Reggie Leonard: Making impact through career services

How a local leader is creating opportunities for students to prototype their careers

This article was originally published by Community Builders, a collaborative publication highlighting the Charlottesvillians who bring us together. 


Reggie Leonard is the Associate Director for Career Connections and Community Engagement at the University of Virginia. His goal is to expand job and internship opportunities and facilitate career connections for all undergraduate and graduate Engineering and Data Science students. No small task.

Outside of his role at UVA, Reggie is also an incredibly well-connected member of the Charlottesville community and does a ton to give back. Here’s his story:

Andy Page: Reggie! How’s it going? Could you introduce yourself?

Reggie: Sure! I get to do that to people all the time in Career Services (ask people to “tell me about themselves”)! I’m Reggie Leonard from Maryland. I work in career services. I’ve been living in Central Virginia for about eleven years now and I moved to Charlottesville three years ago for my job at UVA.

AP: So what do you do? What’s your job?

Reggie: The title is long and ambiguous. I’m the Associate Director for Career Connections and Community Engagement. Essentially what that means is I “live” in Career Services.

My role is unique in that it is split 50/50 with the Data Science Institute and the School of Engineering. My focus is to create opportunities for students to explore their professional interests and prototype their careers. In practice, this is an entrepreneurial employer relations role, where I build relationships with alumni and with companies for the purpose of helping to create more nodes in the network of UVA students and alumni. This also encompasses the traditional goals of helping students get jobs, internships, fellowships, and externships.

The breadth of opportunity is a big part of why the role is specifically broad and ambiguous. There may be new models of doing those types of things that don’t kind of fall into the realm of traditional career services, and I have the flexibility to explore them.

AP: So this is going into the Data Science Institute’s fourth year? And you’ve been here since the start?

Reggie: Fifth year actually, we’ve graduated four cohorts and have started the fifth. Yes and I got here the month after the first cohort graduated. As the first cohort was graduating and heavily in the midst of job searching, they posted the position for my initial role in May, and I applied, interviewed, and moved to Charlottesville a month after that first cohort was graduating. It was such a quick process.

AP: Could you go a little bit more into your story? How did you get from Maryland to Charlottesville?


Reggie: That’s a good question! I grew up right outside of D.C. I was 15 minutes from Alexandria, 15 minutes from D.C. and thought I was going to stay in Maryland my entire life. I just didn’t have a very large, expansive view of the world at all.

I didn’t see a lot of things in terms of career options, in terms of the places that people went to school after high school, and things like that. I saw a very limited scope of what my opportunities were.

In 11th grade, I took a psychology class and loved it! I always knew that I wanted to help people because I saw all of these problems in the world. But I also saw past those problems into a better version of the world. So I wanted to figure out how I could be a part of that narrative of moving towards a better version of the world. I knew that I wanted to do it on an individual basis. I wanted to actually get to know people and work with people one-on-one as much as possible.

So when I took this psychology class it was my first exposure to psychology and the first class that helped me understand people more. That’s when I decided what I wanted to study in college.

I ended up going to a historically black college (HBCU), Bowie State University in Maryland, about 20 minutes from where I grew up. I studied psychology there. In studying psychology, everyone who I talked to in my community and from my university said, “You know you can’t do anything with a psychology degree, so what are you going to study in grad school next?” I didn’t know enough to question them, so grad school it was.

It was around that time that I learned about professional counseling in my Psych 101 class my freshman year. I had literally never heard of counseling, until I was 20 years old, and it was exactly what I had been looking for.

Backtracking a bit, in high school, I went into my senior year with a 2.53 GPA. People continuously told me that I needed a good GPA to get into college. I ended up earning a 4.0 my entire senior year of high school because it was something that I wanted to do before I left. Reflecting on that, I remembered that the guidance counselor at my high school helped either underachieving students or high achieving students, but not average students like myself, which is the majority of students.

I thought about how much potential was being left on the table with this lack of service to these “average” students. The students who were coasting and who were “good enough,” so they were fine without receiving a lot of help, so a lot of spaces they were in just let them do their thing. I couldn’t stop thinking about how many of those students weren’t having their potential fully realized, and what the world was subsequently missing out on as a result of that.

What was the implication of that (lack of cultivation of potential) for the world that we live?

At that point I was pretty sure I was going to end up as a high school guidance counselor.

I went into an MED school counseling program for my grad school, but ended up loving the counseling classes so much that I did some mentoring with undergrads through the diversity office at my university, and fell in love with working with the university population. Through that process I learned about career counseling as a field, and pivoted towards that direction during my first year.

