Another Side of Cy

January 3, 2020 Dan Miller

5-minute read

Cy Wakeman at the Workhuman Executive Forum

You probably know Cy Wakeman as an international keynote speaker, drama researcher, New York Times best-selling author, and global thought leader with a revolutionary approach to leadership.

But what you may not know is her human side – the life she lives outside the public eye with her dreams, inspirations, and pursuit of living her true, whole self. We spoke with Cy in the lobby of Hotel ZaZa in Houston, after her discussion with senior leaders at the Workhuman® Executive Forum.

Read part one of our exclusive interview with Cy below.

Workhuman: You summited Mount Kilimanjaro, the highest mountain in Africa, in July. What inspired you to make that climb?

Cy: My husband and I were first asked if we wanted to go on a safari with a group we do yoga retreats with when we’re in Mexico. Once my husband heard the safari was close to Kilimanjaro, he floated the idea of the climb and I said ‘sure’ without really thinking it through, but it committed me to a great opportunity. We took five of our eight sons. We took the slowest route, so the hike was eight days and seven nights.

We circled the whole mountain, which was crazy because you see all different sides. And it was meaningful to me because when I’m hiking, there’s a lesson every 10 minutes. Hikes are full of metaphors for what we can bring back to our life. They’re physically challenging, and you really get in touch with your monkey mind and all the crap in your head. It’s just you and your mind on that mountain, even if you’re with a hundred people. It’s just you and your mind making decisions, keeping commitments, editing your stories, choosing to continue, and so it’s a choice over and over again.

The third day in was pretty tough and one of my sons said, ‘Mom, it’s all just walking.’ It sounds so cliché and simple now, but in that crux of a moment, I was like, ‘It really is just walking.’ Be present in the moment, one foot in front of the other, enjoy all that is around you.

Workhuman: What was it like when you summited?

Cy: It’s a 16-hour hiking day. You start out at midnight and hike all night in the dark to get to the summit. The peak is Uhuru Peak, which is also called Freedom Peak. We summited on Independence Day, watched the sunrise on the way, then headed back down because you can’t stay in that oxygen level.

The experience was a great reminder that I have to be careful about how my ego brings new stories of limitations in, whether it’s about my age or where I’m at in my career. What the hell is a 54-year-old mother doing, summiting a mountain? Basically, I like to travel and hike to have a great adventure, challenge myself, and remind myself I can do very hard things and be a role model to my sons, who are in their 20s. I hope when they see my celebration of life, they’re like, ‘My freaking 54-year-old mom hiked Kilimanjaro.’

That’s what I want my legacy to be – one that is vibrant. I want to keep moving, keep growing, keep thinking, and keep inventing.

Workhuman: What’s it like to be a mom to eight sons – four of your own and four stepsons?

Cy: Challenging and rewarding. When we first got together, our youngest was 6 and our oldest was 18. I often surprise people with the fact that we have eight sons. They can’t even conceive what that must be like, but it isn’t as hard as it sounds. My husband is a great dad to his sons, so my role is mainly just being a resource to them. My sons and I have been on our own for quite a while, so they are all really supportive of each other. 

We have done some intentional things. We standardize everything we can get our hands on so it’s scalable. We want our kids to know we support their individuality, so in order to do that we’ve standardized things like all white towels, all ivory sheets, all white socks to free us up for the important stuff. For a while, all my boys got a Chevy Malibu. When we standardize things, we free ourselves to do the real work of parenting. We weren’t spending time on variances. We’d do the research once – what’s a good car for a kid to get – and then go with it.

Researching different cars could have taken four weekends – time we didn’t have. And with the same car, we can call the same car guy who knows how to fix it, for example. This gave us more time together as a family, like enjoying our boat. I always use this as a business lesson – standardization frees us up.

Workhuman: You often talk about playing poker with your sons when they were grounded. What are the tips to playing good poker?

Cy: Not sure my tips would help anyone else as they won’t work for you in Vegas.  At our house, we’d play Texas Hold ‘Em, and I had a bit of homefield advantage as I intuitively know everybody so well and can read their body language because they’re my family members. As a mom, I have this unfair advantage because I can tell with every kid when they’re lying or bluffing. But here’s my best poker tip: People get focused on their cards and what they’re playing and that’s the big distraction.

Your cards – the hand you’re dealt – give you very few options. Play your cards quickly and forget about ’em and really tune into how everybody else is playing their cards.


Workhuman Book Club: “No Ego” by Cy Wakeman

In Cy’s Eyes: A Q&A With the Best-Selling Author & Global Thought Leader

About the Author

Dan Miller

Dan Miller is the director of content marketing for Workhuman.

Future of Work