“Saya is a wonderfully engaging speaker… enthusiastic while down to earth; entertaining yet insightful; relatable, thought-provoking and real.  When she shared her dream job wish-list and how she turned that list into a reality I found it not only inspiring, but motivating in a way that made me say to myself, “What a great idea!  That’s a roadmap I can actually follow myself.”

SayaHillmanBCMag2012 (1)

Called “a breath of fresh air” and the “accessible Oprah”

Saya motivates individuals and organizations to stretch themselves and do their best thinking, and supports people in finding fulfillment and groups in creating a positive culture. Positive orientation = positive results. From organizational luncheons to client appreciation events, conferences to company off-sites, Saya keynotes and presents, just as comfortable on stage as she is at the whiteboard. An accessible speaker, not one who hides in the green room or leaves as soon as they finish their time under the lights, Saya is delighted to interact with attendees and participate in conversation. Clients include companies such as Eventbrite and Microsoft and groups such as the International Live Events Association and Missouri’s Municipal Trust.

For big-picture ways Saya can help your group, head here. If you’re interested in Saya being more of a discussion-leader and/or activity-facilitator rather than a speaker, say at your company off-site or staff retreat, check out her Facilitator services.

“We are so grateful to have been able to invite Saya to be one of our CreativeMornings/Chicago speakers this year. Our attendees were engaged, entertained, and inspired as she recounted the tales of forging her own path with Mac & Cheese Productions after being met with rejection. Her words made an impact on everyone in the room; there were multiple folks who, after Saya’s talk, told us that this was the best CreativeMornings event they had ever been to. She was a pleasure to work with, always communicating early and directly with us, and handled technical difficulties on-stage with grace and humor. She’s a wealth of knowledge, experience, and heart, and has so much to give to anyone who is willing to listen.” 

📷 : CreativeMornings/Chicago


Looking for big-picture, inspirational, and high-energy? Saya’s keynotes

Through the power of humor and vulnerability, Saya is a master at getting others to “Me too!” and to discover and utilize their own voices and superpowers. Her messages are memorable and inspirational, resonate universally, and is wisdom you in turn want to share. With her charisma and down to earth’ness, she has you laughing and nodding, no matter how different you are from her. After years of hiding in the shadows, Saya now embraces her literal and figurative stretch marks — a real person with everyday experiences who has inspired thousands with her stumbles and triumphs.

Life of Yes℠ Keynote (45 to 90 minutes) 

Steps to create a fulfilled, balanced, productive, and engaging life for yourself, framed through Saya’s personal experiences and philosophies. Presentation duration depends on amount of audience participation and interaction desired.

Life of Yes℠ Keynote (45 to 90 minutes) Professional edition

Steps to create a successful workplace environment using tools already in your possession, framed through Saya’s personal experiences and philosophies garnered over her many years of business ownership (she’s run a business since 2004). Presentation duration depends on amount of audience participation and interaction desired.   

Areas of focus:

– community engagement

– how to build and leverage relationships

– how to make “the worst!” — networking, self-promotion, sales, asking for help — pleasurable, or at least less terrible

– how to use soft skills to increase income

– how to replace self-doubt with confidence

– how to create a dynamic, if perhaps non-traditional, marketing plan

How To Be a Successful Pioneer Keynote (45 minutes) 

A minute into her talk How to be a Successful Pioneer, Saya had completely reassembled the notion of “success” with a hilarious candor that easily won over the audience—even this jaded agency professional. She reaffirms what our collective gut has always known: when it comes to success we tend to check all the wrong boxes—someone else’s boxes. Her radical mission: to have the world value you for doing what you love. Her vision, to trigger transformation from within by coaxing you out of your comfort zone into your joy zone, challenges the winner/loser narrative that has reigned for too long in our quest for success.”

“It was an absolute pleasure to attend Saya’s talk, I hadn’t laughed that much all week and it really set the tone for my day! Her talk was vulnerable, encouraging, and really made me pause to think about how I want to approach a meaningful life of yes. Her enthusiasm and infectious smile rippled through the audience and proved her passion for helping those who seek purpose. It’s rare that a speaker makes such a lasting impression, especially at 9 am on a Friday, but Saya proved herself a compassionate and dedicated individual and I’m so excited to see what’s next!”

Looking to dive deep and for specific how-to’s? Saya’s seminars

Saya breaks down oft-overwhelming and “scary” areas into digestible and actionable bites. Seminars can be delivered in person or online. The latter is perfect for organizations with remote members.

Productivity Cape – Outfit Yourself With ‘Make Life Easier’ Tools & Philosophies (60 to 90 minutes)

Saya’s first conversation with her now husband was about their love of spreadsheets. A Huffington Post article called her “Chicago’s productivity-guru” and she was included in the Gmail Genius series.

She shares big-picture philosophies as well as specific tools to manage life. If you’ve ever felt “There has to be a better way” or like a hamster in a hamster wheel, this session is for you. Saya narrows the daunting field and presents her favorite resources for you to choose which you’d like to implement and learn on a deeper level. From email and To Do Lists to shopping and travel, she makes life’s mundane yet necessary tasks easier and more enjoyable.

