One lawyer’s unconventional path to career satisfaction

Sometimes the road ahead is winding, full of blind corners, and paved with uncertainty. For lawyers who find themselves dissatisfied with the traditional career trajectories of in-house counsel or the partner track, finding and embracing alternatives can be nerve-wracking, to say the least. But sometimes it all works out for the best.

We spoke with Jenn Peru Gary, a practicing attorney-turned-eDiscovery consultant, to hear about her quest to balance career with family, and how an unexpected option can turn out to be a perfect fit.

Law at the DOJ: the early days


They say it’s always best to start at the beginning: in your case, at the Department of Justice. How did you get in there?

I started my career through the Attorney General’s Honors Program, with the US Department of Justice. I was with the Criminal Enforcement Section of the Tax Division. I started there back in 2000, and it was extremely cool because at the time, Janet Reno was Attorney General, and she was the person who swore me in and appointed me. I will forever be so grateful that I was appointed to the Honors program during her tenure. She was the person who signed my certificate and handed it to me, and it was really just one of the great honors of my life. She’s truly a presence in every sense of the word.

And so for the next six years, I was a federal prosecutor with the DOJ.

That must have been exciting – and intense. What was it like? 

I loved being a part of the Justice Department. I got to be involved in lots of interesting and challenging work, and I met so many accomplished, fascinating people. Most of all, though, I loved what it felt like to stand up in court and say that I represent the United States of America. My dad is a retired Air Force veteran, so I was raised with a great sense of patriotism. The privilege of representing our country in federal jury trials is a feeling I’ll never forget.

What were some of the challenges?

Basically, what ended up happening for me was that as much as I loved it, I also slowly began to realize that representing the United States of America meant that the only time I was dealing with other people (aside from my colleagues) was when I was in full-on trial prep, working with IRS Special Agents and Revenue Agents, and interviewing witnesses that I was going to put on the stand. I’m very much a people person, so the fact that you sort of have to work in a vacuum so much of the time wasn’t great for me. I wanted to have the opportunity to work with a broad range of clients.

The other major challenge was the amount of travel that was required. We were deployed to various US Attorney’s offices throughout the country. I covered the southern region, and early on I loved being able to travel and meet new people and experience different places. As a young, single attorney, there’s so much luster to that, but it starts to lose that luster after you’ve been living out of a suitcase for six years. 

Once I got married and we started talking about having a family, I realized that I was ready to put the suitcase away and settle down. And that I really wanted to do something that would let me engage with people much more than my work at the DoJ could. So I decided to explore the private sector.

The move to Big Law


Was that when you transitioned to a law firm?

Yes. I reached out to a friend I’d gone to law school with, who was at Blank Rome in Philadelphia. And I really just sort of shared all my thoughts and fears with her. The DoJ was all I had known, but I felt that I owed it to myself to at least give the private sector a try and see what law firm life is like. And call it what you want: serendipity, luck, whatever. I’m a strong Christian, so for me it was all part of God’s plan. They’d just lost a key person who was doing criminal tax work, and the Partner was looking for a replacement. My friend was like, your background couldn’t be more perfect, let’s put you in touch with them. I literally had an offer within three weeks of reaching out to her. 

It was fast and furious and crazy, and I was totally scared, but I dove in head first and took a leap of faith and joined their DC office as part of the white collar defense and internal investigations practice group. And I was so fortunate to work with an amazing group of people, and to have an incredible mentor in my life, whom I still love dearly. I had the opportunity to work on a lot of interesting cases, across the entire gamut: from FCPA to mortgage fraud to healthcare fraud and abuse, maritime law, environmental crimes…I really enjoyed being able to to do such a broad range of white collar work.  

But by the time I had been there for seven and a half years, I was pregnant with my second child.  When I’d been pregnant with my first, I’d been a member of a team that was handling a large insurance bid-rigging case, which culminated in a nine-month-long trial. Having experienced that as a new mom, I knew I didn’t want my professional life to be so all-consuming the second time around. It was just so exhausting and intense. The hours were unbelievable, and it really made it clear to me that as much as I enjoyed it, and as much as it satisfied my desire to engage with clients, the intensity just wasn’t compatible with the kind of mom – and wife, because I actually do like my husband! – that I wanted to be. That lifestyle was going to be unsustainable for me. I knew that I needed to make a career change. I just didn’t know what that was going to look like.

The perfect fit: life on the service side


But now we know what it looks like, of course: you’re at Trustpoint.One. 

Yes – and to tell you the truth, never in a million years would I have thought that I’d end up at Trustpoint, or at a company like it, or doing what I’m doing now. It never would have occurred to me that this was even an option. 

You’ve been in three very distinct worlds now – what are some of the unexpected positives, and what are some of the challenges?

That’s a great question – I’ll start with the positives. I shared that I’m a person of faith, and anybody who knows me will tell you I’m very open about that fact. I don’t ever put my faith on anyone else, but it’s an integral part of my life. And it truly feels as though Trustpoint is where I’m supposed to be. I love the camaraderie that we have – it really feels like a family. We all roll up our sleeves to get things done. You’ll never hear anyone say “that’s not my job.” There’s never been a hierarchy – we’re all just members of the same team, and I love that the people I work with have a genuine desire to do the best job we can. 

