Women who have scaled great heights in their legal careers can be intimidating. There they stand, atop the pile, secure at the end of a long, ambitious journey. Depending on where you are on your own climb — or detour — their successes may be inspiring, dispiriting or perhaps no longer relatable. The case against careerism has not been lost on me.

This led me to seek out younger women still in the process of figuring it all out. Women who may be reaching for the top of the pile, or may be contemplating a major change in direction — perhaps married, perhaps not, perhaps raising children, perhaps still deciding what they love and how to pay the rent while doing it. I don’t think you’ll read any of the interviews in this series and think these women have all the answers. Finding meaning is an ongoing process, even for those who seem to have solved the puzzle.

For the first installment, I spoke with Heather Dietrick, who left the security of firm life and dove into the turbulent waters of Gawker Media. She signed on as general counsel, then added the title and responsibilities of company president, making her — at just 34 years old — the most senior woman in the company. I was intrigued, and her job seemed enviable, at least until I walked in the door.

Arguably, she traded Big Law for big problems: A lawsuit by Hulk Hogan over publication of his sex tape; disputes over editorial direction played out in public; resignations; unionization. Last week, a chilling piece on Gawker’s so-called “problem with women” was published. When asked for a comment, Heather said only that she welcomed the open discussion but that these were matters “to be addressed internally.” And now, the company has announced a major pivot in its editorial mission, swapping pop culture for politics. Heather has not adopted the penchant for over-sharing the company is known for. But reading between the lines, I realized that detours can be as disquieting as staying the course. But that’s not news, that’s life.

This interview has been edited and condensed.

Heather Dietrick: In law school, I was interested in the First Amendment, technology law and intellectual property — and was the managing editor of the University of Michigan’s telecommunications and technology journal. I was also very interested in journalism. I wanted to put all of those things together.

I thought that a law firm was a good place to get initial training. At the firm I went to after graduating law school, I worked with a partner on a First Amendment case that was going before the Supreme Court. Rumsfeld v. FAIR was a group of lawsuits challenging the Solomon Amendment’s requirement that universities allow military recruiters on campus [to receive federal funding]. We unfortunately lost that case, but we challenged it, saying that it was a violation of the First Amendment rights of the law schools, who were essentially forced to bring these recruiters on in contravention to their beliefs.

Initially, I applied just to law school, then I decided to add an MBA. I thought that, at some point, I might want to take my career in a more management-focused direction. It wasn’t entirely clear to me how it would work out, but I thought the MBA would open some doors and teach me relevant skills. I took the GMAT in the fall of my first year of law school.

I loved the firm. I loved the people. It was just what I was looking for in a law firm. People were really passionate about the work and struck a nice balance between their work and their home lives. They also had a growing IP practice, which interested me. Then I had a second summer, at Weil, Gotshal & Manges. I wanted a contrast, to see what a different kind of firm was like. It was much larger — I think my Heller summer class had maybe 10 or 12 people. At Weil it was 107 or 108, or something like that. Both were good experiences, but I wanted to start somewhere with a large national practice and a smaller office.

I wanted a firm that was big enough to have first-class clients but small enough to develop personal relationships, both internally and externally. As a young lawyer, I thought there would be more opportunities to do that at a smaller firm. That’s probably too general of a statement, and I think experiences can differ across firms. In a big law firm, you might be part of a small, targeted group that has good relationships inside and outside.

Heller felt right, so it wasn’t that difficult of a decision for me. As it turned out, maybe I chose wrong, because in November of 2008 — at the end of my first year — Heller collapsed. It was a bit serendipitous that I was already looking for a new firm.

A seat at the table: Heather hopes to foster a more inclusive environment at a company that has been criticized for lacking gender diversity. Photo: Hannah Thomson

I was very happy there. I liked the work; I liked the people. It had a nice, family feel and it seemed like somewhere I could stay for a while, develop my skills and figure out the next step. But I was thrust into figuring out the next step much sooner than I expected.

