Saya Hillman – Creator of Mac ‘n Cheese Productions

[quote style=”boxed”]I would build a client base while I still had a paycheck and health insurance, instead of having to find clients while also worrying about where I was going to get rent money.[/quote]

Saya Hillman–a native of Evanston, Illinois, a Boston College graduate, and a Chicago resident–is an accidental entrepreneur who has cobbled together a career hanging out in coffeehouses with passionate people, playing board games on her couch with slipper-wearing strangers, and performing bad improv in front of 700 people. She has eight years of ridiculously fulfilling self-employment under her belt via her company, Mac ‘n Cheese Productions, through which she helps people live a “Life of Yes!” She has discovered how to turn her love for creating community, challenging herself and those around her, and enjoying life to the fullest into what she “does for a living.” Saya is one of Brazen Careerist’s Top Twenty Young Professionals to Watch in 2012.

What are you working on right now?

Mac ‘n Cheese Productions helps people live a “Life of Yes!” through creative offerings–online to in-person, individual to group–on a one-time basis, semi-regularly or regularly. The common thread among these offerings is their goal to support others in living full lives. Imagine what the world would be like if everyone reacted to every situation by saying, “Yes! I can….”

I just took the scary leap of saying goodbye to what’s been my financial “bread and butter” for eight years (producing videos and teaching digital media to low-income Chicago public school students) to focus 110% on my creative offerings.

The two main projects I’m curating right now are: 1) Fear Experiment: people who are “bad” at a particular art-form sign up solo to learn said art-form with a group of strangers, and then perform in front of 700+ people as a way to meet others, challenge themselves, and be rockstars, and 2) Inspirationals: retreats for solo-attendees, for rejuvenation, education and connection.

Taking Mac ‘n Cheese outside of Chicago is another current area of focus, so I can finally say “Yes!” to all those who’ve asked for Mac ‘n Cheese to come to their city.

Where did the idea for Mac ‘n Cheese Productions come from?

In 2004, I was let go by my company. That unexpected life hiccup was the best thing ever. Unsure what I wanted to do, and knowing I no longer wanted “boss” to be in my vocabulary, I made a list of things (regardless of how silly they sounded) that I wished I could get paid to do. And they’re all part of my professional life today. That list-making experience, and the subsequent success of my business, molded the philosophy I’ve adopted for my approach to life. There are no obstacles. I drank the “Life of Yes!” Kool-Aid and love sipping with others.

None of my income streams started out as income streams. They began as ways for me to experience Chicago beyond bars, TV, and dinner and a movie, and as a result of wanting to satiate the desire of people to grow their community via non-traditional, affordable, comfortable and fun ways. For example, Fear Experiment grew out of wanting to cross “Dance a hip-hop routine on stage” off my Life To-Do List; I’m a horrible dancer and knew no one would come see me dance badly by myself, so I rounded up a group of similarly-spirited people, and we danced badly together in front of a 350-person audience. What I thought would be a one-time thing now sells out to crowds of 700+ people!

What does your typical day look like?

The best thing about being self-employed is that there is no typical day! But here’s a good representation:

At 7:00 a.m. I wake up naturally (no alarm needed). Then I eat a leisurely breakfast. At 7:30 I do computer work in my pajamas. After that comes random house stuff (watering plants, loading the dishwasher, cleaning, etc.). Then I do more pajama computer work. At noon I walk to yoga or the gym, and then at 1:15 I shower and leisurely eat lunch. At 1:45 I return to my computer work, and at 2:30 I do errands that everyone else does on the weekends (at the post office, Trader Joe’s, etc.). At 4:00 I have coffee with another entrepreneur, and at 6:30 it’s time for dinner. During the evening I do computer work, coordinate events, and/or go to an improv show or literary performance.

How do you bring ideas to life?

I just do them. I don’t dwell on questions like, “What if this doesn’t work?” or other types of worries. I jump in and adjust or tweak as necessary. I don’t fixate on what I don’t have: any letters (PhD, CPA, CPCC, ESQ) after my name, an easy time saying no to doughnuts, an MBA, a mistake- and regret-free past, a business plan, a lot of money, “the answer,” and a response other than “nothing” to the question, “What are you certified in?”

Instead, I capitalize on what I do have: a supportive, vast and diverse network of folk from Rwanda to San Francisco, fingertips that leave behind entrepreneurial and/or bonding smudges, a growing community of people who’ve experienced goodness due to said fingertips, a vocabulary that lacks the phrases “I’m bored,” “I’m sad,” and “I can’t,” a lifestyle that allows selfishness (i.e. no kids, no pets), a product/service that others market for me, time, creativity and passion.

