The Generational Mindset Gap Around Career Changes with Morgan Hall [TFLP019]

On the latest episode of the Former Lawyer Podcast, I got to talk to Morgan Hall, a former lawyer, and sales executive at Twilio. We had a deep conversation about her experience working as a lawyer, navigating the general mindset gap around career changes as she made transitions, and how she ended up leaving the law altogether to work in tech sales. 

A recurring theme that came up during our conversation that I haven’t gotten the chance to cover before is the generational mindset gap of career changes. And honestly, this mindset applies to anything related to work.

Morgan also has a lot of good advice for any unhappy lawyers who want to leave the law for good. Let’s get started!

Influenced At An Early Age 

Morgan believed from a young age that she had three career options to be successful: doctor, lawyer, or engineer. By high school, she had weeded out the other career options and was determined to become a lawyer. 

Morgan was enamored with the concept of being a lawyer. But, she was attracted to things that just don’t depict the truth of what being a lawyer is truly like. 

Morgan didn’t like law school, but she thought that was normal. She remembered being forewarned that “everyone hates law school”.  

Making Career Changes To Find The Right Fit

After law school, Morgan worked at an employment firm. She quickly became dissatisfied but didn’t immediately link it to leaving the law. Instead, she thought that a career change within the law would do the trick. 

So, she left to work in transactional work, which also bored her. Shortly after, she was offered a job at a prosecutor’s office. With the new dream of becoming a judge, she decided to give the law another chance by making another career change. 

But, even after a year, she still wasn’t feeling fulfilled. Morgan knew that at this point, it wasn’t just the job, it was the law as a whole. And with that, she decided that leaving the law was the best decision. 

The Obstacles Of Leaving The Law 

Before leaving the law, Morgan had to consider what else was out there. She also had to overcome some common obstacles to leaving the law.  

Forgetting Sunk Costs

The first thing standing in Morgan’s way was the common concept of sunk costs. After all, a lot of time, effort, and money go into becoming a lawyer. 

But at the end of the day, you need to ask yourself if it’s worth your sanity. Once you think about what your priorities are, you’ll be able to forget all about sunk costs. 

Rethinking Things 

As you know, being a lawyer can make up a huge part of your identity. It’s all Morgan had known since her teenage years. Removing the law from her identity involved rethinking her priorities and learning to live for herself. 

Morgan started to read lots of books like Mastery By Robert Greene to help her through the journey. This book is about tapping into your childhood interest and allowing them to guide your career changes moving forward. 

Ignoring The Opinions Of Others 

Morgan was never too worried about the opinions of others. However, she had a hard time telling her parents about leaving the law.  

Morgan wasn’t of leaving the law, she just didn’t want her parents to feel disappointed in her. And while her mom eventually came around, generational differences made it harder for her father to understand.

The Generational Mindset Gap Around Career Changes

Something we haven’t yet covered on the podcast is the generational mindset gap surrounding making career changes. I know a lot of you out there experience this disconnect, whether it’s at work or home.

Early Expectations and Influences 

Morgan mentioned the generational mindset gap around career changes that expects children and teenagers to know what they want to do with the rest of their lives at such a young age. Now that we’ve experienced this, Morgan and I can tell you that this mindset just doesn’t make sense. 

And like so many children with strong personalities, Morgan was often told that she should be a lawyer because she “liked to argue.” This is yet another part of that generational mindset and its influence. 

The Stigma Of Making Career Changes

To generations before millennials and Gen X’ers, making career changes is seen in a negative light. To most of our parents and grandparent, you’re supposed to work at one company until your 60s.

Many perceptions like this are coming to an end. The idea of working at a company for decades and retiring with a pension is phasing out. Younger generations just don’t think that. And there are different ways to ensure a comfortable retirement.

Doing What You “Have” To Do

Older generations often separate happiness from the nine to five life. Their “do what you have to do, no matter what” mindset doesn’t account for other priorities. Morgan recalled a conversation with her father, who was in the army. 

He mentioned having to do things he did not want but still had to do. While Morgan understood that, she argued that just because she had bills to pay, she didn’t have to be miserable in her job.

Finding An Alternative Career In Tech Sales After Leaving The Law

Morgan enlisted the help of a business developer friend, who helped Morgan to understand what a job in sales looks like and what would be expected of her. 

Morgan found an open position at a tech company called Salesloft, a tech company that sells Sales Automation Software. She was attracted to its great reviews in terms of workplace culture. So, she went in for an interview and applied right away. 

Within a month, she got an offer and worked there until just recently after her episode of the podcast came out. Now, you can find her at Twilio, a communications company.  

Advice For You, If You’re Unhappy In The Law

Morgan’s first bit of advice to anyone making career changes or leaving the law is to be okay with where you are. Acknowledge that you need to do something differently. 

Be okay with the fact that you may not be a lawyer anymore. From there, be intentional about what you want your next chapter to look like.

