Drew Caitlin Dudley

Today’s Shero Spotlight is Drew Caitlin Dudley, senior account representative at Highspot! Drew graduated from the University of Washington in 2019 with a Bachelor’s degree in English, a minor in Spanish language and culture and a professional certificate from the Michael G. Foster School of Business. 

Not only is she excelling in her business career, but she also published her first book entitled “Dream Smaller” in December 2019. In her book, Drew used her experience being told that she couldn’t be successful both professionally and personally to flip the conversation and empower young women to design lives that they are genuinely excited to live. I am so excited to feature Drew on the blog today!

While in school, what other organizations or internships were you involved in on campus?

I was involved with gamma phi, I led the Husky Sales Club, which was a part of the sales program and in a certain respect, it was the community for students who were in the sales program. I also led a circle on campus called the Creators and that was kind of related to my book, actually, that’s how I wrote the book. 

Was the Creators group the first time you had considered writing a book?

I have always written short stories and things which is part of why I wanted to go into majoring in English with an emphasis in creative writing. The summer before my freshman year of college, I was very into historical fiction and thought I was going to write this historical fiction novel based off of something that was related to my family’s experience in World War II, but I never really thought that at 22, I could be a published author. 

Eric Custer, the professor of entrepreneurship at Georgetown University, reached out to me and [asked if I had ever considered writing a book] … I took the call with him and we started talking about different types of books and the difference between writing fiction and nonfiction and we started with this macro goal of like, Where do you want to be? Where do you see your life going? What direction do you see your life going? What are some of the ways that you can work backwards to accomplish that goal? … It really boiled down to I have this love of writing that I want to explore in the format of writing a book and I also really enjoyed business and sales and the interpersonal communication there and networking and helping people and impacting their businesses. So, I really see myself being a sales leader with this writing habit on the side.

Can you describe the inspiration behind “Dream Smaller?”

Photo by Jacinta Harshe

[I remember a time when I was at a networking event and someone asked me where I want to be in 10 years.] It boiled down to I want to be on my way to being an executive sales leader, if not an executive sales leader at the time, I want to be a published author … and I also want to be a parent with two little kiddos that love to travel with me wherever we’re going.[This man’s] response to that was kind of like, a half laugh, like, wow that’s a lot you really want to accomplish, you might want to think about scaling that back or dreaming a little bit smaller. I told this story to Professor Custer and he just stopped me [and asked how it made me feel] and I paused and I was like, you know, for the rest of that meeting felt like I had to posture to get his validation and I had to ask the right questions and I had to prove my value in a different way than other people in the room because he knew something personal about me and didn’t agree with that. 

Professor Custer in that moment was like, that’s your book. Someone told you to dream smaller and I want you to go find all of the women who dared to design their lives in a way that they’re really excited about living every single day and go tell their story. So, I decided I wanted to tell the stories of other women who were maybe told to dream smaller in their own way, and then actively resisted and worked against that to create lives that they were really excited about and were fulfilling to them in their own way.

What advice would you give to someone who might be in a similar situation and is being told to “dream smaller?”

I would say you have to build up your resilience. I have to understand that people are speaking from their own experience. So, what I understand now about that man’s response was that he was speaking from his own experience where he went to school for film, couldn’t make it in the film industry and had to pivot into sales, an industry he wasn’t really interested in at all, and then started a family later in life. So his experience was not aligning to the ideas that I had for myself, so he thought that wasn’t attainable. What you have to do is you have to seek out mentors and other people in your life who will push you to accomplish the things that you want for yourself without letting their experience impede your decision making. 

What sort of impact do you hope your book makes on readers?

I wanted the women who I interviewed to feel as if they’ve shared their story in an authentic way that spoke to who they were as a person, and contributed to a larger conversation around how different each individual’s life can look, and that there shouldn’t be a generally accepted way to have it all. I wanted all of us together to contribute to a larger conversation on what it means to “have it all” in your own context and kind of flip the script on society to challenge other people to not judge people quite so harshly. From the reader, I wanted them to have actionable, tangible examples of what it looks like to create a life that you are really excited about living. There are strategies and pearls of wisdom at the end of each story to allow the reader to take away a strategy or an action they can take in their own life to be able to start building that for themselves. You’re not going to see yourself in every story, but you might see a strategy that someone used in their own life and be able to apply that to your own.

What advice would you give to young women in business?

Go get as many mentors as you can, network as much as you can to figure out what’s truly interesting to you and then have a life outside of work. I know that sounds silly, but letting your hobbies and your interests die because you have a full time job is so not worth it and so uninteresting. So, never lose those hobbies and outside interests and figure out how you can nurture them to be the most interesting version of yourself you can be.

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As a senior studying magazine journalism at Ohio University and a passionate feminist, I created Freely Femme as a way to use my love for storytelling to highlight some of the most inspirational women in my personal life and beyond.

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