EXJ Conversations: Jordana Confino on coaching the chronic perfectionist, people-pleaser, and overachiever.

ex judicata: It’s a real pleasure to have with us today. Jordana Confino, the founder of JC Coaching and Consulting. She’s a Yale Law School graduate, professional coach, speaker, advisor and an adjunct professor at Fordham Law School. In addition to private clients, she also frequently counsels law firms on relaying a message of positive goal attainment and wellness to their attorneys. 

As we’ve talked in other exj interviews, there is a cottage industry of former practicing lawyers that are now coaches, and it can oftentimes be hard to distinguish. But based on what I’ve learned and the glowing client reviews, Jordana is among the best. So, it is great to have her with us today. Jordana, thanks for being here.

Jordana Confino: Oh, it’s my pleasure, Neil. Thank you so much for having me!

ex judicata: Let’s begin at the beginning. Growing up, did you always want to be a lawyer?

Jordana Confino: Oh, no. When I was little if you had asked me, I would have said I wanted to be a movie star who works part-time at SeaWorld. I was a total creative spirit and animal lover back then.  And even once I grew up, and was in high school and had caught the overachiever bug, it still didn’t even occur to me to practice law. My mom was a lawyer, but I had no interest in it. I gravitated towards psychology and that’s what I majored in in college because I was fascinated by it.

And then I got to junior year, and all my friends at Yale College were going off to their banking and consulting summer internships, and suddenly it didn’t feel like the things that I was interested in were shiny or prestigious enough.  At that point I said, I don’t know what I want to do. I’m a good test taker. I’m type A-plus, very meticulous, detail oriented, all those things. And then everyone’s like ‘you should go to law school’.  So, I took the LSAT and I was fortunate enough to get in. That was how I ended up in law school.  No more thinking than that.  Don’t get me wrong, I love what I’m doing now and, yes, it’s tied to my having gone through law school and everything I learned through my legal experience.  But whenever anyone comes to me and asks, ‘Should I go to law school because I don’t know what else to do?’.  I say, ‘No, that is a bad reason.’

ex judicata: Yes, certainly, a common reason people go to law school particularly history and English majors is because they are unsure of what they want to do.  Absolutely true in my case.  Did your mother try to influence you?

Jordana Confino: Neither of my parents were pushing me towards law school when I was in undergrad. It’s interesting. I spent time in Biglaw when I was in college.  I won’t say which firm.  And my only conclusion from that was that I didn’t want to go to a law firm, because that’s where happiness goes to die.  But by the time junior year rolled around, I had taken to driving myself so hard and people seemed to be really excited about me saying that I wanted to go to law school, so I bought in.

And then, of course, the second that I decided that I wanted to do that, I had a lot of cognitive dissonance because–although I can admit to myself now the true reason why I went–I never would have said that to anyone at the time. And I don’t think I really wanted to believe it myself.  So I ended up concocting this whole idea about what I wanted to do with my law degree such that by the time I walked into law school, I was fully: ‘I want to be a federal criminal prosecutor. That is my passion. What do I need to do to get in?’ I’m willing to kill myself to check all those prestigious boxes to get there.’ And at the time, I think I really believed it.

ex judicata: So, you go to Yale Law School, you have a summer associateship at this super prestigious Biglaw firm, and then two clerkships, Southern District and Second Circuit Court of Appeals. Next stop, potentially US Supreme Court law clerkship.  And then you get off the bus. What happened?

Jordana Confino:  Well I also spent my summer between my first and second year at the US Attorney’s office in the exact unit that I had decided I wanted to work in—the Civil Rights Unit working on sex trafficking prosecutions. That was the stated mission. I wanted to become that person. Then I got there and I was like, ‘Wait a second, prosecutors do a lot of solitary writing.’  I didn’t like that.  Writing gave me tremendous anxiety at the time, which I now can see was linked to my insanely high level of perfectionism.

So, I knew I didn’t like the writing but I thought. ‘Okay, maybe I’ll love the arguing and court part. Maybe I’ll get a rush from it.’ Then I took trial practice during 2L fall at Yale, and I realized, ‘Wait, I actually hate this.’  I came to realize that I really like working in a supportive, nurturing environment and,turns out, criminal prosecution did not offer that. It felt wrong, but I just kept going because, back in college, I’d come to believe that in order to be successful, I had to forego every single aspect of my well-being. So I didn’t expect it to feel good. I didn’t think it could or should.

