‘Winning The Game Of Work’ With CEO, Coach, Speaker and Author Terry McDougall

Andrew Wayfinder Hryniewicz
10 min readSep 28, 2021

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The Destiny Awakening Interviews is a podcast with Andrew Wayfinder and his guests.

Every week (sometimes more) we have a short focused interview with an expert, author, speaker designed to bring you powerful insights, inspiration and ways to break free, live life by your vision and values, and make a difference in our changing and challenging world.

Listen to the podcast at: https://www.andrewwayfinder.com/blog/DA0037

Andrew Hryniewicz

So hello everyone, and a very warm welcome to another edition of the Destiny Awakening Interviews.

I’m Andrew Wayfinder Hryniewicz and I’m joined today by Terry Boyle McDougall, corporate leader, executive and career coach, speaker and author.

And a very warm welcome to you, Terry, where are you hanging out today?

Terry McDougall

Well, Andrew, great to be here I am in suburban Chicago, and it doesn’t quite know if it wants to be winter or spring yet here.

Andrew Hryniewicz

It’s probably not minus 40 anymore, though, is it?

Terry McDougall

Now? No, it’s just flirting between 70 degrees and 40 degrees? Frustrating. It’s difficult.

Andrew Hryniewicz

It’s a crazy time of the year.

Terry McDougall

Yes.

Andrew Hryniewicz

Okay, well, let’s get on to your work.

Terry Boyle McDougal is an executive and career coach, CEO of Terry B. McDougall coaching.

She helps high achieving professionals remove the obstacles that’s keeping them stuck. So they can enjoy more success and satisfaction in their lives and careers.

Before becoming a coach, Terry was a long time corporate marketing executive, leading teams developing strategies and advising senior leaders to drive increased business results.

She’s the author of the bestselling, “Winning the Game of Work: Career, Happiness and Satisfaction on Your Own Terms”. And she also hosts the “Marketing Mambo Podcast”.

So thank you, Terry, for your time today. And the title we’re working with is “Winning The Game of Work”. And Terry’s going to unpack that topic by answering six questions.

So your time starts now, who is your ideal client? And what’s the transformation your work helps them achieve?

Terry McDougall

Well, I work with high achieving professionals who are successful but not satisfied. And what I mean by that, is that if somebody looked at them from the outside, they say, “What does that person have to complain about?”

They’ve got a great title, they’re working for a great company, making a lot of money, they’ve got all of the external trappings of success.

But when I talk with them, or when they come to me, they’re not satisfied, they’re unhappy… They may be feeling like they’re paying too high of a price for that success in terms of stress, burnout, sometimes the impact on health and relationships.

And so what I help people do is shift their mindset and learn skills that help them recognize that they can have a happier coexistence with their success.

So that they feel personally satisfied, they feel happier. And, in turn, that helps them have the energy to show up and perform well at work.

So there’s much more of a balance between that success, but they also have the time and space to enjoy their lives.

Andrew Hryniewicz

Right. So question number two, what’s the biggest challenge they’re facing? Is there a number one pain point when they come through the door?

Terry McDougall

Well, usually it’s that stress. It’s that they don’t believe that they’re tolerating something in their current role that is painful… It’s stressful, maybe they’re having some anxiety around it.

And even if they don’t show it on the outside, they’re feeling it. And they don’t believe that they can do anything different.

So that’s the biggest issue.

And it could be anything from, you know, not getting along with their boss… overwork…. I’ve had people that have worked, you know, 70 hours a week and are like, I don’t know if I can keep doing it.

And, you know, we’ll look at that and say, “How can we shift things?”, “How can we put processes in place that support you, so you don’t have to work such ridiculous hours?”

Could be anxiety about presentations… I mean any aspect of work where people feel stressed. Or feel like they can’t make a change, but yet they have to do this in order to perform, is an issue.

And what I help people do is start to shift that mindset to believe that change is possible.

Well, first of all, to get clear on if you’re not happy in the situation that you are in. What would you like it to look like? Like, get really clear on what that goal looks like.

And I really try to hold the space for people too. So that they don’t immediately pile on to that goal or that dream and say, “Oh, here’s the 101 reasons why that can’t happen.”

Because I often see that where when I asked somebody, well, “What would you like this to look like? Or what would you like to have happen in your career?”

They may have a very clear vision of what they want. But they immediately will say, “Well, I can’t do this, because, you know, I wouldn’t need to go back to school”.

Or, “I want to be promoted, but my boss is not going to leave until he retires” or whatever.

I mean, there’s lots of reasons that people tell themselves that they can’t have the thing that they want.

And if we can separate the goal from how we’re going to get there, that gives the goal some time to live and breathe.

And a lot of times, you know, we start to see possibilities pretty soon after that goal is set.

Andrew Hryniewicz

Okay, what actually sounds like you just answered question number three, what’s the number one insight you would share to help them right now?

And it sounds like what you’re saying is… separate out, where you’re headed, the goal, the vision, the dream, from how you’re going to get there?

Terry McDougall

Yes.

Andrew Hryniewicz

And allow the “how” to kind of present itself?

Terry McDougall

Yeah, because I think that one of the things that people don’t recognize, as they think, that if they set that goal that they immediately have to have all of the information to get there.

And there’s usually a period of exploration. You know, we don’t know what we don’t know.

And one of the things that I think is really helpful, and it helps people garner the energy to go on their journey towards this goal, is if we can find people that can give us insights

You know, whether it’s going to your boss and saying, “Hey, I really want to be promoted to the next level, what’s that going to take?”

