Your Most Reliable Lawyer Will Eventually Rebel: A Conversation With Gretchen Rubin

Gretchen Rubin clerked for Sandra Day O’Connor. Then she left law to write a book, and the moment it became real was a notice in the mail.

The New York State bar fees came due. She asked her husband (whom she met in law school, and who was leaving law for finance at the same time) whether they should pay them. He said, why would we pay our bar fees?

“And I was like, okay, we’re doing this. We’re not paying our bar fees. We’re going rogue.”

Twenty years and several books later, she was backstage at ClioCon 2025, having just led a keynote conversation with Esther Perel in front of a few thousand legal professionals. “I’m having a real law week,” she told us. Yale Law School on Wednesday. A pharmaceutical company’s legal team on Thursday. “My heart is still with lawyers.”

We sat down with Rubin to talk about the four kinds of people in every law firm, why the associate who never complains is the one to worry about, what to do with a rebel in a profession built on precedent, the 10 minutes at the end of the day that fix the start of the next one, how to schedule your worrying, and the 18 months she spent doing two careers at once.

The conversation has been edited for length and clarity.

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You clerked for Sandra Day O’Connor and Pierre Leval before you left the profession. What’s it like being back in a room full of lawyers?

Gretchen Rubin: I love it. I feel like my heart is still with lawyers. I so identify with their outlook on the world and their issues. For me it’s always a special pleasure to talk to lawyers.

And it’s interesting to come at it from the relationship side, because one of the big things I always write about is how relationships are a key to happiness—maybe the key to happiness. So much of what Esther was saying on stage was explicitly about relationships. It was interesting to see how she went deeper into that and broke it into these different parts. How does trust lead to belonging? How do you think about a group being resilient and an individual being resilient? Then the importance of recognition, which you think of as very different from belonging, but I thought she did a really good explanation of how all these things fit together.

Everybody has their own vocabulary and their own approach, so it’s very interesting for me to think about how those dovetail.

 

The Four Tendencies split people into Upholders, Questioners, Obligers, and Rebels. A firm owner looks around at 20 employees. Where do they start?

Gretchen Rubin: That’s something a lot of people are frustrated by, because they say, “I don’t have time to manage everybody individually. I need to find a way to communicate with everybody.”

So think about it this way. If you’re going to announce some change you want to make—we need to switch to a new software program—you need to explain what the timeline is, because that’s what Upholders and Obligers need. But you also need to explain why you’re making the change, because Questioners won’t get on board if they don’t understand why. And then for the Rebels, you have to explain that this is good for you, this is what you would want, you’re going to make more money, you’re going to save time.

When you’re communicating, you want to hit those different notes. And sometimes people say, “Who’s got time for that?” It’s the relationships. In the end, if you’re not communicating with somebody, they just aren’t going to cooperate. They’re not going to do it in a timely way, or they’re not going to do what you want.

Or take something like micromanaging. What one person absolutely resists and feels is intrusive and a waste might be, for another person, a very helpful set of accountability. These people are different. You can’t have a one-size-fits-all solution, because people are just so different from each other.

 

A lot of lawyers are Obligers. Whatever you ask me, I’ll do it, call me at 3 a.m. What can they do for themselves?

Gretchen Rubin: Obligers are great. That’s why I’ve had people who want to screen so they only hire Obligers.

If you are the Obliger yourself, there are a couple of things you can do. One is to say, “I have to say no to somebody, so I get to pick who I say no to.” My team wants me to stay late, but my family wants me to come home for dinner, so I have to say no to someone. You don’t treat it in isolation, like “I have to stay late because of my team.” You always ask, well, who am I saying no to? Because once they know they have to say no to somebody, they can make a choice.

Another one, which I thought was interesting, is to say, “I’m going to say no in order to give someone else an opportunity.” So it’s not that I’m being lazy, it’s not that I’m letting you down. I’m very senior, I’ve done this kind of thing many times, but here’s a junior person, and for them it would be a really exciting challenge. It would be a major step up. You’re still doing it in the service of other people. You’re still meeting that outer accountability. But you’re explicitly invoking it to get yourself off the hook. You’re reframing the obligation and the expectation.

Or it’s, “If I burn myself out, then I might let you down. If I get so wiped out that I have a physical collapse, I’m not going to be able to represent you well. If I burn myself out, maybe I’ll quit my job and desert you altogether.” It’s the oxygen mask thing. I have to serve myself in order to serve you.

I will say, as an Upholder, I used to resist it when people would say, “I have to take care of myself so I can take care of others.” I’d think, take care of yourself because you need it! You don’t need to worry about other people. Who cares about them? But that’s not very compelling to Obligers.

 

And what should the person managing them be watching for?

Gretchen Rubin: In a group setting, it is often the case that Obligers are exploited and taken advantage of, because other people go to them. They know they’re the ones most likely to agree.

