Virtual Campfire With The Queen Of Adaptability, Terry McDougall


Just because you’ve achieved something doesn't mean you're happy inside. Finding your career can be difficult, having to adapt to so many different environments and people, it can be a pain. This wasn’t the case for the queen of adaptability, Terry McDougall. Terry is an executive, career coach, and CEO of Terry B McDougall Coaching. Before becoming a coach, Terry was a longtime corporate marketing executive who helped teams develop strategies and strong marketing campaigns. how she adapted to being the new girl in school, how she managed changing careers, and how she became who she is today.


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Virtual Campfire With The Queen Of Adaptability, Terry McDougall

It is my honor to introduce you to my guest, Terry Boyle McDougall. Terry is an Executive, career coach, and CEO of Terry B McDougall Coaching. She helps high-achieving professionals remove obstacles that keep them stuck so they can enjoy more success and satisfaction in their lives and careers. Before becoming a coach, Terry was a longtime Corporate Marketing Executive where she led teams to develop strategies and advised senior leaders to drive business results. She is the author of Winning the Game of Work: Career Happiness and Success on Your Own Terms. She's also the host of the Marketing Mambo podcast, which is a podcast for self-professed marketing nerds. She lives in suburban Chicago with her husband and three kids, as well as her puggle. I want to welcome you to the show, Terry.

Tony, thank you for having me. I'm excited about our chat.

Me, too. I always love bringing on people who come from these backgrounds that are powerful like marketing, finances in different places and then seeing how they transition into a different world and seeing what made them make that change and what lights them up. On the show, there's an element of seeing how that story evolved through what we call flashpoints, points in your story that have ignited your gifts into the world. How does that sound to you?

It sounds great. This is certainly a topic that I have thought a lot about with myself and I try to guide a lot of people I work with to find those for themselves as well.

I'm excited. What we are going to do is we are going to give you the space to share your story. Along the way, we are going to pause and see what's showing up. With no further ado, I will pass it to you and let you share what's on your mind.

It's funny whenever I think about my story, it does go back to before I was even born. My mom was in tenth grade when she got pregnant with me. She ended up having to drop out of high school. She turned seventeen two weeks after I was born and my dad was 21. They’ve got married. They were young kids back in the ‘60s trying to figure out how to make things work. My dad ended up getting a job with a telephone company. He's a handy guy. He can do welding and electrical type of stuff. He got a job on one of these construction crews. At the time, we are traveling throughout the whole Southeast burying long-distance cables.

He was working on these big construction projects one after the other. We moved more than 40 times by the time I was eleven years old. Until I was in second grade, we lived in a trailer. It made a lot of sense because if you are going to be living someplace for a month or six weeks, you can't be running apartments or whatever, especially with the family. That was a nomadic lifestyle. I wasn't brought up around extended family. I would make friends and then we would have to move away. I thought a lot about that. I remember as a child being sad every time my mom would tell me that we would move and I can remember crying my eyes out because I had my little friends and so forth.

As time went on, I learned to be self-sufficient and adaptable. As I’ve got into school, my parents made it so that we would live in one place for the school year but I went to a different school every year until I was in fifth grade. We are not talking about the next district over. I was going to a different school in a different state every year. I was always the new girl. I don't think that I even realized that I had this gift. I am quick about being able to go into a situation and size it up. I'm sure that that was honed from being a little kid, going into the new classrooms and having to understand what the dynamic was and what this new teacher expected. Also, learn the layout of the brand-new school or who were the nice people in the class and who were the bullies.

Happiness does not necessarily come along with achievement.

That’s something that has definitely helped me throughout my life. I don't think that I ever even gave myself that much credit for being as adaptable as I am. Certainly, as time has gone on, I recognized it as one of my superpowers. Before I recognized that, I was a good student in school. Because we moved around so much and I had so little control around that part of my life, I liked the structure of school and I liked having the teacher challenging me. Being able to pour my energy into that, I felt like I had control. I have always embraced that part of my identity as being a good student and being a high achiever.

I talk about the fact that I work with a lot of people that are successful but not satisfied. Certainly, if I look back over my career, I recognize that in many ways, I was addicted to achievement. I thought that if I kept putting off gratification that eventually, I would get to something that like, “I'm successful. I'm the Chief Marketing Officer of this company," or whatever and that I would be happy. What you begin to realize is that you can grab the brass ring and then you have it and you were like, “What am I supposed to do with this now?” Happiness does not necessarily come along with achievement, especially if you are not being thoughtful about what that achievement is, what that means to you and why you want it.