Making Career Changes Is Okay

You’re allowed to change your mind and make career changes. Don’t let the generational mindset gap of your loved ones hold you in a place you don’t want to be in.

Don’t attach yourself to your job so much that you’re willing to suffer until you retire. You owe it to yourself to be happy. Everything else will fall into place once you surrender to that.

Leaving The Law For Good? Come Join Former Lawyer

If you’re struggling with leaving the law for good, just know that there is a light at the end of the tunnel. You just have to pull the trigger. 

And, if you need some help figuring out a new career path, come join us over at Former Lawyer. You can also join the Collab, to get extra support around leaving the law and making a career change into something that you love. 

Until next time!

Show Notes:

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. I'm really excited to share my conversation with Morgan Hall with you this week. Because she and I talked about some really important things that we haven't really talked about much on the podcast before, including specifically some of the challenges that come along with generational differences in how we perceive and think about work, work-life balance, and these sorts of things along with lots of other really interesting things from her own experience; going from working as a lawyer to a sales executive tech company. I'm excited for you to hear it. The one thing that I wanted to mention also is a little bit later in the podcast, you'll hear my sponsor spot for The Former Lawyer Jump Start. I just wanted to let you know that the price of that is going up on January 1st. If you buy it between now and the end of December, you will save 30% on the price that it will be starting in 2020. If you're interested and have been thinking about it, I would love for you to jump on that and save that money. Okay. Let's get to this episode.

Hi, Morgan. Welcome to The Former Lawyer Podcast.

Morgan Hall: Hi, thanks so much for having me.

Sarah Cottrell: Why don't you introduce yourself to the listeners and let them know a little bit about you?

Morgan Hall: Yeah. My name is Morgan Hall. I went to Emory for law school. I practiced for about four and a half years until I decided to jump ship. Now, I am working as a sales executive for a tech company. I am happier than ever. So, super excited to speak with you, your listeners, and share my story.

Sarah Cottrell: Yay. I'm excited already. Okay. Let's go all the way back to the beginning and talk about what made you decide to go to law school in the first place.

Morgan Hall: Yeah. My parents raised me to believe that I pretty much only had three options to be successful, that was either become a doctor, a lawyer, or an engineer. As long as I can remember, those were really the only true career paths that I ever really considered. My mother is a physician. Of course, every little girl wants to be like her mom. That was my initial desire. I wanted to be a doctor until I realized that I can't stand the sight of blood. After that, I knew that I wasn't really strong in math. Engineer was never really considered at all. Then, as I went through school reading and writing were always my strong suits.

Then of course when you have a strong personality, you "like to argue", you got to just get pushed in the direction of becoming a lawyer. That's how I ended up very early on—when I say very early on, I mean probably, in high school, that's when I determined that I was going to go to law school. Pretty much every summer job that I had, every internship that I had, was to prepare me for that goal to go to law school. I thought that I had made a pretty intelligent decision based on going to all of these, or attending all of these programs, and having all this experience at such a young age. I thought that it aligned with my natural skills, abilities, and personality. That's how I ended up in law school.

Sarah Cottrell: That is such a common story. I've heard it a lot in my actual everyday life. Lawyers that I worked with in the past but also even on the podcast—a quarter or more of the guests that I've had—that is one of the main things that they were told. Like, "Oh, you're good at arguing. You should go to law school," or some variation of that, which I think speaks to what people imagine the life of a lawyer is like, or at least, that's my experience. I did not really know any lawyers or have any in my family or in our social circle or whatever. I think sometimes when people say, "You're good at arguing, you should be a lawyer," they aren't necessarily speaking from a position of knowing what actually working as a lawyer is like. Has that been your experience?

Morgan Hall: Absolutely, I think you hit the nail on the head. There's a perception for those that are outside of the legal profession, there's a perception that being a lawyer is making all of these impassioned speeches in court and there's this very glamorous lifestyle where you're, I guess, living out this personality trait of yours where you're arguing and you're winning. That's really not how it is. The day-to-day of a lawyer is very different. You're in your office, you're reading case law, you're researching, you're writing briefs, and you're responding to requests for production and interrogatories. It's very different. I think that gets lost because we seeLaw & Order, all these tv shows and movies that make the profession look a lot different than what it really is.

Sarah Cottrell: Yes, much less paperwork and sitting at your computer and much more dramatic.

Morgan Hall: Absolutely.

Sarah Cottrell: You got to law school that had been your goal for a very long time. When you got to law school, did you like law school? Did you feel like, "I'm on the right path," or was that a point at which you started to think, "Maybe this is not actually for me"?

