Q&A with Stef Caldwell

Jun 24, 2020

Tell us a little bit about yourself…

I’m Stef! Chi-based Author, Speaker, Side-Hustle Entrepreneur & Full-Timer in High Tech/AI. I help people and businesses get unstuck, navigate ambiguity and achieve big outcomes (while having fun along the way). My three personal pillars are High Vibes, High Tech, High-Value. I want my legacy to be that I helped many women own their stories, find authentic communities and step into the women they were born to be.

What is your story?

When I was sixteen I attempted suicide. Fortunately, I failed. Though at the time, I did not feel that way. Less than one year later and completely by chance, I witnessed a man set himself ablaze in a public parking lot and despite trying to save him, he succeeded in ending his own life. Sixteen was a hard year for me. I had incredibly low self- worth despite having an upbringing filled with love. I grew up in a beautiful home with two successful, self-made, upper middle class parents and two hard-charging brothers. People who knew me at the time would have told you I was pretty, smart, funny. I was an honors student, an athlete, and a social chameleon navigating and charming the likes of the cool kids, the jocks, the bookworms, and the theater kids with ease. What they didn’t know was that I was battling an inner dialogue that I couldn’t shut up, and she played like a broken record in my head every day. “You are not enough,” she repeated to me over, and over, and over.

My failed suicide attempt was the front bookend of the worst year of my life. The back bookend was when I witnessed a man succeed in doing what I had so badly wanted for myself. When I woke up from the trauma of the experience of seeing a man literally set himself and his life ablaze, it was as if my negative inner dialogue had moved out and was replaced by a more positive one. “His fate will not be your fate,” she said to me. “You are meant for more,” she promised me, just in time for me to accept a scholarship to play Women’s Rugby for the premiere NCAA Division 1 team in the United States of America and to move my life to Charleston, Illinois, where I would spend the next four years discovering who I was and what I wanted for my life.

College had its challenges, but none as bad as high school. Sure, there were days when I questioned my ability to per- form intellectually, socially, on the field, in the weight room. And yes, there were moments when I compared myself to my teammates, my classmates, my sorority sisters and felt I had come up with the short end of the stick, but all in all, my soul was happy and my mind fed me more productive narratives about myself and my worth. By my junior year, I had worked my way into leadership posi- tions on and off the field. I was honored with the Most Improved Player award, I lost thirty pounds, and had the fastest mile time on the team. I was vice president of recruitment for my sorority, I was president of the American Marketing Association, and on top of all of this, I had a nearly perfect GPA and was a model member of the university’s honors program. When my rugby coach asked me to lead an initiative to help our team raise money and awareness, I came up with the idea to create a line of T-shirts with empowering phrases written in bold letters across the front of them in a variety of colors. “I Am Fearless” read one. “I Am Powerful” read another. “I Am Unstoppable” read mine. And when I wore it, I felt it. There was nothing I couldn’t accomplish, I was certain of it: I. Am. Unstoppable. As my college experience neared completion, I found myself overcome with anxiety. I knew who I was here. I was finally hitting my stride. I felt worthy here. I felt enough here. Every step forward in my life had been prescribed up until this point. What would life be like after college? What steps were next? What would I do with no one to tell me what to do?

It was at this crucial moment in my life that I received a gift from the universe: my very first piece of Lululemon gear and subsequently, the Lululemon goal setting program. The Lululemon Goal Setting Program encourages people to set goals on a ten-year horizon. The reason for this particular length of time is that over such a long horizon, you are more capable of taking the excuses of time, money, and knowledge off the table for yourself. Therefore, you feel more confident to dream big and know that if you work hard, you can actu- ally accomplish massive goals. The program also suggests you should define goals across three different dimensions of your life—your professional goals, your personal goals, and your health goals—and write them in the present tense. For example, “In ten years, I am . . .”

I was twenty-two years old, and I sat down to spend hours thinking about what I wanted to accomplish in my personal, professional, and health life over the next ten years—so, by age thirty-two. “In ten years, I am making a six-figure salary and working for a company I love whose mission motivates me.” “In ten years, I am married and living in a beautiful home with a man I love.” “In ten years, I am healthy and fit and I have completed a marathon.” When graduation day came around, I confidently accepted my diploma knowing that whatever came next, I was prepared. I had a self-prescribed guide for what came next and was ready for the next chapter of my life.

Fast-forward five years from college graduation, and I am twenty-seven. I am engaged to the man I love, living in a beautiful apartment in Chicago with a beautiful second home in southwest Michigan, one block off of Lake Michigan. Together, we have the most adorable Pomeranian named Cooper, and I have successfully completed the Chicago Marathon. I am making six-figures and working my dream job for, objectively speaking, one of the most innovative AI compa- nies in the world, calling on executives from some of the most interesting technology companies in the world. Life is good, and I am deeply proud of having achieved every single one of my ten-year goals, reaching my personal summit five years ahead of plan, and then my phone rings.