Then I went to Goodwin, where I was totally focused on IP and litigation — which formed a nice basis for some things I do now. I arrived in 2008, so I was probably one of the last people hired before belts were seriously tightened. After I started, I got a federal clerkship offer with Sandra Townes, in the Eastern District of New York. I was at Goodwin for about two years, then I started clerking. While I was clerking, I realized that I really, really wanted to move into media law.

Clerking is a very busy job, but you have more time to think about what you want to do next. And you’re encouraged to do so because you have a hard stop at the end of the clerkship. Knowing I had to make a change, and that it was time to figure out, strategically, what that change should be, made it a clarifying moment for me.

I was looking for First Amendment opportunities, but this one came about socially. My husband met someone at Hearst who had the fellowship a few years earlier. (She actually now works with us at Gawker.) And he said, “Hey, my wife has been looking for this type of opportunity,” and put us in touch. That was very early in my clerkship, so I said to her, “I’m incredibly interested in this for when you’re hiring your next round of fellows.” We stayed in touch and I applied at the right time in their cycle. And it was just an amazing, life-changing opportunity.

Not in a strong way, no. It was a possibility that I would go back to firm life.

They have one slot for a fellow every year. The New York Times also has a First Amendment fellow. I think Gannett does, or did at one point. But it’s pretty rare. These are extraordinary opportunities where you are completely immersed in First Amendment law. Hearst starts out teaching the fellow FOIA, essentially, open-access issues. Then you branch out, working on other First Amendment litigation, mostly on the defense side. The legal team supports Hearst’s huge variety of newspapers, television stations, magazines and websites. It operates like an internal law firm, handling almost all of the litigation, soup to nuts, in-house. At the time, the team was composed of about seven people, plus some support.

They probably get a lot of capable applicants. I’d say the defining factor is a true interest in journalism and free speech — a real belief in it. I think they’re also looking for someone who believes in strategically advancing the law in different jurisdictions, making access to courts easier and access to information easier. Also, someone who really believes in supporting journalists and the work they do.

Good question. Part of it was my background in journalism, which I didn’t take very far, but I worked at my high school paper. And my commitment to seeking out this type of work when I was in a law firm. First Amendment work can be a little difficult to find unless you’re in one of the few practice groups that really focus on it. It’s not a huge industry; the bar is fairly small, and it’s a tight-knit group.

It was, yeah. I knew our, now former, CTO as an acquaintance through other contacts. I said to him, at least a year before, “I’m really interested in this type of work. When I’m ready and feel like you’re ready, I’m going to send you my resume.” And I did. When I heard that the person overseeing legal at Gawker was moving, I sent my resume over and he connected me with the right people here.

You always hear how valuable it is. I think it’s really hard to understand how networking might work out for you when you’re early in your career, whether it’s law or otherwise. I wasn’t focused on it in a targeted way; I think it was just natural for me. I’m a people person and like to learn what other people are doing and keep in touch. But now I realize that it’s just invaluable — both understanding what opportunities are out there and helping to run this company.

When I came on, there was another lawyer who was a little more junior (since then, we’ve built out a team). There was some apprehension — but the company’s willingness to defend its journalism was a defining factor for me. Even though it was a big job, I thought going to a company that shared those beliefs about free journalism and what’s newsworthy would make sense for me.

More than apprehension, I was attracted to the fact that the writers here aren’t afraid to reveal the world around them. Deadspin’s motto is “Without access, favor or discretion,” but every site really lives that. They don’t acquiesce to pressures that make it difficult in this country to cover politicians, celebrities or other subjects that are meaningful to readers.

I think it was a legally defensible piece, but it stepped over a line editorially that we don’t want to step over. We drew a line in the sand, and the founder made the decision to take it down. I voted to keep it up, not because I supported the content but because I thought if we left it up, we could have a conversation around how this wasn’t the type of journalism that we want to do.

Yeah, it was challenging for the whole company because one of the defining features of this place is that every person believes in the editorial mission to tell meaningful stories that reveal something about the way the world works. That piece was an extreme anomaly, but we learned something from it and we’ve recalibrated our editorial and refocused on the kind of stories we want to do. I think it’s important that people took something away from what was a tough time.

Well, I mean, since I’ve been here, we’ve never before talked about taking down a post. But I work closely with editorial. I defend the things that they do, and I vet a lot of the content. We have a team of people here who also help with that, even more since I’ve taken on other responsibilities. But I still work quite closely with edit, reviewing the content from a legal perspective. Sometimes you end up having conversations about the editorial direction, but ultimately that’s up to the editorial folks and our executive editor.

I think a legal operation in a media company can work one of three ways. You can be a complete service organization for editorial. You can swing to the other side of the pendulum and sort of force judgments on them. Or, you can work in partnership — which is what we try to do here. It’s as much our goal as it is edit’s goal to get stories out. And to tell those stories in the voice of edit but, of course, in a way that’s within the bounds of the law. I think that’s what we’ve done here building the team.

I don’t think they roll their eyes. If they send a piece to legal, the thing that is affected the most is time. It takes time to review, ask questions, go back and forth, and maybe do a little more work on the story. But I think the writers believe that we want to get these stories as much as they do.

It’s very fast-paced. The legal team handles all the legal work around here, but talking specifically about vetting content, you want to take your time with it, so you rely on the writers and editors to communicate a timeline that’s reasonable.

Sometimes they’ll say, “This is a really hot story, we want to figure out a way to get this out the door quickly.” Other times, you have a little bit more time. We don’t review every single piece of content that goes out the door — that’s just not necessary — but we constantly work with the writers and editors to make sure we’re all on the same page. That they’re able to make the calls and say, “Hey, this looks like something we should kick over to legal, let’s work with them on this.”

I’ve been president since the beginning of 2015 and I think it came about for two reasons. First of all, working closely with the editors — which I had already been doing — is a natural fit for leadership because the whole company is behind the editorial mission. And I still work very closely with the writers to support that mission. Secondly, what you do as general counsel ends up touching every part of the business at a place like this. So, I started learning every part of the business in detail, which is why it made sense to step into this larger role.

It’s a mix. You learn the nuts and bolts of finance, management, that kind of skill in an MBA program. But actually doing the job is a fluid experience. It changes day to day, so you’re learning on the job too. Gawker’s a special place. I don’t think you could just walk in here. You have to understand the culture and how it works.

I take the position of being the most senior woman in the company very seriously, and I think a big part of my job is to help other women grow here — make sure they see a path for themselves and understand how to advocate for themselves. That’s a work in progress.

When I said it wasn’t a big deal, I meant that the management here has supported me and advocated for me. Now it’s my responsibility to do that for other women in the company. My personal style is very hands-on. If I could meet with every single person in the company once a month or more, I would. Time does not always allow for that, but I try to foster a place where people know that I always have time to talk and develop relationships with people that I don’t necessarily work with day-to-day.

That’s true internally, which is what I meant. Externally, there are certainly lots of times when I’m the only woman. In a room full of a dozen male lawyers, you need to remember to project confidence and hold your own.

Well, you have me in this role, which is meaningful, and right now nearly half of our site leads are women. But we wanted to go further down in the company. One of the things we’ve discussed with the union — I don’t know if you heard; the writers voted to unionize — is creating a group that is focused on diversity, because it has to be more than just the people at the top talking about it. I think everyone in the company should be thinking about it. We don’t want one viewpoint on the world; we want many of them. And it’s something we need to incorporate into our interview process.

We met in law school. We both worked for law firms for a while, and I think there’s an advantage to being married to a lawyer — they understand that sometimes you’re beholden to court dates and last-minute blow-ups sometimes take you away. We’ve been fortunate to have differing periods of busyness.

He currently works in-house, in the genetics department of Mount Sinai. His schedule is a little more predictable than mine is, but we still have to focus on making time. We don’t have kids, but if we don’t affirmatively make sure to carve out time, work ends up consuming it.

I actually have never caught the baby bug. For many years, I was waiting to, but I think I’ve come to terms with the fact that I just might not. And I think that’s okay. We’ll focus on other projects together.

I hope it wouldn’t be. We live in a world where maybe, ultimately, it is. But I’d like to help foster the environment at this company so it’s not an advantage. I have enormous respect for the people who work here, at all levels of the company, who have kids. A lot of them have busy jobs — the news cycle moves very quickly. I always try to make sure they have plenty of time carved out in the system to spend time with their family.

It’s really flexible; we don’t have the pressure of face time that you see at law firms. That being said, the editorial group, at least, is sometimes beholden to the news cycle. But I think they’re very understanding of each other, and take on responsibilities when someone needs to spend time with family. In our legal group, one lawyer has three kids and it’s just a matter of being flexible so she can go home and see them every night. I might take over some stuff if something pops up when it’s time for her to do that.

We really let the writers decide for themselves. The idea originated with them. They created their own public debate about whether they should unionize. We essentially set up a thread on one of our sites. And they debated it and communicated; the way they communicate best is on our website. We thought, “We’re about the freedom to think and to speak, and so we should absolutely let everyone do that and figure out what they feel is best for themselves.”

Staff working from laptops in the screening room creates a laid-back atmosphere more reminiscent of dorm life than firm life. Photo: Hannah Thomson

Sure, and just to clarify, if people don’t know the circumstances, this 30-minute video arrived and we published a little over a minute and a half, with just a few seconds of sex. The idea was to show what is actually happening. Before we ever published a word, there was a lot of speculation in the media about the existence of this tape, who was in it, and what the circumstances were. Hogan had been out in the media talking about his sexual prowess and various sexual encounters, and also about this woman in the video — particularly saying he never slept with her, when he actually had. In this media conversation, there was misinformation about the video.

There was speculation that this was a sting operation, that he was catching his wife in the act. It turns out that his friend in the video had actually blessed the encounter. So when the video arrived on our doorstep, we did what news organizations do, take the new information and clarify the story. You have the subject of a story lying about part of it. You have rumors flying that aren’t true. So we published a bit of the video and then the narrative: “There’s interest in celebrity sex in this country, but it’s actually quite mundane — here’s what’s happening in this particular video.”

They sued us in federal court a few times; now we’re in state court. But we got a few federal decisions, and the state upheld its decision in our favor, saying this is protected by the First Amendment. It’s a matter of public concern. People are talking about this, the subject of the story’s talking about it already, and celebrities and politicians in this country aren’t allowed to say, “Hey, I’m the only one who’s allowed to talk about this subject,” or, “You have to talk about it in exactly the way I want you to.” Once the topic is out there and people are speculating and discussing, journalistic organizations are permitted to — and supposed to — say: “Here’s what’s happening: We’re revealing something about this celebrity, this person in power.” Which is what we did and the courts have agreed that that’s protected by the First Amendment.

Litigation is ongoing; we’re going to trial on March 7.

I think it would for the reasons I just described. Celebrities are incredibly powerful figures in this country. You see them, and their PR machines, shut down stories or direct the coverage about them. Which is fine, that’s their job.

But it’s a news organization’s job to reveal something about who they are, especially when you have one of the most famous people in the world presenting one image in public and doing something else in private. That is fundamental to all sorts of stories, ones that we do, ones that the New York Times does — and, frankly, underlies basic reporting about people in powerful positions.

Very involved.

Either I, or our other litigators, take a very hands-on approach. We have really excellent, top-notch First Amendment outside counsel. But there’s a lot of coverage on the company, and we want to make sure we’re always telling our story in our voice; it’s important. Whether it’s on our sites or in court papers.

I would say: Take risks. I think a law firm can sometimes be the path of least resistance. And law firms provide really excellent training, so I don’t rule them out entirely. But keep your eyes open to other opportunities and be willing to take risks. I am aware that there is a lot of serendipity involved in my path — along with keeping an eye out for opportunities that matched what I wanted to do, even if there was a little risk.

Law firms obviously are some of the most highly paid jobs — especially for young lawyers — but I think it’s worth sacrificing to pursue something that you really want to do.

My husband and I both taught undergrad English classes at the University of Michigan. And the university treated us essentially like PhD students and comped our tuition for three of my four years and for two of my husband’s three years. That was a very good point, because me being able to say, “Take risks,” is reliant on not having the crushing student-loan debt a lot of people have coming out of law school.

Every single day, I love walking into this place, and I want to make it a place where every person working with me feels that way too. I think that’s really true here; it’s just a very special place.