilt or self-reproach.

Because a life that honors all your passions isn’t just possible—it’s the whole damn point.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

I had to unlearn the age-old tale of the starving artist.

On the first day of college, my theater professor—we’ll call him Ron (because that was his name)—stood in front of a packed auditorium and declared, “If you choose this career path, you will never make any money.”

Looking back, I wonder how many hearts broke in that moment.

Such statements are insidious. They become self-fulfilling prophecies, especially when you spout them at humans who don’t yet have a fully formed prefrontal cortex. It was the start of a belief that if I wanted to pursue creative work, I’d have to accept that money wouldn’t be part of the equation. That success would come only after years of consuming nothing but beans and malt liquor in a drafty apartment with mold and cockroaches.

Worse yet, I internalized that if I wasn’t struggling, I wasn’t working hard enough.

And those rags-to-riches stories didn’t help either. Stephen King wrote Carrie while working in an industrial laundry and living in a trailer with no phone, making it near impossible for his first agent to call and make him the offer that would change his life. Ash Ambirge tells the story of living in her car while launching her business, which miraculously took off with her very first launch. I attributed that beginner’s luck to the depths from which she’d had to claw herself out.

I even came to believe I didn’t deserve to make money if my suffering wasn’t as egregious as theirs! Wild, right?

Then one day, I was listening to a podcast episode on money stories, and I heard someone say:

“You don’t have to suffer in order to be rich. You don’t have to earn your worthiness.”

And it stopped me cold.

Because it had never occurred to me that that belief was… optional. That maybe I could love what I do, be so good at it that it felt easy and get paid well, without army crawling through the Swamp of Sadness.

Since that moment, I’ve been on a mission to rewire that story—not just for myself, but for every multipassionate creative who still feels like they need to get a “real job.”

I want to be proof that we can make beautiful things and beautiful money. That joy and abundance are not mutually exclusive. That art is valuable because it’s sacred. Not because we have to bleed for it, but because it connects us to something greater than ourselves.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

Three books in particular have rocked my entrepreneurial world and helped shape the values I bring into both my life and my work.

Existential Kink by Carolyn Elliott

This book mindboggled me with the idea that the things we say we don’t want might actually be giving us a secret thrill—and that identifying and befriending those desires is the key to real freedom. It introduced me to the shadowy stuff we don’t talk about: the subconscious payoffs of self-sabotage, the strange comfort in complacency, the fear of outshining others.

EK has profoundly influenced the way I help clients who feel like they’re constantly battling the same old demons. And, while I’m not recommending anyone follow my path, I’m confident it is the only therapy I will ever need again.

The Middle Finger Project: Trash Your Imposter Syndrome and Live the Unf*ckwithable Life You Deserve by Ash Ambirge

Ash’s writing was one of the first times I saw someone like me–irreverent, sweary and no-nonsense—succeeding on her own terms. This book gave me permission to burn the rulebook and trust my own instincts, even when they flew in the face of convention. She frames marketing as an offer to help, greatly reducing the ick factor that accompanies self-promotion for most of us. And you will walk away with the sense that you are worth WAY more than you believed you were going in.

This book has undoubtedly helped shape the foundation of Down the Rabbit Hole, where “telling it like it is” is the order of the day and F-bombs are added for sparkle.

Four Thousand Weeks by Oliver Burkeman

This book shook me to my Type A, color-coded habit tracking, fully optimized core. It dismantled the entire premise of hustle culture I’d been both seduced by and complicit in—the idea that if I just found the right system, I could finally do it all. Four Thousand Weeks made it clear that belief is a trap.

Burkeman reminds us that the list will never be done and our obsession with optimizing every second only robs us of presence.

This philosophy is now baked into everything I teach: that joy—not output—is the only compass worth following.

I work with multipassionates who often feel like failures because they can’t do everything at once, and Four Thousand Weeks finally gave me the language to say: You were never supposed to.

Contact Info:

• Website: https://JennieOConnor.com
• Other: Follow me Down the Rabbit Hole: https://jennie-oconnor.kit.com/0e2e46123b

  Join me on Substack: https://d0wntherabbith0le.substack.com/

Image Credits

Custom-branded images by Jennie O’Connor Creative, built with AI.