Morgan Hall: Yeah. It's funny you ask that because I did not like law school at all but I thought that was normal. I remember being forewarned, "Everyone hates law school. Law school sucks." It's like pledging and then once you get through that process, that's when your life is a lot different. Even though I didn't like it, I didn't think that there was anything wrong with not liking it. I now know that was incorrect but everyone around, we were all miserable, especially 1L year. We all know that's the worst year of law school. I believe it was the end of 1L year, I got a really bad grade in Property. I remember I was crushed. That was the only time I really considered dropping out of law school. But I thought, “Well, if I drop out, that means I'm a quitter.” It was just one bad grade but I don't think that I looked at it holistically.

Also, as I think about it now, the reason why I didn't do well in that class—and I was by no means at the top of my class 1L year—was because I wasn't into it. I remember all through grade school and college, I had really, really good grades. A lot of my friends hated school. I enjoyed school. I didn't mind it. I actually loved school and I did well in school because I like to study. I like to problem solve and figure things out. When I didn't have that same passion for schoolwork when I got in law school, that should have been a red flag right there. But instead, I chalked it up to, "Well, this is the haze of law school and I just have to deal with it."

I remember I talked to my boyfriend at the time who was in law school with me—he's my husband now—we both figured, "Hey, this is how things are. Law school is hard," but I think had I been more honest with myself and if I wasn't worrying about how it's going to look if I'm a quitter, then I likely would have made a different decision.

Sarah Cottrell: Yeah. I think that that is a really common story, and even not necessarily with law school, but even with the profession of law, I know I've talked with other guests about the fact that being miserable is seen as normal. It's not seen as an indication that anything's wrong or that you should think about doing something else. Because it's like the “Well, everyone hates their job” mentality. Like you said, I think it's really unfortunate because if you are in law school and you're not liking it but you think that that's what you're supposed to be experiencing, then you aren't able to use that information in a way that helps you make a different decision because you think that's just how it's supposed to be.

For you, what job was it that you ultimately ended up going to after law school? Was your expectation that you would like that job more than you liked law school?

Morgan Hall: Yeah. The first job that I had out of law school was at an employment firm. I did a lot of plaintiffs employment work. Actually, employment law and employment discrimination were my favorite classes in law school. I thought that it would be a great fit. I actually didn't hate it. The facts of the cases were always exciting. It was never a dull moment. I learned a lot. But again, the day-to-day of being a lawyer was what really got to me. I did not enjoy the actual act of litigating cases. Even though talking to my clients and having settlement conversations over the phone with opposing counsel. Even though that was exciting to me, when it came to actually putting together a complaint and everything that just comes with the litigation, because that's how you spend the majority of your time as a lawyer, I very quickly became dissatisfied.

But I thought, "Well, maybe I just need to find another job." I didn't immediately attribute it to "I don't like being a lawyer". I thought I just needed to find another job. I think that's the motion that you go through. You spend all this time and money in law school and your family. It is part of the decision too. They also invest in you to make sure that you can get to the place that you're in now so you're not going to throw in the towel that quickly. I thought that I would like it more than I did just because of the subject matter but that wasn't the case.

Sarah Cottrell: Yes. I really relate to that because I also started out in litigation. I chose it because I like research and writing, which is a terrible reason to go into litigation. Because as you said, the vast majority of the work that you're doing in litigation cases is discovery and motion practice essentially, writing angry letters about insufficient interrogatory answers. I relate right there with you. How soon after you started at that job did you realize, "Oh, this really isn't for me"? When did you leave and where did you go?

Morgan Hall: After that job, I went to a firm that did mainly real estate transactional work. That was even worse. I was bored to tears because transactional work is no litigation at all, of course. You're literally just reading the fine print. Think about when you buy a song on iTunes—or I guess not so much anymore now that they're streaming music—but when you buy a song on iTunes and you had the fine print, that's how I convey it to others who are outside of the law, who don't understand how boring transactional work is, at least, for me. That was even worse.

But there was a partner in the firm that also did a lot of business litigation. He had this one case that was really interesting to me. He was working on a joint venture agreement. I got to be involved in that. That was where I got the bug. I was just thinking about two business owners, they want to create some agreement so that they can create this new business venture that would make them lots of money. I remember thinking, “Well, as a lawyer, I'm just here on the sidelines making it work for them while they are living this out.” They're benefiting from it, not only financially, but this is a creative venture for them. They've come together and they just go to the lawyers to say, "Hey, this is what we want to do. You all figure it out."

I remember thinking, "Wow, I would love to be on the other side of the table." That's where I started to think, "Hmm, maybe something in business would be a little bit more exciting." But again when you worked your whole life to be a lawyer, it's very difficult to think, “Well, what else could I do?” I didn't really have any idea of what else I wanted to do. That was why I was stuck. Shortly after I thought to myself that doing something in business might be interesting, I got an offer to work at a prosecutor's office. I thought to myself, "Well, I would love to be a judge."

That was actually something that I wanted to do when I was in law school. I wanted to be a judge. I thought, "Well, if I become a prosecutor, that will be a really good way for me to make the connections that I need and get the courtroom experience necessary to become a judge." I took that job with the plan to try to become a judge. I studied the paths of a lot of the judges in the area and I saw that the vast majority of them were at one point prosecutors.

