Jennifer Alvey: From Lawyer to Legal Publishing to Career Coach for Lawyers [TFLP 014]

This week I’m going to share with you my conversation with Jennifer Alvey. Jennifer worked as a lawyer for a number of years and then she left and was in legal publishing. About 10 years ago, she works now as a career coach for lawyers. 

She has a lot of interesting stuff to share from her career journey and how she made that change as well as the things that she has learned coaching lawyers out of their own legal careers into other careers that work better for them. 

I’m really excited for you to hear this conversation, so let’s get to it.

Jennifer’s Journey In The Law

Jennifer went to law school with the idea that she would work in congress. But, when she got to law school, the pressure was on for her to get a job at a firm and didn’t have a lot of support to find something else. 

She also got caught up in the dream-crushing debt that law school brings. So, she got a job in a firm, working in intellectual property law. She began to feel that something wasn’t right when she noticed that misery was quite normalized in the law. 

At the time, she felt that if she had more hands-on work that things would be better. So, she moved to a smaller firm to work in patent law. However, their patent got withdrawn, and Jennifer’s job essentially disappeared. 

So, she had to find another job. She did, and this job had everything she wanted. She even got lots of compliments from her superiors. But, Jennifer was still miserable with her job in the law. This prompted her to do a lot of soul-searching and even seeing a therapist. 

Leaving A Job In The Law For Writing

When Jennifer finally started getting serious about leaving the law, she realized that she needed to find something completely different. She thought about what led her to law school in the first place. The first thought in her mind was writing and the power of words. 

After seeing an ad in the Legal Times for BNA (pre-Bloomberg), she answered it, and got the job! She wrote pieces on tech and eCommerce, back in ‘99 when the internet was still pretty new. 

Jennifer was there for two years and then had a few other writing jobs as a freelancer. Eventually, she worked as editor-in-chief of a legal association magazine. Around 2007, she went freelance and started her own blog. 

After blogging and freelancing for a couple of years, she realized that this could be a full-fledged business. So, she got some more training and continued to work as a freelance writer until she had another realization and made another change. While she still does freelance writing and editing, most of her work is coaching lawyers. 

Career Coach for Lawyers

Remembering her own level of misery in her time in the law, Jennifer really wanted to help others in the same position. So, she got the necessary training and began coaching lawyers. She helps them to put the pieces together and motivates them to find what makes them happiest. 

Want Out Of The Law? Here’s Jennifer’s Advice:

For people who are flirting with the idea of leaving, Jennifer says that it’s very helpful to try and separate what’s the environment versus what’s the actual work and what each one is doing to you or for you. 

Dealing with a really dysfunctional environment is much more common than not in the law for a lot of different reasons. Try and separate your environment from your thoughts of “I don’t like this.”. The best thing you can do is just be really brutally searingly honest with yourself. I have to tell you that’s difficult. 

For people who are sure they want to leave law, the most necessary, which also tends to be the hardest thing, is figuring out what you really want, the big picture question. You have to be invested in your new goals if you want to leave the law for good. 

Lastly, Jennifer said that one of the best things you can do for yourself when transitioning out of the law is to make non-lawyer friends broaden your horizons, and see the different values in people who aren’t lawyers. They can also give you a better perspective on all of the options you have based on your personality and interests. 

And, if you have no idea where to start with leaving your job in law, download my free guide: First Steps To Leaving The Law. You’ll learn exactly what you need to do to finally make that transition. You can also email me if you have any questions. I’m always happy to help. 

Until next time, take care!

Connect With Jennifer:






Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. On this show, I interview former lawyers to hear their inspiring stories about how they left law behind to find careers and lives that they love. Let's get right to the show.

Hey, everyone. Welcome back to the podcast. This week I’m going to share with you my conversation with Jennifer Alvey. Jennifer worked as a lawyer for a number of years and then she left and was in legal publishing. About 10 years ago, she transitioned into career coaching for both lawyers and nonlawyers, but mostly lawyers. She has a lot of interesting stuff to share from her own career and how she made that change as well as the things that she has learned coaching other lawyers out of their own legal careers into other careers that work better for them. I’m really excited for you to hear this conversation, so let’s get to it.

Hi, Jennifer. Welcome to The Former Lawyer Podcast.

Jennifer Alvey: Hi. Thanks for having me. It’s great to be here.

