On dreams, can’ts, 5 years of business, and 4 years in New York City


Today marks my 4-year New York anniversary, and this month marks my 5-year business anniversary.

How time flies around and through us. How things change, but we stay largely the same.

Back then, my decision to be self employed, and then self employed in one of the world’s most expensive cities, received similar responses…

“Why would you do that?! Is there any money in writing?”

“You’re going to be so broke. And cold. SO COLD.”

“What about the TAXES?!”


“I love you, Hill, but I don’t think that’s going to work. Maybe look into real jobs? You know, just to stay afloat…?”

… but I suppose my dreams were louder; creating a constant racket in my skull and soul, saying “This is your one chance to do the work you love in the city you love.”

Then, on a bright summer afternoon in 2012, I realized: This really was it. I had to go.

So after almost exactly 1 year of business, I sold my car, packed up my stuff, and took a flight to live life on Expert Mode in NYC.

And in a way, the responses were right at first: 
I WAS broke.
The first couple of years of my business I DID work myself (quite literally) sick, multiple times.
The taxes DID kinda suck.

But I was also insanely happy.
I was free, and full of love and the fire of ideas.
And New York City rose up up to meet me; cradling me in her electric rhythms, charging me up with creative energy like nothing ever has.

Even if no one believed I could, I was hell bent on making it work.

The only way I was going home would be bruised and bloody, after pounding on every door and window it took to succeed.

And slowly, very slowly, I began to blossom; pushing my flowers and leaves through the cracks in the NYC concrete, teeth bared, determined to grow whatever the cost.

Gradually, I made it out of “broke” with my credit score intact.
I started making headway.
Clients who found me weren’t just excited to find a writer with a malleable style; they were excited to work with ME.
I switched business models twice, and found a way that fit my sanity.
And last year, I broke 6 figures for the first time.

Now I look around this room I’m in these years later, in my beautiful apartment I share with my amazing partner, and my heart is even more full full of love as it was when I stepped off my flight in Newark 4 years ago, breathless with anticipation and possibility.

Every day I am grateful for the friends, family who, while sometimes confused by my choices, gave me the steadfast support I needed to survive. I am grateful for the times I had to eat dirt and humble pie, and make it through the crying spells, and the winter snows (both literal and metaphorical.) And most of all, I’m grateful for the grand adventure.

Yes, New York City can be a hard place. But as the saying goes — no pressure, no diamonds.

I guess the moral of this story is: if your dreams are louder than the voices saying “can’t”, take heed.

Just be prepared to throw yourself after them with everything you’ve got, and everything it takes — and everything you want just might be waiting around that corner.

Like what you see?

Sign up and never miss another post (and get a crazy cool freebie)

  • This field is for validation purposes and should be left unchanged.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.