I said, "Okay. Well, I'm going to give it another shot. Maybe business litigation and transactional work isn't my forte. Maybe I need something more fast-paced. I'll get in the courtroom. I'll now be working to attain this, not a new goal, but maybe a renewed goal of becoming a judge and I'll be happier." For a while, I was a little bit happier but I think it was just more so it was a break from the monotony because I spent a lot more time in court.

I worked there for about two and a half years but I want to say probably after the first year, I just had this same restlessness in my spirit that something just wasn't right. I did not feel completely fulfilled practicing law. At this point, I'm saying, "Okay, I've done business litigation, I've done transactional work. Now, I've been in the courtroom and I am no longer at the point where I can say, ‘It's the job, it's just the job.’" I think now I'm at the point where I can definitively say, "No, it's the career. I don't like being a lawyer. I've done it for four and a half years at this point. I've been at a number of different offices and it's still not working out."

That's when I really started to consider what else is there for me. But it was very, very difficult to even arrive at the decision to leave because I didn't know what else to do. Again, I've been working to be a lawyer since I was like 13 or 14 years old. I didn't know anything else. I was never—and I don't fault my parents for this—but they never even encouraged me to explore any other possibility. I had no idea, it was almost like I was starting from scratch. Getting to the point where I am now or to the point where I was when I finally left was a whole new journey in and of itself.

Sarah Cottrell: Yeah. Let's talk a little bit more about that because I know that there are a couple of things that most people struggle with when they get to that point that you're talking about, where they are willing to say to themselves and other people, "I don't want to be a lawyer anymore." One thing is dealing with the identity piece, which especially if you've been planning to be a lawyer for a long time, I think that can be a really significant struggle. I'd love to hear from you how you worked through that piece of things.

Then the other piece, which you've mentioned some already, is this question of what will other people think? Whether that's law school, classmates, family, friends, all of the many people who might have an opinion about whether you should leave your job as a lawyer. I'd love to hear you talk a little bit about how you dealt with the identity piece and also the way other people reacted or were going to react.

Morgan Hall: Yeah. In terms of the identity piece, that was a real journey because you're right, when you've wanted to be something for so long and everyone has known you as that, "Oh, you're the girl that's going to law school," or "You're the girl that's on the mock trial team and the debate team because you're going to be a lawyer one day," or "We know you as future judge," so and so, that also becomes a part of you. That's not just how others know you but that's also how you begin to see yourself. Reversing that was a real challenge.

During that period, I started to read lots of books and there were a couple that really resonated with me. But one that stands out to me the most is Mastery by Robert Greene. Essentially, the book is about how to learn a new skill and apply the discipline necessary to become an expert at it, basically, to master your craft whatever that craft may be. He talks about how you have to take on a mindset of apprenticeship is what he calls it.

But before going into that, he starts the book by talking about one's responsibility to find their life task. He talks at length about instead of just haphazardly choosing a career, you really have to tap into the drivers that interested you at a very, very young age. When you're like five or six years old, what were some of the things that you enjoyed doing? That's what you need to tap into and allow it to inform your career moves moving forward.

I remember that when I was coming up, one thing that I did really well was that I used to sell CDs when I was in middle school for just extra money. But this is back when Napster and LimeWire were big. People would buy blank CDs and pop them in the CD player when it was illegal to do all that. I used to make those. I used to sell them in school. But I never thought of it. My parents, they knew I did it for extra cash but they didn't really think about it either to say, "Hey, Morgan. Maybe you need to look into a business or maybe you should consider going into sales."

That, I kept in the back of my mind, but I also had a hobby when I was younger; building web pages. I taught myself HTML. Of course, now HTML is a lot different than what it was back then, but I used to spend hours on the computer just building websites from scratch. I was thinking, "Wow, that's something that I did just for fun." I thought, “What is the intersection between those two?” I had a natural inclination in technology and selling stuff. I thought, “Well, maybe I can get into tech sales.” So that's how I landed where I am now.

But I think that as anyone, not just people who are unhappy being attorneys, but anyone who's thinking about what they may want to do differently in terms of a career transition, I would say read Mastery by Robert Greene because that really helped me out a lot. It also helped me to become comfortable with the fact that you owe it to yourself to fulfill whatever your purpose is. Because I think there are people who can compartmentalize, there are people who say, "Hey, I just want a nine to five. I don't have to love coming to work. I just want to make my money, get a paycheck and go home," because they get their fulfillment elsewhere.

But I'm the type of person where I feel deeply connected to the work that I do every day. I can't be unhappy at work. Some people can, I can't. I don't care how much money I'm making—well, maybe I won't say I don't care how much money I'm making because if you pay me $50 million, I will be unhappy, but lawyer money just wasn't enough for that—but it doesn't matter how much money I'm making. If I'm unhappy, it's very hard for me to hide it. It's going to show through. I think that I owe it to myself to do more than just work to pay bills and be unhappy.