Life of Yes℠ Bootcamp: Sales & Self-Promotion (2 hours) 

Do you revert to “would rather do anything else” mode when

      • You have to write copy about yourself
      • You have to ask someone to spend money on you
      • You have to ask someone to spend time on you
      • You have to market yourself (email, social media, conversation)
      • You have to figure out how to make money off of yourself

Do you fear the moment when

      • Someone asks you how much you charge
      • Someone asks you what you do
      • Someone asks you what your qualifications are
      • You’re about to enter a “networking” event
      • You make your thoughts, service, or product public
      • People realize you’re a fraud, that you don’t know what you’re doing, and/or you’re not worth the price you’re asking

But have you long wanted to

      • Make (more) money off your business, side-hustle, and/or interests and passions
      • Reach more people
      • Increase authentic connections that propel you forward
      • Feel more confident talking about yourself and engaging in small talk

This Bootcamp is for you. It’ll teach you avenues to self-promotion and sales that work with what you already possess. No having to get certified in this or having to attend that. No e-book or fifteen-step program to buy or coach to hire. No waiting or analyzing or running things by others. You can excel, now.

Life of Yes℠ Bootcamp: Public Speaking – What & How To Share (2 hours)

      • How to choose, create, and share content
      • How to best communicate your thoughts and stories in ways that are engaging, memorable, comfortable, impactful, and inspiring
      • How to best complement your speaking (slides, handouts, etc.)
      • How to be less fearful of the stage and the spotlight
      • How to make public speaking work with you instead of against you

Life of Yes℠ Bootcamp: Public Speaking – The Business Side (2 hours)

      • How to feel comfortable calling yourself “a Speaker”
      • How to figure out what to speak about
      • How to get speaking gigs
      • What tools you need to be a Speaker
      • Creation/updating of your Speaker Page
      • How to feel comfortable talking Speaker money — asking to get paid, what to charge, when to give a discount/speak for free

Life of Yes℠ Travel: Minimize Expense, Maximize Experience (60 minutes)

Saya and husband Pete have traveled together, from Omaha to Oslo, since 2010. Taste-wise, she’s Four Seasons, he’s Motel 6; budget-wise, they’re somewhere in the middle. Light and frugal travel is their jam. Saya’s learned to pack everything in a carry-on, Pete’s learned that being pampered can be nice. Together they enjoy street-food, bike tours, and local recommendations you won’t find in guidebooks.

They use their mutual love of spreadsheets and the latest apps to make on-the-road adventure a priority and an attainable reality. This session will help you travel within your budget. While other topics will be touched, the session is financially-focused. It includes philosophies and strategies, specific tips and tools, and Pete and Saya’s personal experiences.

The Everyperson’s Guide to Easy Networking (60 to 90 minutes)

Would you rather do almost anything else than “network”? You’re not alone. Traditional “networking” is something that fills many with angst, dread, and fear.
That used to be Saya. But now, not only is Saya proficient at networking — she attributes much of her business-owner success to her ability to “get out there” — she enjoys it and loves to show others how to transform networking into an enjoyable experience. 
The ability to connect with others can completely change your life; fortunately, it’s a skill that can be learned, enhanced, and mastered. At its core, networking is about creating win-win scenarios. Thusly, networking isn’t just for the professional arena — enhance your connection skills, enhance you overall life.
Saya narrows down the overwhelming world of “How to be a better networker” and shares what’s worked, and hasn’t worked, for her through personal case studies and insight, as well as thoughtfully-culled resources and activities. Her focus is on creating win-win’s with what you already possess so that you can get started now.
The Everyperson’s Guide to Easy Networking is a clear, accessible, easy to implement blueprint.
“There’s no point in going to something where you’re just going to stand along a wall and look like you have Irritable Bowel Syndrome.” — Get Bullish

Event Curation (60 to 90 minutes)

How to create successful, memorable, low-stress, well-attended events

Evernote – the Complex Digital Filing Cabinet Simplified (60 to 90 minutes)

“Evernote is a cross-platform, freemium app designed for note taking, organizing, and archiving.” That makes life so much easier! But it can be overwhelming and frustrating at the start, and you are not alone if you want to use it but aren’t sure how or you tried to use it and gave up. Saya was both of those people and now can’t imagine her productive, efficient life without Evernote.

Because your brain should be for generating ideas not storing them.

      • Why you want Evernote in your life
      • How to set up Evernote (or re-set up Evernote, if you’re like Saya and your initial system left much to be desired)
      • How to get the most out of Evernote features and capabilities
      • How to set up the rest of your life to sync seamlessly with Evernote
      • Specific examples of ways to use Evernote, both personally and professionally, most rooted in efficiency, productivity, and time management
      • Where to get ongoing support and continuously add tools to your tool belt


Something you’d like Saya to speak about that you don’t see above? Let her know and we’ll see what we can do — the only guaranteed no is to the question you don’t ask, right?!

