How Rachel Carries Her Teaching Past Into Her Legal Career

September means a return to school for students and teachers across the United States—a routine that former teacher, employee benefits, and executive compensation associate Rachel Mann knew well. After graduating from the University of Pennsylvania in 2012, Rachel spent six years as a teacher, getting her start in the profession through Teach For America.


She still maintains ties to her education life, counting universities among the firm’s clients she serves and keeping up with former students as they embark on their own journeys into adulthood. Rachel shares with us her path to becoming a lawyer and lessons she brought with her from the classroom to the legal profession.

How Did You Decide To Join Teach For America?

In college, I majored in history and absolutely loved it. I did a history honours thesis program and while deciding if I wanted to go the Ph.D. route or something else, a professor told me that he thought I would be better off being a high school history teacher than going the Ph.D. route.

In high school and college, I had a part time job teaching Sunday school at a local synagogue and so I really liked teaching. I was a camp counsellor. There are a lot of people in my family who are in the teaching field and Teach For America recruits very heavily from Penn’s campus, so it kind of all converged onto that.

What Were The Most Rewarding Aspects Of Your Teaching Career And What Were Some Of The Hurdles To Leaving That Career?

The most rewarding thing also made it the hardest to leave, which were the relationships that I built with the people, particularly the students and the families. Anybody who is a teacher knows it is a service profession where you are completely giving of yourself—your heart, mind, and soul 24/7 to the kids. I was teaching high school, so I was helping students get ready for college. It’s such a transformational point of life that you can really help them shape themselves and think about “What path do I want to be on? What do I want to do? What do I want to be?”

How Did You Decide On The Field Of Law That You Are Currently Practicing?

It was definitely the people. I have a good friend who is an employee benefits lawyer and she was a big mentor of mine through the whole process of deciding that I wanted to make this career switch. I had never heard of employee benefits law and she sort of looped me in.

The summer I started law school I had a research job for a professor at Penn Law School and he had a former student who was an employee benefits lawyer at Morgan Lewis at the time. She was amazing and she introduced me to everybody in the group. I didn’t fully understand what they did at the time, but thought they were great and smart, and I wanted to work with them.

What I find rewarding and satisfying about this area is that it’s always changing. A new regulation will come out and nobody knows what it means, nobody knows how to follow it and we’ll be the first to read it. For example, when the new ESG rule came out last year, nobody knew what it meant or how it applied, and so clients were coming to us for a first look, and that was so cool that they would put their trust in us and what we would say mattered.

More recently with SECURE 2.0, our Plan Sponsor Task Force was all over being the first people to figure out about what it means. That’s a very exciting, interesting part of our practice. It feels like we’re helping to shape thought leadership that’s out there in the world that other lawyers and companies are following.

What Were Some Of Things You Pulled From Your Time In Schools Into Your Current Career?

I think there are a lot of overlapping lessons from teaching to law. One is they are both service professions. I think not everybody realizes that about law, especially when you are coming from law school and been in the books. But we are here to serve our clients when they have an opportunity or a challenge that they need help fixing. That’s just like teaching—where I am serving the kids and serving the parents. Those were my clients. The idea of client service and what is doing best for the client. As a teacher it’s not about what is best for you, it’s about what is best for the kid. And the same in our profession, it’s about what is best for the client.

Two is public speaking and explanation skills, the ability to take something super complex and break it into bite sized chunks that someone who doesn’t know a lot about the topic can understand. Obviously, it’s a different topic I’m teaching about now, but I do really think about lawyers teaching our clients about the law and how the law applies to them in a way that makes it sticky and engaging.

Then after getting up in front of a room of 11th graders, you aren’t going to fear anything in life!

What Piece Of Advice Looking Back Would Lawyer Rachel Give Teacher Rachel?

Lawyer Rachel would say to teacher Rachel, "Don’t change anything about your past.” People ask me all the time, “Do you regret teaching for six years?” I don’t regret one bit. I learned so much. I built great relationships with people. I had my mind expanded in all sorts of different ways that I never could have imagined. I enjoyed it. I learned a lot and I wouldn’t take back that time for one second.

Also, it wasn’t my intended path. I didn’t go into teaching thinking, “I’m going to use this to get into law school,” and I’m really glad I didn’t because it would have sort of cheapened the whole experience I had with teaching. It wasn’t a stepping stone. I went into it with the intention that I was going to stay, and I was going to be a teacher for life and in the end I didn’t. But I wouldn’t have stayed one fewer year or gone straight through. I was passionate about it then, but that passion changed and shifted, and I shifted along with it, but I got so much from the experience.

What Does Back To School Prep Look Like For You Now?

I have a 7-year-old going into second grade and a 3-and-a-half-year-old who’s going to preschool. I try to keep summers light and fun and try to hang onto that summer vacation feeling when they’re home more and we get more quality time as a family. School will pick up, extracurriculars, and sports will be upon us soon enough.

Our top picks

Slide 1/5

Get results tailored to you


You might be interested in...

Thumbnail for Shoosmiths - Focus on Edinburgh

Shoosmiths - Focus on Edinburgh



All employers