Leaving the Law: What Drove One Lawyer to a High School Classroom

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From LawHub, this is I Am The Law, a podcast where we talk with lawyers about their jobs to shed light on how they fit into the larger legal ecosystem. In this episode, Kimber Russell interviews a lawyer who stopped practicing law full-time to take up teaching given his family obligations and changing priorities.

Kimber Russell:

Today we are joined by Jaye Lindsay, who is a 2011 graduate of Southern Illinois Law School in Carbondale. And today's episode, we're doing it a little bit differently. In our normal I Am The Law episode, we talk about lawyers and how they got to be where they're at and what they're doing, but today, we're really going to be learning about what is it that's pushed him outside of the legal realm and into a high school classroom?

So Jaye, let's talk a little bit about why you went to law school in the first place and a little bit of background here. We know that you spent some time in the service in the Army and you were also a truck driver. So you've got this wide, varied background. What made you go to law school?

Jaye Lindsay:

So I had been planning law school since before I even went into the military, which was back in 2000. It was sort of a long-term plan. It was something I had always dreamed of doing.

Kimber Russell:

What is it about the law that appealed to you even back in the days when you were driving a big rig?

Jaye Lindsay:

Well, driving a big rig came after undergrad. I had chosen to go to the military first before I went to college. When I got out, I did a couple years, finished up my bachelor's degree, and I immediately realized that the cost of law school was going to be pretty daunting if I didn't come in with some sort of capital. So I took two years off to drive across country and truck driving is one of those few careers where you don't have to necessarily have a home or rent. With a post office box and living out of a work truck, you're able to save a whole lot of money in a very short period of time.

Kimber Russell:

What area of law were you thinking of practicing when you first set foot at SIU?

Jaye Lindsay:

Oh golly. I think like most entering law students, I didn't really have a clearly defined concept of what a lawyer does. Like many students, I'd seen the TV shows and movies and my mother had worked as a paralegal for a few years when I was younger. So I had these maybe somewhat glamorized ways of looking at the legal profession. And I'd say the two areas that I wanted to go into were perhaps criminal defense, being a champion for the rights of the underprivileged, or something to do with environmental protection. I think that interested me a lot because I had lived in Florida for years and I had grown up around the wetlands and watching the mangroves be decimated. I think maybe I had a concept that I was going to make wide sweeping changes to the world around me.

Kimber Russell:

Now when you did graduate from law school, you landed a job at a fairly large personal injury firm with about 25 attorneys and about 70 or so other staff. What was your initial position at this firm?

Jaye Lindsay:

So for the first two months, my position was technically classified as a law clerk. I worked in the break room using my own computer. I worked on a small fold out table. I sat on this metal folding chair. I was right next to the emergency escape, which had a big window and I like to call that my window office. My role was doing mostly legal research, answering discovery requests, pretty much any random thing that the attorneys would ask of me. It was fairly well understood that provided I got my bar results back and I had passed, I would be brought on as an associate attorney.

Kimber Russell:

Now as glamorous as that particular position sounds, did you get upgraded to a cubicle once you got your bar results and were able to become a full-fledged attorney?

Jaye Lindsay:

Absolutely. I definitely got a cubicle.

Kimber Russell:

And what kind of cases were you working on at that point? How did your experience as a new associate differ from your experience as a law clerk?

Jaye Lindsay:

Not really that much except for I could sign pleadings and show up in court. The day that I swore in at McCormick Place in Chicago, as I was leaving the ceremony, I got an email from one of the attorneys at my office saying, "Are you official yet?" I said, "Yes." He goes, "Good, we have a motion to dismiss with an argument coming up at two o'clock this afternoon in courtroom 2009. You need to be there."

It was a case I'd worked on, so I was familiar with the facts. I wasn't unprepared. I had done most of the drafting on the motions, but it was a fairly significant case and I essentially had to catch a cab across town to immediately get there in time to argue the motion. So I can't by any means say that I didn't get good experience. It was a phenomenal opportunity.

Kimber Russell:

Well, tell us a little bit more about the casework that you did. What was the practice area that you focused on when you were at your first position?

Jaye Lindsay:

I worked for a small group that had about five attorneys at any given time, mostly younger attorneys with a senior mentoring attorney, and we handled mostly PI cases or injury cases involving seniors. So you had nursing home cases, abuse, neglect, bedsore cases, hip fractures, falls, malnourishment cases. I would say the line share though about 70% were nursing home negligence cases.

