Outworking Your Imposter Syndrome

Question of the Week

Outworking Your Imposter Syndrome

Happy Friday, everyone! I hope you’re staying cool.

I’m so happy with the MDB Episode we dropped this week. I chat with long-time friend and fellow lawyer-turned-entrepreneur Jesmond Riggins. Jesmond founded Legislative Logistics, a legislative consulting company for small and medium-sized businesses.

In the episode, Jesmond tells his inspiring story, from graduating high school near the bottom of his class to graduating from law school and now starting his own business. He also provides insight into the motivational mindset that helps him achieve success. It’s one of the most open and vulnerable conversations to date, and I can’t wait to share it with you.


Episode Highlights

Who you were does not determine who you will be.

By the time Jesmond reached high school, he was entirely disinterested in school except for playing football. In a pivotal conversation, his football coach convinced him not to quit the team, which he now attributes as a key factor for why he stayed in school and eventually graduated. However, he graduated with a GPA of 1.3 on a 4.0 scale and a rank of 443 out of 459 students.

“Graduating from high school, I felt lost,” Jesmond said. “I remember thinking to myself, ‘I’m going nowhere. I’m left behind.'”

While his friends went off to college, Jesmond joined the military. After his time in the service, he worked full-time and attended community college while sleeping in the living room of his mother’s apartment. Because of his poor high school performance, he had a lot of catching up to do and took several remedial classes.

Despite the difficulty, Jesmond kept pushing and landed a scholarship to continue his education at St. John’s University in Queens, NY, where he decided to study government and politics. His professors saw a brilliance in him that they cultivated, which led him to attend Rutgers University law school and land a job after graduation in the Department of Justice.

“I was lucky enough to find myself in the Civil Rights Division,” he said. “I was the only Black male civil rights analyst who implemented and enforced section five of the Voting Rights Act.”


Outwork your imposter syndrome.

Even as Jesmond worked toward a future he wanted, he struggled with self-doubt and imposter syndrome. To overcome those feelings, he gave his studies his best effort and gained confidence as his effort reflected in his grades.

“I was deathly afraid that people would find out that I was stupid, that I’m not supposed to be there,” he said. “So I worked hard. I studied every single day. And when I got my first report card back, it was straight As.”


Create a business that solves a problem.

Jesmond’s law career spanned various government and politics-related roles, where he noticed that many people from organizations didn’t know how the political system worked and how to influence it best.

“I had no idea that what I was observing would turn into a business idea,” he said. “It was just something that I noticed, and all of us complained about.”

Once he realized he could create a business to help small and midsize businesses that can’t afford lobbyists, he came up with the dollar amount he needed to save to cover the essentials for himself and his family while he got his business off the ground. Then, he saved as if his life depended on it.


Quote of the Week

“If you wait for the right moment, you may never do something.” – Jesmond Riggins


Task of the Week

Don’t miss this episode. And you can find out more about Jesmond here.

I’d love to hear what you think. Does Jesmond’s struggle with imposter syndrome resonate with you? Have you ever had more courage than you ever thought you could muster?

Let me know at the links below.