Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. I practiced law for 10 years and now I help unhappy lawyers ditch their soul-sucking jobs. On this show, I share advice and strategies for aspiring former lawyers, and interviews with former lawyers who have left the law behind to find careers and lives that they love.

Hello everyone. This week on the podcast, I am sharing my conversation with Mike Whelan. Mike is a former lawyer, although he hates the term former lawyer so let's just pretend I didn't say that, who now runs a legal marketing agency or a marketing agency for legal tech companies who are interested in marketing to lawyers.

You'll hear a lot more about that in the episode. You'll hear about what it was like for Mike to start law school as a 30-year-old with 4 kids in 2008 right before the Great Recession hit. We also talk about how he ended up deciding in law school that he was going to be opening his own law firm when he left law school and then how he went from being a solo practitioner to doing the work he does today.

I am really excited for you to listen to this conversation. One of the things that I appreciated most about the conversation is the fact that both Mike and I have a deep appreciation for the need for lawyers to really be able to know who they are apart from their job for you to really have an opportunity to figure out who you are apart from your identity of being a lawyer.

It really is a huge part of the process for all of my clients who are trying to figure out what it is that they want to do that isn't practicing law. The conversation with Mike I think highlighted how important that is, so without further ado, here is my conversation with Mike.

Hey, Mike. Welcome to The Former Lawyer Podcast.

Mike Whelan: Hi. I'm really excited to be here because I'm lonely. It's a terrible reason. I recently hired my wife, as an aside, and you'll see as we talk about my history. My wife is like a through story, I missed her so much. She was off at work and I was like, “You know what, you could just work for me,” and so now I literally pay my wife to hang out with me because working on your home is tough.

Sarah Cottrell: Yeah, it's a whole thing. I am not an extrovert, I am an introvert and so lots of just working on my own actually is probably helpful for me energetically. But even so despite that, there are times where it's like, “Okay, human contact.”

Mike Whelan: Yeah. I'm happy to be here talking to you. That is the take-home.

Sarah Cottrell: Alright. Well, why don't you introduce yourself to the listeners, and then we will go into your story?

Mike Whelan: Sure. My name is Mike Whelan. I wrote a book called Lawyer Forward: Finding Your Place in the Future of Law. At the end, the way I summarize the book is that it is about systematizing self-acceptance. It's really about trying to figure out that your freak flag is the thing that's actually really useful in the legal space and around it, and that all that pressure that you feel to change who you are is actually the system being broken, not you being broken.

The background of the book is this narrative of me figuring that out about myself but then also giving advice from my logistics background pre-law into how you can do that and build a business around your uniqueness as well. I also have turned that into an agency that I serve mostly legal technology companies so I'm in marketing now, I do content marketing and community building for these legal technology companies who want to speak to lawyers.

Sarah Cottrell: Yeah, which marketing to lawyers is a whole thing and I know we've talked about this previously when you and I had a conversation. We will talk about that but let's go all the way back to the beginning which is what we typically do on the podcast, can you talk about what made you decide to go to law school?

Mike Whelan: Sure. What the heck is wrong with you? Got it.

Sarah Cottrell: Yes, basically.

Mike Whelan: My wife and I met when we were fairly young. We got married within three months of having met each other and then we got pregnant three months after that. We started life rolling really quickly. We lived here in the Kansas City area and I was working at a trucking company and wasn't on the path that I wanted to be.

When we got pregnant with our second child, I realized if I didn't go back to college, then I was just never going to. It was just part of my identity growing up that I would go to college. My mom called me the professor when I was a kid and so I had that as part of my identity. So I decided we're going to go to school.

I grew up Mormon and what people do who are Mormon is you go to BYU and I didn't know anything about that. But we just packed up and moved to Utah. I'm first gen everything and so I thought you just showed up to a school because I'm an idiot. It turns out, there are kids who spend their whole lives trying to get into BYU and I just showed up.

I ended up getting in, it ended up working out, and while I was at BYU, I was pre-dental. The way I convinced my wife to allow me to go to school was I'm going to be a sexy orthodontist like the sexy orthodontist she was working for at the time and she's like, “Cool, let's go do that,” and then I realized that they stab each other in the mouth with needles. I'm not doing that and so I switched to Middle East studies as you do and then we had this whole plan.