Jordana Confino: So I kept at it—I  out-studied and outworked everyone in the room. And increasingly I started to feel like I was dying inside. I honestly felt like I was the loneliest person in the entire world. I remember feeling so lonely it physically hurt.  I wasn’t enjoying anything that I was doing. I had no sense of meaning or fulfillment. And I was just growing more and more anxious and unhappy by the day.

And then I get to the Biglaw firm that second summer and I’m looking around and realzie I’m not the only one person that seems so unhappy. There are so many people around me that seem miserable, but no one seems to care what is happening.  It made me feel uneasy.

At the same time, I’d also started to have crazy anxiety about the fact that I had committed to two years of clerking after graduation. 

I knew this was going to be nonstop, lengthy writing assignments because that’s literally what clerks do.  And, at the time, that was my worst nightmare. So, I started meeting with a therapist that second summer when I was working in the Biglaw firm.

Ex judicata: So, all this time the pressure is building and building.

Jordana Confino:  Yes, my anxiety was so high, I remember describing myself as a hamster in a pressure cooker.  I thought that I was going to explode. All sorts of chronic physical health issues had also started to take root when I was in law school. They got much worse in my first couple years out.  I started thinking, ‘When is this going to end?’

Then, that summer, I did a values alignment exercise with my therapist where she basically asked me to look at this list of 100 values and identify my top values. This was a question that I never thought about in my entire life: What do I care about and why?  And I realized that my top values were love, connection, authenticity.

Meanwhile, I’m the loneliest person in the world and walling myself off from any feelings of connection both immediately and in terms of future.

ex judicata: What did you do?

Jordana Confino:  In the midst of all this, I’d discovered positive psychology while googling ‘how to be happy,’ which I did because I truly had no idea, and I really wanted to know. And once I discovered positive psychology, my brain exploded and I was just like, ‘Oh my God, how come lawyers and law students don’t know this? They all need to.’

I saw that there could be a fusion between my psychology background and my law school and law firm experience. And I realized that this is what I wanted to do in some way professionally. It gave me something to pivot towards as opposed to just fleeing away from the practice of law.

ex judicata: And when you decided to leave the law did people ask you if you’d lost your mind?

Jordana Confino: Yes. So many people said things like, ‘Are you crazy?’ And even worse than that, some people immediately just stopped talking to me because I was no longer interesting to them anymore.

ex judicata: That’s funny. I would think you’d be more interesting. But anyway…

Jordana Confino:  It depends how you define interesting. I will also say that a number of those people, fast forward many years, are now very interested in what I’m doing because they see that there was something to it. The funniest thing is that one person asked me if I was doing this because I was afraid that I wasn’tt going to meet a man if I was in a high-powered legal position. I kind of equate that with, ‘Are you crazy? Why else would you possibly be doing this?’

ex judicata:  Yes, that sounds about right. Yikes.

Taking charge and making change is what we are all about at ex judicata.  It’s taking the leap. It requires a lot of courage, and many times you have no idea where you’re going to wind up.  But you just know instinctively this is the right thing to do. What was your path out. I know you had a series of law adjacent jobs that sounded cool. If you could walk us briefly through some of them.

Jordana Confino:  Well, I should note that I waffled for a bit. I was absolutely terrified to make the move out of law. And some people are telling me that if I just remained in place a little bit longer, then more doors would open. But the truth is that when you’re trying to keep doors open, you’re keeping other doors closed. And at a certain point I realized that I had to do it now because I didn’t see a space in time when I’d be better equipped to do it. I realized that the chasing gold stars would have just continued on forever.

So the first thing I did was a heck of a lot of volunteer work because it turns out it’s not as easy to go from law to a law adjacent job as one might think. I thought I was a hotshot with all these credentials, but I found they only really mattered in that world.

If you’re transitioning or pivoting, you may have to take a step back.  Not always, but often.  I wanted to work with law students focusing on well-being and I wanted to be in New York.  Every job I was looking at wanted 2 to 4 years of experience working in a school, so I started doing some volunteer work during my judicial clerkships. I ultimately, ended up going to Columbia Law School, where I worked in student services.

I loved it.

While I was there, I underwent a certification in Positive Psychology, and as my capstone project I developed a syllabus for a course on Positive Lawyering that I really wanted to teach. But that was not a possibility for me at Columbia. Then, my second year at Columbia, I was asked to serve as the acting Clerkship Director. I did this for awhile, but it was not really what I wanted to do.

During that time, I got much more actively involved with lawyer well-being initiatives and work outside of Columbia.  And then ultimately through a very indirect, fortuitous path, I ended up connecting with someone at Fordham Law School. They had just issued their strategic plan saying that they wanted to double-down on community building, well-being and student professional identity formation. And they wanted to launch a new office of professionalism, and they needed someone to build it and run it. So they hired me in that role.

