Kara Loewentheil, J.D. is a Master Certified Coach and Host of the UnF*ck Your Brain Podcast, which has been downloaded almost 4 million times in 18 months. Three years ago she did what every Jewish parent dreams of for their child: She left her legal career running an Ivy League think tank to become a life coach. Now she teaches women how to undo the effects of patriarchy on their brains and create true authentic confidence from inside. She has grown her coaching business from zero to over seven figures annual revenue in the last 3 years, and is passionate about teaching women how to overcome anxiety and self-doubt so they can take on the world.
Let’s start with the basics. What are you doing now? In a sentence or so, describe your work/practice(s).
I’m a confidence coach for feminist women. I teach women how to not only to recognise the thoughts they have that are created by social messaging and the patriarchy, but how to change those on purpose so they can create true confidence from the inside out. That’s the only way it works even though we’re taught that accomplishments or external validation is what will make us confident. The truth is it has to come from inside of us. We have to truly believe it and to do that we usually have to rewire our brain. So that’s what I do, I’m a life coach and that’s what I teach.
Did you always imagine yourself going to law school?
I don’t think that I always imagined myself going to law school when I was growing up. I loved literature and I was an English major with a Creative Writing concentration. I strongly considered being a writer and I strongly considered a career in psychology, which is interesting given where I ended up. I was very active in the reproductive rights movement. By the middle or end of college I knew I would go to law school because that seemed like the next thing I could do for the reproductive rights and reproductive justice movements. I come from a family of lawyers and it certainly seemed more plausible than medical school.
At what moment did you realise you wanted to take your legal education and career in your own direction?
I didn’t set out to become a life coach. I have always been very interested in the human experience and what I would call human interiority or what our subjective interior experience of reality is like. I was always reading self help of going to therapy or working with coaches but I definitely planned to stay in the legal career. By the end of my legal career, I was an academic and on track to become a law professor. When I found my current teacher and mentor’s work, it just changed my life so much applying it that I knew I wanted to teach it to other people. This was the best way for me to make an impact in the world.
What were the steps you took and opportunities you seized in order to get where you are?
To get from there to here, I went and got certified as a life coach. That was the easy part. You just had to pay money and show up learn which are things I’m good at. Coming out to my family and telling them and telling all my colleagues and friends was more challenging. Telling law professors you’re going to leave the academy to become a life coach…you get to watch people try to control their facial expressions. That was the biggest challenge and hurdle I would say. Plus becoming an entrepreneur. I really had to learn a whole new way of thinking about myself as an entrepreneur instead of an employee. Lawyers are so obsessed with getting everything perfect before anyone sees it and being an entrepreneur is the exact opposite. You have to fail all the time. I really had to change my entire way of thinking of being in the world. It was like a death and rebirth in some ways.
What makes your current practice “lawfully uncommon”?
I’m not entirely sure what that means but being a life coach is a pretty uncommon thing to do although more and more lawyers are these days. I’m not a practicing lawyer anymore and I just registered myself as retired from the New York State Bar. I don’t practice at all; I have a different practice now.
Is there anyone influential in your life that helped you realise your goals? Mentors or role models in the field that inspired you?
The most influential person in my life in this way has been my teacher. Her name is Brooke Castillo. She has a podcast called Life Coach School Podcast, my podcast is called UnF*ck Your Brain. You can see how our branding is slightly different! I was applying her podcast to myself and doing the work on my own for 18 months before I decided to go get trained as a coach. She has been my mentor and teacher the whole way and continues to be my mentor and teacher. She has been my biggest influence. I also had to build a whole new professional network from scratch. I don’t get my clients through my network, I’m not referral based, but when you work for an organization you take for granted that there’s all these people working who you can talk to and bounce ideas off of and you have bosses to give you instructions on what to do. When you’re an entrepreneur you don’t have any of that. Having colleagues and friends and other entrepreneurs and other coaches to talk to and get ideas and advice from and to give those things too has been super important to me. I’m in a small mastermind of other life coaches who trained with my teacher and whose businesses are at
$1 million a year of revenue and up. That has been really helpful and inspiring.
What got your juices flowing or tickled your fancy while at law school?
I’ll be honest; I did not enjoy law school that much. But I did discover critical legal studies in law school in 1L year. I took a seminar with Janet Halley at Harvard. That kind of blew my mind and resonated with me because I’ve always been a very pragmatic realist person. I was so alienated by all the legal formalism. My mother was a Federal Public Defender for 20 years so I grew up with an inside view of what the American criminal justice system is like, what it does and how racist it is and how unfair it can be. To show up at law school and have everyone acting like the law totally made sense and was so just and they had these abstract principles. I was like, what the hell is going on here? When I discovered Critical Legal Studies and Critical Theory in general, I think that was just an important step in my intellectual evolution. I still use those tools in some ways in my practice.
What made your blood boil or made you snooze while at law school?
What made my blood boil was everyone pretending everything made sense, especially after law school! I clerked for 2 years at a Federal Appeals Court. Most Harvard professors have clerked on a Federal or Supreme Court. After that I was like, HOW and WHY are you perpetuating this fiction that the law is coherent and makes sense when you see how the sausage is made? When you’ve been on the inside and you see how 3 justices on a 3-judge panel fight about what the opinion is going to say and they negotiate and they edit. Their clerks preparing the basis for these opinions have just gotten out of law school and don’t really know anything. It was shocking to me how much wilful denial goes on. That was my strongest reaction to law school.