First of all, there's something about this that I want to dig into and it has to do with that resilience that you have and showing up to these new environments all the time. Was there something about this that also had you trying to shine bright and showing up bigger because when you show up in an environment, you want to be seen? Would you fade in the background and blend in as much as possible? I'm curious if that was something that showed up early in your life and then continued.

I am not somebody that likes the spotlight and I certainly wasn't going in and saying that I wanted to shine so people notice me. We moved so much that what I cared about was what was important to me. I was self-contained and self-sufficient. Meaning that if I was trying to achieve something, I was doing that for myself. That felt good to me to get an A on my test or to work on my diorama for fourth grade. I did that for myself. I feel like I was a little shy and sometimes, the attention that I’ve got for being a good student felt a little bit uncomfortable. I’ve got the opportunity sometimes to be the lead in the play or something like that. I wanted to take it but I also didn't feel super comfortable with it and I feel like that, in some ways, held me back a little bit.

I try to encourage a lot of people like, “Take the bushel basket off to your light and let it shine.” For so long, I was shining within the bushel basket and I was the one that could see it and I was okay with that. I was a little modest and as time went on, I said, “Take that basket off and let yourself shine.” You are not bragging. You are just being and that's okay. I didn't like the attention sometimes. It felt uncomfortable. I felt vulnerable because if people start noticing you, sometimes people can be envious or want to knock you off a pedestal if you feel like you are on a pedestal. I was like, “I like what I'm doing and I'm enjoying it myself. I don't want to put myself out there.”

We are focused so much on the earlier side of your progression but that is a dramatic part of this, which is the early journey. What comes to mind is this element of building trust? When you are feeling as though your journey is like, “I'm in. I'm out,” and moving on so quickly. How does one build trust or have a relationship of trust when within a year or maybe even less, you are moving on to something else?

VCP 105 | Queen Of Adaptability

It's definitely something that I have had trouble within my life. We didn't talk about this but you can imagine having a mom who was a teenager. She didn't necessarily know what she was doing. I was often emotionally volatile, so there were some trust issues there too because sometimes, I didn't know if I could trust her to be consistent, so I relied on myself. When I met my husband, he definitely helped me build that trust. In my adult life, I feel like I have relaxed a lot more, open up more, be who I am and not feel like somebody is going to criticize me or anybody even has the right to, quite frankly. That all comes down to true self-acceptance to say, “I'm okay the way I am and I like myself the way that I am.”

I want to move the story forward and see what happens. You have this person who's built this strong self-reliance, resilience and adaptability. You have moved through your journey. What happened as you’ve got into the workforce? Maybe some things happen along the college journey that was shaping you. Tell me what happened next. What are your next flashpoints?

From fifth grade on, we moved to Delaware. I was a good student and I ended up getting into college, early decision. With my mom being so young and my dad didn't go to college, I was a first-generation college. This is back before the internet. It wasn't even like you would hear about a college and be like, “Maybe I will apply there.” I applied to a school in Virginia and I’ve got an early decision. I ended up going and it was great. I loved it. I made lots of friends. I had a boyfriend in college who was from Boston. When I graduated from college, I did not have any intention of going back to Delaware because I grew up in a rural area and few professional job opportunities.

I went to visit my boyfriend in Boston. While I was there, I thought, “I will look for a job while I am here.” I ended up getting a job with a publishing company and I worked there for a couple of years. That was great. This is somewhat of a flashpoint. I wrote about in my book a little bit that I worked there for about eighteen months. I worked in the ad sales department of a publishing company. I was the sales assistant for five salespeople and I liked it. It was fun. I was learning about this publishing industry. My boss who is a Sales Manager liked me.

After about eighteen months, he said, “I'm going to promote you to marketing assistant.” I was excited not to be an admin anymore. Unfortunately, he had a little tiff with the new president of the publishing company and he got fired. He had been there for eight years or something. All of a sudden, it's one of these things like they are walking him out of the publishing company. Unfortunately, when the new sales manager was hired, understandably, he didn't want to promote the old guy’s person. There was somebody that got hired from outside to take that role.

I decided to quit my job because I felt like I paid my dues for almost two years at that point. I wasn't going to stay there and be an administrative assistant. I’ve got a part-time job as a waitress and a part-time job as a telephone pollster. One of our big clients was Mike Dukakis. When he was running for president, I was doing telephone polling and see what people thought about him. I saved up my money and I moved back to the DC area where a lot of my friends from college were. I’ve got a job at the publishing company and ended up working in marketing. That was great.