I was very intentional about tapping into that. Then in terms of what others will think, that didn't really worry me too much. Honestly, the biggest issue for me was my parents. I'm very close to my parents. I've shared this with them. I've told them that I wish that I was exposed or I was encouraged to explore other options when I was younger but I know that they just wanted the best for me. That was their idea of what would give me a comfortable lifestyle. But I wanted to make them proud. It wasn't, "Will they be ashamed of me?" I always wanted to make them proud.

I still do have these conversations with my parents because they don't understand it, especially my father. But I know I have to live my life for me. Even though my parents did not agree with it, my mom has come around a lot faster than my dad, but even given their sentiments, I wasn't willing to just be unhappy so that other people could be satisfied with my decision. My husband was very, and still is, very supportive. That helps as well but I think that you have to live life for yourself because it doesn't matter, your parents or your friends, they have their opinions but they don't have to get up every day and go to work. You have to live that life. You owe it to yourself to do what you need to do to make yourself happy.

Sarah Cottrell: Yes, I think that's a really important insight. My husband is also a lawyer and that has actually been very helpful because I think other lawyers, even lawyers who want to continue as lawyers, instinctively understand why someone might not want to be a lawyer. You don't really have to go into a long explanation. It's similar to the point I made earlier, other lawyers know that most lawyers are miserable. They understand why. I think it can be trickier when you're talking to someone who doesn't have that experience.

It can be really helpful to have other lawyers in your life who get it. I speak from experience because, like I said, my husband is also a lawyer. That was definitely very helpful in feeling it's not crazy to feel like “I don't want to be a lawyer.” You said your mom has come around to it but your dad still struggles with it. How long has it been since you left the law for the tech sales job?

Morgan Hall: I've been out of the law for two years now. I'm so much happier. When I have these conversations with my dad, it's really interesting because I think he's not unlike so many other parents, especially those that come from a little bit of an older generation. Think about it, to this day, you might see a little kid and say, "Hey, what do you want to be when you grow up?" The question in itself assumes that there's one thing, there's one answer. You have to be able to answer that as young as kindergarten.

Now, of course we know that when you're five and six years old, that answer will change as you grow up. But I think that it's really warped to me when you expect children to be able to answer that question so soon. Even in high school, to think that maybe you take classes to prepare yourself for a certain major or you decide on which school to go to based on the fact that this university has a great program in nursing or art, for example, but I think a lot of times, those decisions are premature because even at 17 years old, you're making a decision about what you want to do for the rest of your life. That's a heavy decision to make.

If a 17-year-old said, "This is the person I want to marry," you would say, "Hey, you've got your whole life ahead of you. You'll meet new people. You probably won't know until a few years from now who you want to marry." Or if your 16-year-old daughter says, "Hey, this is the tattoo that I want," you're going to be like, "Hey, in five years, you may regret getting that tattoo." But I don't think we put that same emphasis on the question of what do you want to be when you grow up.

There's nothing wrong with being aspirational, but I think the problem is a lot of times, you make these decisions and they can be very costly, either because it requires you to take out a lot of loans, like those of us who went to law school, or even for jobs that are a couple levels above entry level. It'll say, "Hey, in order for us to hire you for this position, you've got to have experience doing X, Y, and Z." It may be very difficult for you to break into a different industry if it requires you to have some prior experience in the field.

The idea that you have to make these decisions so early on before you even know who you are is crazy to me. I don't know the answer to it but I think that those students who go into college maybe with an undeclared major, they are a lot braver than we think. I used to look at people like that and say, "Oh, you don't have your life together. You don't even know what you want to major in. You're wasting your time here in college" kind of thing. But now I think that they were the ones that were probably smarter than the rest of us because they took their time to understand, "What is it that I want to do and how is this going to impact me for the long haul?"

I think that there should be a different approach to the way young people make those decisions because here I am, in a job now that has no requirement for a professional degree but I'm hundreds of thousands of dollars in debt because I made an uneducated decision when I was much younger.

Sarah Cottrell: I want to take a quick break here and talk to all the unhappy lawyers who are listening. It's so easy to complain about how much your job sucks but feel too tired and overwhelmed to do anything about it. The only problem is that means you stay stuck and unhappy with no end in sight. You're not alone. So many lawyers get stuck in this paralyzing cycle. That's why I created The Former Lawyer Jump Start. It's designed to help you ditch the overwhelm and accelerate your progress towards leaving the law for good. Inside, you'll find a step-by-step process for going from "I don't want to be a lawyer anymore but where do I start?" to confidently moving towards your goal of leaving the law. I've got you covered. Want to stop feeling like you'll never get out? Go to formerlawyer.com/jumpstart and buy it today.

