Three Lessons Learned in Three Years

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I celebrated three years at the Entrepreneur Center (EC) by (finally) reading Lean In- a gift given to me by a close friend and mentor. I have learned a lot these past three years, as you should when your life is suddenly marked by the reality of the working world. The transition into my first full-time job was quite smooth, relative to many post-grads on the job hunt. I knew I wanted to stay in Nashville and my familiarity with the EC from a past internship granted me an initial contract position to assist with Steve Case’s inaugural Rise of the Rest tour, of which Nashville was the final stop (I like to think he saved the best for last).

Therein began my role as “event planner”, a path I thought I loved and wanted to continue in for a long time. Spoiler alert: This turned out to be very false. I still enjoy events, but now much more from the vision and strategy side and less from the “what color linens do we need?” and “how much beer should we buy?” side.

As I read Lean In, I was inspired by the way Sheryl’s description of her career and her learnings from disappointment and success were such universal lessons. Her recollections made me curious about my own journey and the events that have impacted my growth. In the grand scheme of things, three years is not very long. However, I am such a different person than who I was on graduation day. Though my passions and personality remain relatively consistent, I came to realize three main lessons that are continuing to impact the woman I am today- both personally and professionally.

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In three years, my title has changed four times, my desk has moved three times, and I have worked for four different CEOs. I don’t think a single day has looked the same as another. Through all of this, I have realized that this is where I thrive.

Let me be clear, my use of the word thrive does not imply comfort. There have been countless uncomfortable scenarios of learning on my feet, of taking on responsibilities that I’ve never done before or been trained in. There has been ambiguity and miscommunication, failed attempts and false starts- but the learning, the iterations that have come from those learnings, have been invaluable.

I have always been so eager to learn my entire life. My mom reminds me often of what I kept chanting the week before I started kindergarten, finally getting to join my two older sisters in school, “I want to learn, I want to learn!” That mindset, that excitement and curiosity, has remained true 20 years later. It makes sense that I would thrive in the gray- when the things around me aren’t prescribed or proven, ready for repetition. I guess for me, comfort and stability become monotonous and monotony depletes my energy and creativity, stifling my growth.

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For the majority of my life, I have been drawn to the idea of social justice. This passion grew in high school with my involvement in Invisible Children. My sister and I started a club that organized fundraisers and awareness events around the child slave soldier epidemic in Uganda. It was the first time I really understood that the individual decisions and actions we take, big or small, can have an effect on people all over the world. From there, my involvement grew to include sex trafficking prevention in Eastern Europe, homelessness in Nashville, equal rights for farm workers in Florida, and unconscious bias that exists for female entrepreneurs and entrepreneurs of color.

I applied for a pretty competitive internship with the International Justice Mission in DC the summer before I graduated college. To me, this opportunity would have been a dream come true, symbolizing the pinnacle of my volunteer work to that point and potentially an answer to the question of what direction I would go once I left college. After making it to the final round of interviews, I was not offered the position. I was disappointed, to say the least, especially after the admitted build-up in my head.

I resorted to looking in Nashville for a summer internship and ended up landing a job at the EC... the catalyst to getting an actual job here after graduation. An event that I interpreted as a lost opportunity actually lead me to accepting a position that would be a critical factor in the formation of my leadership.

The mission of the EC is focused on the growth of startups, an investment in entrepreneurs. This is very important work. Startups make a huge economic impact, employ many people, and often create solutions to the world’s most pressing problems. Nevertheless, when I began my full-time, "working woman" life there, I assumed that this was the work that allowed me to make a living, and I would need to find ways to fulfill the social justice passion in other ways. I have come to realize that many injustices are made right through empowerment. And what better form of empowerment than entrepreneurship, whose definition is literally taking a risk to make a profit. Risk results in growth, and for many people, growth is the way they move out of a position of oppression.

Unfortunately, even entrepreneurship is laced with bias, especially for founders of color and female founders. About a year into my working at the EC, I was introduced to the work of diversity and inclusion in this field, particularly within the tech industry. As I began to learn more, have more conversations, and ask more questions, it was clear that this was the way my day-job would allow me to be a part of work that aligned directly with my passion.

I tell this story in an effort to show that working on the things you are passionate about don’t need to be restricted to the before or after your 9 to 5. There is a high chance that you can find ways that your career can integrate with your passion, whether that be through special projects you get assigned, people you are in a position to meet, or volunteer activities you plan for your team. Get creative. And when you feel like life is handing you a rejection, it is most likely just opening a door you didn’t expect, that will teach you things you never imagined.

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Growing up, I always considered myself a leader. Never afraid to speak up in class, lead a group project, join clubs, facilitate meetings… you name it, I felt capable to rise to the occasion. When I started working at the EC, that changed. It was as if all of the sudden, I convinced myself I was not capable. I entered a new world with people who had been there longer than me, were educated more than me, read more than me, and knew more than me.

Who was I to take ownership?
Who was I to lead?

I could feel myself retreat or hold back in times that I might be the center of attention. It was hard for me to speak with authority or own the things I knew to be truth. After a mentor suggested I read Brene Brown’s The Gifts of Imperfection, I learned that this feeling resulted from my being a perfectionist. My desire to control other’s perception made me alter my truest self.

The way I have felt this the most has been through the practice of leaning into conflict. Conflict is not my thing. I don’t enjoy it, I am not competitive and the motivation of my personality is to ensure that the people around me feel good and comfortable. Conflict, as I have known it, is quite the opposite. It invites everyone taking part in it to speak confidently on behalf of their needs, desires, and perspectives.

As I have been practicing this leaning in, however, I have learned the freedom that comes from it. Each time you speak out or act in a moment you are tempted to hold back from, you experience growth. You act out bravery and the things that seem big in your head start to shrink. Owning your voice, for some people, can look like a practice that is outside of your comfort zone, especially in the earlier stages of a person’s career. But we all have a unique perspective that will add to the decision-making process. That doesn’t mean you will always be right and it doesn’t mean you will articulate it perfectly every time, but it will allow you to root deeper into yourself, and that is something that will benefit any team you are a part of.

Jocelyn Youngdahl