The Story Of Cherie Healey: From Corporate Employee To Advising Fortune 500 Leaders

Cherie Healey the founder of SIREN gives professional development advice.

Cherie Healey, a seasoned executive coach, encourages positive change at global giants like Google, YouTube, Stanford GSB, Apple, and more — guiding great leaders and teams to amplify their influence and reach. 

She is a board-certified coach, a brand strategist, and the founder of SIREN, an Imagination Studio. We had the privilege to sit with Cherie Healey and hear about her 25-year journey from a corporate employee to advising successful leaders and their teams. Here are some highlights from our conversation:

Can you tell us more about your background and journey?

I knew what I wanted to do when I was a kid. All I cared about was talking about life and figuring out why we're here. When I went to college, I had to decide what I was going to focus on. I wanted to do some version of psychology, sociology, and theology. I wanted to get into what it is to be a human being. My dad was like, how are you gonna make money in that? And he said, you got to do business. And he got to me. He had me worried enough that I was like, alright, I'll take marketing because he says business and that's business psychology.

I ended up going into advertising and marketing. Then, at some point, I found myself as an ad director. We were in a board meeting. I looked around the table, and I was thinking, I just want to know why all of them got out of bed today. And if they're happy and if they feel like their life has meaning, Does this job mean anything to them? There I am, crating around with a giant old PC, taking it to advertisers to show them a thing, and I thought this doesn't really match up with why I'm here. 

At that time, opening your personal business was not a big thing. But it began when Tony Robbins wrote the book, “Awaken the Giant Within.” I read that book and was like, this is my job! I get to talk about life all day. So I started studying like crazy and added in more training. I'd go to take immersions and courses. And at some point, I said, okay, I think I'm ready enough to launch my own thing. I left corporate, and I've been doing it ever since, coaching and helping the people who want to make the world a better place.

What advice do you have for students/new grads trying to figure out their career paths and make decisions about their future?

I'll say, go back to when you were a kid. How did you play when you were a kid? That's a big clue. There's a lot in us before we're seven. It tells us what we're here to be and do. This [for me] goes back to my mom coming into my room and taking my little pink princess phone out of the wall every night because I wasn't doing my homework because I was talking on the phone. And it's a hilarious joke now because I'm literally paid to be on the phone or on Zoom, helping people with their lives. That's exactly what I was doing with my friends. So it's really important to go back in time. 

Cherie Healey the founder of Siren and executive coach.

You can also go forward in time and imagine, “what would my 90-year-old self say when I look back on my life”. What do I want to say I did? Is there a group of people that I care a lot about? Is there a cause that I'd like to support? You can't be very logical when you do this because the logical mind is so overfed in our world. I always tell people that there's this really great, easy strategy that you can do. That is the source of Disney's success. They say that they separate the dreaming room and the critic room. [What we do is] we put the dreaming room and the critic room together in the same room. Instead, what we have to do is go into the dreaming room, where no critics are allowed and where every single idea is brilliant. Then you can take some people you really value—people who are going to not believe in one of those ideas. You go into the critic room [with them] and weigh what's the best idea. 

Self-doubt is common among young adults. How can we overcome self-limiting beliefs and gain confidence in their abilities?

We doubt ourselves or get into this “I'm stuck place” or “I'm not worthy” because we forget who we truly are. We're in the critique room with this part of ourselves. It's saying, do what everybody's telling you to do—don't be a revolutionary today. 

Parts theory suggests that we all have many different personalities inside that are phenomenally useful. So if you have to go do something new that you're afraid to do, that one ego will be like, “Oh, no, we are not safe. Let's not do this.” You have  to say, “Okay, cool. I hear you.” You're doing this talk inside yourself. [You need to ask yourself] what part of me do I need to put in charge? Sometimes, you put that part that is really creative, like a beginner's mind, into the dreaming room when you sit down and give yourself 45 minutes to do a sprint. Then, later on, another time, you allow yourself to set the timer again and do the critical work, be analytical, and go into the left brain. Think logically or ask for somebody who's really logical to help you into that process. But at the end of the day, I’m just talking to those voices in my head, to those little parts, and putting a different part of me in charge of whatever's in front of me.