Kimber Russell:

That's a pretty complex work. What was your compensation once you moved up from the hourly wage of a law clerk? What were you getting paid as a new first year attorney at this firm?

Jaye Lindsay:

You're asking me to go back quite a few years, but if I remember correctly, as a clerk, I was brought in at maybe $15 an hour, no benefits. When I transitioned to an attorney in October, I think it went up to about 18. And then by December, around Christmas, the firm gave me a promotion to $20 an hour. Let me give you the caveat that although it was $20 an hour, I was told I could work as many hours as I would like. However, there'd be no time and a half.

Kimber Russell:

Let's do a little math here. How many hours a week did you find yourself working, understanding that they didn't put a limit on that, and what did that translate to for an annual salary?

Jaye Lindsay:

Well, interestingly, like most hourly jobs, the work was structured pretty evenly so that nobody would be working too much. I would say that I was working probably an average at about 50 hours a week. So you're looking at about a thousand dollars, I would say about a week. But that thousand dollars a week, keep in mind, I did not have health insurance through the firm at this point.

Kimber Russell:

Were these types of positions typical when you were out there hustling to get your first job?

Jaye Lindsay:

Most of the jobs I was looking at were worse. I applied for dozens of firms. Just the options were deplorable, Kimber. They were 12, $13 an hour jobs, no guarantee of future work. So when I did find this opportunity, I looked beyond the salary and said, if this is an opportunity to work with really prominent lawyers and get really solid experience and they're going to let me go to court, they're going to teach me how to practice law the right way, I can suck it up for a while. I can humble myself.

And I have to say I was very successful. In 2012, I was making the $20 an hour. Towards the middle of that year, they did kick in and start offering full Blue Cross Blue Shield health insurance, which during that year, my wife became pregnant and we had our first child in October. So we were able to enjoy having wonderful comprehensive insurance. And by the end of 2012, starting 2013, I was given a pay raise to a salary of 50,000 a year, which included small cuts or fee splits on cases that I would either bring in or cases that I would settle or win recoveries.

Kimber Russell:

What was it that caused you to decide to move on from this firm? It sounded like you were on an upward trajectory, you were getting paid more, you had insurance, you were getting great skills, what was it that gave you that push to go?

Jaye Lindsay:

Well, two things. First of all, it's lifestyle. At this point now, I'm a husband and father, we have a young child. We had bought a home out in the suburbs because frankly, there was no affording much any closer to Chicago on 50,000 a year. My wife really couldn't continue working because the money she was making would not even justify daycare. So we had gone from being a two income family to being a one income family with a child. What began as a 50 hour work week when I was hourly, quickly mushroomed out of control when I was salary.

When I jumped to the 50,000 salary, I started noticing that my caseload got a lot bigger. I went from having maybe 15 to 16 cases to at one point, 40 plus cases, all of which were significant responsibility. Mind you, these are not cases I'm coworking with some senior attorney, these are cases that I am solely responsible for. That's a lot of responsibility to put on a second year attorney. I found myself working late. I found myself downtown a lot. I was leaving the house around five in the morning and I was getting home around eight o'clock, nine o'clock at night, and I admit, some of the commute was part of that. But as a whole, my lifestyle, it started becoming very clear that this was going to take a toll on my family.

So I was offered a position in rural central Illinois closer to my wife's family, and the job paid the same as I was making, but the cost of living would've been far less, and there was a very short track to partnership as the attorneys were looking to hand over the reins within a few years. So in my mind, I was thinking, here's an opportunity to lower our cost of living, live closer to family and make the same or more money and eventually build into an ownership role in a firm, which was not something that was available to me in Chicago.

Kimber Russell:

What were the terms of the original agreement when you took on this new position? What were going to be your duties there and what practice area were you going to be taking over?

Jaye Lindsay:

Well, like many small firm practices, it was a general practice. It had been around for a hundred years. There were two attorneys who were older and looking to retire. The expectation was that I would bring some of the litigation skills that I developed in Chicago to the firm. They did a lot of defense work. They really weren't a plaintiff's firm, so there was a learning curve there. They did everything from municipal work to family law to criminal defense. It ran the gamut of general practice so there was a lot to learn. Then that was the expectation is that I would come in, work, learn the areas I didn't know, meet the community, become a part of the community, and eventually take over that practice.

Kimber Russell:

That was the plan, but that's not exactly how things worked out, right?

Jaye Lindsay:

No, indeed it wasn't.