And honestly, I will tell you that a lot of times people, they don’t even want to have that conversation. Like they want to be promoted, but they don’t want to share that they want that, because of their fear and a lot of reasons, right?

Maybe they’re afraid that their boss is going to give them feedback that they don’t want to hear. Or they think whatever they hear is going to be so insurmountable, it’s going to cause them anxiety.

But, you know, if we can find people that have done the thing that we want to do, that’s a really great place to start…

Just to go and say, “Hey, I admire what you do, or I admire how you’ve managed your career, I’d love to talk to you more and hear about your story and what you did? What challenges you faced? How you overcame them?”

And one of the things well, actually, there’s a couple really great things about that. One is that somebody who’s further ahead on the path can tell us about the pitfalls. They can tell us about, the things that you should do to be more effective on your journey.

But also very often, that causes people to become advocates for us.

Because, you know, very often when somebody has overcome a lot of obstacles, and they’re down the path, they want to help people that are coming up behind them.

And, they may be able to provide insights or connections to resources that can help us get to where we want to go. And, before we hit record, I was just mentioning that I had a client who got a job offer this week.

And I’ve seen this happen multiple times, that when people start to engage with others about promotion, or insights, or getting a new job, or whatever…That a lot of times the change that they’re looking for can happen very quickly, once they engage others, because we’re surrounded by possibilities.

And so often we’ll just sit there and like kind of wish, “Oh, I wish things are different”.

But once we start taking action, it’s sort of, you know, stirs up the energetic pot. And a lot of times it can get that energy going towards the thing that we really want.

Which is amazing. And even though I’ve seen it multiple times. I’m still amazed when it happens. And feel really thankful that things work that way.

Andrew Hryniewicz

Okay, great. Yeah, I agree. You know, the universe is on our side, but we have to let it know what we want.

Terry McDougall

Yeah, absolutely.

Andrew Hryniewicz

So question four, in your own development, was there a concept, book, program, talk or experience that was most impactful?

Terry McDougall

Oh my gosh, there’s so many. But I’m going to go back to the beginning of my career… I am a first generation college graduate. I had my sights set on going out and working in an office in the corporate environment.

And when I graduated from college, I was just so anxious to hit the ground running and get my first job that, I would adjust certain things just to get a job and get a paycheck.

And my boyfriend at the time, his mother had done some career counseling, and she gave me the book, “What Color is Your Parachute” by Richard Bolles, as a gift.

And she said, “Do not apply for any jobs, and do not start interviewing until you’ve read this book and done all of the exercises.” And that was really the best career advice that I ever got. Because it exposed me to this idea that was foreign to me at the time.

That you should pursue a career that aligns with your strengths, that aligns with what you like to do, and what you’re good at. And that wasn’t something that I ever thought about before that.

And I’m so thankful, because it did get me started on a path where, as a creative person, that I could channel my creativity into something that I get paid for.

And so, I actually, my first job was in a publishing company, but I soon moved over and did marketing for the rest of my career. And it was really fun to be able to, be creative, and get paid for it.

You know, it wasn’t like I was doing art all the time, but to be able to use words and colors and imagery and conceptualize and make things happen. That that was very well aligned with what I got energy from.

Andrew Hryniewicz

Reminds me of, when I used to be an architect back in the day… There were some times when you would get paid to bring out the colored pencils.

And, color in a big… you know, now it’s all done with computers. But before, if you had to do color renderings on a presentation drawing and things, you’d be there with the coloring pencils or the watercolor.

Terry McDougall

Yeah, it’s fun to be able to do that. And for me, I think it was always like, seeing my concepts come to life, which I imagine in architecture, it’s sort of similar, right?

You envision something, and then to actually see it happen. And, in marketing, it’s everything from, advertising and all of that, to B2B marketing. And so we did lots of events.

So you know, conceptualizing, “Okay, where are we going to have this big conference? And who are going to be our speakers? And what are we going to do for leisure time activities?”

It was just fun to come up with the ideas, involve everybody in the organization, and then actually see it happen.

Andrew Hryniewicz

Okay, great. So question number five, what free resource would you like to share with the audience?

Terry McDougall

Well, I’ve got a couple chapters of my book that are available on my website at terrybmcdougall.com. And so people can go there and download them.

Andrew Hryniewicz

Okay, great. And then sort of last question, question number six. What should I have asked you that I didn’t?

Terry McDougall

Yeah, well, you know, one of the things that people sometimes ask me is, “What words of wisdom do you have for people?” And the thing that I would say is that, “Your Happiness matters”.

And so often we’re so focused on the goals of surviving and so forth, that we don’t step back to say, “How am I feeling? Am I enjoying this experience”.

And you know, my mission in life really is to help people realize that “It does matter if you’re happy”.

You’re put here on earth with certain unique gifts. And I believe that our purpose here is to use those gifts. And if you feel like you’re in a place where you’re really stuck, and you know, you’re so focused on all I’ve got to get this paycheck or whatever.

I encourage you to step back and recognize that you can have both… “You can make a living and be happy.”

And I would encourage you to step back and start thinking about “What would that look like?” And maybe start thinking about, “What small steps can you take to move towards something where you have joy and happiness in your life?”

Andrew Hryniewicz

That’s a great idea. And I definitely concur with that.

So that was perfect Terry. Thank you so much for your time today.

Terry McDougall

Andrew, thanks for having me.

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Andrew Wayfinder Hryniewicz
Andrew Wayfinder Hryniewicz

Written by Andrew Wayfinder Hryniewicz

Philosopher. Shaman. Architect. Therapist. I love time spent with friends and family, creating beauty and magic, and this amazing planet we all share.

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