Courage is the journey

This week I welcome Jessica Dawson to The Trailblazer conversation.  Jessica is an accomplished, dynamic entrepreneur, coach, and author who is no stranger to courage.  She shares her journey to cultivate a life of impact for herself and her clients in the Chicagoland area.  

MM: Thank you for joining me to co-author this blog conversation with and for trailblazers. I had the privilege of reading a chapter in your upcoming book and knew that I had to interview you for this blog.  What’s the name of the book and when will it be released?

JD: First, I want to thank you for allowing me to hold space with you. I am appreciative of the opportunity!   I’m so excited about the book! It is called Voices of Impact and will be out around Mother’s Day of 2023. 

MM:  Tell us a little about yourself and your coaching practice.

JD:  A little about me. I am a Jersey girl who still claims her East Coast roots. Growing up so close to New York and having a father who was an investment banker, finance was the push and definition of success. And, I embrace the Midwest as I have been living in Chicago since 2014. 

I have been described as a spiritual intuitive who oozes executive presence. I get a kick out of that because it’s true I am very spiritual. I’ve done a lot of inner work and that journey continues. I’ve also been in corporate America for, let’s just say, a while, (smile).

For a little over a decade, I worked in the learning and development space as a consultant, where I coached, taught, and gave keynotes, and executive presentations for some of the world’s largest organizations.

Pre-2020, I was on the road about 75% of the time and could be resourced anywhere in the world to do this work. It does sound glamorous being on the road. However, it was hard and lonely. At the same time, I am so grateful for it because it pushed me to grow. I learned so much about myself, and I did it all because of my passion for developing human beings. 

Today, I am an entrepreneur with a coaching practice, Empowered for Sales, where I am a Success Strategist and Business Coach for entrepreneurs and executives. Coaching is embedded in who I am. It chose me.   What I love about my work today is that I get to work with two ambitious populations to get them to the next level. 

I help entrepreneurs sell with greater ease using their strengths, strategically add to and scale their offerings, and have unwavering faith and belief in their ability to grow and sustain their businesses.   I also help executives battle imposter syndrome, own the room when speaking, and navigate the pressures and relationships of the corporate landscape.

It’s very rewarding work. As coaches, we have arguably the best jobs in the world!

MM:  I agree that coaching is a radically rewarding journey and I love coaching trailblazers.  

Please share a bit about your story in finance and the moment when you decided to take a different path.

Great question and it almost feels like another life because I am so different today. When I graduated from college, my definition of success was working in finance and living in New York City. I knew almost immediately that I did not like being a stockbroker, but I stayed.  I think a lot of other people can relate to that because it’s easy to stay and just coast. 

The deciding factor to pivot came in 2008 when I was working for Lehman Brothers, and as the company was collapsing, I was retaining client assets.  I said to myself there had to be a better way. 

It was a very rough transitional period where the layoffs seemed to come daily and I saw firsthand people’s misery.  There is a saying about passion or mission being birthed by extreme rage. I was deeply troubled that talent was being squandered and discarded. The organization had arrogance around people who should feel lucky to still have a job.  That experience changed me and I’m grateful for it, even though it was painful.

MM:  Based on your experience, what is one of the most important qualities that trailblazers can develop to make an even greater impact?

Being a trailblazer requires a lot of courage and most people have been conditioned to suppress their courage. It’s easy to follow the crowd, it’s easy to do what’s been done and not go against the grain. I love Dr. Brené Brown who talks about the notion of courage as being brave and afraid at the same time.

Trailblazers create an opportunity to meet the needs of others. I don’t think people get how much courage plays a part in being a true trailblazer. The other piece is your faith and being able to follow your instincts and intuition. That gets conditioned out of us too.  We look outside of ourselves for answers but our power is ultimately in us.  I believe that there is something inside of a trailblazer that pushes you to do things that quite frankly you may not do if you didn’t have it inside of yourself.

Bringing more stillness into life helps you can hear your inner guidance and brings forward more trailblazing moments. Start small by following your impulses and seeing what happens. 

MM:  So often women leaders and entrepreneurs feel isolated, exhausted, and afraid to take up too much space because they experience backlash for showing up as their full selves.  How do you coach your clients and how do you manage these challenges?

