The University of Virginia’s School of Law checked in with some of its alumni to see how they are doing five, 10, 15 and 25 years after graduation.

See how Jake Gutwillig, Ashaki Holmes-Kidd, Tanya S. Wang and Douglas Eckert are using their degrees now.

Five: Jake Gutwillig, Class of 2013

Associate, Sullivan & Cromwell

New York, New York

(Photo by Samuel Stuart)

Describe your work: My work focuses primarily on white-collar criminal investigations. On a given day, my responsibilities include preparing presen­tations to government authorities, conducting witness interviews, and working with clients and co-counsel to chart the course of investigations. It’s an exciting job that has taken me around the world and allowed me to work with wonderful, dedicated colleagues, from whom I have learned a great deal.

What activities do you enjoy outside of work? Anything that allows me to be outside. In recent years, my wife, Victoria Morphy Gutwillig (Class of 2014), and I have gone on a number of ad­ventures, including visiting national parks in the U.S. and hiking in South America and New Zealand. However, these days, our time outside work involves our newborn daughter, Eleanor, so we’ve happily traded Machu Picchu for walks in Central Park.

Are you where you expected to be at this stage of your career and life? Not at all! Ini­tially I was set on a career in corporate law focused on mergers and acquisi­tions. However, following a year at Sullivan & Crom­well doing transactional work, a federal clerkship inspired me to change course and pursue litiga­tion with the hope of be­coming a prosecutor. Re­cently, I accepted a position as an assistant U.S. attorney for the Southern District of New York, which I expect to begin in the coming months.

What do you like about your life five years after law school? UVA Law has given me so much: a tre­mendous education, a sense of professional purpose, wonderful friends and, of course, Victoria and Eleanor.

Ten: Ashaki Holmes-Kidd, Class of 2008

General Counsel, Parkway Property Investments

Orlando, Florida

(Photo by Dynamite Studio)

Describe your work: As general counsel, every day pres­ents a new challenge, which I find enjoyable. When we were publicly traded (until October 2017), I oversaw our SEC filings and com­pliance matters. Now, as a private company, on any given day, I am negotiating joint venture agree­ments, loan agreements, and/or purchase and sale agreements for the acquisition of new assets. I also oversee all internal legal matters, ranging from employee-related matters to establishing and imple­menting internal policies and procedures. I particularly enjoy being part of the executive man­agement team that decides the company’s current and future investment strategies.

What activities do you enjoy outside of work? I love to travel, and my husband and I visited our seventh continent, Antarctica, in December 2017. We are expecting our first child in October and are looking forward to bringing him along on our future travel adventures. When we are not traveling, we enjoy partak­ing in Orlando’s burgeoning food scene and attending performances at the Dr. Phillips Center for the Performing Arts and the Orlando Shakespeare Theater, where I was recently asked to serve on the board of directors. I am also a member of the Smithsonian’s Orlando Host Committee, which focuses on bringing some of the extensive offerings of the Smithso­nian to Central Florida.

Are you where you expected to be at this stage of your career and life? Yes and no. I knew early in my career that I wanted to work in-house and eventually be general counsel of a public company, but I did not expect the right in-house position for me to be in Orlando, or to be named general counsel at age 33. I also did not expect that my company would go private a year after I assumed the general counsel role. My career path has had several unexpected twists, but I am thankful for the journey and where I am today.

What do you like about your life 10 years after law school? I love that I enjoy my job and the people with whom I work. I also love that I have a supportive husband, loving parents, wonder­ful friends and the cutest dog in the world, Minnie.

Fifteen: Tanya S. Wang, Class of 2003

Senior Attorney, IRS Office of Chief Counsel, Criminal Tax

Dallas-Fort Worth, Texas

(Photo by Ardena Castillo)

Describe your work: After my time at UVA, I got an LL.M. in taxation from New York Uni­versity. Since graduating from NYU, I have been with the IRS Office of Chief Counsel. I worked in one of the civil divi­sions for many years, advising audit teams on legal questions and litigating in U.S. Tax Court. Despite being the hardest class in the LL.M. program, partner­ship tax was my favorite work. Starting this year, I transferred to the criminal division. Now I am working on issues that I have not thought about since law school, like probable cause. I even dug out my notes from Professor [Anne] Coughlin’s Criminal Investigation class and remembered her discuss­ing whether a man could fit in a washing machine.

What activities do you enjoy outside of work? My husband and I have a 6-year-old son and a large German shepherd. They are both a handful – lots of activi­ties and mischievous deeds to keep us occupied. I also teach Zumba classes a few evenings during the week. Being a fitness instructor is a fun creative outlet for me. I am thinking of starting a legal FAQ blog for fitness instructors, to combine my legal knowledge with my hobby.

Are you where you expected to be at this stage of your career and life? The only thing that I was certain about at graduation is my dislike of litigation, and after 15 years, I am still right on that one. When I left UVA, I wanted to do estate planning. I definitely did not think that I would be with the government this long. But I have enjoyed working in an environment where reaching the right result is more important than winning the case. The flexibility of the government job also made life a little easier as a working mom.

What do you like about your life 15 years after law school? I like that my life is very balanced. My work is challenging and interesting, but I leave the office at a rea­sonable hour. And my evenings and weekends are mine to spend with my family and teach fitness classes. 

Twenty-Five: Douglas Eckert, Class of 1993

Executive Vice President and General Counsel, Hoar Construction

Birmingham, Alabama

(Photo by Liesa Cole)

Describe your work: I am a partner in an ENR [Engineering News-Record] top-100 contractor based in Birmingham, with offices in Houston, Austin, Nashville, Orlando and Washington, D.C. My work has gravitated from pure legal counsel to responsibility for shared services – legal, human resources, risk management and sales/marketing. Day to day, I supervise professionals in each of these areas who lead the compa­ny’s efforts. As general counsel, I deal with traditional corporate functions but, more frequently, am involved in contract negotia­tions.

What activities do you enjoy outside of work? I have always enjoyed sports, watching and playing. Unfortu­nately, I blew out my knee just before law school and have spent the last 25 years having many knee surgeries, so my focus right now is golf. I also love to travel, whether it is for golf or sightsee­ing, and our family has a tradition of extended vacations overseas during the summers.

Are you where you expected to be at this stage of your career and life? I am thrilled to be where I am, but I can’t say I saw this path. I enjoyed the tradi­tional practice of law at a great law firm in Birmingham, Bradley Arant, but also loved the manage­ment side of the practice. I really loved acting as outside general counsel and helping clients solve business issues before they became litigation. That probably led me to private business.

What do you like about your life 25 years after law school? My family. I have two daughters, one who just gradu­ated from UVA and one who is still there. That has permitted me to reconnect to the school. I love our choice to move to Birming­ham instead of a larger city, as it has been a wonderful place to raise a family and for my wife, Kathryn, and I to get deeply engaged in the local community. I am thrilled to be at the point in my career where I worry more about the development of those who work with me. One thing I do love about UVA Law School is how connected the alumni are – to this day, many in my Class of 1993 are close friends, and I think UVA Law had a huge positive influence on each of us.