Take the bushel basket off your light and let it shine.

I had another flashpoint after several years. I worked for one publishing company and then got a job with the insurance administrator but it was in marketing. I remember I was in the Art department and my boss was the Art Director and there was a graphic designer that worked with us. She was my best friend at work. I was the Production Manager. Meaning that I bought all the printing from the printing companies for our direct mail. My friend got married and she moved away. I had worked at this place for about 4.5 years and I'm sitting there, looking around and realizing that if I don't do something, everything is going to change around me. I'm going to wake up like that frog in the slowly boiling water. I'm going to look around and be like, “Everything has changed and I don't like the situation I'm in.”

I picked up the phone and called the University of Maryland and said, “When is your MBA program deadline to apply?” It was two days. This is before the internet. I'm so old. I called my boyfriend and it’s a different boyfriend at this time. I had broken up with the one in Boston. He was going to school at the University of Maryland. He went by the office and picked up the application for me. They had told me that if I start the application that they would hold my space. I ended up getting into the University of Maryland Business School.

I quit my job and started going full-time. I didn't even know how I was going to pay for it but I did figure it out. Luckily, in the ‘90s, it wasn't as ridiculously expensive as it is now. I was able to figure out how to pay for it. I went to school full-time for 1.5 years and got an MBA. That set me up for a whole new trajectory of my career. I moved from being a bit of a worker bee to getting more on a management track. It was a great decision, even though it was risky. I look back and I'm like, “I quit stuff left and right.” I think of myself as a quitter.

It's funny you say that because quitting is not giving up. It’s knowing that you are making a decision that is in service to you. At the moment, it feels weird because it's like, “What am I doing?”

It is scary. That was the realization that I had when my friend got married. I realized that I could stay there and all of the joy that I had with her and my boss because we had such a great working relationship. We had a lot of fun and did a lot of cool creative things in that job. I realized if I stayed there, everything would change around me and it wouldn't be the same thing. Sometimes, you have to let go of something to be able to reach for whatever the next great thing is.

I like the way you put that. It had me thinking of this visual of a caterpillar. A caterpillar could stay in the cocoon and stay as a caterpillar but ultimately, at some point deep inside, it's not a caterpillar anymore. It's a butterfly. It needs to get out and start becoming the butterfly. In some ways, that's where you found yourself. You are the queen of adaptability. You know that ultimately, you need to adapt. Sometimes, you stumble on this place of like, “Should I? Shouldn't I do that?” The shoulds start to hold into place.

It was a comfortable job. There were a lot of great things about it. Being a buyer, I bought millions of dollars with the printing but the printers loved me. I went to lunch in every nice restaurant in Washington. Over the years that I worked there, I used to get football tickets and hockey tickets. I had a lot of nice perks with the job but at some point, that's not a reason to stay in a job because you get free baseball tickets.

It's funny you bring this up. Oftentimes, I talk to people and I hear them say all these amazing things about the jobs that they have. I don't mean to be anti-corporate but those are the shackles that hold you in.

VCP 105 | Queen Of Adaptability

They call them golden handcuffs for a reason.

People need to put that frame on like, “That's great but what is it that I want?”

From that job, I ended up getting married about 1.5 weeks after I graduated from business school and then within a year, my husband and I had moved from the Washington DC area to North Carolina for a job that I’ve got there doing marketing for a big bank. That began a 21-year career doing marketing for two large banks. That was a great path for me to get on. Even though before I worked in financial services, that seemed like the most boring thing in the world but once I’ve got into it, I realized that it was fascinating. It was a nice combination of an intellectual challenge because I worked in the B2B area and there were a lot of exotic products and stuff that we had. I was challenged to understand how a company would use some of the things that we had and I had to be able to explain it because that's what you do in marketing. Also, being creative and analytical was great.

I moved up to lead marketing in the last place that I worked for some businesses there. I wasn’t the lead marketing for the whole company but I did lead it for several businesses. That was where I wanted to go. I wanted to be a chief marketing officer but the funny thing is that from afar, you can say that's what you want and not know until you get closer to it like, “That's a little different than I thought it was going to be.” I liked being able to set goals for myself, achieve them and keep moving up. There are a lot of great benefits that go along with being successful in a corporate career.