Kimber Russell:

So how long did things work out before you noticed there was problems brewing?

Jaye Lindsay:

One month, Kimber.

Kimber Russell:

Wow.

Jaye Lindsay:

The position lasted a month. The attorneys went through about four paralegals in the month I was there. At one time, one of the partners began screaming profanities at the paralegals to the point where they were crying. There were occasions where one attorney just wasn't around at all, and I found out he was looking to phase himself out down to two days a week within a few months. And this was an attorney who was going to largely be teaching me the trust and state aspect of the practice. So I would be left with one attorney to mentor me, and that happened to be the attorney who, at least in my opinion, was not somebody I wanted to work with. It was not a comfortable environment and certainly not a place I wanted to work. So I made the difficult decision to start a practice of my own despite the debt and the wife and the child in tow.

Kimber Russell:

How long were you a solo? And did you stay in Central Illinois? Because you had picked up your entire family, move them out there for this other opportunity and to have things fall apart after just about a month, that must have been a pretty difficult time for you.

Jaye Lindsay:

It was pretty devastating. Our family went through a lot of turmoil. It took a toll on my wife, for sure. Fortunately, my little practice actually didn't do too bad. My old firm was very kind and referring me a lot of business. Well, I may have made $15 an hour when I started, but now years later, the relationships I built and the trust I built there translated into significant referrals that kept me above water.

Around October of 2013 is when this took place. By Christmas, I had moved back to Chicago. I found an apartment in the suburbs. My small solo practice finally got an office space in Chicago, and I began hustling a lot of probate work, doing a lot of referral work, local court appearances, and I was able to float myself for a while until I was able to sign on with a different firm in January of 2014.

Kimber Russell:

What type of practice did this firm have?

Jaye Lindsay:

It was a niche practice, a little tiny boutique firm out in the west suburbs. Wonderful owner. He hired me in there because he and the other three attorneys in the firm had very little litigation experience. Mostly what they did was high net worth estate planning, asset preservation, but over the past five, six years, they'd found that their practice was leaning a lot more towards will contest, litigated guardian ships, really nasty fiduciary cases, and they needed somebody who knew how to take good depositions, who knew how to handle themselves in court. And I was permitted to continue operating my own practice so long as there were no conflicts with that firm.

Kimber Russell:

It sounds like this was a little bit of a pivot for you from what you were doing before, even with your litigation experience. How long did it take you to get up to speed?

Jaye Lindsay:

Well, I didn't have a lot of time to get up to speed and I didn't before either. It was baptism by fire. In both experiences, I was handed files and I hit the ground running. The difference is in this job, they did definitely pay for me to go to training. There was a lot of mentorship, trying to help me learn the elder law side of the job. And I have to be honest, I found that I did not really care for doing estate planning and trust building. I really did prefer litigation, which makes it tough when you're working in a firm where litigation is not supposed to be the primary focus. But at that same time, it was a shift. Litigating a will contest is certainly different from a personal injury case.

Kimber Russell:

In what respect?

Jaye Lindsay:

Well, for instance, in a personal injury case, you're on a contingent fee. From the client's perspective, they don't really care how much time you devote to their case, and if you're being paid salary by your employer, you're not billing hours, you're not using time matters that keep track of every 10 minute phone call you make. The expectation personal injury is this case is worth 200 grand. We've got X amount of dollars we can devote to developing the record, taking depositions and doing whatever else you need to do to get this case settled or to trial. So yeah, you have to be efficient. You don't want to take 75 unnecessary depositions and blow all your profits. But at the same time, if I want to work a hundred dollars a week and just slave away on this case to get it done, my firm's not hurting. The client's not hurting. I am.

On the other hand, when it comes to traditional litigation where you are billing a client by the hour, there's a little bit of a struggle there that you have to deal with. I've got a client who comes to me and says, "Hey, my mother who has Alzheimer's disease just signed a will giving away her multimillion dollar estate to some caregiver that we don't even know. We want you to go after them." I have to have that unpleasant conversation saying, "Well, it's going to be a $20,000 retainer. We are going to spend probably two years fighting this battle, if not longer, depending on if they get a good attorney. And we're going to have repeated court calls, tons of motions. This could be a 50 to $70,000 litigation case." Try finding a client in today's economy who can just cut those checks.