They also hired me as an adjunct professor and said I could develop and teach courses related to professional identity formation. So, I got to start teaching my Positive Lawyering course.  And I very quickly realized that teaching that course was my favorite part of the overall job.

I’m still teaching that class, and I also teach a class on peer mentoring and leadership.  

And then fast forward a few years, and my students started graduating and calling me from their law jobs, saying they wouldn’t be surviving without what they learned in those classes. It was early Covid, and I found myself spending like 20 hours a week on the phone with former students, talking with them about their situations.  

At that point, I was like, ‘I think there’s a profession for this.’  So I got my coaching certification and began coaching.  Around the same time, I started working with law firms because I realized that the things we were focusing on in the classroom were just as relevant to them, as well.  I was doing this on the side at first until, ultimately, this past year I decided to step down from my Dean role. I’m still teaching my two courses at Fordham, but aside from that I’m now doing the coaching and consulting full time.

ex judicata:  I have a couple of questions. Was it ever hard working in a law school with all these high achieving kids around you, knowing you were once them.  Did you ever second guess your decision to change paths?

Jordana Confino: No, definitely not. And actually, the question I’m most often asked is the opposite of that – people ask, ‘Are you telling your students that they should leave practice of law?’

And the answer is absolutely not.  I teach students about the importance of values alignment and strengths alignment.  And when thinking about their careers, how they can separate what really matters from what just FEELS shiny because they’re immersed in a particular world.  For some Big Law may actually be the ideal path. Whereas for others, like me, it was a mismatch. I just want them to be honestly asking themselves these questions.

We also talk about cultivating well-being and understand that it is not a distraction from, but actually an essential element of, professional development.

For me, practicing was never the right fit.  But I’m so glad I went to law school because I did make some wonderful friends and going through law school made me well situated to do the work that I do. In front of a population that so desperately needs this work

ex judicata:  For sure.  I think a number of people listening to this would be interested in what exactly is involved in proposing a course and becoming an adjunct professor.

Jordana Confino: I was in a special situation where I was being hired as an administrator to direct the Office of Professionalism, and I was also being hired as an adjunct as part of it.  But it’s an excellent question and one that I get a lot.  Most places will want to see a syllabus as part of a proposal to teach a class. You’d then send that syllabus to the right Associate Dean or whoever oversees the academic adjunct curriculum.

I love teaching my course, but people should realize it’s not a full-time gig. It’s something you do for the enjoyment and the benefits of being affiliated with the particular institution, not the pay. If you want to be a full-time professor, you have to pursue the tenured  faculty route, which is a whole other beast.

ex judicata: How did you get that all important first client?  Was that one of the students that you had been working with from law school or did it come about another way?

Jordana Confino:  Interestingly, my first client was actually my most random client.  I had just launched my website and I was still nervous to even announce it to anyone.  And then it occurred to me how am I going to get clients if no one knows that I’m doing this?  It was a family member that posted about my business on their LinkedIn. And someone saw it and I got my first client that way.

ex judicata:  So, luck sometimes plays a role, but you put yourself in a position for something to happen.

Jordana Confino:  What’s been most helpful in terms of getting clients is talking to people about the work that I do, which is easy because I absolutely love it.  I’m really an open book.  My goal is to help people know who I am and what I’m about, so that they can determine if I’m the right fit.  The coaching page on my website says ‘coaching for the chronic perfectionist, people pleaser and overachiever’. And people ask ‘Isn’t that a little narrow?’  And I point out that, first of all, in the legal profession this is a lot of people. And second of all, I don’t need to be for everyone.  But I figure that if I speak directly to my people, that will make it as easy as possible for them to find me.

ex judicata:  So many lawyers fit that profile that a boatload of coaches is needed. In your coaching practice, I have to imagine you’ve got a number of young attorneys on the cusp of making a major career change but they’re unsure if they should proceed or should not?  Is there one particular theme or themes that that appear at the heart of why it’s so difficult to leave law?

Jordana Confino: There’s a couple of different things. One is that a lot of people are like me and they never thought about what else they might want to do. And when you’re in the thick of things at work your brain space and time are stretched so thin that you have zero capacity to do that.

So, when you ask people ‘What are you interested in outside of work?’  They’re like, ‘What?’  Outside of work they have literally nothing going on. So, the thought may be to run away from their law job but if they do, they don’t know what they’d be running towards.