Sarah Cottrell: I am so excited to have you here. I have been reading some of the things that you have written about advice for people who are looking to leave the law. Why don’t we start with you just introducing yourself to the audience?

Jennifer Alvey: Okay. I graduated from law school in 1991. I’m officially kind of a dinosaur, I suppose. I practiced for about eight years. Probably the last two or three of those, I knew I wanted to leave law but I just had no idea how to do it or what I wanted to do. But once I did, I went into legal publishing and that turned out to be exactly the right thing for me to do at that point. Although it’s really funny because a lot of people around me were like, “What could you do with that? What’s the career progression?” I’m like, “I don’t know but it’s gotta be better than this.”

Sarah Cottrell: What drew you to law school in the first place?

Jennifer Alvey: I had this idea, I had interned in my state legislature when I was in college and I thought, “Oh, I want to go work in The Hill in congress.” It was a great theory. But then I got into law school and my school, which was Duke, and I think a lot of schools are like this; the pressure is, “Oh, get a job with firms,” and there wasn’t a lot of support at that point, and of course, there was no internet for looking at other possibilities. I got caught up in that and also the fact my loans were scary. I thought, “Well, I’ll work for a few years for a law firm and try and find something on The Hill.” I guess in a way it panned out because when I was a legal journalist, I did cover a lot of stuff on The Hill but I never worked for a committee.

Sarah Cottrell: Got it. Do you live in the DC area?

Jennifer Alvey: I did for 15 years. I did start with the DC firms and stayed there for quite a while, then left DC and moved here to Nashville where I live now.

Sarah Cottrell: What kind of law did you practice and how did you find that law? Did you just go towards a firm and end up where they needed someone? How did that work?

Jennifer Alvey: It was a combination of things. I had a clerk on the Federal Circuit, which is of course, known for intellectual property and I was interested in intellectual property, but mostly, the trademark and copyright side because I’m not an engineer and I never wanted to be one. Then I went to what was then Howrey & Simon. I did some intellectual property stuff there. But they were mostly, I would say, at least 85% or 90% litigation at that point. I did get a lot of that thrown on a whole bunch of cases that needed bodies as well.

I spent one summer doing document review with actual boxes of documents. I spent every morning of that summer pretty much crying all the way into work, which I thought was kind of normal. But then I went to see my doctor because I had been having a lot of digestive intestinal issues and she had asked me something and I told her that and she just looked at me and she said, “You know that’s not normal, right?” And I was absolutely floored. I was like, “Really? I thought it was.” I think that was the beginning of the end in a way, although it took a long time.

Sarah Cottrell: Yeah. That’s so interesting that you mentioned that because there are so many people who I’ve talked to who talk about how misery in your job as a lawyer is very normalized, particularly in certain environments like law firms, to the point where it’s almost like, “Well, why would you think that’s a reason that you shouldn’t be doing this? Because literally, everyone is miserable,” essentially. I think it does contribute to being in situations where you could cry going to work everyday and you think that there’s nothing abnormal about that. Because honestly, I think in a lot of ways, it’s not that abnormal.

Jennifer Alvey: No. I think it’s abnormal but it’s incredibly common.

Sarah Cottrell: Yes, yes.

Jennifer Alvey: The amount of depression and anxiety. It was really high then. I think that technology has probably just increased some of that.

Sarah Cottrell: Yes. You said that when the doctor said to you that this isn’t normal, that that was the beginning of the end, but you also mentioned that for the last couple of years, when you were practicing, you knew you wanted to get out but you didn’t know what you wanted to do. Can you talk a little bit about how you figured out what to do next or what the process was for you in doing that?

Jennifer Alvey: Sure. My theory on why I was so miserable in law initially was, “Oh, well, it’s this really big impersonal firm and I’m not getting any very much substance of work and I would just be better off if I had more hands-on experience.” Someone I knew once said that I was like a stealth risk taker, and that’s probably somewhat true. I found a job with a little company in a suburb and they wanted some patent enforcement work done. I was like, “I know about patents. Enforcement, that’s like litigation, super.” Then their patent got withdrawn from issue, which as a wet behind the ears sort of young lawyer, I had never heard of. It is rare but it happened and that just meant that my job disappeared, I found another gig and it had everything I wanted. I had client contact. I got to do lots of substantive work, all that stuff.

