Author, Coach, and Strategic Partner


Today, we help tell Terry Boyle McDougall's story over a cup of coffee.

Terry smiling and signing her book Winning the Game of Work.

If you enjoy reading her story and want to support, please use her personal referral code on our website. You’ll receive a 10% discount and Terry gets a 10% commission! And you get coffee!

Terry Boyle McDougall, PCC, MBA, is CEO of Terry B. McDougall Coaching, a Chicago-based consulting firm specializing in executive coaching, leadership development, talent optimization, and team building. She is the author of Winning the Game of Work: Career Happiness and Success on Your Own Terms. Before founding her firm, Terry was a long-time financial services marketing executive. She is a popular keynote speaker, blogger, and podcast guest. She lives in suburban Chicago with her husband, children, and a puggle.

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We asked Terry some questions that reflect on her life’s work, provide advice, and of course, ask why she drinks coffee. Here’s what she had to say.

1. What are you building to make the world a better place?

As a coach and author, my mission is to help people lead careers that are both successful and satisfying. My view is that if someone isn’t currently happy in their job, it’s because work is a game and they are playing by the wrong rules. I aim to help people to embrace what’s unique about them and to learn the real rules of the game of work so that they maximize the intersection of professional success and personal happiness. We’re all here on earth for a reason, and we make the world a better place by having the courage to show up as our authentic selves and do what we’re here to do.

2. What do you want the world to remember you for doing?

For encouraging people to show up just as they are in their glory and imperfection knowing that they are good enough.

3. What inspires or motivates you to do what you do?

When someone I’m working with suddenly starts to believe that their desires are possible and starts acting “as if,” more often than not, they achieve their dream. Helping a person have that moment of realization that, indeed, anything they imagine is possible is the reason I do what I do.

3. Tell us about your biggest failure and how you overcame it.

I don’t buy into the notion of “failure” because you only fail when you stop trying. I prefer to think in terms of setbacks or obstacles rather than failures. The biggest obstacle that I deal with is my fear and doubt about my ability to achieve my goals. I wrestled with that fear a lot while I was writing my book — many days, I sat stuck in my fear of what other people would think and whether it would be “good enough.” I got through it by continuing to move forward. Some days it was only a millimeter of progress, and some days it was miles. Forgiving myself for not being perfect and continuing to move ahead is how I deal with setbacks.

4. Why do you drink coffee? Is it the taste, experience, or caffeine?

I work from home, and I’m usually on the phone all day with coaching clients. Coffee is part of my morning ritual. It’s comforting to come downstairs and get the coffee started before I settle into my coaching chair. I love the smell, choosing one of my favorite mugs, the rich flavor of the brew, the warmth, and the jolt of energy to get my brain and body engaged for the day. Strangely, coffee feels like my companion to help get my day started.

5. What is one tip that you can give our readers on how they can challenge the status quo and become successful?

Get focused on your innermost desires for your life and nurture that feeling — believe that it’s possible and let it grow within you. In my line of work, way too often, successful people become fixated on what is expected of them externally, and they lose contact with their internal desires. In these cases, they become “successful but not satisfied” with their efforts — there’s no joy in that. To me, real success in life is finding a way to show up authentically and share the gifts that make you truly unique.

Do you like the above quote?

If so, we have a series called Roasted for Visionaries, where we take the best quotes and compile them into a never-ending dose of inspiration.

More About Terry

 Terry giving a talk to an engaged audience.

Find Terry on her Website, Linkedin, Instagram, or Medium.

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Are you building value for the world, love coffee, and want to be featured? Send us your story hereAlso, if you love what Terry is doing and love coffee, here is her personal referral link for coffee to support her. She gets 10% in commissions for each referral and you’ll get 10% off your order by using promo code TERRYMCDOUGALL.


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