Honestly, that’s why I got so excited when I discovered your whole platform, ex judicata. I’ve come to learn that the subject matter of one’s work is far less important than what you’re doing on a day-to-day basis, who you’re working with, what those people are like, what those relationships are like, and how work fits in with the rest of your life. But when it comes to thinking practically about what else is even out there, people don’t know where to start.  That’s a huge challenge for anyone who wants to leave law.  Another big challenge, especially for people in Big Law, is being able to create enough space and have enough time to process exploring alternatives, not to mention actually applying for jobs.  Finally, there’s overcoming the fear, which is itself a huge challenge.  Because they’re potentially blowing up this thing, which, even if it’s making them miserable or slowly killing them, has provided their sense of validation or worthiness for quite a long time.

ex judicata: We’re here at ex judicata to try to help lawyers overcome those challenges that you just referenced. Switching gears for a moment, when working for law firms what’s the main message that they want you to convey or that you want to convey? And who comes up with the messaging?

Jordana Confino:  I feel strongly about the integrity of my work so I always come up with the messaging. If a firm asks me to convey something I’ll only say yes if it’s something I would have communicated on my own. And it’s tricky in the wellness space because there are some organizations that want to do something ‘well-being focused’ solely to check a box, rather than because they actually care about the well-being of their employees. I try to only work with the latter.

There are two core messages at the center of the work that I do. One is positive psychology for peak performance. So that’s the science of positive psychology and the huge body of impressive and compelling research that shows that our well-being enhances our performance, and that self-care or well-being and success are not mutually exclusive. 

I talk about the foundational elements of our well-being—things like positive emotions, engagement, a sense of meaning, connection, and then physical vitality.

Then the question becomes how we can cultivate these things in the context of an extremely demanding profession?

For organizations the message is FIRST, your people will not only be happier and healthier, but they’ll also perform better if you give them a sense of meaning and purpose in the work, and if you make them feel like they matter and  thattheir work matters. And SECOND, here’s how you can practically do this in the context of your work.

My second core focus is on the perfectionist mindset and de-glorifying perfectionism. I’m helping people understand that there’s a big difference between drive, high standards, and commitment to excellence on the one hand, and fear-based perfectionism on the other hand. I show people that perfectionism is really a fear and shame-based hustling fueled by self-criticism, which is very different than things like intrinsic motivation and wanting to do a good job.  And I show them that this first kind of perfectionism not only hurts our well-being, but also holds us back from most effectively doing whatever it is that we want to do.

This is something that I was still experiencing firsthand when I first got to Columbia Law School even though it was a non-legal job.  I’d already made the leap from practice, so in my mind I was thinking, ‘Okay, I’m honoring my values.  I’m following positive psychology.  I’m off the treadmill.  Everything’s going to be amazing now.’

And then I burned out really hard within six months of being there.  And it was because I was still tearing myself apart on the inside. I was still driving myself into the ground.  So I realized, you can take the girl out of the toxic work environment, but if you don’t take the toxic boss out of the girl’s mind, she’s not going to be happy.

That’s something that I share with people at the law firms, but I actually think it is really important for anyone on your site and listening to this.  Leaving law very well may be the right thing for you but if you’ve spent any amount of time in law, or even if you just went to law school, you’ve probably internalized this perfectionist mindset and will likely carry it into your next job. 

So you have to make an intentional effort to rein in the old mindset. This is challenging but totally possible.  So, there are really two things to focus on.  First, moving out of the law and figuring out the right career fit for you.  And second, being in the right mindset to set yourself up to thrive in your new environment.

ex judicata:  That makes a lot of sense.  One last question, Jordana. It’s the one we always end on.  How did your law school training help you as a professional?  Not the surface fact you went to law school and practiced law.  I’m talking about the skill set you gained when getting your law degree.

Jordana Confino:  It’s interesting. I think there are the problem-solving capabilities and analytical skills that are helpful in anything.  But for me personally, what also helped after leaving law were all the things I did in law school that were not on my resume. The mentorship programs I got involved with, the teaching opportunities within student organizations, all the things I did because I actually liked doing them. So if anyone out there is struggling to figure out what you might want to do next, go back and look at those things you did just for the sake of it.  They will offer some clues.

ex judicata: And then connecting the dots, you focused on doing things you liked doing as you grew in your new career opportunities.

Jordana Confino: Yes.

ex judicata: And that is a perfect place to leave it. Jordana, thanks so much for doing this and all the valuable insight you shared for lawyers and law students alike.

Jordana Confino: My pleasure. Thank you so much for having me.

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