I walked into my office one day right after I had finished this great draft of something, and got lots of compliments from the partner. I was like, “Oh, my god, I still hate this.” That was like, “Oh my god, what am I going to do about this?” I started doing a lot of soul searching and saw a therapist, and all of that stuff. I highly recommend therapy for every lawyer out there because I think a lot of us get news messages along the way and some of them are not even from our law environment, they are from our “Let’s build a resume checklist” way of life that most lawyers really pursue. You get a lot of good feedback if you’re getting As in all your classes and you’re doing the quiz team or the Spanish club or student government or whatever it is you’re doing. No one’s seeing their goal, “Well, yeah, you’ve got a lot of really good academic skills but what do you want to do in your heart? Are you connected with yourself?” People do not ask you those questions when you are in high school and college and you’re doing well, they just don’t.

Sarah Cottrell: Yes. I think I really relate to what you said about moving to a job where it had “everything” in it that you wanted and then you realized, “Hey, I actually still hate this.” Because when I first decided I wanted to leave Biglaw, I also was like, “Oh, maybe I’ll like it more at a smaller firm with more hands-on blah-blah-blah.” I started to do interviews and I basically went to this interview at this place that was ostensibly like the kind of place that I would want to be. I realized that as I was walking in, I don’t actually want to be here. The things that you’d say, “Oh, yes, I really want to be doing more depositions,” or whatever, I was like, “I don’t actually want to do those things.” It was sort of this moment of, “Oh, yeah, it’s not just that I want a different type of legal work, I need to be doing something else entirely.”

I think for some people, making a change to a different type of firm or whatever, might be the solution. But I think for me, at first, I didn’t necessarily have the imagination to think any further than like, “Oh, a different kind of law firm work.” It was only once I started doing interviews that I realized that “Oh, yeah, I can’t actually tell these people that I want to do this work because I don’t.”

Jennifer Alvey: Yeah. I congratulate you on listening to that voice because that voice got just completely squished down for me in my life. But when I finally started getting serious about it, I realized that I just needed something completely different and I tried very hard to figure out why I went to law school at the first place, and in the end, the only thing I really came up with was the power of words and that I really like to write. Writing briefs and stuff in firms was the thing that I hated the least, although really most legal writing is not that wonderful constitutional law that you can see in law school. It’s very different. But at least, there were some principles and some nice soaring language and a lot of those opinions. But most of what lawyers do is nothing like that as we know. It's highly paid technical writing really.

Sarah Cottrell: Yes, airy letters about interrogatories and such. Tell me how you found your way into legal publishing and what it was that you did there.

Jennifer Alvey: I actually saw an ad in Legal Times and answered it, and did it right before I was going out of town for [inaudible]. Completely forgot to, or somehow, my resume did not go, but my cover letter did. It was faxed because that’s the world I lived in. I got back and there was this very nice request. It’s like, “Thank you for your cover letter. Do you think you could send the resume?” I was like, “Oh. Yes.” It was to BNA, which was just BNA then and not Bloomberg BNA. That was for a job covering basically like technology and all these brand new internet ecommerce stuff in 1999. I thought, “That actually sounds kind of fun,” even though it was very scary because I’d never ever, ever taken an editing test in my life. That was a standard thing that they did for all candidates and I did okay on that. They hired me.

It was tremendous in many, many, many ways. I got to write a person talking to somebody else instead of this very formal language. I got to interview people and I didn’t have to make sure that I got this one admission or the very formulated things that you have to do in depositions. It was mostly curiosity driven. I love that. It was very different and a lot of fun.

Sarah Cottrell: That sounds super interesting. How long did you do that? My understanding is that’s not what you’re doing now. Do you want to walk me through the progression from there to where you are now?

Jennifer Alvey: Sure. I did that for two years. It was a ton of fun. I had a daily deadline for a story. I would tell you that that was the best thing for me ever because you didn’t have two weeks to think about a brief and then sit and procrastinate for 10 days. You just had to do it. You had to get out of your own way, and that was wonderful because it taught me a lot about being a writer. But in the end, it was kind of exhausting. There was some stress involved. I can’t imagine these folks who actually do journalism now and they have to turn in like three or four stories a day. But at that point, I took a long distance freelance job for a little while and then I found a local job for a magazine that was about the electric utility industry. That is an industry that is super law heavy so I just kind of fit right in. It was great because I learned all about how magazines get published. I loved it because it combined a visual with words and longer interviews. It was terrific training.