So you find yourself really being frugal, trying not to bill for anything you don't need to do, struggling to find ways to be more efficient. And it's not even like representing a big insurance company or a major bank. These are people, school teachers, plumbers, mechanics, cops, firemen. These are people with real lives that maybe can't give you 20 grand. So you find a way to make the five or 6,000 they come up with at least get some sort of result. So I guess the short answer is I would often have to get a result that was less than what I knew I could achieve because it was the best the client could afford. Maybe I have to settle for a small result that makes them somewhat whole because to get any more would require more money than they can afford.

Kimber Russell:

So did you find that it was difficult to maintain that caseload then? If you know you can achieve a result but the client's by and large can't afford it, were there fewer cases for you to cover?

Jaye Lindsay:

There was always plenty of work, but not necessarily work you could bill for. And by that I mean I might get a dozen cases in the door where people want us to go after some brother or sister because there's a perception that they stole money from a parent, but we often had to turn those cases down because the client had no money for retainers. Or we'd take the case and find that within two or three weeks or two or three months, the client had run out of money and we're sitting on a dinghy out in the ocean without a sale, and we'd have to have those conversations where thank you for $15,000 but you don't have any more. What are we going to do?

Even with the best management of client expectations, clients still would often become very disillusioned, and I would find that the workload I expected for the following week just went from a full week of work to two of our clients just quit on us and don't want to keep going.

I was being paid $32 an hour, flat pay, with no benefits whatsoever. So if I'm just tinkering around on my computer all day, I'm certainly not helping the firm, but I am billing them $32 an hour. So there's an ethical dilemma for the attorney and not even as an attorney, just a human being. Do I sit here and bill my wonderful employer $32 an hour so that I can watch videos about how to use time matters? Or do I just say, well, there's not really anything I can do for the clients today. There's nothing I can bill for and profit the company, I guess I'll take time and go home and see the family and just lose money myself.

Kimber Russell:

Well, what was the work-life balance in that case? It sounds like you were able to have more of a work-life balance if the hours weren't as insane as they were at your original job.

Jaye Lindsay:

Oh, that's absolutely right. The work balance was better. There's plenty of autonomy. I could certainly come and go and the idea being if I'm there, I'm making money. If I'm not, I don't. I could take two weeks off anytime I wanted provided there were no court appearances, provided there was no deadline on a pleading, but that would mean losing money.

Kimber Russell:

Were you ultimately going to be given a salaried position at some point?

Jaye Lindsay:

I don't think his idea was any of us would become partners. The idea was for us to make a solid living wage. I think for some people that might be great, but if you're looking at trying to support a family, and at this point, keep in mind, that by the end of 2014, I had a second child. With the changes in the Affordable Care Act, he had dropped his health insurance right after I started. So I quickly found myself making about the same money as I had at the previous firm, however, paying all of our healthcare and dental costs out of pocket. And so when you really look at the numbers, even if I had maintained 40 or 50 hours a week and made somewhere in the low 60,000 range, to take a vacation, it would've cost me four or five grand out of my pay. To pay for monthly premiums on health insurance, I was paying around seven, $800 a month with huge deductibles. So very quickly, that $32 an hour job gets reduced to almost an impossible wage in the Chicago suburbs for a family of four.

Kimber Russell:

So was it at this point that you decided to make this big, big change?

Jaye Lindsay:

Probably around the time that we had our second daughter, she was born in November. In the months leading up to that, I noticed that my wife and I, all through her pregnancy in 2014, we struggled to find quality healthcare. The health plan that we were on that we could afford through the exchanges was unfortunately just poorly accepted. We had a very limited option of doctors for her. The out-of-pocket costs were so high that we started struggling, and it really made us rethink what it meant to be poor. We really had never thought of ourselves as poor. So we started really rethinking our lives.

November, our second daughter was born, and by December, I set my wife and two kids to live in Florida with my family. My wife started looking at jobs down there in the education system. I took a couple of teacher certification exams, which I was able to do up in Chicago from testing centers. And by March, I had left my firm and by about April or May, I was fully moved down to Florida.

Kimber Russell:

You've been out of law school for just about four years. What was that decision making process like?

Jaye Lindsay:

Well, I think first of all, you have to understand I didn't really pack it in. Even though I have taken a different career path, I'm still a licensed attorney. I still have clients. I still represent people occasionally. In fact, I have right now about 27 pending referrals in Illinois where I have referred cases for a fee and about 16 probate cases I'm managing, which do not require my presence in the state. I have a group of about three contract attorneys at any given time who can cover court appearances on these cases if I need them to.