Were there challenges you faced in the transition from law school to the profession?
Clerking is crazy to me. You don’t know anything. Ironically, the fancier the school you went to, the less concrete knowledge about the law you have. Maybe your analytical skills are strong, but I remember when I started clerking, one of my co-clerks had already clerked for a District Court for 2 years which had been a big education for him but he also had gone to a state law school. He actually knew stuff about the law whereas I had mostly been taught theory. Part of that was me, I self selected into that because I was into Critical Legal Studies and theory but I had taken Fed Courts and Property and Corporations and I taken the basics you’re supposed to take beyond the requirements. And I had very little concrete knowledge. You basically learn the whole thing on the job. The law should be an apprentice system.
The other challenge that a lot of lawyers face is that people who go to law school tend to be hyper critical, perfectionistic and risk averse. Then you start work and you’re still like that and it makes you crazy. I had a hard time getting my first draft opinion done for my judge. That took a lot longer than it needed to. It was before I discovered the coaching work I do now so I had a lot of anxiety for the first 4 or 5 years of my legal practice because I didn’t have tools for managing my mind. I didn’t know how to change my thoughts and I still believed that my job was causing my stress (turns out that’s never the problem, it’s your brain). Law school drills into you that any mistake is fatal which is not helpful for that mind set. I would say that was the biggest challenge, navigating that anxiety and perfectionism.
Do you still see the law all around you?
Of course I see the law all around me. I was a big fan of the Mnookin article called Bargaining in the Shadow of the Law. It’s about divorce negotiations and I think it’s from the 1970s but it was one of the first articles to talk about the way in which law shapes not only legal processes but all of the decisions and negotiations that we make in anticipation of or to avoid or thinking about legal consequences or alternatives.
I’m a structuralist in some ways so I see that all around me. It’s also interesting being a life coach who was a lawyer. I think I think about my legal obligations much more than most entrepreneurs. I’m still a very small company but I have two full time employees when most people have independent contractors at this stage because I read the legal definition of the two different types of jobs. I look up my ERISA obligations, I ask a lawyer. Most life coaches with 2 employees don’t know what ERISA is. It does still shape the way I think about things. I for sure still see it around me.
What advice would you give to a first-year law student?
I would say if you don’t want to be a lawyer then drop out of law school. Being a lawyer is not like being in law school necessarily so if you don’t like law school it doesn’t mean you won’t like being a lawyer. But if you went to law school because you just didn’t know what to do with yourself, it’s a very expensive way to pass the time. It’s challenging and teaches you to think in a different way and changes your brain and not always for the better. I wouldn’t do it if you don’t actually think you want to be a lawyer.
If you are going to stay in law school, try to make sure you take preventative measures to protect your brain from the way law school teaches you how to think. Law school teaches you to be super analytical and logical, which is very helpful, but it also teaches you to be very pessimistic and always worry about everything going wrong and that’s less helpful. Go to therapy, get a coach, read some books about positive psychology or listen to my old podcast which was called The Lawyer Stress Solution and still available wherever you get your podcasts. Don’t let law school steam roll your brain. Try to stay on top of seeing how you’re taught to think and questioning that and introducing a positive bias into your brain to counteract the negative bias in terms of how you’re being taught to think about things.
If you were given the blessing and curse of an extra hour every day to do whatever you wanted, what would it be?
I don’t feel like I don’t have enough time in life and that’s mostly because I manage my mind and my thoughts about it. I also work for myself and I love my work so some days I work a lot and some days I work less. If I had an extra hour every day, I really wouldn’t change what I’m doing. I don’t suffer from believing I have a lack of time.
No regrets, absolutely none. Regret is an emotion that is caused by our thoughts. We can choose whether we want to believe the thoughts that cause it. I have always chosen to think and believe and love believing that everything in my life brought me to where I am today. That doesn’t mean that there was a reason like a divine intervention. It just means my life now is a sum of all the experiences that I’ve had and I wouldn’t be me without them. Because I have done the work to love who I am, I would never want to change that.
I actually think that law school made me an amazing coach in some ways. I had a lot to overcome but it taught me how to be totally unflappable in the face of questioning and disagreement. When I work with very smart, high-achieving, feminist women, my clients aren’t just “oh whatever you say” and I’m teaching them a pretty radical view, that you can really control your own life. You can create what you want in it and create your own feelings. We do a lot of debating and law school taught me how to handle that.
More importantly, when I first found this work, the reason I believe in it so much is that when I first encountered it, I brought my lawyer brain to bear on it. I tested the ideas from every angle. I worked through all my own possible objections and devil’s advocate arguments. I took it to the extremes mentally and it stood up. I saw how it stood up for me. I’m so glad I had those critical tools and part of what makes me an amazing coach is that I ask great questions, it’s almost like Socratic questioning but for your own good and it feels better. All of the tools I learned in law school are so interestingly useful for being a coach other than the negative biases. All of the analysis and logic and questioning makes me a better coach. I think it turned out to be super helpful.
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