Meet Saya Hillman

Saya Hillman, Evanston, Illinois native, Boston College graduate, Chicago resident, and self-employed since 2004, has discovered how to turn her ability to create community and challenge herself and those around her into her “job.” Mac & Cheese Productions℠ is a lifestyle company focused on you finding your tribe, expanding your horizons, and feeling full through in-person events. Via social gatherings, weekend getaways, two-hour workshops, three-month classes, and speaking engagements, Saya shares how despite hurdles and despite lacking traditional success, you can have the life you desire. She was one of Brazen Careerist’s Top Twenty Young Professionals to Watch, has been featured in Forbes and the New York Times, and is a TEDx speaker. She’s married to someone she met at one of her own events, and they pulled off an almost 100% bartered wedding, as featured in the Chicago Tribune and Huffington Post. She’s not living the dream; she’s living her dream. A dream rooted in a lifestyle where she doesn’t have to don pants most days and can go to the post office, yoga, and Trader Joe’s at 10AM on Tuesdays. 


What inspires you? 

While I absolutely love, love, love being self-employed and working from home, I admit. There are (some silly) things I miss about office-life –

  • Birthday lunch from your choice of restaurant and hokey birthday card signed by your coworkers
  • Professional development
  • Regular paychecks
  • Group discounts
  • Ice-breakers (yes, I like ice-breakers!)
  • Someone else shopping around for the best health insurance
  • Pats on the back

It’s nice to be recognized. And as adults, we don’t have someone putting our 85/100 math quizzes on the fridge anymore. So what inspires me, especially on days when all I’ve done is nag people to complete forms, make a payment, or return an email, or on days filled with peers Facebook’ing about bonuses or company outings, is the heartwarming sharing from Cheese-Its (as I’ve monikered those who participate in my offerings). 

Whether it’s in an application or in a Thank You note, I am continually surprised and touched by how honest, courageous, and vulnerable people are with me. And quite often, it’s people whom I’ve never met or barely know. It’s these sentiments that tell me I’m doing what I’m supposed to be doing and inspire me to keep on keeping on.

What makes you laugh? 

I am totally in the bag for improv. And I feel so lucky to live in Chicago, where every night of the week, a plethora of accessible, good improv-comedy exists. There is something so magical in improvisers beginning with a simple just-discovered word, phrase, look or action, and watching everything unfold and fit perfectly together as if yes!, of course the performers had practiced for “trombone” being the audience suggestion. The quick wit, the remembering of details, the teamwork, the fun the improvisers have with one another…

And the golden rule of improv, “Yes and,” where you never deny your fellow actor but instead accept his/her ideas and then add to the scene, is one of beauty. It’s beautiful because it’s applicable to every nook and cranny of life. Since I’ve started Yes and’ing in all that I do, I am infinitely happier and fulfilled. Professionally, socially, romantically, whatever-ally. So much so that the tagline of my company is “Helping people live a Life of Yes!”

I also love impoliticly correct humor and using laughter to tackle sensitive subjects and help people work through hurt. My boyfriends, Key & Peele, are masters in this arena. So are my best friends Jon Stewart, Stephen Colbert, and Louis CK.

Then sometimes it’s wonderful to just laugh at silly. I cannot stop guffawing at this Whose Line Is it Anyway segment.

Biased of course, but my husband is wickedly funny as well. We met at one of my events, thanks to improv actually. My one professional challenge over the years has been keeping up with the number of female Cheese-Its, as I prefer to balance the gender ratio for the dynamic it producers. Single, married, dating, gay, straight – doesn’t matter, I just always need more guys! So I turned to the male-dominated field of improv, posting one of my events in an online comedy-forum. Husband saw it, came, and here we are four years later. One of the first things that attracted me to him was his high-brow humor. He does Workplace Improv, where companies bring him in to work on team-building and business skills via laughter, being silly, and letting go of judgment – of yourself and of others. How cool is that? swoon

I am a fairly-happy person 100% of the time, but man, there is nothing like the feeling of laughing ridiculously hard, especially with a group of people. Adults don’t have enough of that.

Have you ever stolen anything? 

Besides boys’ hearts? Ha. Just kidding. I don’t think I’ve ever stolen a boy’s heart (Holler if I stole yours, it’d really do a number on my ego!).

A bit of background before this admission – 

Growing up, all I wanted was to be normal. Everything about me – name, biracial’ness, single-parent’ness, everyone else had money’ness, curly hair, towering height, overflowing weight, lack of anything that plugged in, e.g. a vacuum, microwave, or TV, due to my earth-loving mother – was abnormal.

Instead of Kraft, my mac and cheese was egg noodles, flakes of thyme, and just-grated cheddar. Instead of Skippy, I had oil on top, impossible to spread organic peanut butter. Instead of Barbies, I had some off-brand dolls who couldn’t hold a candle to the real ladies. 

So when the opportunity to have a Barbie, a real Barbie, arose, I took it. 

Age nine’ish, I was in Osco Drug. I made sure to check that no one was watching, slyly glancing up and down the aisle. Then I stuffed one of the pink boxes in my bag. I made it through both sets of automatic-doors; home-free! 

I was halfway down the block when a boy a few years older biked up to me and said, “If you bring back the doll, my uncle won’t call the cops.” Turns out “Uncle” worked at the drugstore. I slowly walked back, eyes on the ground, put Barbie back on the shelf, and slunk out of the swishing double-doors.

What do you geek out about?

  • Both using productivity and efficiency tools and having people go “Ohhhhh, cool!” when I share productivity and efficiency tools. One of my favorites is MightyText, which lets you text via computer. I love not having to pick up my phone to check a text, it pops up right on my monitor, and being able to type texts. I get asked so often how I manage to keep my sanity herding as many people and curating as many events as I do that I now teach a workshop, Time-Management & Efficiency, to share how I deal with deadlines, To Do lists, collaboration, frugality, focused workflow, all that good stuff.
  • Bypassing bad traffic by knowing what good streets to take (hello Canal, Loomis, and Leavitt!). Shhh. Don’t tell.
  • Direct and indirect passive income. Getting a notification that someone just paid to put something in my newsletter or that I got a credit because someone took their first Uber ride or booked their first cleaning/handyman service (use code SAYA3359 for $25 off your first use at!) is all sorts of awesome. I can’t even imagine the sensations I’ll have if, er when, my book comes out and it goes FLYING off the shelves. Kaaaa-ching! While doing nothing!
  • Smart multi-tasking. It’s easy to fall down the rabbit-hole of inefficient multitasking these days, when doing too many things at once makes you less productive. When I’ve got the slow cooker going, the dishwasher churning, I run to the post office to knock out both exercise and an errand, and a CD is burning for my Life of Yes! Camp, I’m in heaven.

Who helped get you here? 

Mom. There’s so much I could say about Debbie Lyn. I’ll concise it up in list-format –

  • She gave birth to me alone, at home, by choice; I was a full month late
  • She’s never had a car and just got her driver’s license at age fifty
  • The last ‘office’ job she had was when her water broke with me; raising me as a single-mom, she sold homemade dried flower arrangements at craft fairs, typed phD dissertations for Northwestern grad students in the pre-computer age, was the sole female apprentice in a woodshop, and eventually settled down as a self-taught organic gardener.
  • When asked how she got home after her water broke, she said, “I don’t think I rode my bike. Did I? No, I must’ve taken the bus.”

Check out a video I made on her.

Want more? Connect with Saya on Twitter and Facebook and Instagram and learn about her company + how to live a Life of Yes! on herwebsite.

Photo by: Angela Garbot Photography