Each day, people like you have ideas on how to make the world a better place, but don’t know how to put their ideas into action. To help you take the first step, we profile budding social entrepreneurs who are tackling issues that are important to them, one step at a time.

The idea

I’m horrible at improv comedy. If someone were to tell me that I should sign up for a class by myself, with a bunch of random strangers, and perform to a crowd of 700 plus people at the end, I’d tell them they were crazy.

Which is why I probably need to do it. Saya Hillman from Chicago-based Mac ‘n Cheese Productions agrees. After she convinced friends who didn’t know each other to dance a hip-hop routine on stage with her so she could check it off her life to-do list, she saw the immediate bonding that came with shared vulnerability. Fear Experiment, where you perform an art form that terrifies you, was thus born.

Dancers from the first Fear Experiment show at Park West Theater in April 2010. (Photo via Rich Chapman: richchapmanphoto.com/rwc)

There’s no one succinct way to describe Mac ‘n Cheese Productions. Besides Fear Experiment, other offerings include: minglers, an ideas salon, meetups, dinner parties, events for women entrepreneurs, a newsletter of referrals for local businesses, and most recently, retreats. Her long-term dream, though? A summer camp for adults.

“It can be awkward to go to stuff. I try to remove all the “ick” factors in traditional ways of meeting people and getting out there so to speak,” she says.

Saya is also big on giving back. Fear Experiment participants volunteer as pen pals and teachers to an underserved population, and the students are treated to dinner and the show. Folks from her network, called Cheese-Its, also regularly sponsor a Rwandan boy’s education, and she started a Chicago chapter of BC Cares, the volunteering arm of Boston College alum.

Whether it’s providing opportunities for community service or confronting your own perceived limitations, Saya is all about getting others to “Live a life of yes!”

“I’m trying to help people not be paralyzed by fear and low self-esteem. It’s really hard for people to see the positives in themselves often,” she says. “I hope I’m able to bring that out in themselves. And not only recognize it, but to own it and do something good with it as well.”

Obstacles

Eight years ago Saya got laid off from her job as a video producer. She had no plans of being an entrepreneur; the only thing she knew was she didn’t want “boss” in her vocabulary anymore.

Motivated by having to pay rent and the possibility of being forced to move back home, Saya’s first step was to figure out how long $300 in savings and unemployment checks would last. Turns out not long; Saya had to just jump and figure it out along the way.

Here are some of the challenges she faced:

Obstacle: Plan or no plan?
Solution: Saya started out wanting to create her own video company for special events. She didn’t know the first thing about running a business, and people advised to have a plan. But while she loves lists, having a plan wasn’t her thing. So she researched other companies. Shadowed videographers. Contacted a local business development center. Used collaborative tech tools like Creative Cow.

A year into being self-employed Saya was continuing  with her tradition of throwing dinner parties for friends who didn’t know each other when strangers began wanting in. It was then Saya realized she could make it into a business. Mac ‘n Cheese soon morphed from a media company to a people connector company. “I didn’t imagine any of it, but that’s what I love about it. There’s always something new and exciting,” she says.

Obstacle: Financial insecurity
Solution: From buying video equipment to coordinating events, Saya continually opted for the most economical ways to get things done. She was careful not to get herself into situations that would cause a huge debt to hang over her head.

She would also occasionally do pro-bono video jobs, and anytime she has given something away for free or low-cost, it has always come back to her in a positive way. “More often than not people say ‘yes’ to my outlandish requests and go above and beyond what I was expecting,” she says.

Obstacle: Working solo
Solution: Saya knew not having co-workers to bounce ideas off of was going to be hard for her, so she immediately started reaching out to her networks. She kept with this trend, and a few years later, began going to events in the city by herself as part of an experiment called the “The Solo Life.”

The amount of people she knew in Chicago increased exponentially, and now connecting and collaborating with people from all walks of life is her bread and butter. “When you go into situations where you’re meeting people, I learned the power of listening, and the power of not going into something just thinking about what you need out of the situation,” she says.

Advice

Saya is thrilled that she was fired all those years ago. From meeting her fiancé to inspiring a woman to start a dog walking business, the amount of friendships, partnerships, and startups she has encouraged through her events are numerous and far-ranging.

“I love infecting people with ED, entrepreneurial disease,” Saya says. “It’s the best thing in the world.”

Saya introducing Fear Experiment. (Photo via Rich Chapman.)

Here’s how she thinks you can move forward on your idea:

Starting out

• When you can’t find something that you want, create it. Or attempt to create it at least.
• Make lists. What would you love to get paid for no matter how crazy it sounds, what your ideal job looks like, super-connectors you know, skills you have.
• Ask. Once you have your lists, email the super-connectors. “People won’t know how to help you if they don’t know you need help.”
• Steal ideas. “When you’re designing your own life of yes, there are a lot of smart people who’ve already created a lot of amazing things.”
• Figure out what your priorities are. Know what you can and cannot sacrifice, because you’re not going to do or have everything you want in the beginning.
• Don’t worry so much about money. “If you can find other things that you do have, such as a skill, people are really willing to trade and barter these days.”

For the ladies

• Refer, refer, refer. “Word of mouth is something women are really good at. This will come back to benefit you ten-fold, as it’s usually win-win-win.”
• Don’t be afraid to self-promote. It’s totally fine to boast.
• View others as collaborators, not competitors. There’s always an opportunity to work with someone new.

Staying motivated

• Meet people without expectations. “If you go to a networking event with the idea that you want to get three new clients, it will be a total disaster.”
• Don’t wait for the perfect time. Stop coming up with excuses; it’s never going to feel like the right time.
• Take the leap. What’s the worst that can happen?

“You have to figure out what’s good advice and what’s bad advice. What’s good for someone else might not be good for you,” Saya finally says. “Trust your gut.”

_

Want to live your own life of yes? Feel free to chat with Saya about entrepreneurism and self-employment through @sayahillman on Twitter. She is also available for speaking engagements.