Sarah Cottrell: Yes. Oh my goodness. You made so many good points. I don't even know where to start. Okay. I think one of the things that you mentioned that I think is so helpful and something we haven't really talked about on the podcast yet is the generational difference in terms of thinking about career because I have had a very similar experience to you, I think, with respect to like I think my parent’s generation sees moving around trying different jobs as "job hopping" in a negative way. But I think a lot of those thoughts and expectations about jobs and careers were formed at a time where, for example, pensions were much more common and so companies were incentivizing people heavily to stay in one career with one company for decades and decades.

We've seen that mostly go away. We've seen even pensions fail where people had the expectation they would be there and they weren't. I think generationally, the way people think about work and career is very different. Sometimes, if some of the people in your life, some of your loved ones are in a different generation than you—which for most people, that is likely the case—when you're having these conversations, you might not even be speaking the same language because they perceive stability in things that you don't perceive as having that same level of stability and vice versa.

Morgan Hall: I agree. They also separate happiness from the nine to five. I remember—because my dad was in the army—I remember he said to me, "Well, do you think that I wanted to do everything that I had to do when I was in the military? No, but you do what you have to do." I'm like, “Yeah, I get it. I know that I have to have a job in order to make a living but there's more than one way for me to do it. Just because I have to pay my bills doesn't mean that I only have to pay my bills by being a lawyer.”

Sarah Cottrell: Yes, 100%. I feel like there probably are a lot of people out there who have maybe had some of these conversations because I know that I have had some of these conversations. Because I do think, like you were just describing, maybe there is also a little bit of a generational mindset gap where our parents' generation would say, like you said, "Well, do you think I loved every moment of my job? No, but I did what I needed to do."

To your point, which I think is also a very fair and valid point, it's not that you're not doing what needs to be done, it's just that doesn't mean you need to stay a lawyer forever, you can do many different things and support yourself. I don't know how old you are. I'm 36 and I think I'm like a very old millennial—I actually don't really identify as a millennial because back in the day, I didn't have the internet and whatnot in grade school—Anyway, that's neither here nor there. The point is that I think that my generation, and certainly people who are coming up in their 20s, place a very high value on certain aspects of lifestyle, like valuing time more than money in ways that maybe wasn't necessarily the case for the majority of people in the generation above.

It can be a very fraught conversation because I think often, it's perceived as a judgment, like, "Oh, I'm judging you for having this different set of thoughts or values with respect to work and money," or that there's this perception, like you said, that if someone is putting a lot of value on liking their job, that they're just being totally unrealistic, expecting to be able to love every moment of a job, and it's just a job. It's not as black and white, I think, as sometimes, those mindsets can get solidified into.

Morgan Hall: Yeah, I totally agree. I think the tension for me is that my parents always raised me to be so confident and sure of myself. They've always said to me, "You can be whatever you want to be. You can do whatever you want to do." Now, I challenge them and I say, "Hey, you raised me to be this way, right? This is what you've said that you wanted me to become. Now that I am fearless and now that I am ready to step out on faith because I am confident in what I can do and who I can be, why is this no longer applicable?" That's when they're silenced.

I think like you said, there's such a disconnect that you just have to agree to agree to disagree. I wish it didn't have to be that way because I still do want to make my parents proud, but you can't fight every battle. I think that at the end of the day, you have to understand that, like you said, we're speaking two different languages because gone are the days where you retire after working for 35 years at UPS. Those days are no longer here.

Now people have certain expectations, and as a job seeker or as an employee, you very much expect a mutually beneficial relationship with your employer, and one that will accommodate you because you understand that, “Yes, I'm an employee here and I'm doing work, but I also want to be able to spend time with my family, or be able to work remotely as long as I'm producing the results that I should,” or whatever the case may be. If others don't understand that, it just is what it is.

Sarah Cottrell: Yeah. I think there is a level of confidence that you have to have in what is the right decision for you. I know a couple weeks ago on the podcast, we had a conversation about how often, if you're inordinately worried about what other people will say or allowing it to prevent you from making a career move that you need to make, it can sometimes be caused by the fact that you are not actually fully confident in your own thoughts or beliefs about needing to make that change.

Instead of focusing on how can I convince other people to think that what I'm doing is the right decision—I think this is the point that you're making, Morgan—what you really need to be thinking about is how can I bring myself to a place of confidence in my own thoughts and beliefs about my career and what is the right fit for me?

Morgan Hall: 100%.

Sarah Cottrell: I think that's super important. So many good things. Let's talk a little bit about your job now, how you found it, what tech sales are. Because I have no real experience in that, I don't know that I could even necessarily explain what your day-to-day looks like. I think that would be really interesting and helpful for the listeners.

Morgan Hall: Yeah, I work for a technology company in Atlanta. We actually sell sales automation software. Basically, what we do is our software helps salespeople to be more efficient and productive. Essentially, they could talk to more customers, hit quota, and be more effective in their job. That's the way I'll put it without being too long-winded. But in terms of my day-to-day, I have a few hundred accounts that are assigned to me and my goal is to break into these accounts and essentially close deals, get them to buy our software.