I won a Fulbright Grant to go to Jordan for a year. I was admitted to a PhD program for Middle East studies. I was going to become the professor. My wife, she got really ill in this mysterious illness and that again has driven a lot of our decisions since then and said, “We can't do the PhD. It's too much debt. We don't know what the job options are going to be,” so I was like, “Well, let's go to law school then.” In 2008, way worse debt, way worse job prospects. That choice has driven a lot of the choices since then.

Sarah Cottrell: Yeah. I know people who have listened to the podcast will know that I graduated from law school in 2008 so I'm familiar with a different side of that experience. Okay, tell me had law ever been floating around in the background before then? Did you know lawyers? Do you know what I mean? Was it that made you go, “Oh, law, that's the thing that I'm going to do since I'm not going to go get my PhD?”

Mike Whelan: No, no. It was the smart kid's path to making money that didn't involve pulling organs out of people's bodies.

Sarah Cottrell: Yeah, for sure. I was going to say you were talking about being a Middle Eastern studies major and I was an International Studies major. A lot of people I talked to on the podcast and people who I work with were some type of liberal arts major and didn't necessarily know exactly what they wanted to do but knew they wanted to do something and do some advanced degree and law is in that way of thinking, like, “Well, that just makes sense.”

Mike Whelan: Well, it was slightly more deliberate than that in the sense that we had four kids when I went to law school. I was 30 when I went and so I couldn't be self-indulgent about it. It had to have a path to making a nice middle-class, upper-middle-class wage.

At the time that I went in 2008, I went to the University of Texas. You had a guest Laura Evans on, she and I were in the same class. When I went in 2008, it was September of 08 and if you'll remember, it was October of 08 when the banks collapsed. We had no idea when we went. Everything made sense. I said I wasn't going to do it if I didn't get into a highly-ranked school.

I got into Texas, you're in the middle of major markets, all the math said you're going to get a big firm job if you're in the top half of the class and big firms at that time were starting at $160,000, I think, so all the math worked, it just happened to be that there was a major financial catastrophe in the middle of it and I'm super grateful that there was because I would have been miserable if I had gone down the path that I had in my head.

Sarah Cottrell: Okay. I know for people who've listened to Laura's episode, we talked some about the reality of what it was like to be a first-year law student at that time and some of the realizations that you had to have related to what the job prospects might be like.

I know that was happening for you because it was happening for everyone at that time and it also sounds like you didn't necessarily go to law school thinking, “This is the thing that I have always wanted to do and is just going to be super fulfilling,” it was more like, “This is something that could be interesting. I would be good at it and it will help me support my family in a way that makes sense.” Is that fair?

Mike Whelan: Yeah. The first year of law school is when I decided I would open my own firm for all those reasons that you mentioned. There's an old Above the Law post where the comments were still enabled then so people just ripped me apart.

Sarah Cottrell: Back in the horrible, horrible days.

Mike Whelan: It was bad. I had sent Above the Law a note about an experience. They had asked how is 1L job searching going and I had this experience where I was going up the stairs at the University of Texas and it was so dark. It was just a graveyard, this environment of going to on-campus interviews.

There were these two lawyers who were standing in this stairwell who were interviewing law students and one of them said to the other, “Well, how many interviews do you have?” “Oh, I have a hundred. How many interviews do you have?” “Oh, I have 80.” “How many are you hiring?” “We're hiring two. How many are you hiring?” “We're not hiring anybody,” and then they laugh awkwardly because it was so confusing. They're still going through all the motions.

I don't think they meant it this way in retrospect, but I remember it as a cackle as these kids because they're younger than me, these two lawyers who were standing in this stairwell and these kids are self-rationalizing, “Well, at least we got out of the war before it really got bad.” Honestly, those two lawyers probably got laid off a year later.

But it was really hard and everybody was trying to figure out emotionally. I remember I sent to Above the Law and I said in the conclusion to this statement, “I'm going to just open my own firm,” and all of these people in the comments were just ripping me apart for how broke I was going to be and how miserable I was going to be. You got into your tier two law school or whatever, you're not in the top three or whatever. You remember what the law was.

Sarah Cottrell: Oh, my gosh. Yes, I do.

Mike Whelan: Because I went to a T-14 school or whatever, I'm just a loser and so you're going to fail and burn. I was so mad. I was so mad and so motivated because I had worked. I knew business. I knew how to run a business. I decided at law school that I would start my own firm and that I was going to help other students at the law school start their own firm when they got out. That's when I created the Future Solo/Small Firm Club and that decision changed a lot of what I've done since then.