What’s one trend that really excites you?

Workshifting–being able to do your job from anywhere in the world. (Here’s a site I love: My dream is for my fiance and me to stay rooted in Chicago but bring our passions to San Francisco, London, Amsterdam, and New York for a few months at a time.

What was the worst job you ever had and what did you learn from it?

I guess I’m lucky in that I’ve never had a bad job. They’ve all been so different, and it’s hard to classify any as “the worst.”

I’ve had bad experiences at all of my jobs–from a customer overhearing me call her a not-so-nice word after she was not so nice to me (when I was a college ice-cream scooper) to not seeing eye-to-eye with a co-worker or a boss. The main takeaway from these experiences was that I prefer to be my own boss and to collaborate with others as an independent contractor, rather than on an hourly or daily basis.

If you were to start again, what would you do differently?

I would build a client base while I still had a paycheck and health insurance, instead of having to find clients while also worrying about where I was going to get rent money.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I put life in perspective.

Is the thing I’m complaining about really that big of a problem? Yeah, it sucks when my pedicure gets messed up 20 seconds after I get it, but having the time and money to beautify my toes is amazing. Yeah, it can be frustrating to deal with coordinating large groups of opinionated people who ignore all the instructions I give, but I’m so lucky to make a living helping others feel better about themselves. I constantly remind myself to be appreciative of what I have, and I am so grateful I’ve been able to “make it” as an entrepreneur.

What is one problem you encountered as an entrepreneur, and how did you overcome it?

I’m sure I’ve done many things wrong over the years that have cost me time and money (like doing my own taxes, not having a financial planner or a lawyer, buying “A” when I should’ve bought “B,” and “wearing all the hats” and not letting experts do what they’re qualified to do). Maybe a mixture of luck and hard work has allowed me to prevail. I’m not sure if I have overcome these types of missteps. Time will tell.

What is one business idea that you’re willing to give away to our readers?

You can have them all! I don’t view anyone as a “competitor,” because a “competitor” is someone who does something similar to what I do, and who therefore appeals to a similar crowd and values similar values–and that’s someone I want to know and brainstorm with, not shut down! The main ingredient to my offerings is me. No “competitor” has that.

One business idea is an adult summer camp–relive the days of Capture the Flag, talent shows, and campfire sing-a-longs! And I would love proceeds from the adult summer camps to fund a summer camp for inner-city kids.

If you could change one thing in the world, what would it be and how would you go about it?

I would lessen the disparity between the poor and the rich. Everyone should make enough money to enjoy a steak dinner, vacation, and massage every once in a while–not to mention to go to college and own a home. I’m clueless about how to make this happen.

Tell us a secret.

I love the MTV show Teen Mom, and often plan my trips to the gym around its schedule. And a bonus secret is that I like to drink pop straight from the two-liter bottle.

What are your three favorite online tools or resources and what do you love about them?

I had a hard time keeping it to four! I live for efficiency.

  1. has the widest range of the most helpful and interesting resources.
  2. is a Gmail add-on that allows you to see a person’s photo and connect to his/her LinkedIn, Twitter, and Facebook accounts right from your inbox.
  3. Google Docs makes collaboration efficient and organized, so no more emailing attachments or being without an important document, as they’re all in the cloud!
  4. for scheduling groups of people (no more sending bazillion emails back and forth to ask what dates and times work for everyone).

What is the one book that you recommend our community should read and why?

The Accidental Entrepreneur: The Life & Times of Saya Hillman. It’s not out yet, or even in any shape of existence beyond a few scribbled thoughts, but people keep telling me I should write it. And it’d be so helpful in furthering my entrepreneurial self if you bought it.

Three people we should follow on Twitter and why?

  1. @lifehacker for tips, tricks, and downloads for getting things done.
  2. @alexisgrant offers great insight into entrepreneurs, writing, travel, careers, and social media.
  3. @teachingyoushit because not everything has to be taken so seriously; it’s good to laugh.

When was the last time you laughed out loud? What caused it?

Last night at an improv fundraiser show (for two friends who lost their apartment and dog in a fire).

Who is your hero?

Anyone who is good at improv.

What are some suggestions of non-traditional ways to meet potential clients?

At a guitar class, an improv class, a volunteering gig, or fast-paced pitch events a la Pecha Kucha, Potluck! and Ignite.

How did you meet your significant other?

At one of my events! I’m not only the president; I’m also a client.


Saya Hillman on Twitter: @sayahillman
Mac ‘n Cheese Productions on Facebook:
Mac ‘n Cheese Productions’ website: