The Legal Department Podcast with host Stacy Bratcher

Stuck At Work? Tips To Reboot Your Career With Ellen Yang [E84]

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Stuck At Work? Tips To Reboot Your Career With Ellen Yang [E84]

You’re at a great company, with a fancy title and what seems from the outside to be exciting work. But all that glitters is not gold. No matter where you are in your career–whether you’re just starting out or at the top of the career ladder, you can feel stuck.

Ellen Yang shares advice for attorneys and managers alike on how to recognize that you (or your team) might be feeling stuck and how to break through that to find something more fulfilling. She has specific advice for senior level lawyers, deputy GCs and associate GCs, about how to fill out that resume to get GC ready.

Ellen also did the unheard of: she returned to a law firm after more than a decade in-house. Tune in to learn about that experience and whether a return to the “dark side” is right for you. Lots of great stories and advice here to help you level-up, whatever that means to you.

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Listen to the Podcast here

 

Stuck At Work? Tips To Reboot Your Career With Ellen Yang

As we move into the end of the year, it seems like everybody else’s priority is fighting for number one on their to-do list. The client wants their deal done, the project has to get across the finish line by the end of the year, the holiday parties to attend, the presents to wrap, the travel to book, it’s all too much. Although everybody else wants your time, I’m going to encourage you to take a moment for yourself.

I talk a lot about not sleepwalking through your career, not working on autopilot, but thinking intentionally about where you are and where you want to go. That’s why I wanted to have this conversation with Ellen Yang. She wrote an article that resonated with me called Stuck at Work. In this conversation, we break down what that means, what the mindset is, and how to get out of it. I thought it would be a great conversation for you as we move into the new year, and you may think about how to turn a fresh page. I hope you enjoy it.

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My name is Ellen Yang. I am a partner and general counsel at a boutique law firm called DTO. A fun fact about me is that one time, I entered a grilled cheese contest, which is making, not eating, grilled cheeses. I tested out so many different grilled cheeses that I couldn’t eat grilled cheeses for two years afterwards.

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The Taboo Topic: What It Means To Feel “Stuck at Work”

On this episode of The Legal Department, I’m excited to welcome Ellen Yang. She is a partner and general counsel at DTO Law. Before returning to a law firm, she spent most of her career in-house at big companies you would know, like Taco Bell. We are going to talk about something that is not widely discussed among the in-house crowd, which is feeling stuck at work. This episode grew out of Ellen’s article for Bloomberg Law called Stuck at Work. Ellen, how are you?

I’m good. Thank you.

I’m excited to have this conversation. You posted about the article on LinkedIn. We know each other through some mutual friends, but your post generated a lot of comments and engagement. That told me that this is something that a lot of people are thinking about. What inspired you to write the article?

There are so many things that people experience in their careers that don’t get widely talked about. Who wants to go to a party when somebody asks you, “How’s it going at work?” You’re like, “Meh.” It’s not.

You’re scanning the room, looking for someone else to talk to.

It’s just not. You’re going to be the Debbie Downer at the party. There are a lot of topics relating to people’s profession and career that don’t get talked about. Maybe people might talk about it with their inner circles. I’ve got an inner circle of professional girlfriends all in-house that I used to talk a lot about, and they made me feel better. In general, I wouldn’t say they’re taboo, but they’re not something you talk about widely because you’re probably admitting something about your current employment that you don’t want to do in public.

I was approached by Bloomberg Law to write a column. They asked me what I wanted to write about. There are so many practitioners out there in legal practice areas who do a great job. I was like, “I don’t know if I actually want to do that.” I feel like a lot of people come to me for advice. I try to be very candid and honest with them. I give them the good, bad, and the ugly. I was like, “Maybe there’s something there because I feel like this is an underserved area, one that’s not spoken about often.” That’s how I approached it. I approached it as I want to be the Carrie Bradshaw for the legal profession, but with a lot more clothes on and a lot more inexpensive clothes, unlike her brand names. I was telling you I might be dating myself because I don’t know if people even know what Sex and the City is anymore.

Unpacking Lawyer Restlessness: Why The “Grass Isn’t Greener”

You’ve got a friend in me. I get the vibe. I love the framing. It makes lawyering sound a lot more hip. This feeling of being stuck intrigued me for a couple of reasons. First of all, the grass is always greener. Law firm lawyers have a perception that in-house lawyers have a very regular schedule. There are fewer demands. There are no billables, but it must be somehow easier. People who are in-house look at the general counsel like, “That’s such a prestigious role. That person must be engaged every day. It is so exciting. They get to mingle with the C-suite and the board.”

As you and I have talked before, the grass is not greener. Sometimes, we all have a feeling of being stuck, bored, or feeling uninspired. I want to talk a little bit about digging into your article. You observe that this is another phenomenon. Lawyers, in particular, when looking at their careers, feel, “There’s nothing else I can do. This is what I am. What else would I do? How could I do anything differently?” You probe that. First of all, why do you think lawyers, in particular, are in a rut?

I agree with everything you’ve said. A career is a trajectory. It’s like a roller coaster. There are times when it moves fast, and you’re accelerating down the hill. There are times you’re climbing. There are times of inertia where you are at the platform getting on and off. I didn’t go into the article here because it is a little more complex. People also have different needs at different points in their lives and in their careers. I know when I was pregnant with my two kids, that wasn’t for me the optimal time to be going around interviewing because I was trying to get out of a pile of dirty diapers.

A career is like a roller coaster. There are times where you're accelerating down the hill, and there are times of climbing. Then there are times of inertia where you are at the platform, getting on and off. Share on X

Taking that part aside, lawyers are all trained to be overachievers. We cannot sit still. I guess we experience professional restlessness or anxiety. I was talking to a colleague who had been complaining to me that he’s so busy, he’s got a lot of billables, and he was trying to figure out how to balance it all. I talked to him, and his calendar cleared up. With all this newfound time, he was stressed that he wasn’t busy enough.

Sometimes, I’ll come home, and I’ll be like, “I don’t know what to do. I’m unhappy or whatever.” My husband’s like, “You’re not busy enough.” It’s like clockwork. He can tell if there’s something that is a lull. He observes. It’s the same thing that you’re talking about with your friend. You feel overwhelmed sometimes when it’s super busy. If it’s slow, it’s almost like that billable anxiety. “I’m not going to make my hours this month.” That’s very interesting.

It’s funny. I guess this is why lawyers also need therapists. We’re trained to always be looking at the next thing, always be developing, and always be productive. Going back to feeling stuck, it can be different for everybody. It can mean in terms of your development, your professional expansion of your coverage areas, and your practice areas. For me, knowing my ambitions, especially beginning and middle of my career, I was trying to be deliberate and to fill out my resume. If I felt like there was an area of my resume that I didn’t make any headway on, and I wasn’t adding new things, projects, practice areas, or experiences to my resume, then I felt like I wasn’t developing.

I would feel stuck and make intentional moves to try to fill in those gaps. That’s one type of stuck. Another stuck may be advancement, especially in-house. In some places, particularly when the legal team is leaner, you need somebody to retire or to leave for you to advance in their place. That can be tough, especially when you don’t have a lot of openings or positions above your level, particularly with DGCs. You need your GC to leave. That may not happen. That could also be feeling stuck.

It could also be that you’re tired of doing the same work over and over again. You were mentioning repetitive work. I always wonder about that because this is probably a personal thing, and maybe we share this, that I’m happiest in the days when there’s a lot of variety. One of the things I like about the GC role is seeing the landscape and not just doing one thing. I’ve also observed that some people have a lot of comfort in doing the same thing. People are different. I always tell my kids people like different things. As you’re saying, there are several varieties of stuck.

Particularly if you’re in a large organization, folks can be siloed. The company wants you to do that one thing, but it depends on your personality. For me, when I was at Taco Bell, I was working on their commercial transactions. I pretty much ate, drank, and breathed contracts all day. I would have people come into my office and say, “I don’t know how you do this every single day.” It didn’t bother me until everybody started saying that. It’s like “How do I do this every day?”

I used to think I had a great job until everyone told me it was boring.

It’s different for everybody. It’s more about not feeling challenged, engaged, or fulfilled in your job. Going back, feeling stuck sometimes takes a little bit of self-analysis to figure out what you truly are feeling and why. Only through that can you address it. There are so many things that people can do once they figure out why they are feeling this way.

Feeling stuck sometimes takes a little bit of self-analysis to figure out what you truly are feeling and why. Share on X

Actionable Tactics: How To Break Through Career Inertia

I want to dig into that. As you can probably imagine, I talk to a lot of lawyers. I’m very inspired and motivated by professional development. I love helping people do that, which is one of the reasons I do this show. I frequently encounter lawyers, when we talk about “I can’t do this,” or “I’m tired of this,” with a feeling of inertia or helplessness about “There’s nothing I could do. My GC is only 42. I’m never going to get that chair. What else am I supposed to do?”I want to talk about the things to do. Especially in-house, there are a lot of different tactics and opportunities. Let’s dig into those.

For leaders like you, and others out there tuning into your show, I want folks to be aware of this cognizant that this happens, because as a manager, and as a good leader, your job is not only to ensure that your employees are happy with what they’re doing, or they’re satisfied, particularly if they’ve been there for a while. I would also argue to challenge them a bit. You will find some people who are like, “This is my job. I love doing it. I’m the master in this domain.” That’s fine.

For many others, it’s helpful when managers challenge their direct reports, because while it might be uncomfortable while doing that, in the end, they’ll be happier. They’ll be glad. They would have you stretch them in ways they never would have imagined. That’s where you get engagement, loyalty, and appreciation. When you have employees who feel those things, studies have shown they are much more likely to stay in their job, even when they could get a higher comp somewhere else.

One example of that would be from a manager’s perspective. I keep using Taco Bell as an example. The general counsel there, a number of years back, told me when I first started that occasionally, every six or seven years, he would mix things up. He would have the lawyers trade spots, almost like musical chairs. I could see your face, which is jaw-dropping. That’s exactly the face. I’m like, “Are you crazy?” He would do a little switcheroo, like Wife Swap. It’s Lawyer Swap.

I thought he was nuts as I was intrigued. If you look aside from somebody’s own personal development, if you have worn different hats, you’ve had different experiences. Most often, this comes from externally from outside the organization. As a lawyer, when you have these different roles, you’re able to see and analyze situations, problems, and projects from a much broader perspective. You’re able to spot many more issues. I do see that there’s a benefit.

As a lawyer, when you have these different roles, you're able to see and analyze situations—problems, projects—from a much broader perspective. Share on X

Be open because you’re going to learn more, even if it’s scary and uncomfortable to switcheroo.

For the lawyers there, it’s actually an amazing growth opportunity. Who does that? The lawyers were kept engaged and learning. It stretched them in areas that they hadn’t done before. Attrition was low. You also need to have the mentality where, even though you’re switching roles, you still have a support network.

It’s not like, “Go figure out ERISA Law by yourself.”

I may change jobs if it were ERISA. Yes, that might be a good example where you can engage outside counsel because nobody should go through that brain damage. Also, it’s okay to make some mistakes early on. I remember talking to an in-house lawyer somewhere else. She said her in-house department operated off a ticketing system. Everybody was trained on pretty much all issues. When the ticket came in, it got assigned out, and you had to handle it. I thought that was crazy, but I could see the utility in it. Certainly, if you had somebody go on leave of absence, you would have cross-training. Going back, if somebody is feeling like they are stuck or in a rut, it’s good to try to get to the source of what they’re feeling.

There are so many things that we can do. Some of them are easier than others. Some of them require greater change than others. It’s sometimes worth listing them out so that way, folks can remind themselves of their options. It’s good to raise your hand when at work to have that conversation. A manager would be a fool not to want that conversation or to discourage it because you want to hire people who are ambitious, who are lifelong learners, and who want to grow. Those are the type of people you want. If somebody is raising their hand and saying, “I’ve been doing this for a while. I’d love to expand my scope,” perfect. That might even mean a little bit less work on your plate. They could transfer over, but it would provide so much for that person the opportunity.

The Power Of Asking: Expanding Your Scope (The Employment Law Example)

I want to underline that point because we shouldn’t be suffering in silence, first of all. To your first point, do some self-reflection and think about what it is that’s bothering you. If you don’t open your mouth and tell somebody, it’s going to fester. As you said, the biggest pain in the neck for a manager is having to replace somebody. I don’t think that line lawyers or folks out of a leadership role realize there’s a big drag.

It’s finding the right fit, onboarding that person, and developing the relationship. There are the financial costs, the friction, and the disruption in the team to lose somebody. It may seem scary to raise your hand and say, “I don’t want to do these commercial contracts anymore. I know I’m good at it and I have happy clients, but if I see one more of those come across my desk, I don’t know what I’m going to do,” or “I want to learn employment law,” which s one of the things you did. Maybe you could share that example. That’s a good, concrete, exciting example.

When I was at Public Storage, I’d been there for probably five years. I knew the regulatory landscape for self-storage inside out because, believe it or not, every state has its own self-service storage facilities act. It’s like an eviction process. Every state had its little nuance. I had been doing that for a while and knew the ins and outs. We could have a separate episode, maybe not on this show, but a more salacious one about what goes on sometimes in self-storage.

I am intrigued. We’re going to put a bookmark in this conversation for sure.

Talk about being the life of the party, working at self-storage. You’ve got a lot of stories to tell. I raised my hand. I need to write a post about this. Thankfully, my boss was pivotal in my legal career to set me up for success. His name is Ammar Kharouf. He lives in Europe with the European sister company. He encouraged me. He never would ever discourage me. I didn’t know any other way because of his support. He’s the one who also told me to get involved with ACC, which is also another example of what you can do, but I can go into that in a second. I raised my hand with him. He said, “Sure, let’s have you.” He probably, in his own mind, was laughing and thinking, “Sucker. Let’s try to do employment law.”

You’ve got this thing that you figured out. You’ve got your job manageable because you knew all the rules. You want to come into a little more excitement. Every day is a party.

The way you probably use the word excitement, but it’s craziness. I also started doing some marketing stuff and sweepstakes contests, but those were lower volume. I started doing employment work. There’s so much employment work, especially in California.

Overcoming Competence Anxiety: Embracing The Fear Of New Areas

One of the barriers is to say, “I’ve been a commercial contracts lawyer or whatever for five or seven years. I’d love to learn employment, but that’s scary.” We were talking about this before we got on that we’re used to being very competent and feeling like we know what we’re doing. It can be uncomfortable to think about branching into a new area. How did you deal with that?

The CEO of a company once said a common phrase, but I relish it. He said, “If you’re not scared, it’s not worth doing.” I try to remind myself of that because I feel like women are much more inclined not to take something on unless they know it or they feel confident they can do an amazing job. There’s that study that women don’t apply to jobs unless they can check eight out of ten requirements.

'If you're not scared, it's not worth doing.' Share on X

Men just write their names in.

Beating heart?

I got that. Check.

I have to remind myself of that all the time. I tell myself, “Think of all the other areas of the law that I didn’t know, yet I know well.” I could do that. Lawyers are trained to be methodical in their approach to understanding something.

We’re good learners.

We’re smart and analytical. For anybody out there who’s afraid of tackling something, if you get an assignment and it’s totally an area you’ve never done before, break it down into little bites and figure out how to approach it. Use your network. Talk to people. That’s where networks like the Association of Corporate Counsel, many other organizations out there, your friends, or colleagues will help out and give you the lay of the land, or give you an approach. These are untapped resources who are happy to help you.

You’re not expected to be perfect. That’s the other thing, especially if you moved from an area where you were very competent and could do the job in your sleep. To do something new where you’re not going to be a master right out of the gate is intimidating.

There’s nothing wrong with doing little checkpoints, too, to say, “Am I on the right path? Does this sound reasonable?” to give you some confidence as you’re learning.

General Counsel Aspirations: Filling Resume Gaps And Executive Growth Strategies

Learning new practice areas and raising your hand is solid take-to-the-bank advice. As a manager, I would be thrilled. It would make my day for someone on my team to come to me and say, “Stacy, I would like to learn this or do this.” It would be a gift to me. We talked a little bit at the opening about DGCs or senior management level lawyers who might be stuck because the next seat up is occupied by somebody who has no intention of retiring or leaving. That is a very clear snag. That’s quite obvious as a snag. However, there are guaranteed opportunities for that person to grow even in a company with a sitting GC. I would love to hear what your thoughts are on that. I have my own ideas, but I’d love to hear your thoughts.

If somebody has aspirations to be a general counsel, I would have them do a little more self-reflection and maybe talk to some people. If they know what industry they want to go to, chances are they probably need to have certain buckets of practice areas, skillset, and whatever they need on their resume. Those areas are not filled out. For example, I didn’t have as strong a transactional experience. I started as a litigator at Quinn Emanuel and then had a litigation and field operations role at Public Storage, very much business interfacing, as well as litigation practice areas. I did employment, but I didn’t have as much transaction experience. I knew I had that gap in my resume.

I went to a company where I filled that gap, Taco Bell. If you want to be GC, look at your skillsets, your areas, and see if there are gaps and how you can best fill them. Sometimes, you can fill those out internally in the company, which is great. If you were the flip side, maybe you were doing more advice, the product counseling work advice, but less so on the interfacing with business colleagues or whatever, then maybe you can switch around a little bit internally to build out some of those areas. If not, you can get some experience externally first to help build out that resume. That could be board work, whether it be nonprofit boards.

There are also public boards. I had been volunteering with the organization way back when and raised my hand to see if I could get on their board. It was called Read to a Child Los Angeles. I can get some board experience, and I can check that off on my resume. That way, you could show future employers you have experience communicating with a board. Talk about high-level strategy, long-term planning, and the process of working with the board.

If there are other areas, say you want to fill out some privacy, data security, there are external certification opportunities that you can get. I saw that gap in my resume. I had some experience, but I wanted to show that my experience was robust. I got CIPP US certified. I did it sooner versus later because I knew there were going to be many more laws passed. I was like, “I got to do it when the list is somewhat short.”

Those are all great. The other suggestion I would have, and something that I didn’t necessarily raise my hand for, but helped me grow out more of my practical skills, was taking on a function outside of the legal department. If you’ve been in a company for a while and people know you to be a smart, competent, practical business partner, they might want your help on another function.

When I was at USC, we restructured some of our risk functions. I got risk management. That is definitely legal adjacent. As part of that, I learned about insurance. I placed our insurance tower. I helped manage OSIP, which is an owner-secured insurance product. Those are great skills. They serve me in this role. It was something that I could fill out on my resume to show how I was an executive-caliber attorney, even though at the time, I was a deputy or associate general counsel.

That’s a great example. No wonder you weren’t bored.

USC had a lot of stuff.

We had a panel through ACC SoCal with the general counsel of Epson because she took on sustainability in addition to audit reports. Sustainability was a big one, as well as the general counsel for ECOS, and now the GC at El Pollo Loco. Back then, she was a GC. They all took on sustainability and how they approached it. They said it was such a great growth opportunity. Given the legal and regulatory requirements, it did make sense that legal took on that function for many companies that didn’t want to, if they didn’t have a standalone function with its own separate executive, and how it gave them an amazing growth opportunity and also a mission.

It is something a little deeper.

Also, legal will frequently take on the people team, sometimes in addition to risk. Those are all great examples of where you can show up, raise your hand, add value to the company, yet give you a broader experience that may help with somebody’s aspirations to try to move on to whatever their next phase is in their career.

The Unexpected Move: Ellen Yang’s Return To Law Firm Life After 17 Years In-House

On the topic of phases of career, and you led off with that, you’ve moved from an in-house role. You’re back at a law firm. That is so intriguing. I want to hear all about that. Back to the grass is always greener. When you’re in a law firm, you’re like, “I would love to be at a company because then I could make sure they follow the advice, or I get to see the project all the way through.” Sometimes, when you’re in-house, you’re like, “It would be so nice to be at a law firm because I could give the advice and then not worry about it.” Let’s talk about your transition. What has it been like?

It has been good. It has been, at times, uncomfortable. We talked about this at the outset. I haven’t been at a firm for seventeen years. It has been a minute. It’s uncomfortable in terms of there being a learning curve. I was in transition. My last company was wound down. I was in the market. I was interviewing around. I knew generally, I could go into any company and immediately start adding value, contributing because I had done it at four different companies and even in different industries. Being in a different industry did not scare me.

I was trying to figure out what challenge I wanted, and where I felt like I wanted to be challenged, particularly because I’m not a spring chicken anymore. I figured wherever I’m going to end up, maybe I had one more play, but I didn’t see this as being an interim thing. I wanted to make sure I had enough there for the long haul, enough that would keep me interested growing and learning that I felt like I would be satisfied for a little while. That’s hard to determine what is going to fill my inner cup.

You don’t have a crystal ball with the future is going to hold.

In that sense, coming back to a firm, I knew it was a much bigger hill to climb. I anticipate I would feel uncomfortable, but I try to relish it. I try to lean in because that’s where I’m challenged personally. While at times they may not like feeling that way, I always know that at the end of the rainbow, I’m better for it. It has been good in terms of I hadn’t practiced law in a while, because part of what makes a good in-house lawyer very effective at their company is being a good business advisor, partnering with the business, and trying to be creative and figure out a way to get something across the finish line.

Part of what makes a good in-house lawyer very effective is being a good business advisor. Share on X

I always say I’m a lawyer light. You’re not pulling out your Rutter Guide or your statutes, the civil code, or whatever. You know the law at a high level, if you’re not a specialist, and then you try to figure out how to solve the problem and accomplish the business goal. You’re not steeped in reading cases, statutes, and regulations all the time. I call it lawyer light. At a law firm, I don’t pay you for being a lawyer light. I want somebody who knows, instead of making it up, as many of us do.

You go with your intuition a lot. I’ll tell you, Stacy. Having been back at the law firm, there are no more hardbound copies of Rutter. Books are probably for show. They have file cabinets. I open them up, and they’re empty.

We had these. They’re more of an accessory. It’s staging. I asked somebody for a hanging folder. They had no idea what I was talking about.

It has been fun. I missed practicing law. I missed debating about the nuances, strategy, and what angle to take, especially in litigation. It’s like a game of chess, a little bit. I missed legal writing, persuasive writing.

Instead of just emails. I’ve had a kick ass email or Slack.

My last company is very Slack. It’s like picking out the perfect emoji. I miss that long-form writing. That has been fun, sitting around a table and debating about which argument to raise and which to put in a footnote.

The In-House Advantage: How Corporate Experience Makes A Better Law Firm Lawyer

You probably didn’t use too many footnotes at Public Storage. I’m curious as to whether your in-house skills have helped. Have you used those, or is in-house that different?

A hundred percent. I’ll give you a few examples for a smaller company. I’ve been in that role where it’s a privately held company, a little bit smaller. The owner started it, and the owner knows all the employees. It’s very personal. Any lawsuits would be an affront to that person’s character, how they conduct business, and how they are as a business owner. They take it personally. I’ve been in that role where I’m in-house and having to explain all this and deal with the emotion behind it. One of my clients had switched counsel and now uses us. He said to me, “Ellen, when I talk to you on the phone, I feel like you care so much and everything is going to be okay.”

What a high compliment.

I made myself feel so much better. I told him, “It will be. We’ll get you there.” I guess it’s because I lead in that situation. I also lead with empathy because I know that it’s important to him. He has built this. I visited his headquarters. When we walked around, he stopped and talked to all of the employees, asked them about the kids’ soccer game, and asked them about how the wife was doing. A person who has those relationships with their employees takes a lot of pride in their business. They don’t run a shoddy business generally. I lead with empathy, which he appreciates rather than it being business.

That’s one example. For bigger clients, I told one very big client, their in-house counsel we’re interfacing with, “I read your outside counsel guidelines. I know we have to submit budgets on this day and updates on this day. I wanted to understand what level.” It’s like, “I might as well have the music stop playing, or the record stop.” It was like, “You read our outside counsel guidelines to a T, you know our due dates, and you want to bring up the budget in advance?” I was like, “Yes. I’ve managed those cases before and understand how critical having an accurate budget is and how you rely on that. Your department is held accountable to that.” She was taken aback because no outside counsel had ever asked her about it.

They’re like, “What? I just signed it. It’s part of our agreement.”

She appreciated the detailed part of us handling the matter and how she felt assured. I know in-house. You never want surprises, whether that be the prizes for something that gets sprung up in the lawsuit or the fact that you’re going to be over budget.

You’ve been in their chair. You know what’s important to them. On the client service side, you can deliver. I wonder about the first example of empathy. That should be available to law firm lawyers. I do wonder, though, because we’ve been in the business. You work so closely with the operators, the senior executives, etc. You know what their jobs are. I’m wondering if your approach to your first client was a little more informed. An outside counsel can certainly show empathy, but maybe not perceive the same things that you were.

That’s right. I’ve worked for privately held companies that have maybe one or a few owners. I know the pride of ownership they have in that company, versus I’ve also worked for public companies. For that, particularly if you have a CEO who is the former CFO, it’s a numbers game. I approach that very differently. You have to look at it from the big picture numbers game. You could win the battle, but lose the war. For that situation, I wouldn’t go in with empathy. I would go in with numbers.

For a smaller company where you have that pride of ownership from the company owner, you can’t just lead with numbers. You can’t because they take this personally. You have to acknowledge that. Sometimes, they don’t all hear the comments like, “We’re going to spend more in attorney fees than what it costs to settle. How does that make any sense?” You’re like, “You have to understand they’re not ready to settle. You have to get them there and show them.”

There are different approaches. First of all, I feel like everybody has a new chapter in their professional book, and nobody should feel like they’re pigeonholed. Sometimes, it’s disruptive to make a big change in your life, but we’re lawyers. We are smart people. We’re adaptable. We can manage almost every situation. We made it through COVID. Talk about getting new things thrown at you from all different angles. We survived that, adapted to it, and have made changes since then to the workplace.

Everybody has a new chapter in their professional book, and nobody should feel like they're pigeonholed. Share on X

From a personal level, anybody can take that brave move. They’ll adapt and make a change. In my situation, I made this change. I’m able to incorporate all of my skills, try to apply them to whatever new application I’m currently in, and try to be the best lawyer that I can be. That was the mindset I had in going back to private practice.

While I’m the general counsel of the firm, people sometimes ask me, “What’s it like being general counsel for a bunch of lawyers?” Actually, it’s the easiest thing. Show them one little bit of risk. They’re like, “Take care of it. Fine. Conversation done.” That’s very easy. On the other side, practicing law again and having some clients, I get to be the outside counsel I always appreciated. People ask, “Is this where you’re going to land and then eventually retire?” I don’t know, but that’s okay. I’m having a blast while I’m doing it now. That’s what matters.

That’s awesome. You are so many examples of how to reinvent your career. Although being a lawyer has its drawbacks, it opens up so many opportunities. I feel like there are more opportunities with a law degree and having practiced law than in many other careers. Onto a lighter question, the last question. I ask everybody this because I use music to get myself pumped up for the day. What is your pump-up song? The Eye of the Tiger is off limits.

You can have the tigers. My Spotify account has been usurped by my two teenage kids, so my algorithm is so messed up. I blame them. What I’m trying to say is I don’t get to play the music I want to play in the car anymore. I am last on the totem pole of who gets to. My kids and my husband battle it out for the first, and I’m last. The song that, when I listened to it, gets me in the zone would probably be Joy Division’s Love Will Tear Us Apart. It is a little surprising, but I feel like that song puts me back in time. Everyone says music is the fabric of life. It puts me back in time where I could drop my head back and forth without getting a neck pain that lasts a week, and pumped up for whatever I was going to go out to that night.

Thank you so much. This is a great conversation. Ellen’s article in Bloomberg Law is called The In-House Career Rut Is Real, but You Can Stop Feeling Stuck. Ellen, thanks so much for being here.

Thank you, Stacy. You’re amazing.

Thanks.

 

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About Ellen Yang

The Legal Department | Ellen Yang | Reboot Your Career

Ellen Yang is a Partner and General Counsel at DTO Law, a boutique firm with offices in Los Angeles, San Francisco, and New York. She brings 17 years of in-house experience, including roles as Chief of Staff and Legal Counsel at Cruise, General Counsel at Penske Motor Group, Director of Contracts at Taco Bell (Yum! Brands), and Corporate Counsel at Public Storage, a NYSE REIT. Ellen began her legal career at Quinn Emanuel Urquhart & Sullivan after graduating from NYU School of Law. She served on the Board of the Association of Corporate Counsel, Southern California Chapter, for eight years—including four years on its Executive Committee—and recently completed her term as Chapter President in September 2025.

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