From corporate America to creative entrepreneurship

A practical breakdown of my journey

Last week, I shared my thoughts on leaving corporate America. And I got a lot of questions asking exactly how I transitioned from corporate to full-time poetry.

I wish I could offer you a clear framework on HOW TO LEAVE, but here’s the thing, leaving is inherently messy. No rupture is clean. There’s no perfect way to get divorced or quit a career or pack up your home and strike off in a new direction. If someone promises you a 3-step guide, they're full of shit or selling you something. Probably both.

I’m going to tell you how I did it, but I can’t tell you how you should do it. 

First, let’s clear up a couple of misnomers: 

Myth 1: All artists must starve

There’s a pervasive belief that permeates MFA programs: creative work isn’t valuable and people won’t pay for it. That myth keeps writers and artists severely undercharging for thoughtful and meaningful work. 

What people will pay for is artistic expertise—carefully considered work that displays nuance, complexity and direction. That’s deeply valuable. You must find what you’re good at and what people desire and the only way to figure this out is ideation, iteration, and experimentation. No one has a winning idea from the get. One rarely eurekas in isolation.

Myth 2: Marketing oneself is unethical

Marketing oneself is only gross if you make it gross. Manipulation, fear mongering, scarcity models, exploiting pain points, overpromising—all that is pretty icky and you shouldn’t do it. But sharing your gifts with the world and being compensated for that contribution? Friends, that is simply what we’re here to do. Make a clear and honest offer. See who steps in to receive it. 

Myth 3: If I do creative work, I’ll automatically love my life

I’m grateful to no longer be in a toxic workplace, but making a living as a writer isn’t easy. It puts a lot of pressure on your dreams. And sometimes making money and making art don’t go hand in hand. You don’t have to make your creative passion also pay your salary. There’s wisdom in having a boring, balanced, not-horrible job and letting yourself make joyful art elsewhere. You can still be a credible writer/artist/creative, even if you don’t make it your livelihood.

Myth 4: You’ve got to leap all at once 

Truthfully, baby steps are okay. It’s okay to build yourself an exit ramp. Just also give yourself a hard date—whether it’s 3 months, 6 months or a year. Pick a deadline and work your way free. Otherwise, you’ll keep kicking the decision down the road, and you’ll find a million reasons why now isn’t the right time to leap. 

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Here’s what my journey looked like: 

I went slowly. I dropped to part-time at my agency and used the extra time to ideate, test, experiment creatively. Here’s what I tried:

Typewriter poems: Surprisingly, there’s a market for this. For about a year, I typed live poems on the fly inspired by party guests. I got booked for birthdays, festivals, weddings and corporate events. This proved unsustainable with my carpal tunnel issues, but check out Scott Andrew James and The Poetry Society of New York for examples of typewriter poets absolutely thriving.

Commissioned poetry online: For awhile, people commissioned me to write poems for their lovers, kids, dogs etc., and this was actually quite lucrative. When I finally stopped, I was charging $300/poem and still had a waitlist. But experimentation doesn’t just tell you if a concept can make you money, it also reveals whether or not you enjoy doing it. In the end, I realized I didn’t actually like writing poems for other people. If I was going to make art, I wanted it to be for me. 

Poetry prints: My Mother Says was my first  poem to do really well online. I did a test print run and discovered that people wanted more, so I made posters and pins too. I partnered with a local print shop and, as my Instagram grew, those orders paid my rent for a while. If I hadn’t gotten my book deal, I’d still be offering prints.

Writing workshops: I started teaching writing workshops based on craft questions I received. When those workshops filled, I expanded the container to a month-long course. At the end, I surveyed all my participants and learned that my writers were craving ongoing community where they could develop craft and connection. This took me to my next project. 

Sustenance: Finally, Sustenance was born. Embracing this community allowed me to let go of other revenue streams and freelance gigs. I priced membership at a rate that would make members value it and also incentivize me to make it my full-time work. I also wanted to bring in the best authors in the industry as guest speakers and pay them appropriately for their time and expertise.

A year later, Sustenance has over 170 poets and essayists who are invested in honing their craft and building connections with other creatives. Every month, we bring in guest speakers like Maggie Smith, Brendan Constantine, Danusha Laméris, and Courtney Maum. I offer weekly office hours and generative sessions to help support each writer’s growth. Want to join us? We’d love to have you. Sign up here. 

Bottom line: In the end, it was a terrifying series of leaps that landed me on my current path. Through constant experimentation, I feel like I’ve finally discovered my Ikigai—that Japanese concept that suggest that one’s true purpose is a combination of what you love, what you're good at, what the world needs and what you can get paid for.

Just remember, there is no one way to leap. Scoot if you have to, but if you’re anything like me, you won’t be satisfied until your feet have finally left the ground.

How do you hustle creatively? What’s worked for you? Have you found Ikigai? What else do you want to know? Let’s share some wealth in the comments. 

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P.S.

You can now preorder Instructions for Traveling West

My book, all about big leaps and flinging into the magic dark, is officially available for preorder. Preorders help the book have a big life when it’s released and help ensure that there will be another one. You can order here.

Want to write like your hands are on fire? 

My writing community, Sustenance, is gearing up for a special month in October. Our theme is THE GLOWING METAPHOR, and we have Brendan Constantine teaching us about the Authority of the Metaphor. We also have

Writers at Work with Sarah Fay

coming to teach us how to offer value on Substack and I’ll be leading an intro to poetry workshop. You also get generative writing sessions with me as well as office hours where you can get feedback on your own work. Join us here. 

Here’s a run down of October’s events! Join us to creatively kick off Fall!