The personas that I'm reaching out to are CROs, chief revenue officers, VPs of sales, business development leaders, sometimes people in marketing. My goal is to get them to buy the software for their team with the expectation that it's going to help them to drive more revenue for their business. It's different, of course, from practicing law because I'm not in an office reading or writing. My office is an open office plan so everyone is just like out in the open at our desk. We have our computers and we're hitting the phones. We're having business conversations, we're running product demos. Every now and then, we're meeting customers in person. I have a base salary. Then on top of that, I have a quota.

My overall income is base plus commission. That part of it is very stressful because, of course, you don't have that guaranteed amount of money coming in every month or every year. It's pretty much you make what you put into it. If you're hitting quota, you're closing deals, you're closing big deals, then you're going to get paid a lot more. It's all about the level of work that you put into it. That part is a little bit different. But there are some things that are similar—and when I say similar—there are aspects of my job as a lawyer that really transferred nicely to what I'm doing now. The ability to communicate effectively, overcoming objections, being persuasive, all those are skills that come in handy for what I'm doing now, and I really like it.

One other thing, the reason why I really wanted to work at a tech company too, is that—I'm 31. When I started this job here, I was 29—a lot of these new tech companies are run by millennials and everyone, most of your co-workers are around your age. I really like that part of it because it's very much a work hard, play hard culture. Everyone here is very smart, very driven. We work really hard, but because we're all around the same age, there are certain perks that I love. We have a casual dress policy. When I was in college in law school, I had a nose piercing and I took it out when I was practicing law, but now that I'm here working at a tech company, I was able to get my nose piercing back. Of course, those little things don't necessarily matter as much but I like the fact that I am able to, more so, bring my full self to work and engage with my co-workers in a way that is just more authentic. It's not as stuffy and corporate as working in a law firm.

Another thing that I really like about being in sales which I did not like about working in law is that when you're a lawyer, it's very adversarial. You've got you and an opposing counsel are at two opposite ends of the spectrum and the goal is to win-win-win. Of course, as a sales executive, your goal is to win too, but it's not in an adversarial way. You don't have to fight somebody. There's competition, but it's not that direct interaction that you have with opposing counsel. It's more like, "Hey, you and a customer are working together to get a deal done."

I'm very competitive. I was a competitive swimmer growing up and I love car games and stuff like that. I thought that would play nicely for me as a lawyer. But I actually did not like that aspect of practicing law. I remember I would be on the phone with an opposing counsel. There were times when I felt that they were condescending and just all types of tricks that lawyers play to show their bravado so I don't miss that part of it. I would say those are the main differences that stick out to me.

Sarah Cottrell: That's super interesting. How did you find the position that you ended up taking this tech sales job?

Morgan Hall: When I was still practicing law, I remember that I was listening to a podcast. I think I heard a Mark Cuban interview. The question he was asked was, "If you lost 100% of your wealth today, are you confident that you could become a millionaire again and are you confident that you can become a billionaire again?" He said, "Billionaire, no, because a lot of that was luck. I was in the right place at the right time. But could I become a millionaire again? Absolutely. The way I would do that is I would get a job in sales because I know that I would quickly be able to make enough money to be able to open up my own business, and that's how I will become a millionaire."

That stuck out to me because I knew that I had an interest in business because ultimately, what I want to do is I want to be an entrepreneur. I haven't figured out what kind yet but I know that that's what I aspire to do right now. I want to have my own business. I thought to myself, like Mark Cuban said, “The best way for me to learn business without going back to school—I have enough debt—so without going back to school to get an MBA, I can just get a job in sales. There are transferable skills and I'll make it work getting into sales.”

I had a friend that worked for business development for Uber. She lives in Silicon Valley. I said, "Hey, girl I need your help. How do I get into tech? I want to get into tech but I don't know how." She helped me to understand how to identify the top tech companies in Atlanta—that's where I live—She helped me to understand what exactly it means to be in sales, what day-to-day life is like, what would be expected of me. I was very calculated and methodical in my decision making unlike when I decided to go to law school. This took place over a couple months. The place where I work now is called Salesloft. That's the tech company that I work for. It had great reviews on Glassdoor in terms of the culture.

I came in for an interview. The vibe was just right and I applied. It was the only place I applied and I moved very quickly throughout the interview process. Within a month, I got the offer. I haven't looked back since. It happened quickly once I decided this was what I wanted to do, but getting to this point was lots of research, reading, listening to articles, and talking to people. I think that I definitely went about it the right way because I'm certainly happier than I have been. This is the only place that I've been since leaving law.

Sarah Cottrell: Talk a little bit about when you say that you're happier in this job than working as a lawyer. Can you talk a little bit more about the specifics? Like some of the main reasons that you think this is such a better fit for you than practicing law.