In addition, it satisfies everything I was trying to achieve when I thought about making a career transition, in that even though I still work crazy hours sometimes, I still have more predictability in my schedule than I ever had as a practicing white collar criminal defense litigator, particularly where travel is concerned. Any litigator will tell you that your schedule is driven by deadlines – and often they’re immovable. And particularly in white collar criminal defense, you’re always working with clients in crisis. You never hear from a client who has exciting news or is seeking your help with protecting a cool invention of theirs, as an example. It’s always “I just received a subpoena, and I’m under investigation.” Or “The vessel’s oily water separator was being bypassed and a crew member knew that.” They’re always completely stressed – they’re scared. So if you’re a person who cares deeply about people in general, the way I do, you really take all of that on. You become their therapist, their friend…it can become overwhelming. And that’s the part that has been great about this role: I get to remain connected to the law and the legal community, but I also get to maintain some distance from that intensity. While my clients are working with people that are in crisis, I am removed from that level of intensity to a degree. And that’s been a real relief for me, in a way that I didn’t fully appreciate while I was practicing law. I knew the stress was there, but I didn’t understand how much it was affecting me, in every way. Exhaustion. Health. Time away from my family. Coming to Trustpoint has truly been such a blessing.

What about the challenges? 

I’ve come to believe that there’s really no such thing as true work life balance – it’s never perfect. There will be times – and sometimes it varies from day to day, sometimes moment to moment – when you feel like you’re doing your job on the most badass level, and then you’ll have the most tremendous guilt. Be it Mom guilt, wife guilt, or pet parent guilt. And then at other times, you’ll feel like you’re crushing it on the mom front by chaperoning a field trip, and then realize that you missed a call from a client. There’s never going to be a time where you feel like you’re doing it all perfectly. 

And of course, in a client services role, when you genuinely care about the people with whom you’re working, you want to make sure that every client is being given the attention that they deserve. I take my work for each of them very personally, and I do whatever I can to ensure that their matters go well – almost as though they’re my only client. So those challenges still exist. 

That said, one thing has been something of a pleasant surprise: I’m always humbled by the fact that my background resonates so much with clients. There’s almost this sense of instant credibility, and it never ceases to amaze me that as a result of my professional experiences in the “federal prosecutor posse,” they look to me to provide a consultative approach in matters of legal strategy. That’s been really cool and exciting, and such a refreshing surprise every time it happens. 

Do you think there’s a specific type of background, or a specific type of person that thrives in this environment?

You’ve got to like people. You need to truly like engaging with people and being social if this kind of work is not going to feel like work to you. Building relationships and connecting with people has to come naturally. And you also need to have thick skin, because client relationships are tricky. Anyone who’s in any kind of business development role will tell you that you have to find that balance between staying top of mind, and not being a pest. You don’t want to become one more thing on their to do list. Especially during 2020 – I mean, during a pandemic, business development seemed so inconsequential to me. So instead, I just focused on checking in, connecting with people, and just making sure everyone was ok.

So what would you say to someone who might be about to embark on a similar journey? 

I often hear from attorneys – especially women – who are struggling to juggle practicing law and do a genuinely good job, while simultaneously maintaining a home, and a marriage, and a family. And in 2020, we were all presented with a whole host of new challenges. We were all thrust into a new reality, with zero ability to plan, and you’re talking about people who, for a living, plan and advise and strategize. So it was extra tough — for all of us.

What I always say is, I understand the fear. I understand the insecurity. But if you’re miserable on a daily basis, and you’re starting to see the effects of that on your mental and physical health, you owe it to yourself and the people you love to make a change. 

I never want to minimize how daunting that is, because I’ve felt it. I mean, it took 9 months to get my first client matter at Trustpoint, and even though I’ve been really successful here over the past seven years, those first 9 months were grueling. So I truly understand how difficult it is to make that change. But I’m so, so grateful that I stuck with it and gave this a chance. 

And when things are tough, I often remember something a very wise woman once told me. She’d been in the business for many years, and she said, Look, you have to think of this like gardening. People refer to business development as hunting, but it’s not hunting. It’s gardening. You plant the seeds by developing the relationships. You water them and fertilize them over time, by keeping in touch, by having discussions, by finding ways to form a real human  connection. People are not robots. And while a partner at a law firm or General Counsel at a corporation may seem intimidating, at the end of the day we all put our pants on one leg at a time. Remember that, and continue to reach out and make those connections. Find that common ground, and eventually, the fruit will come in and you will see a harvest.


Jenn Peru Gary is a former federal prosecutor and white collar criminal defense litigator with over thirteen years of experience conducting internal investigations and leading or defending against government enforcement actions. As a Managing Partner at Trustpoint.One, she strategizes and partners with clients to provide a measured and thoughtful approach to handling their e-discovery and document review challenges in the most efficient and cost-effective manner possible.