After that, I threw my hat in the ring for editor in chief of a legal association magazine and got that position sort of as a surprise but I did and I was excited. It was even more fun because it was a bigger magazine. It was an association for in-house counsel so I knew a lot about their lives but certainly not everything. I learned a lot just managing, like columnist and generating an editorial calendar and having a real team to work on this magazine. I loved it. The only reason I really left that job was because my husband and I were both extremely tired of the big city commute. We also had a two-year old at that time. I’m like, “Okay, he needs room to roam.” All the houses we’re looking at are like three quarters of a million dollars. That scared me. At that time, it was around 2005, 2006 right before the big bubble burst—the first of many. I thought I wanted to be on the hook for that and I don’t want to live this stressful life anymore. We moved to a suburb of Nashville and that part has been wonderful. I had one last official publishing job with a firm here that does a lot of employment-related publications.

Then I ended up going freelance and starting my blog as just an outlet, really. That was in late 2007 I think. After I’ve been doing that for a couple of years, I was like, “Oh, this could be actually a fun business. Maybe I should get some training and do this.” And I did. I do freelance editing and writing from time to time, because I like to keep my hand, and I do like that work. But most of what I do is coaching. It’s mostly unhappy lawyers. I have clients from other professions but I have to say that the misery level of lawyers is so much higher.

Sarah Cottrell: It’s a special kind of misery.

Jennifer Alvey: It is. It’s very complicated and intricate.

Sarah Cottrell: Yeah. I think being a lawyer really helps you understand where other lawyers are coming from. I realize that sounds obvious.

Jennifer Alvey: You know it’s not though, because I’ve had clients say, “I love talking to you because you get what I’m saying without having to spend 45 minutes explaining it to my therapists who can’t believe that people really act like that.” I’m like, “Oh, yeah, they do.” It does shock therapists who have not dealt with lawyers a whole lot.

Sarah Cottrell: Yeah. Talk a little bit more about your business, and building and growing your business. Do you write on the blog now similar things to what you were writing starting out? Tell me a little bit more about how you developed the business side of the blog.

Jennifer Alvey: I definitely write somewhat differently than I did to start with. I think as I learned things about brain science for example, it’s just exploded in the last two years, I’ll read these articles and look at the data and go, “Oh, okay, so that’s kind of this thing going on with lawyers,” or “Oh, that’s what lawyers could do to feel better.” It’s always good with our profession to have some data instead of just woo-woo feeling because lawyers are critical thinkers, and that’s what makes them good at their jobs. I blog for a long time, depended a lot on SEO, and now I’m more branching into a much bigger social media presence. I’ve recently started a column which I’m having a ball with. I hope the people whose letters I answer, not [inaudible] and advice column, I hope the people that I answer their letters are enjoying them as well. But it’s fun because it’s much of the same stuff that I write about on the blog in general but I think having a specific situation to apply it to is perhaps more useful for readers.

Sarah Cottrell: Yeah. In terms of your coaching, is it specifically career coaching? Is it broader than that like more generalized life coaching? What type of coaching do you offer? Talk to me a little bit about that.

Jennifer Alvey: What I learned quickly about coaching is it’s all connected. It’s like you pull a thread in a fraying garment and they all start coming apart. I certainly can talk mostly about career, but unless somebody’s been doing a lot of other work like therapy or some other kind of self-improvement, development work, I’ll really only be able to help in so much with logistics because there’s probably something staring at them that they need to address in some meaningful fashion. Whether it’s looking at some beliefs about what they can and can’t do, or about money, I’ve had many, many, many clients who’ve talked about how they cannot possibly not have their kids at private school, we have conversations about that, and about whether their kids’ private school is worth having a really miserable parent, things like that.

It depends a lot on the client. It can be pretty focused on just, “Okay, what kinds of things do you like, what kinds of things do you hate? Have you thought about this? Have you thought about this other thing? Okay, if that sounds interesting to you, go explore this idea or this idea.” I always give homework. Things that allow people to at least get a taste of what they’re thinking about without having to quit what they’re doing right at that minute. If they have a good experience, then I’m like, “Okay. Here’s where we are, here’s where you want to go, what do you see that needs to happen between those two points?” I’ll help them brainstorm about that as well. It can be that straightforward but I find that people end up doing better if they really get down and dirty with some of the bigger issues that are bubbling under the surface.

Sarah Cottrell: This episode of The Former Lawyer Podcast is sponsored by my free guide: First Steps to Leaving the Law. I know that there are a lot of unhappy lawyers out there who are overwhelmed at the thought of leaving the law and literally don’t know where to start. You can grab this guide and take the guesswork out of it. Go to and grab it today, seriously. You can get it and start today.