The graduate program I completed was the MA in Professional Counseling, at Liberty University in Lynchburg, VA, where my curiosity led me to complete 72 credits for a 60 credit program.

My time there was interesting, because most of what people know about Lynchburg is Liberty University, and most of what people know about Liberty University is it’s very strong religious leanings and equally strong political involvement.

I had a pretty unique experience both in Lynchburg and at Liberty because I lived downtown (away from the university) in a fairly low-income part of town that was mainly comprised of locals who had zero ties to the university. I really wanted to be in the community.

As a result of living in the downtown area, my friend and I started something called LynchVegas which was kind of tongue-in-cheek way to highlight things to do in Lynchburg. We built a website and social media presence to create and distribute cool content. We did a lot of blog posts, photography, videos, and exclusive interviews with owners of businesses. One of my favorite questions to ask folks was “What do you want more people to know about your business?” There were always so many misconceptions that people wanted to correct, it was really fascinating.

That was a fun entrepreneurial venture, that even led to of a couple of restaurant menu items named after us that we helped create.

AP: So somewhat related question. You went from Maryland to Lynchburg to Charlottesville. For being a young person moving into Charlottesville, what was that like? How did you become part of the community here?

Reggie: That’s a really good question. When I got here, I only knew one person that I had worked with before.

I’m definitely an ambivert. I love being around people but I love not being around people as well. When I am around people I love having more intimate conversations rather than “working the room.”

To that end, I knew that I would probably default towards introversion when I moved to town, so I decided not to do that. So I asked myself “What is deciding to not do that look like?”

I figured that it meant living downtown, close to the action. I knew that it also meant living with other people and not by myself, and it also meant becoming a regular somewhere.

Shortly after moving here, I became a regular at Oakhurst Inn, a coffee shop that was within walking distance of my office. I knew that one of the things that helps you stand out in a new place is ordering something unique. So, I always ordered a Cuban Cafecito with a little bit of foam. By my second week in town, as soon as I walked in the door, the staff would just ask me if that’s what I wanted. Then it got to the point where they just stopped asking, and they’d greet me with my coffee. It really helped me to feel like I had a place even before I’d actually started making friends.

After that, I was really interested in getting involved with the art and tech scene here. So I went to New City Arts with the one person I knew. I ended up loving what they were doing, and showed up to a lot of their events. Eventually, I was asked to be on the Board a year later which was crazy! That gave me the opportunity to meet a ton of people in town.

AP: Wow that’s a very good advice for anyone who just moved to a new location. That’s awesome! Going back just a little bit to the career services — What’s something you wish more people knew about the career services world?

Reggie: That’s a good question. I think that a lot of the perception around career services stemmed from it not being something that’s mandatory. The way that it’s usually introduced is almost like this shameful or punishing task. It’s a place that you go if you don’t have an internship or can’t get a job. In reality, career services is a resource to help you grow no matter what situation you’re in.

We’re reading the same design thinking books that everyone else is. We’re inspired by the same types of people that inspire the startup founders. The language that we use in career services is language like “career exploration” and “career prototyping.”

We don’t talk about you deciding on your career. How could you know how you want to spend the rest of your life, right now? We want people to develop a skill of learning how to keep their eyes open so that when they see things that peak their interest, they know how to process that. We want to help them develop decision-making frameworks to figure out what they want to do with that information. To help them figure out if they want to pursue it as a career or something on the side or just something that they know about and they value.

So I think it’s very open ended and we get so excited to have students come in and explore with us. They don’t have to be at any specific point in the game. They’re free to come see us whenever.

I think that those are some things that I would want more students to know about career services. That and the fact that we’re humans. I live in the same world that they live in. The same things that they’re seeing and that they’re affected by are affecting us and are also inspiring and driving us as well.

AP: All right, so now just a quick speed round. Favorite restaurant in Charlottesville?

Reggie: I would have to say the Brasserie Saison.

AP: Favorite thing to do on weekends?

Reggie: Get outside just in general. I’m boring on the weekends. I don’t want to have plans. That’s why I live downtown, so I can just roam and whatever comes up, comes up.

AP: Favorite coffee shop in Charlottesville?

Reggie: It’s actually just outside of Charlottesville, but I’d say the Mudhouse in Crozet.

CommunityBuilders is a publication that shares the stories of young makers, builders, and creatives who are making a difference in their local communities.

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