I decided to leave that in 2017 mainly because I had a few years of what I call working hard to do my job. I felt like I was having to make business cases left and right to do what I was charged with doing as head of marketing. By the time, I’ve got an okay on things. I was so exhausted that I thought, “This isn't how I want to be spending my energy.” Some of the changes that were going on at the company, I was able to leave without having a job at the time. I spent that time thinking about what I want to do next. It was nice to stop, take a deep breath and intentionally consider, what do I want to do next?

That question is one that many people ask themselves and sometimes it's like, “Do I change my environment and go get the same job someplace else? Do I truly break the pattern and do something completely different?” It takes some real intentional pausing and a second path.

I had interviews for the next step up from where I was and I kept coming in second for these jobs. Quite truthfully, whenever I go on the interviews, I have a knot in my stomach about it. I was trying to convince people. I could have totally done these jobs but I didn't want to do this job.

Sometimes you have to let go of something in order to be able to reach whatever the next great thing is.

You weren’t convincing yourself.

I feel bad because I didn't get the offer but then I think, “Maybe you don't really want the offer. Maybe this is the reason why you've got the knot in your stomach.” It did get me thinking, “What are you good at and what do you like to do?” As a manager or as a leader, I’m always investing time and energy in the people that I worked with. Often, as marketers and financial services, creative people are working with analytical people. A lot of times, it could be difficult for marketers. I spent a lot of time helping people figure out how to influence within the organization. It was important for people that were on my team to feel confident and feel like they had some agency over what they were doing.

I’ve got feedback that I was good at what I did. My teams always had high employee engagement scores compared to even average within the company or in the department. I realized that maybe coaching might be something that would be a good fit for me. I had hired coaches and that had certainly helped me at different points in my career, so I decided to get the coaching certification. Frankly, at first, I thought, “This is something that I have in my back pocket and I will get another job. I will use the skills in my next job. Maybe I will have a couple of clients on the side or something like that.” In going through the training, which was about six months and about eight months until I’ve got the certification, as you are among other people who are starting an entrepreneurial journey, it becomes contagious. I'm looking around and I'm getting inspired by people that were committed to starting their own practices. At some point, I thought, “Why don't I do it, too?” It's worked out. It's coming up on four years since I quit my job and coming up on three years since I’ve got my certification.

That's a testament. I've got friends who are coaches, who will tell me most people who go after coaching or become a coach quit because they realize that this is not an easy journey. Once you decide to become one, the real fun begins because you have to go and dig into like, “Who am I really? How do I become the person who can serve somebody in a way that's going to get them to see who they are?”

There are a lot of self-discovery that happens and there are a lot of questioning sometimes, too. If you are working with somebody and they are not getting the results that you would like them to get, you have to have some good boundaries and recognize, “Is there something that I can do here? Am I doing the best that I can do and this person doesn't want to come along on the journey? Are they moving along on their journey more slowly than what I would like?” It's not about me as a coach. It's not even about me in terms of judging what their outcome should be. Sometimes, people may come and say that they want a particular outcome and then they decide something different and that's okay.

Sometimes, people misunderstand coaching and think, “If I hire a coach, this coach is going to make sure that I get this goal.” It's like hiring a coach to get you a gold medal in the Olympics. They can teach you, guide you and try to hold you accountable for practicing and doing all the things that you need to do but you still need to go on the journey. The coach doesn't pick you up and carry you across the finish line. They can just be there to give you feedback, teach you tools and keep your mindset in a positive place where you've got the energy to focus on that goal.

It makes me think about entrepreneurship as a journey anyways in its own right. That's why people often say, “There are a lot of entrepreneurs who fail and a lot of people don't make it through those first three years.” Part of it is because there's an element of like, “It sounds like a great idea starting your own business, work for yourself and all these great things, these platitudes that people think of.” You have to commit to doing the work of being that person who creates that thing day in and day out, whether it's that storm, the ups and downs that it requires to be that person, which is both internal and external in the way that it shows up.

VCP 105 | Queen Of AdaptabilityI use this analogy a lot. I have never been to Mount Kilimanjaro but I have known at least a couple of people that have done that. You can see the top of the mountain for a long way but you are hiking for days and days. You can envision, “This is the thing that I want. I want to be up there at the top.” You still have to walk every step of the way and you are going to, at times, feel like you are not making any progress at all because it looks like the mountain top is still as far away as it was before. You might fall off the path and you have to climb your way back up. Along the way, there can be some beautiful things that happen. Entrepreneurship has taught me a lot about life. It's about the moments. Sometimes, things are a slog and sometimes, things happen quickly and miraculously as well and that's amazing.