“We’re dissolving the business development team,” my boss informs me, and my world came to a screeching halt. Cue: devastation. This was my dream job, which I had managed to procure at the ripe young age of twenty-seven, and with this change, I would be moving onto a new team starting the following day, doing something entirely different—and my new manager? TBD.

I felt stuck and I had no idea how to get myself unstuck. I thought my only option would be to leave the company. But, the universe had another plan, and it was during the months and the year that followed that I started Manifest and unlocked the next- order version of myself, the version that whispered to me, “Remember, Stef, you are meant for more,” and so instead of leaving, I leaned in. And in one calendar year, I managed to unstick myself, start a company that helped more than one hundred women unstick themselves, and publish a book to share these ideas for getting unstuck with women like the readers of Simply Unstoppable. And I did all of this while not just working for the company that I mentioned above but performing so well that I advocated for and received promotion and a raise.

You accomplished many of your goals much earlier than you anticipated, what was that journey like?

It was focused, it was intentional and it was fun. I used the Lululemon program to break down massive ten year goals into more tangible elements which I could make progress on. The tangible progress created momentum. That momentum carried itself from one outcome to the next. It wasn’t perfect, it wasn’t linear, but it was fun and it was intentional.

What inspired you to create Manifest? Where did the idea come from?

When I was going through that job transition, I was really struggling with where I was in life. I wasn’t sure of my future and I was feeling stuck. I started talking about this with my friends and in every conversation I had I realized more and more that I was not alone. It made me start questioning – why hadn’t I talked about these feelings with my friends in the past? How come women struggle to authentically open up and be raw with other women? Especially those who are in a position to help them get unstuck and navigate ambiguity and realize their dreams or at least support them on their way? I realized that there was an opportunity to create more of that authentic dialogue between women in Chicago and beyond.

Did you ever have moments of doubt? How did you continue to push yourself to follow your dreams?

Of course I have doubt! All the time. I remind myself that doubt only shows up when you are doing something outside your comfort zone. Outside your comfort zone is where growth is… you are either growing or stagnating. The two are mutually exclusive and collectively exhaustive. I’d take growth over stagnation any day… so really self-doubt is a compass for growth. When you look at it that way, it’s not nearly as paralyzing, you can appreciate it when it shows up… “What’s up self-doubt! I appreciate you being here to try and keep me safe, but I’m going to grow anyway ;)”

How do you balance everything that you do? What does your self-care routine look like?

Balance is a farce! If you seek balance you will always be chasing an unrealistic expectation of what life is really about. Chase joy. Try to live in as much joy as possible – work can bring you joy, home can bring you joy, relaxation can bring you joy, chase a joyful life and joyful activities that light you up in side. Don’t fall victim to this idea that work has to be work – there can be a lot of joy in your work. You just have to adopt that mindset. How does your work bring you joy? How does your exercise bring you joy? How does making good food decisions or good financial decisions bring you joy? Don’t focus on balance, balance doesn’t exist… focus on living in joy 🙂

What did you learn throughout your journey that may help others with similar ambitious?

We tend to get all up in knots because we have a big big dream and we don’t break it down into parts. You could have the biggest dream for what your life looks like 10 years from now — you could want to change your career entirely which may include going back to school and a ton of other things… Well how could you start taking action tomorrow towards that big ass dream. Could you spend 20 mins doing research on the field you are looking to get into and what the educational requirements are? Could you do that once per week for the next month? Great! That’s a start. Trust that the path will light itself once you start walking it.

What advice do you have for others that has helped you throughout your journey? Are there any quotes you live by?

There’s an old adage “Trust that when the student is ready, the teacher will appear.” that is just the most true thing ever… You just have to start and then the path will become clear. → Also, don’t be afraid to ask for help! If you don’t ASK you won’t ever GET. The smartest people I know know where they are strongest and where they are weakest and they hire/surround themselves with those who fill in their gaps.

What is next for you and Manifest?

This summer we launched our podcast, we are publishing our first book (ManifestHer: The Ambitious Woman’s Guide to Getting Unstuck, Navigating the Ambiguity of Your Post-Prescribed Life and Manifesting Your Biggest Dreams) and we are launching a virtual community which anyone can apply to and then become part of… we can’t wait to spread our mission and our valuable resources and content to more ambitious women! We’ve also got another book in the works, some new programming and more!

What does being Simply Unstoppable mean to you?

Impossible to keep something from happening → it’s inevitable because there will be no stopping of the actions that are creating that new reality. It’s empowering!

Tell us about your upcoming book launch.

Book is dropping Sep 1!!! Available anywhere books are sold – physical, ebook and audiobook all available. You can pre-order now on the www.manifest-her.com site.

How can readers get in contact with you to continue this conversation and learn more about Manifest?

Site: Manifest-her.com, email: hello@manifest-her.com, IG: @Manifest.Her

Get in touch with me: @bystefcaldwell on IG, www.bystefcaldwell.com