Book Saya

Saya is based in Chicago and travels everywhere. Interested in exploring further?


Hit escape to return to this page without submitting your answers (they may not save though so you might want to compose elsewhere and then copy and paste here).

📷 : CreativeMornings/Chicago


“Saya Hillman is natural born storyteller. She practices what she preaches in her ‘Life of Yes’ approach to living by being vulnerable and generous with her audiences and by taking risks to share what she’s discovering about the world and herself in a way that hands others along just a little further in their journey toward self-understanding. And she does all of this with a great sense of humor. She inspires us to want to live more boldly.” — Kirk Kicklighter, Producer and Host, Flick Lit: Reel-to-Real Storytelling for Movie Lovers 

“Saya Hillman spoke to our very diverse group of over 120 business owners in Illinois. She was not only able to hold their attention, with people rapidly taking notes, hanging on every word, but after the event we had many guests tell us she was the most relatable person they have ever heard speak to them before. We are still receiving positive feedback from the event we invited Saya to give the keynote presentation at and we couldn’t be more thrilled. Saya has cultivated her relatable real life experiences into presentations that can benefit all walks of life. She comes highly recommended.” — Lauren Davis, Winnebago Buy Local

“Saya presented the Life of Yes workshop to a packed room of our members. After the session, the attendees were abuzz discussing the exciting projects they planned to start based on the LOY philosophy. I’m included in that – I went back to my desk and got the ball rolling on a creative project I’ve been putting off for years! Thank you Saya!” — Alison Hanold, Partnerships Director, The Chicago Literacy Alliance

“Saya was our opening speaker at the International Special Event Society’s Day of Education Event.  She made us laugh, made us think, and inspired us all to be the best version of ourselves!” — Barb Siska, International Special Events Society

“Saya Hillman’s class on Productivity was top notch! She took what could have been several weeks of material and was able to condense it into a very informative and eye opening four hour course. I walk away with a number of new tools that I am implementing right away. Totally recommend this course!” — Eric, Coldwell Banker

“Saya has a very informal and confident presentation style, and is more non-traditional in her approach to entrepreneurship, which I think gave attendees another viewpoint on entrepreneurship in general. Also, there was a very effective exercise at the end of the session that got everyone talking with people they didn’t already know in a way that we didn’t have in any of the other sessions.”—Paul Wu, University of Chicago’s SeedCon

“The minute after Saya Hillman finishes her talk on Living a Life of Yes, you feel like you are ready to take on the world with all your amazingness (good and bad). Through her passion, drive, and personal success story, Saya breaks down her secrets for living a happy and fulfilled life into bite-size pieces we can all implement. Between the stories and laughs you will be sure to have a couple of those ‘aha’ moments where the wheels in your head begin to turn and you feel like you now have gained needed tools to success.”—Alexandra Eidenberg, eWomenNetwork

“Saya and Pete were great at the Ideation Conference. They had attendees at our intensive lab get out of their chairs for improv breakout sessions. Each session called on participants to break from their shells and get creative. Improv sessions are a great way to get conference attendees out of their comfort zone and find a commonality with other attendees. We can’t wait to work with them again.”—Jessica Schultz, Groupon

“Without a doubt, your talk was my (and many others’) most memorable and favorite. Priceless!”—Joan Julian, CUSP Conference

“Just a beautiful, honest, open and warm presentation of a designed life.”—Dave Mason, CUSP Conference

Upcoming Engagements

Check out the calendar page for upcoming chances to see Saya speak

Sample of Engagements | Clients

All in the Chicagoland area, unless otherwise noted

  • Featured Speaker, Creative Mornings
  • Keynote Speaker, Annual Conference — Waxing the City, Palm Springs, California
  • Facilitator, Company Off Site — Microsoft
  • Presenter, Camp GLP — Good Life Project, Rockhill, New York 
  • Keynote Speaker, Annual Meeting — MIRMA (Missouri’s Municipal Trust), The Ozarks, Missouri
  • Featured Speaker, Client Forum — Genesis Insurance Company
  • Featured Storyteller, Chicago Women’s Funny Festival
  • Keynote Speaker, Day of Education — International Live Events Association
  • Featured Speaker, Business Event — Winnebago Buy Local
  • Keynote Speaker, Annual Conference — The Association of Premier Nanny Agencies
  • Emcee, ‘Always an Eagle’ — Boston College Alumni Association
  • Featured Speaker, National Public Library Week — Skokie Public Library
  • Featured Storyteller, Listen To Your Mother
  • Featured Speaker, ‘A Better You’ Workshop — Groupon
  • Keynote Speaker, Elevate Conference — BizBash and Eventbrite, New York City
  • Featured Speaker, TEDx — Bloomington, Indiana
  • Featured Speaker, SeedCon: Entrepreneurship and Venture Capital Conference — University of Chicago
  • Featured Speaker, ‘A Life of Yes’ Workshop — College of Lake County
  • Featured Speaker, Staff Retreat — Tru Sweets
  • Featured Speaker, CUSP Conference