Welcome to The Emotional Entrepreneur, a feelings blog about business

June 25, 2024

When I was 15, I would write in the margins of my school notebooks — in tiny writing, where no one could really see it, but it was there if you looked, lining the pages of my homework. Cramped and compelled:

It’s only when I feel alone that I turn to realize that I am. 

It had floated into my brain one day and stuck. I think I was impressed at myself (lol) for how well this turn of phrase seemed to get at the elusive, perplexing wisps of being human and being conscious

My problem back then was this: In the dead air between activities (volleyball, homework, play rehearsals, church, boy gossip), an earworm of doubt would wriggle its way to the forefront of my mind and threaten to ruin it all. 

Doubt about what? 

Well, about everything that mattered to me at the time.

That all this work would pay off with a college scholarship. 

That my friends knew me in a real way.

That God existed. 

That any of this existed. 

One doubt after the other, heavy dominoes crashing into each other before I even realized what was happening.

And then came the shattered glass of my internal world. 

To me, everything was good until I had a thought that it wasn’t. But once that thought cracked through the door of consciousness … I was alone. A single spinning planet in the endless night of space. 

It’s only when I feel alone that I turn to realize that I am. 

But I’d keep on keepin’ on, because there was a part of me that knew those doubt-earworms were not helpful (to quote from my former therapist) and also kinda a normal human thing. 

And maybe also just a little nuts.


I bring this up because being an entrepreneur reminds me of this —  a little. 

Less internal shatter. Less existential. 

But that Schrödinger’s cat mindfuck lonely feeling … there’s a similar version for entrepreneurs. 


You’ve got your vision and your clients and your recurring monthly revenue. Your friends compliment you at dinner, saying things like, “You’ve built a successful business out of nothing!” You take the compliment in stride, because it’s true and you are proud. You’re good, focused, clear — knocking out emails like a champ, onboarding new clients at a respectable pace, and feeling in tune with your Simon Sinek why. Momentum, the plan, your brand. It’s all up from here. With gut-felt gratitude: God, life is fucking good! 

But then comes that splinter in the glass — so inevitable it’s almost cyclical. 

Maybe it sounds something like, What if everything fell apart?  Or: What if I’m not good enough to keep this going?

Probably triggered by some small setback (a no from a potential client, a glimpse at the viral Reel of a more successful competitor, a lower revenue month, a client who needs to part ways). 

Whatever the cause (and sometimes: there is none), this doubt-earworm, if ignored, can wind its way through your confidence for days. 

Your brain leaps to confirm it, eagerly snuffling around and finding the technically possible (if improbable) ways in which it could, indeed, “all fall apart”  in — *checks notes*, wowjust one measly month. 

It’s all on you, you get sweaty as you remember. You’ve opted out of the meager safety net you’d have with a “real job.” Oh my god, have you made a mistake? Have you been deluding yourself this entire time that you could do this? You’ve built a business out of nothing — the compliment has curdled and out of nothing, nothing, nothing, nothing  now reverberates around you. 

“I’m my own boss!” becomes “All the responsibility is on ME.” “I have total freedom in my days!” becomes “I’m aimless and unmoored.” 

The very same circumstances that spread gratitude across your chest just days before have now become evidence that you fucked up and have no one to help you. 

It’s only when you feel alone that you turn to realize that you are. 


It won’t last, of course. Things inside will tilt up toward good again. And next time, the doubt spiral will feel a little less real, manifest a little less catastrophically, dissipate faster. 

And so on. 


Trust me —the dramaticism here isn’t lost on me. (As a writer, a theater dork, a sensitive kid, something I’ve been accused of too many times to count.) But that’s kind of the whole thing:

Big feelings are pretty endemic to entrepreneurship, even if you’re not at heart a dramatic person … because you are out there on your own, taking real risks. 

In other words: that ole’ doubt spiral is never 100% unfounded. 

This life comes with a certain level of vulnerability and self-doubt, no matter how assured you are. 

That’s what The Emotional Entrepreneur is all about, the emotional journey of being an entrepreneur

From a practical, means-to-an-end perspective, sharing about our feelings helps us process and return to groundedness faster. In turn, this makes us better at business. 

But also, it significantly reduces the chance of catching a secondary feelings infection: shame, aka judging ourselves and beating ourselves up for getting “derailed” by a feeling in the first place.


Welcome to The Emotional Entrepreneur, a feelings blog about business. 🙂

P.S. You’re so deeply welcome for not calling this Feelingspreneur.  (Emopreneur? Idk, I kind of like that one …). 

P.P.S. Please email me, share on socials, or otherwise let me know if this resonates. If there’s anything I enjoy more than thinking about big feelings, it’s talking about them with others. <3

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