Granted, it's gone from being a full-time practice to sort of a dining room consultancy, if you will. And there's still a way to make money doing it. A solid side business, maybe 20, 30,000 a year even.

On the other hand, the decision really came from being a parent. To answer your question directly, the first and foremost deciding factor was I never wanted to be in a position again where I could not pay for the healthcare that my children deserve. So that was a big factor. I wanted a job where I had stability and a solid health insurance plan. The second factor was my loans.

Kimber Russell:

Yeah. Talk a little bit more about your loans, because I think that's one of the big issues now. What is your loan burden and how has that impacted how you can be an attorney or live your life in general?

Jaye Lindsay:

I list it as my second motivating factor because the kids always come first. But my student loans, they're not nearly as bad as some people's student loans, but my loans are significant. These are all things I knew going into law school and coming out. It's not a surprise to me, I wasn't ill informed. I think the only difference is I didn't realize that four years out of practice I'd be making in the 50 to $60,000 year range. Especially living in Chicago, I was faced with a situation where I realized if I continued working for these kinds of wages, even if it does go up by 20 or 30% over the next few years and on income-based repayment, my loans are going to compound faster than I can pay any principle.

I realized that to get the first two things, to pay off my student loans as an attorney and to make the kind of money I would need and work for the kind of firm I would need to work for to get comprehensive medical benefits, retirement plan, all the typical benefits that people used to enjoy 20 years ago, to get that, I was going to have to go to a large firm that had maybe 2000 hour a year billable requirement, and frankly, as a young father with two kids, in my thirties now, I'm not a 25, 26 year old law grad, I'm in my thirties, mid thirties, I decided that frankly, that was not an option I really wanted unless it was my only option. So I started looking outside the law to find a better option.

Kimber Russell:

So now that you're pivoting into a new pursuit, what was it about teaching that attracted you? Why did you decide to make that shift?

Jaye Lindsay:

Well, I thought about law teaching a lot. I think that's far outside my likely trajectory coming out of a fourth tier law school, I'd always been interested in teaching, but I never really thought about high school teaching. I think that was probably the furthest thing from my mind most of my life. But I have a few friends from back in the military who did the Troops to Teachers program who are very happy with their jobs. They're not making hundreds of thousands of dollars, but they're family men, they're daddies. They spend time with their kids a lot.

I talked to my friends. I asked one of my friends in Mattoon who's been a teacher for a few years, "What do you like about being a teacher? Because I'm considering it." And he said, "Frankly, I work 196 days a year. I take my kids to school every day and I bring them home every day, and we talk about what they did in school. I don't work all summer. So if I want to go see a grave site or honor somebody at Arlington or pay my respects to somebody, I just take off on my Harley and go do it."

So the picture he painted was fairly decent. My mother being a teacher for 15 years also helped. I had a good sense of what the job would be, and obviously being a state position, it comes with terrific benefits. Well, I have a giant binder of benefits that I'm entitled to, including top-notch Blue Cross Blue Shield health insurance. But the biggest factor that I found was public service loan forgiveness, 10 years. Loan forgiveness in 10 years, not 25. Plus after five years of teaching in a critical shortage area, I get 17,500 of my loans forgiven immediately. So looking at that makes the picture a lot more attractive.

Kimber Russell:

What is this critical need that you're going to be filling in your new position?

Jaye Lindsay:

I'll be teaching exceptional education or special education.

Kimber Russell:

So what preparation do you have to go into the special education? What are you doing now to prepare yourself? Because you haven't yet begun this job, when are you going to be starting?

Jaye Lindsay:

Well, I start in a couple weeks. The kids come back on August 10th. Preparation wise, because I'm an alternative pathway teacher, meaning I did not train for it in college, I have two options. I can go back for more education or I can challenge the exams that are designed to test your knowledge as a teacher. I opted to challenge the exams and I passed them.

Kimber Russell:

It sounds like you're pretty excited to embark on this new career path. What parting thoughts do you have about this whole journey that you've taken? What are some key takeaways from it?

Jaye Lindsay:

If you're a family man or you're a woman who wants to have time with your children, you want lifestyle balance, you want the stability of regular health insurance and retirement, there are lots of things you can do because you're educated, not because you have a law degree, but you got to be creative. You got to ask yourself, what life do I want? Then ask yourself, what jobs fit that? And if you're not qualified for it, get qualified.

So again, I don't really see myself as a lawyer or a teacher. I see myself as a family man who loves his kids and his wife, wants to have a good quality life and have time off. So I chose a way to try to make that happen.

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