Another side of Cy

December 10, 2019 Dan Miller

9-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 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: What was your first concert? And what was your favorite concert?

Cy: My first concert was the Marshall Tucker Band. That will really date me. I loved them and it was good. My favorite concert is Cher. I've been to four of her farewells. Since the time I was a little girl, I would wrap my hair in a beach towel and sing all her songs. I love that woman.

Workhuman: Who would you want to co-star with in a movie?

Cy: I absolutely love Will Smith. He would just make me laugh. Or Will Ferrell. If somebody was a leading guy for me, I would want somebody super funny and entertaining. If my co-star was female, I would go with Reese Witherspoon. She’s brilliant.

Workhuman: Favorite TV show?

Cy: I love ‘The Big Bang Theory,’ so I would love to just sit in with that cast. I think it would be a blast. I’m kind of a geek, so that’s my answer.

Workhuman: Let’s shift to your work, and some of your new thinking. When you say we manage energy, not people, what does that mean?

Cy: Yeah, that's a big, new insight for me. We expect most people to manage themselves, and that gets back to the toggle switch (high self/low self). What I as a leader want to evolve into is not managing you. You come self-regulated, self-accountable. I want to manage the energy of us getting together. And most energy, when we’re in low self, is ‘why we shouldn't have to,’ ‘why we can't.’ It gets us away from delivering to the world what we need to deliver and takes away from our innovation and collaboration.

Leaders manage energy away from ‘why we can't’ to ‘how we could.’

So, if you think of statesmanship in our government, all the energy is going into what's wrong and ‘why we can't,’ where we're divided, and how we're different. Great leaders manage energy into the biggest goal the world needs right now. Let's only manage energy to ‘how we could.’ I think a lot of leaders get into managing people and telling them what to do or try to have their idea win the day, and I think we need a lot more people who are just willing to jump in and manage energy in a big way toward solutions.

Workhuman: Thirty years ago, you talked about change management. And 30 years later, people still can’t figure it out. Why is that?

Cy: For a couple of reasons. We in the industry have failed them because we have proliferated a really dysfunctional view of change. We give mixed messages – at one point we say, ‘Step up. Be accountable. You're unlimited. Your potential's unlimited.’ And then, ‘Oh, wait. Something changed? Sit back down. I'll be back. Don't move. This is scary.’

We have literally enabled people in a negative way – enabled people to be great, unless the world changes. And when change comes, it is the one way our ego has held us captive.

Because our ego is always scanning the environment and it's like, ‘Oh, there's a change, all bets are off.’ But if you're in high self and you're in the flow of things, you don't know the things that are changing or aren't changing. You notice the present moment, which is now.

If you want to exhaust yourself, compare today to the past and then worry about the future. Change is a comparison and an attachment to something, and attachments are the source of all suffering. So, I think the reason we have problems with change is that we have taught people to have problems with change.

Workhuman: Who inspired you? Did you have a mentor?

Cy: None of my inspirations really came out of business – they came out of personal development. Byron Katie is an amazing teacher, with The Work. She inspires me. Eckhart Tolle inspires me. There is a lot good inspiration in business as well. Along with everybody else, I love Brené Brown. But I'm also inspired by a lot of people in science – like many of the astronauts and NASA scientists. Innovative thinkers are my inspiration.

I read a lot more about physics and spirituality than I do about business.

Workhuman: You've got the 2020 Ditch the Drama Tour coming up in four cities. What will attendees learn

Cy: It is a rare opportunity to have me all day. I will teach the principles so everybody's caught up, but I'll teach them in a way unlike people have seen before. So, they'll get our bottom line, but the coolest thing is we're going to do a ton of Q&A where people can bring their questions. They can vote them up or down on what the audience wants to hear me talk to. We'll go much deeper into these topics. And then, I'm going to bring people onstage and do live coaching so that people will really see how this thing works.

Like Workhuman itself, the Executive Forum has become a movement – a vibrant community of senior HR leaders shaping and defining the future of work. Join us in San Antonio, May 11-14, 2020.

About the Author

Dan Miller

Dan Miller is the director of content marketing for Workhuman.

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