Yeah. That’s so interesting because even just since starting Former Lawyer and launching the podcast, I find that often, lawyers’ felt need is “I don’t want to do this but I don’t know what I want to do.” Often, that translates to “I need to figure out what job I should be doing that is not this job,” which I’m incredibly sympathetic to, and I’m certainly not saying that’s not something you need to figure out, and I was in the same position when I realized I didn’t want to be a lawyer, it was like, I literally don’t know what I would do if I wasn’t a lawyer.

Jennifer Alvey: It’s a terrifying moment.

Sarah Cottrell: Yeah. You’re like, “Okay, I’ve been on this path and now what is happening?” But I do think that really, and not to be all like woo-woo, but to your point about mindset and the deeper things and the fact that you pull one thread and everything is connected, I think in most cases, it is not true that the only thing someone needs to figure out is, “Well, what job should I go to that’s not a lawyer job?” For a lot of reasons. One, I think that there needs to be some exploration of how you ended up in that job that was so wrong for you because if you don’t do some exploration around that, it’s very likely you’ll have the same thing happen again.

In particular, if you go into a situation where you’re just like, “Oh, I just want someone to tell me,” and I think this is the point you’re making, if you just have someone tell you, “Oh, you should do this other random thing,” that’s not all that dissimilar from the decision making process you may have gone through to go to law school and become a lawyer, and so if you don’t do that deeper work, you aren’t necessarily going to set yourself up for a better outcome, you might be setting yourself up for a very similar outcome. I also think that, like you said, not only is it not purely a “Well, I just need to know what other job I should be doing,” even though, again, I know that is part of it, but there is also all of this other stuff that’s tied up with our jobs and how much money we make, and all of those things that have very little to do with “What other career should I be pursuing?” and a lot to do with “What do I value? How do I understand how other people see me? How much do I care about that? Why do I care about it?” all of these things that are, like you said, probably something that is worth exploring in therapy, which is a theme that has come up on multiple episodes because I am very pro-therapy for all people.

Jennifer Alvey: Yeah, we are. We all need to [inaudible] from time to time, if nothing else. It’s like you go to your MD for an annual physical, I think the same thing, we will benefit from that same approach of therapy every so often. I have a lot of sympathy for younger lawyers who are starting out with a huge amount of debt, because that’s a real thing. You can’t just wish that way. That does make options somewhat more limited. But I feel like if they’re willing to at least imagine what they want, there are ways to navigate there that are less miserable even though it might take longer than somebody who is eight years out or something like that.

But I do think also that it’s a profession and people sometimes are drawn to it just because you don’t have to make a lot of decisions about your career path. Some people really enjoy that. They’re like, “Oh, here it is. Here’s my little step A, step B, step C,” associate and depending on the size of the firm, maybe there is counsel for a while and a non-equity partner in a quarter, and it’s like, “Oh, it’s a nice little very obvious path.” Even the things that firm lawyers often think of as alternative, government, that’s really pretty lockstep as well. In-house counsel is not a huge leap. I’ll put an asterisk on that because if you go to our in-house counsel for a startup or a small company, it’s going to be a very different experience than if you go to a big pharmaceutical company or a manufacturing company. It might really be a wild ride in a smaller place.

I think we forget that there are hundreds of thousands of college graduates every year. We’re like, “Okay, I’ll take this marketing job and we’ll see what happens.” That’s completely the attitude they go in with and they make all kinds of interesting decisions and moves, and that’s how they develop their career. Many lawyers are terrified of that.

Sarah Cottrell: Yes. You mentioned earlier in our conversation that many lawyers tend to be the type who did well in school and got all the gold stars. I think that the career path for lawyers, the traditional career path for lawyers, very much feeds into that kind of mentality of just getting the next gold star. To be clear, I am not criticizing people for this mindset, because that is what my mindset was. The realization, once I was working at a law firm, for me, was “Oh, maybe just making your life and career decisions based on what the next gold star is on whatever path you’re on in the perpetuity is not actually the best way to make decisions for a happy well-rounded life.” I think that it can be difficult if that’s how you made decisions up to that point, because it’s not just “Oh, I don’t want to be a lawyer,” it’s also, “I have to develop a completely different set of decision-making tools that I don’t have right now.”