We have uncovered many parts of your story. Now I want to think about what are the lessons that you have learned about yourself that you want to share with others that you feel are important?

One of the things that I continue to face is my own fear because when I was growing up, I was constantly in new situations. I’ve got good at evaluating situations. I would even call myself hyper-vigilant. Even into adulthood, I was scanning the horizon looking for risks. At some point, you have to face that there is danger. If you want something, you are going to have to go for it and believe that you will summon what it takes to face whatever comes up.

I have seen this a lot with myself but also a lot of times, with my clients. We can sit and say, “This could happen.” We could try to enumerate all the risks and what will happen 99% of the time is that none of those things will happen. None of the things that you are worried about will happen. Something that you never even imagined will happen and you will figure out a way to deal with it. What will happen if we stop worrying and we focus all of our energy on our goals and start moving forward? It's going to be scary and exciting. You are going to make progress instead of sitting, biting your fingernails down and worrying about what if?

I want to shift gears a little bit for our last question, which is unrelated but definitely something that usually elicits some interesting responses. What is one book that has had an impact on you and why? If you have multiple books, that's fine, too.

Two books come to mind. These are books that I don't even know if you can even get them anymore but they are ones that I read probably in my early twenties. One of them is called Courage Is A Three Letter Word. The word is yes. The book is stories of all these people that overcame things. The realization is that progress is not made without fear. Courage is not a lack of fear. Courage is about moving forward despite the fear. It's about saying yes to things and moving forward. That was inspiring to me.

The other book was one that is called The Art of Selfishness. That opened up my eyes to the fact that it is okay to care for yourself. A lot of us have been raised to think that we always have to think about other people, care for other people first and we should subjugate ourselves to other people's needs. It's not about being a jerk. It's not about always putting yourself first 100% of the time. It's about putting your oxygen mask on first. If you care for yourself and then you have the ability to care for other people. That helped shift my mindset to recognize that I was worthy of my own care and that if I did care for myself that I would be in a place to be able to care for other people.

First of all, you made my job hard because I'm going to have to go find these books and dig them up. Definitely, they have never been mentioned so far in this show. That has been a lot of episodes so far so that's quite a kudos to you. Thank you for sharing.

You are welcome. In Courage Is A Three Letter Word, some of the examples might be a little bit dated there. One thing I do remember is that John Glenn was one of the people. Everybody still knows who he is. He’s one of the NASA astronauts. Some of the examples might be a little bit dated but still inspirational.

Sometimes just the title alone is enough to sell it and it's like, “That makes a lot of sense and that's the reminder I needed now,” so that's awesome. I can't thank you enough, Terry. This has been fun having you on the show and sharing your insights. There are many great things I’m leaving with and I know the audiences, too. I want to allow you to share where people can find out more about you.

I have a website, it's If there are other fellow marketing nerds out there, you can find out more about my podcast at Finally, my book Winning the Game of Work: Career Happiness and Success on Your Own Terms is available at Amazon and

Thank you for coming on. This has been such a pleasure.

Tony, thank you for having me. It was a lot of fun.

Thank you and thank you, readers, for coming on the journey with us. This has been fun. I hope you are leaving with lots of great insights. Go out and consume Terry’s stuff, the book and the podcast. Go check out our website. Have a good day.

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About Terry McDougall

Terry McDougallTerry is an executive and career coach, speaker and best-selling author of Winning the Game of Work: Career Happiness and Success on Your Own Terms.
She works with managers, executives and professionals who want to draw upon their greatest, most authentic abilities to positively impact their organizations. She supports clients who are creating change, driving innovation, and navigating transitions.
Terry relies on both her formal training as a coach and first-hand experience as a corporate leader to support her clients as they work towards their goals. In coaching engagements, Terry serves her clients as a partner and encourager as they break new ground; as a sounding board, supporting them as an objective listener; as a scout, who sees the larger context, their possibilities and potential; and, as a catalyst, helping to spark their commitment and action.

After 30 years of corporate business experience, 15 of which were in senior managerial roles, Terry chose to become a coach to concentrate on helping leaders step fully into their potential to lead satisfying careers. Though the majority of her professional experience is in financial services and marketing, her work exposed her to a wide variety of industries, business climates and corporate transitions such as mergers, acquisitions, divestitures and restructures.

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