Employee Spotlight: On her way to becoming a psychiatrist, Stephanie Dudley Caster changed career paths and found happiness

Stephanie Dudley Caster has always been interested in human behavior. It’s why she has a bachelor’s degree in psychology. It’s why she enjoys being a settlement attorney and it’s why one of her hobbies is acting. We recently had a chance to catch up with Federal Title’s Managing Attorney of the 14th Street office, Stephanie Dudley, the ultimate multitasker—wait until you read about her law school experience!

Stephanie started working for Federal Title in 2013 at the Friendship Heights location and then moved to the 14th Street office when it opened in 2015.

“I have seen so many changes,” said Stephanie, “a lot of restaurants, condos popping up here and there, all different generations; the millennials are here now.” Stephanie said, “When we opened, we were one of the first few title companies. Now 14th Street is pretty heavily saturated with brokers and title companies. Luckily, 14th Street has a consistent flow of business. It is also a community-embracing area. When I walk into Trader Joe’s, the regulars come in. Everyone is walking around the neighborhood, talking with others, probably less due to COVID-19, of course. There are coffee shops; people are sitting outside, just kind of mingling.”

When asked about a perk of working at Federal Title, Stephanie replied, “It would be the relationships I have developed over the years with agents. I started in 2013 and for some agents, I am their No. 1, go-to settlement attorney. I have even developed some relationships outside of the office. We go out and have lunch.”

Being a successful attorney seems to run in Stephanie’s family, but this career path was not what she initially envisioned for herself when she was earning her bachelor’s degree in psychology at University of Maryland. “I wanted to become a psychiatrist,” said Stephanie.

As Stephanie further studied psychology, she realized that it just wasn’t her calling. After a few important conversations with her dad about her future, Stephanie soon realized that she was meant to follow in her father’s footsteps and become an attorney.

“My father was an attorney with the federal government,” said Stephanie. “He was a labor and employment lawyer. I was intrigued by the analytical piece of law and I remember observing him with cases.”

When Stephanie entered law school, she never considered real estate law. She thought she might practice family law. “I got my degree from Catholic University and did not know what to do next. So, I decided to work with a professor at Catholic U. She was looking for someone to come in to work with her title company and that is how it began. And she was based in the Chevy Chase area, right across from Federal Title’s Friendship Heights office. Working with the professor is where I began learning the title business and getting involved with real estate.”

With a strong appreciation for relationships, Stephanie is very close to her own family. “I have four biological children, two girls and two boys. They are 22, 20, and 18 and I have a little one, she’s four years old.”

A few weeks ago, Stephanie remarried and gained three stepchildren, who are in their 20s and in college. “We will have a nice blended family,” said Stephanie.

When Stephanie was accepted into law school, her first-born, a daughter, was two years old.

Stephanie did something remarkable, twice.

“The first week of my first year of law school I had my [first] son, and then the first week of the third year of law school I had my other son,” said Stephanie. “I always amaze myself, how in the world did I do it? That was a feat that I am very proud of, that I was able to get through it. I had three children while in law school, but I also had a great support system at the time.”

With a busy career and home life, Stephanie said she likes to relax when she has downtime. An ideal day off would look like the following…

“When it’s a nice warm day,” said Stephanie, “I like to sit with a nice book, a nice cup of coffee, sun just gleaming. And just be silent, just enjoy whatever I am doing. Just taking it in, not checking emails, not doing anything other than enjoying the moment. Because I have vowed to begin to enjoy moments better instead of, ‘what’s next?’”

Stephanie also loves spending time with her mother. “My mom is my best friend,” said Stephanie. “We like to go to lunch. COVID-19 of course has affected many things. We used to get in the car on a Saturday, and the girls: myself, my mom and both of my daughters would go out and we would go to a mall. I try to keep my mom physically active so that she can remain sharp in the mind and body.”

Along with relaxing alone or spending time with family, Stephanie says she loves to act and has some acting credit.

“For many years,” said Stephanie,” I took acting classes in the DC area at almost every studio theater in the area. I would just sign up for classes, not with the goal of becoming a movie star. It helped me to become comfortable speaking in front of others.”

Stephanie added, “People may not know I am extremely shy, and one way to come out of that shyness, I took acting classes and actually starred in a film for a film festival. In the DC area, local filmmakers put together films for a filming contest and I was a lead actress. It was filmed at a Silver Spring theater. I still have a copy of the film. It was one thing that I enjoyed. I said one day if I felt like it maybe I will take some more acting classes.”

Stephanie concluded our interview with, “I am very committed to the work that I do. I am a very hard worker in that respect and when it comes to the clients that we have, I really have their best interest in mind. I want this to be a win-win for everyone. So, when someone comes to Federal Title, I want to make sure they are completely satisfied with the services that they are getting.”

Stephanie also said, “I think my coworkers would be surprised to know that I am a very funny person. It often shines when I am at the closing table with the intent to have a fun and exciting closing. I think what happens is that when we are in our place of work, we try to maintain a level of seriousness, but I know how to crack a joke or two.”

Stephanie likes to observe behavior patterns, and it seems like Stephanie’s behavior is fascinating, too.