Jennifer Alvey: Right. There’s often the accompanying belief that I don’t have these tools and I can’t possibly get them because I’ve been in this too long, fill in the blank, that’s part of that deeper work that is needed, that’s a passive that they need to do.

Sarah Cottrell: What would be your advice to someone who is working as a lawyer but they’re not happy and they’re thinking they might want to leave? Then also what kind of advice would you have for someone who is working as a lawyer and they’re sure they want to leave but they’re not really sure where to start, what would you tell those people?

Jennifer Alvey: For people who are flirting with the idea of leaving, it’s very helpful to try and separate what’s the environment versus what’s the actual work and what each one is doing to you or for you. There are a lot of people out there who if they could do the job in law that they thought they were signing up for, they’d be pretty happy. Maybe that’s part of their job but then they’re also dealing with a really dysfunctional environment which is much more common than not in law for a lot of different reasons. Try and separate what’s the environment versus what’s the “I don’t like doing this” part of it. The best thing you can do is just be really brutally searingly honest with yourself. I have to tell you that’s difficult. I found it difficult initially. There are still times after all these years that I’m like, “Okay, you’re not being honest with yourself about X, Y, or Z.” That’s important to do.

Looking at the reasons you went to law school can be helpful in that process or it might just be irrelevant. You just have to look for honesty and look for the times that you really actually enjoyed something at work. I had actually a fantastic time on a case that was about early mobile phones and they were about clamshell design. The best time I’d had in that case was writing the brief, but also supervising the photoshoot of the phones. I was like, “This is really fun.” I thought, “Oh, huh, that’s really weird. Who goes to law school to supervise a photoshoot?” But it was really good information to have. I like playing with how things look and how you can create a convincing argument with just pictures. Look for those moments of “Oh, this is fun,” or “Oh, I got really engrossed in that.” And also being really honest about if I have to deal with one more person who walks in my office like I had nothing else to do and says, “I need you to do this right now,” and you know perfectly well that either they sat on it for weeks or it’s an artificial deadline and that makes you crazy. Some people don’t care. I cared a lot about that. You want to look at those things.

For people who are sure they want to leave law, the most necessary and the hardest thing for them is just figuring out what they really want, the big picture question, “Why am I here on earth and what am I supposed to be doing?” That’s a big existential question but it’s really important to start to get some answers around that before you start looking at different jobs, because I tell clients a lot, like, “Look, if you want to get to Palm Beach and you just go online and just buy a random airline ticket and ends up being to Oregon, well, okay, yeah, you can get some other tickets and get your way back to Palm Beach, but why would you do that? Why not just figure out the most direct route to get you to where you want to go? If you don’t tackle these big questions about what it is you’re here for and what you want to do, then you’re going to buy a lot of tickets to Oregon before you get down to South Florida.”

Sarah Cottrell: Jennifer, do you find that people who have been in law for a longer period of time have different issues in terms of making a transition out of law versus those who’ve been in for a short amount of time, or is it essentially sort of a similar set of challenges across the board?

Jennifer Alvey: I think the base issues that they face are roughly the same. But what is different for people who have been in law longer is the difficulty they have changing their mindset a lot of times. It feels much scarier I think to people who’ve been in law for 15 years to think about doing something else. Part of it is that the whole DNA of law when it comes right down to it is looking for downside risk and mitigating, which is essentially a very pessimistic view of life. One of the very few professions in which if you’re a pessimist, you will professionally perform better than if you’re an optimist. That is a huge exception to most work in this country.

The longer you’ve been doing that, the harder it’s going to be to change that mental groove or [inaudible] depending on how you want to look at it. It’s absolutely possible but it’s important for people who’ve been in longer to know that it will probably be harder for them and they just need to be very patient with themselves.

Sarah Cottrell: That is such good advice. I think also there can be identity issues wrapped up in the ability to say to someone, “Oh, I’m a lawyer.” You don’t have to describe what that is. People know what that is. It’s clear. It conveys a certain number of things like I’ve done a lot of schooling, and these sorts of things. That’s something that I have found that people, even early on and also later, that that’s something that they struggle with a lot. For me, there’s been some struggle related to that and it takes you by surprise, especially if you have wanted to leave the law for a long time, because you’re thinking like, “Oh, I’m leaving the law and this is what I want to do.” Then you have to also wrestle through some of those identity questions.