So you really have to be aware of fairness. Look around and ask: Is one person serving on eight committees while everybody else is serving on one or two? Is somebody consistently taking the drudge work? Is somebody consistently working hours beyond what other people do? Are they doing the unpleasant travel? Are they working with the most difficult people? Because it starts as “You’re so good with these difficult people, nobody can handle them like you,” and now they’re dealing with every nightmare client and everybody else is doing the easy stuff.

As the boss, you want to look around and say, is this fair? You don’t want to lose some of your most valuable employees because you’re burning them out and overextending them. Because eventually, they will rebel.

Colleagues can help here too. Sometimes Obligers won’t speak up for themselves, but they’ll speak up for somebody else. They’ll say, “I don’t understand. Why did Peter get put on this deal? He’s already got five deals. What about all the people who aren’t working on it and have a lot of free time?” You can speak up for each other and point out when things aren’t fair, instead of saying, well, if you said it’s okay, then it must be okay.

 

How do you get an Obliger to actually take a vacation?

Gretchen Rubin: Not by saying, “You need to take time for yourself.” That just sounds like more work for me to do.

It’s: “Look, I’m looking at the last 52 weeks and you have taken very little vacation time. I can tell that you’re starting to run on fumes. I want you to come back to me by the end of the week and tell me what your plan is for taking at least a week off.”

So I’m giving you accountability to come to me with a plan, but I’m kind of forcing you to restore yourself. I’m not expecting you to do that on your own. A lot of times people say, well, if it’s important to the Obligers, then they should just do it. That doesn’t work for Obligers.

 

Now the Rebel. A brilliant associate, in a profession built on precedent and rules and structure.

Gretchen Rubin: I could imagine a Rebel starting their own law firm, because they think, I don’t want anybody to be the boss of me, so I’m going to do everything my own way. And then you’re working for a Rebel boss, and that is not easy either.

People say, “I don’t want to have to tailor everything to every little individual snowflake.” But once you know somebody is a Rebel, you can really frame things according to: this is what you want, this is what you choose, this is who you are.

So you’d say something like, “I know it’s really important to you to feel like you are a super-reliable colleague. And when you’re consistently late, you make me feel like your time is more important than my time.” I’m reminding you of an identity that I know is important to you, because you see yourself as a good colleague. Or, “I know you value being a high performer, and you’re really on track to make a ton of money this year. But if you keep this up, you’re just not going to make the same kind of numbers that you otherwise would.”

And as much as you can, let them do their own work in their own way. “Wow, this is a really tough problem. You’ve got the chops to handle it. I have faith in you. If you run into any roadblocks, come to me, I would love to help. But otherwise, I’ll just look forward to you coming to me in a month or two and telling me what your plan is for handling this.”

Sometimes a challenge works, and some people don’t like this because it is kind of manipulative. It’s, “Everybody says that you could never come on time to a meeting for even a month.” And they say, oh, I’ll show you.

But part of it is that just recognizing different people’s tendencies automatically allows you to start speaking their language a little bit more.

 

You write about clearing clutter as a first step to feeling calmer. In a firm full of documents and deadlines, where do you even start?

Gretchen Rubin: Somebody told me about this and I think it’s a really great idea. At their firm—it wasn’t a law firm, it was something analogous, an advertising agency—once every two months they blocked out a Friday afternoon. It was basically, get your stuff sorted.

Everybody would come into the office, and for half a day, they’d bring in some kind of fun lunch, and the idea was that this was dedicated time where your work was to file, throw away, and sort. Because in an office there’ll just be stuff, and you think, why is this dead plant here? Well, I can’t get rid of it because it doesn’t belong to me. So it sits there for 15 years.

So you say to somebody, you’re the one who’s supposed to go around and look in the corners, and on the shelves, and on the tops of the filing cabinets, and just clear. Because everybody says, well, it could be important, so I can’t get rid of it. But it’s been there for 10 years. What’s in it? Nobody’s even looked. And it’s distracting that it’s there, because every time you think, oh, maybe that’s the thing that I need.

It can be really valuable to periodically give people that time explicitly, and to do it as a group, because a lot of the time no one person is going to go to that banker’s box, because they don’t have the authority. But if you say, we’re all doing it, now is the time, then you figure it out, deal with it, get it out, and it’s not sitting in the conference room for the next 10 years. You ask, why do we have this?

What you don’t want is for people to just sit there and clean out their inbox. That’s just working.

 

Is there a practice you use yourself?

Gretchen Rubin: Yes, and this could work really well in the law context. The last 10 minutes before I leave my office, I spend just clearing off my desk. I put pens in the pen cup, I throw away Post-it notes I don’t need anymore, I reshelve books. I put everything back so that when I come in in the morning, it’s all ready.

That’s also very calming. One of the things you see in happiness and habits is that transition points are very draining. That’s why a lot of times people will eat unhealthy food during a transition—you come home from work and you immediately have an unhealthy snack. Transitions are demanding. So anything that helps you have a little bit of a transition is helpful. It’s probably even more important when I work from home, because then I have so little transition between work and home.