Clear communication is crucial in both personal and professional life. How can we improve our communication skills to succeed in the workplace?

Communication is the most important thing for all of us. Taking a course like ”Nonviolent Communication” by Marshall Rosenberg is amazing. Even basic communication classes are really helpful. 

I also developed a protocol after all this time. I'll tell you what the steps are; they're really simple. There's a problem in the way we are communicating because we are wired to agree or disagree. We need to overcome that primal wiring. Let's not simply agree to disagree. Let's listen to learn. This is all built on the idea that we would like to overcome that unconscious way of being and be conscious listeners.

Building a network and finding mentors can be vital for career growth. How can students/new grads start networking and seek out mentors effectively?

First off, you have to believe that people want to help and that you're worth it. Many people fall into that super achiever role where they think they have to do it all themselves, which is never going to work. We're not meant to do life by ourselves. And to believe that is a joy; to help tell their own story, to say I'd love to connect with you or to give you advice. It's a real joy. It's believing that if you have the impulse to do something, there are people who are going to show up to help. But you've got to talk about it a lot, and you've got to have relationships.

Cherie Healey speaks on professional development.

You're going to get hired by and hooked up by people who know you or who were told about you by someone they know. Don't let your age be a barrier. Don't ever worry about the numbers. You're going to be around people who are like you and who are on a path similar to yours. When you're sitting next to other people who are also on a path like you, it upgrades your sense of self and makes you believe in yourself more. Then, it helps you be brave enough to tell people what you're up to and ask questions, and get their contact information. Be bold and say, would you mentor me? Could you sponsor me? Don't ever think it's not possible that that person that you would love to learn from could be in your life.

Change is constant, and it can be unsettling. What mindset shifts can we make to embrace change and see it as an opportunity for growth?

Something that I know got me through life is that I had a vision for my life very early on. I didn't know how I was going to get there, and it is very important to understand that we are not supposed to know “the how”. 

As much as we would love to think we get to make all the action plans in the world, we're not going to know how it turns out. You probably know how you met your love; it’s never the way you would have imagined it. There are some things we know, but that is the magic of life. Sometimes it's a trillion times better than we could have ever made up in that dreaming room. So you need to believe that, no matter how many waves come at you, you keep going.

Goal-setting is a powerful tool for personal development. What advice can you offer on setting and achieving meaningful goals?

The word goal gives me a slight amount of PTSD, like SMART goals and all the things that I was taught. So, I look at them as dreams instead. I have a big idea list, and it's chunked down into seasons. This is just a psychological tool. If there's a big thing you're trying to achieve, you need to break it down into multiple visions. Each one of those visions ultimately leads to the goal, the big vision. This way, you're always trying to find out what's the next best move. 

So when I wake up in the morning, and I look at this beast of a menu of ideas, I go, what's going on in my life right now and what am I most excited about? What just jumps off the page at me? I'm gonna do that either today, this week, or this month. It's very much emergent. 

Failure is a part of any journey. How can students/new grads reframe failure and turn it into a stepping stone toward success?

There's a cliche old saying, “failure is just feedback,” which I think is true. We have the power to assign meaning to anything. Our minds' job is to assign meaning to stuff all the time. Checking your meaning is very important. So, my meaning [to any failure] could have been “How dumb that I did that,” or it could have been, “I need to be able to expect it.”

If you expect it, it means that you just graduated to the next level of life. It's really good. We don't graduate until we go through some hard stuff. I've never had a really great lesson come easy. I sound just like my dad right now. But it's true. So it means you're in; it means you're taking risks, and that's good, and high risk means high reward.

Explore Cherie's expertise and discover more about her approach at 

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