Morgan Hall: Yeah, I said I like how it's not adversarial. I like how I'm not in an office just working on the same types of motions and litigation type exercises. I love the people that I work with—I touched on it earlier—because we're all just the same age. It's just a lot more fun coming to work. One thing I will say about working with lawyers, not even just opposing counsel, but even the lawyers that I worked with at my firms and at the prosecutor's office, lawyers generally have similar personalities. Very type-A, a lot of times we're competitive to the point where it's cutthroat. Just the personality type of an attorney is not one that I enjoy. It's funny because I was one, but that part of it, I didn't like. I didn't even like the people that I worked with too much.

I can appreciate the fact that I actually like my co-workers. I also like the culture here just in general. It's very collaborative, very open, and transparent. It's just a lot more interesting. One thing that I will say about practicing law is that there's only so much room for you to be creative. When you're practicing law, sure, you might be writing a brief and you might say, "Hey, I got this really creative way to articulate an argument," or "I can be a little animated. This is my style when I'm doing my opening or closing on a trial," but you still have to be within the confines of the law. To me, it's very restrictive. Whereas in what I'm doing now, I can be super creative. I can be creative in the way that I engage with customers and potential customers. I can be more creative in the way that I demo the product. To me, it's just a lot more interesting.

I think people in sales get a bad rap like people think, "Oh, you're in sales," or "You're sleazy," or "You're going to be annoying or just overly zealous to try to get my business," but it's really not like that. You have to be persistent but I like that there's still an aspect of winning. Of course, you want to win your deal and you want to outperform your teammates. You want to be at the top of the leaderboard in terms of revenue or percentage to quota. But at least where I'm at, I like that it's collaborative and it's not cutthroat. It's competitive but it's not cutthroat. It's a very healthy competition.

Then also a cool thing about being in sales is that the amount of money you make is up to you. There are lots of my co-workers who have been here and have been in sales for a couple years but they're a couple years younger than me. They're making great, great money, even more money than some of the lawyers that I know that are six years out of school like I am. We've got cool perks, we've got lunch served to us, catered lunch three days a week. If you're a top performer, you get to be in the Sales Club which means you go to Vegas or you go to Mexico. There are just lots of cool things about working at a tech company and cool things about being in sales that you don't get practicing law that really make the job exciting. It makes me excited to come to work every day.

Sarah Cottrell: That's awesome. Morgan, what advice would you give to people who are in the position that you were, where they're not liking their job as a lawyer? I know you mentioned the challenges with your parents and their feelings about you leaving the law and also the fact that you had student loans, and that is obviously a big impediment or like a mental hurdle for people. I'd just love to hear any advice that you have for those people if they're listening right now and not happy but not sure where to start.

Morgan Hall: Yeah, I would say the first thing that you have to do is you have to be okay with where you are. Meaning, acknowledge that you need to do something differently. When I say differently, I mean consider other options, but be okay with the fact that you may not be a lawyer anymore. That's hard for a lot of people for whatever reason. Maybe it's money, maybe it's the loss of prestige, maybe it's their parents, or whatever the case may be, but you have to be okay with whatever you decide to do next. Then from there, you just have to be very, very intentional about what you want the next chapter to look like.

I think the most important thing is understanding that you're allowed to change your mind and we're not put here just to pay bills. One thing that held me back was my student loans. I thought, "Well, hey, I've got all these student loans.” Right now, I'm at a prosecutor's office so I'll qualify for public service loan forgiveness, which is another story. They're not even honoring that anymore. But don't think that you have to be tied down to this because you made the choice. You can change your mind and don't attach yourself so much to your job that you're willing to suffer until you retire just for the title or just for the money. You owe it to yourself to make yourself happy. I think that everything else will fall into place once you surrender to that.

Sarah Cottrell: I think that's such good advice. Morgan, is there anything else that you would like to share that we haven't covered or talked about or any other advice that you'd like to give before we wrap up our conversation?

Morgan Hall: No. Just best of luck to anyone that is embarking on this journey. There is light at the end of the tunnel. You just have to pull the trigger. If anyone wants to talk further, feel free to shoot me a note. I can be found on LinkedIn. My name is Morgan Hall. My current position is at Salesloft. If anyone wants to talk further or have any other questions about the transition, then I'm more than happy to help.

Sarah Cottrell: Awesome. I'll put a link to that in the show notes. Anybody wants to connect with Morgan, they can go there and get that information. Thank you so much, Morgan, for joining me today. I really enjoyed hearing your story. This conversation, I think that we talked about a lot of really important things and hopefully it's helpful for a lot of people.

Morgan Hall: Yes. Thank you so much for having me. I enjoyed the conversation as well.

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. Come on over to formerlawyer.com. Join our community to get even more support and resources in your journey out of the law. Until next time. Have a great week.