Another thing that works well for people is around Monday mornings. Some people get the Sunday blues and find Monday mornings really stressful. A friend of mine who has her own agency just sets that aside for quiet reacclimation work. She doesn’t schedule big meetings, she doesn’t try to do anything really demanding before lunch on Monday. She goes through her inbox, sorts through the mail, does the little bits and bobs, so she can ease into the week.

She said it made Sunday much less stressful, because she wasn’t expecting herself to just throw herself into the week. And she said in the end her productivity was so much higher, because she was really ready, instead of feeling this immense resistance starting her day and feeling overwhelmed by Monday.

 

Lawyers are paid to be skeptical and pessimistic. Can that coexist with happiness?

Gretchen Rubin: It’s what we’re paid for, to be skeptical and pessimistic. And it’s hard, because you really are inculcated in that. It’s what you’re rewarded for and asked to do—to anticipate. What if this marriage ends spectacularly? What if this partnership blows up? What if we come to blows?

So part of it is just being aware that that is your training, and that it’s not the only way to look at the world. Sometimes people forget that they’re especially trained.

The other thing is that skeptical and pessimistic people will often ruminate and be very consumed with worries, because in their own minds they’re very capable of saying, my kid’s going off to a party with his friends, what are all the things that could go wrong? You’re so good at that.

So one thing that can help people who worry a lot is scheduling time to worry, which sounds very counterintuitive. But you literally schedule time to worry. You put it on your calendar at a specific time. If you worry a lot, maybe it’s every day, or maybe it’s once a week. You don’t want to do it before bedtime. And it’s really helpful to have pen and paper, because sometimes when you worry you think of things that need to get done.

Then if you start to ruminate, or perseverate on these feelings—here are all the things that could go wrong, oh, I thought of something else that could go wrong—you say, okay, I’m going to do that when I have scheduled time to worry. You’re not trying to suppress it, because the more you try to pretend that you’re not worried, the more it’ll come flooding back. But you set aside time and say, I’ll worry about that then. I have time for it. I’m not ignoring it. I’m not burying my head in the sand. I’m just not going to let it seep into every moment of every day. It works really well for people.

 

You made a successful legal career and then left it. A lot of lawyers have something else they’d rather be doing. What’s the first step?

Gretchen Rubin: There’s an amazing book written about that by a friend of mine, and I really think it’s an outstanding book. It’s called The Creative Lawyer, and it’s written specifically for lawyers who want to think about pivoting to a different career. Maybe they want to go into nonprofits, maybe they want to write a novel, whatever it might be. It’s about how you do that in a systematic, careful way, because it’s just not realistic for most people to blow up their lives and walk away from their profession and start something new. He takes you through a process of how you’d ease into it.

I’ll say that when I switched from law to writing, I spent about 18 months still working full time in law, writing the book in my free time. So by the time I was ready to try to get an agent and a book deal, it wasn’t like I’d quit my job the first minute I decided. Sometimes you have an overlap, so you can be gaining your skills and your knowledge while you’re still in the old profession. Because I think sometimes people believe they have to burn all their bridges and go all the way. But that’s so scary. It’s not very realistic.

 

Were you anxious it wouldn’t work out? Did you have a plan B?

Gretchen Rubin: Thinking back on it, I wasn’t that anxious about it. At a certain point I decided, I’d rather fail as a writer than succeed as a lawyer. So I need to succeed or fail and see how it goes.

I was at an open place. I had moved from DC to New York, so I didn’t have a job, and I thought, well, this is my chance to really try. But I didn’t worry about it that much. Maybe because I was just naive. I bought a book about how to write and sell a nonfiction book proposal, and I thought, I’ll just follow the directions and see how it goes. And that’s how it went.

There was one day, though. My husband and I met in law school, and he switched into finance when I switched into writing. And we got a notice about our New York State bar fees, which are expensive. And I said to him, should we pay our bar fees?

And he said, why would we pay our bar fees?

And I was like, okay! We’re doing this. We’re not paying our bar fees. We’re going rogue. At the time I thought it was this huge thing. Now I know you can go back—there is a way to go back—so it wasn’t as dramatic as I thought it was. But that was a moment where I was like, okay, we’re doing this.

 

Takeaway: Look at the last 52 weeks

Almost everything Rubin recommends cuts against a manager’s instinct to standardize. Four different explanations for the same software rollout. A Friday afternoon that bills nothing. A recurring calendar entry that says Worry.

One item on the list costs an afternoon and no money at all. Pull up the last year and count. Committees. Drudge assignments. Unpleasant travel. The clients nobody else will take. Vacation days left on the table. One name will keep appearing, and it will belong to the person least likely to ever raise it with you—which is exactly why counting is the only way you’ll find out.

Because eventually, as Rubin says, they will rebel.

Gretchen Rubin led a keynote conversation with Esther Perel at ClioCon 2025. To hear from the legal professionals, innovators, and advocates shaping the future of law, get your tickets to ClioCon 2026 today.