A Life of Yes: 4 steps to blissful self-employment


Freelance Feast's first guest post is brought to you by Saya Hillman, an accidental entrepreneur and all-around superconnector. Thanks Saya!

In the immediate aftermath of being fired a few years back, it didn't feel like the best thing ever. But eight years of the most blissful self-employment later, I see that it was!

I attribute the success of my company Mac 'n Cheese Productions to living a Life of Yes.

How do you live a Life of Yes? Four things: Just do. Shoot for the stars. Put it in the universe. And embrace fear.

Just do

It's never going to be the right time. Your website, logo, or business plan will never be perfect. Don't focus on the what ifs. Share now, tweak later.

I didn't mean to share before tweaking when I started my first Meetup group! But I did. Here's how it happened.

Brainstorming about how to reach new networks led me to Meetup. As I created my first group description, I accidentally went live—and seven people signed up before I finished. As I read through the introductions—"I'm seeking to make great memories now"; "I don't know what I want, but know I want something more, especially more fun and laughter"; "Looking to live my life more proactively"—I realized how many people desire positivity. My first Meetup was five days later, and it received rave reviews! People who were helped + new Mac 'n Cheese sign-ups = double-score.

Shoot for the stars

Why aim for anything that's not exactly what you want? Because you're afraid you can't get what you really want? Well, falling just short of the stars is still pretty good.

I have utopia lists for everything. Housing criteria. Employment criteria. Boyfriend criteria. You may read my lists and exclaim, "Seriously? A four-block radius for where you'll live? Getting paid to play board games on your couch? A guy who smells like a campfire? Good luck, Unrealistic Standards!"

Today I live in a converted toy-factory loft in the target area, I have a job that's so far from a job it's ridiculous (and it pays the bills), and I just got engaged to my best friend, whom I met at one of my own events. He doesn't come with a campfire smell, but close enough.

Put it in the universe

Just ask. You never know. The world has a wondrous way of conspiring to make things that are supposed to happen happen.

I am enamored with the idea of being a professional speaker, traveling the world for obscene money to talk about things I love, but I have a lot to learn before I can do that. I figured that the first step to getting hired as a speaker would be to offer speaking as a service. Worst-case scenario was that no one would contact me, and I would lose the thirty minutes it took to create the webpage offering my speaking services. Two days after I posted the page, I was asked to speak in front of 300 people at the CUSP Conference on design.

Embrace fear

That's the most important question: What's the worst-case scenario if something doesn't turn out as I hope? When you realize that you're not setting in motion the end of the world, you can embrace fear.

After seeing Mimi in Rent sass around the stage, I knew I had to experience that, regardless of my lack of skill and a load of fear. So I tried a dance experiment. I selected sixteen friends, none of whom knew each other, and all of whom were bad dancers and nervous to partake for one reason or another. I hired a choreographer, rented a studio and a theater, and rehearsed with my friends. After three months of rehearsals, we danced in front of an audience of 350 people.

It was a hit! Everyone asked, "When's Dance Experiment Two?" Three shows later, and Dance Experiment has become Fear Experiment, with added art forms including improv, a cappella singing, and stepping. We've sold out shows for 700+ at Chicago's famous Park West and built some beautiful relationships.

Go for it!

You will fail 100% of the time at everything you don't try. So challenge yourself, make a list, ask for what you want, and embrace fear. Then report back.

Speaking of putting it out in the universe, you might be able to help make our ridiculous wedding wish come true. Thanks for thinking about it!

Saya Hillman, an Evanston, Illinois, native, Boston College graduate, and Chicago resident, is an accidental entrepreneur who has cobbled together a career of hanging out in coffeehouses with passionate people, playing board games with slipper-wearing strangers on her couch, and performing bad improv in front of 700 via her company Mac 'n Cheese Productions. One of Brazen Careerist's Top 20 Young Professionals to Watch in 2012, Saya thinks self-employment is the best thing ever.