Jennifer Alvey: You do. It is a wonderful stamp on your passport. It gives you instant respect, you get the instant, “Oh, they’re smart,” assumption. You don’t have to prove it. But it’s not the end of the world either if you can’t say that “Oh, I’m a lawyer now.” I had the inverse experience probably a month ago, I was at an Art Crawl thing and I was talking to somebody I knew and I said something around “Oh, well, when I was in law practice blah-blah-blah,” and she’s just like, “You are a lawyer?” I thought that was hilarious. Exactly what all of that meant was I have a master but it made me chuckle.

Sarah Cottrell: I think to your point earlier about the fact that leaving the law often comes with some deeper work than maybe people realize, especially when it comes to this identity questions, I think you really do have to explore the question of why do I care so much about what that conveys to people I know, to people I’m just meeting? That is going to be a complex question, there are going to be layers.

Jennifer Alvey: Yes. I think the more decided and invested you are, and identify with whatever your new goal is, there’s a little less of that. It was a shame feeling for me for quite a while like, “Oh, I couldn’t cut it,” and that was a very complex knot for me. In the end, I worked through it because I realized, I really, truly did not want to have to make the compromises emotionally. I’m not even sure I would have been capable for much longer to do what it takes to suck it up and just deal and all those other things we say to each other that are really not psychologically very sound, but that are very wide-spread in the male dominated profession like law and a very traditional profession.

But I know within the past six months, I’ve had some sort of dream/almost nightmare about working in a law firm and I’ve been there for two months and I haven’t entered a minute’s worth of billable time. I had been out of law for 20 years but I still have dreams about that which is insane.

Sarah Cottrell: Oh, my goodness. It’s classic.

Jennifer Alvey: Yes. That’s one of the things I hate the most about law practice.

Sarah Cottrell: Yes. I have a whole rant about billable hours and efficiency, but I will restrain myself. Jennifer, as we’re coming to the end of this conversation, is there anything else that you would like to share that we haven’t covered already or that you think that the listeners of the podcast should be thinking about?

Jennifer Alvey: I honestly think one of the most important things you can do for yourself as you think about a transition, particularly if you want to get out of law, but even if you just want to move within it, is to develop friends and people you can hang out with who are not lawyers because the assumptions that lawyers bring to everything is very hard to be more frankly objective, because lawyers see the world a very specific way as a group. Having a set of friends [where there’s] one other lawyer is fine, but having people who have really different values about compassion or giving or trusting, it’s really important to have that in their life, whether it’s a book group with people from maybe your college. I’ve had friends who have the groups that they loved and they were the only lawyers in it. I have a group of folks that I’m with every week and we do creative taffling basically. It’s so fun and there’s not a single other lawyer among them and it’s wonderful because you just have different perspectives.

Sarah Cottrell: Yes, completely because I think lawyers often construct a bit of an artificial world where the assumption is that everyone thinks like them and values the same things. When you can step outside of that or even see someone else who is outside of that or is not a part of it, I feel like it breaks that illusion that that is the world.

Jennifer Alvey: Yes, exactly. I know that finding those folks can be challenging, especially if you are working 60+ hour weeks. Many, many lawyers do. But Meetup is a wonderful tool or if you’re into things like knitting and crocheting and other activities also have similar kinds of things but a lot of times, at shops you can go just do like a sit and stitch, and that’s nice because you get to do a little bit of your hobby and you get to chat with people. It’s just a bit [like spending] an hour, maybe a week, helps you decompress, and talk to people who don’t have a law degree.

Sarah Cottrell: I think that is really good advice. Before we go, Jennifer, do you just want to let everyone know where they can find you?

Jennifer Alvey: Yes. My blog is and then I am on Twitter as @JennAlvey. Instagram, I’m still going to sign up.

Sarah Cottrell: I will link it in the show notes for anyone who’s interested.

Jennifer Alvey: I also have a Facebook page for my coaching. If you just search Jennifer Alvey Coaching, you’ll find that too.

Sarah Cottrell: Awesome. Thank you so much. Thank you for joining me today, Jennifer. I really appreciate you sharing all of your insight from your own experience and from coaching other people in leaving the law.

Jennifer Alvey: Oh, you’re so welcome. I loved our conversation. It’s fairly important.

Sarah Cottrell: Thanks so much for listening today. I absolutely love getting to share these stories with you. If you haven't yet, subscribe to the show, and come on over to and join our community to get even more support and resources in your journey out of the law. Until next time. Have a great week.