I may have a very unconventional way of thinking about this, but I believe wholeheartedly that life is happening through us, not to us, and that everything is a mirror for what our thoughts and beliefs are. Our thoughts and beliefs can bring unwanted experiences and we are giving fuel to those unwanted experiences whenever we give our focus to what we don’t want. Trauma is real and I would never suggest ignoring it AND I believe that Earth is a school. We signed up to learn and overcome many lessons for the evolution of our souls. 

MM:  “Earth is a school.”  That’s a statement.    

Bringing this notion back to coaching, I coach my clients on how to find empowerment in any given situation or circumstance. When you don’t take up space, you are giving your power away and you are resting in a place of victimhood. No oppressed person or group has overcome without taking their power back. For me, that starts from within. That’s where I start with my clients, so we work on expanding perspectives to change the positioning of how you see yourself in the situation and/or circumstance. 

MM: We know that we stand on the shoulders of trailblazers who have gone before us.  Tell us about an influential trailblazer in your life and what you learned from them.

My parents are both trailblazers and I want to talk about my mom.  She grew up in the 60s in south central LA with two parents who worked hard to create a great life for their family. My mom took an interest in math very early on and she had a natural talent for math in school. She was so good. She tutored the kids in the neighborhood growing up. 

My mom was encouraged by her teachers to pursue other careers, such as becoming a teacher. She was essentially given the message that Black people couldn’t excel in math. My mom had other dreams of becoming a mathematician and a statistician. She worked so hard and went to college at the University of California Santa Barbara. On arrival, my mother and my grandmother entered the dorm room where my mom would be staying.  My mother’s roommate and her mother were in the room. The two White women took one look at my mother and my grandmother and decided that they would immediately switch dorms.

My mother persevered until she graduated. She didn’t stop there because education is so important to her. She earned an opportunity to attend Rochester Institute of Technology and moved cross country to pursue her graduate degree in Statistics.  

What is so amazing about my mother is that she is brilliant. She is a Black woman mathematician and statistician who worked in corporate and eventually switched to entrepreneurship. She has tutored and coached so many people on understanding math and life. She had three kids who she would do anything for and she persevered through it. She never leaned into the victim mentality. She always used it to fuel her and she succeeded in a male-dominated academic domain. 

She courageously persevered. To me, that’s trailblazing.

Do you have any questions for me?

JD:  What is something that you have battled with sharing with your readers? Something you feel like your readers should know but you’ve been going back and forth on that you can share now?

MM:  This is a deep question, Jessica.  I can see your coaching skills in action.  I have many stories from my own life that I want to share with my readers. I want to talk about the women in my family who went before me, and I want to explore their individual and collective struggles.  It’s been a long journey of healing for me and my evidence of that healing is that I am ready to share many of them from an empowered and integrated perspective.  Their  experiences are part of mine and contributed to my journey to this very moment.  I was put here to do this exact work and I do it well because of my lived experiences. The same is true for my clients.  

Additionally, I realize that I disempower myself when I don’t claim my full, lived experience.  It’s like you said earlier about feeling like a victim.  If I focus daily on feeling victimized by some part of my life, it means that I’m not seeing the full picture of myself.  

JD:  What is one way that you keep your vibes high within entrepreneurship when times get tough?

MM:  My path into entrepreneurship has been fueled by self-trust.  I developed a new level of confidence and calm that was not available to me before I got intentional about my meditation practice.  It taps into the courage to feel safe so that I can dream and plan boldly.  I also surround myself with a community of trailblazers who are on a similar path.  I also remind myself that I am doing my best at this moment.   Jessica, you and I are in a small Mastermind group together and our dear friend, Erin, has been teaching me to rest.  I’m learning from both of you.

JD:  What do you think is your core genius as a coach?

My core genius as a coach is to spot the patriarchy a mile away and that means that I can help trailblazing women leaders unhook themselves from the limiting beliefs that they internalized throughout their lives.  I’ve seen what’s possible in my life and around the world.  I believe that the transformation that they desire will happen and I let them borrow my belief until they can build up their own. 

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