Sarah Cottrell: Yeah. It sounds like for you again, it was seeing, “Okay, the path to a steady job with a good salary that I was anticipating has pretty much evaporated, what is the thing that will move me in that direction? Because among other things, I have four kids,” which I think you and I may have talked about this but I just think things that are so important when we're having these conversations about the decisions we make in our career and the paths we choose to go down because there's this school of thought or way of talking about careers that I think that is very unhelpful because it tends to be like, “Who cares about the realities of anything? Just do what you love.” I'm like, “Listen, if you're someone who has four kids, that is a real constraint. That is a real factor. It really needs to be taken into consideration.”

I think it's helpful—and we can talk a bit more about this—for people to know that you can account for these real factors and also look for something that is a better fit. That's just a little bit of a soapbox for me.

Mike Whelan: Yeah, but honestly, the bigger factor on that surface, kids are kids. No matter what you do with kids, they're going to feel like they're traumatized. Everybody's got to come out with their own baggage and my kids certainly will. We always say if your kids are humble enough to know they need therapy and financially stable enough to be able to afford it, you've done all you can do as a parent.

But the thing that really popped up during law school again was my wife's illness. My wife, we have since found out that she has something called Ehlers-Danlos syndrome which is a connective tissue disorder that really just makes everything really hard. Some days, those things are hard-hard, but most days it's like a bad flu and it just makes motivation and getting up and going really difficult.

She was struggling when we were in law school. My wife is a woman and when a woman who recently had kids goes to a doctor and says, “I have a brain fog, I feel tired all the time. I don't know what's going on,” the doctors automatically are like, “Oh, you have depression,” and so they start giving her medication for that and that didn't work. They're like, “Oh, you must have manic depression,” and so they give her medication for that. “Oh, you have the other kind of manic depression.”

In the middle of law school, it got to the point that she was so heavily medicated, there was a full year where she was just laying in bed nearly comatose, staring at the wall, and she was miserable. Our marriage was tested at that point because I'm in the middle of law school. I'm competing and it is straight-up competing because it's all on a curve. I'm competing with these kids who were able to spend 14 hours a day studying and here I am, trying to take care of four kids while my wife is really struggling and crying.

I would walk by her while she was in bed and she was just crying. I can't get down there with her which only distanced us more and only made it harder for her. But we can't function if I don't keep going. We can't function if I don't take the kids places and if I don't go get the grades. I've got all this pressure.

In the middle of all of this, to your point about you have to adapt to your real-life circumstances, part of the reason that I needed to run my own firm was I realized I can't work 40 hours a week, much less 60 hours a week. I can't do that big firm life. I have to be able to build my own firm because otherwise, I can't work around this illness.

In the middle of my second year, we put my wife in the hospital for a while. I had to drop down to all but two classes. I withdrew from all my law school classes which meant I had to go during the summer. A lot of it was defined and a lot of my history since then has been defined by this combination of her illness and her goodness and supporting me trying to do the things that matter to me while we adapt to the reality of her body.

Sarah Cottrell: Yeah. I have a few dear friends who have chronic illnesses and I think the experience that you're describing is something that a lot of people can relate to and in particular, the unfortunate nature of we're not really sure what this is and on and on and on until you get some answer.

But like you said, it also makes sense that that was the thing in that period of time, that is what loomed largest. It wasn't like, “Let me self-actualize in some vacuum of whatever,” it was like, “What needs to happen in order for things to, in any respect, stay on the rails?”

Mike Whelan: Yeah. I don't want to undersell my wife's goodness in the background because she knew I needed to self-actualize. She knew that I have interest in the way I see myself and the kind of work that I want to do, which is largely teaching, we knew that I couldn't do the PhD path and go get the degree. We knew I couldn't teach in a law school. We knew that I couldn't go work in that big firm and do that environment. There were a lot of boxes that were crossed off, options that we just couldn't do.

But I spent the rest of my legal career, and getting back to Lawyer Forward, to the book, I spent a lot of this time with this struggle of why am I doing legal services? Is that what it means to be a lawyer? Because I actually don't enjoy legal services. I don't actually enjoy reading through documents really carefully to make sure the comma doesn't screw somebody down the road or finding some esoteric case from the 1800s, none of that was interesting to me. I didn't enjoy it.

The part of my practice that I enjoyed was the teaching part, both the teaching I was doing to clients and the teaching that I was doing with the Future Solo/Small Firm Club at Texas which became a conference and then a book and all this other stuff. It was those activities that I felt honestly shame about because this wasn't paying the bills, this wasn't stuff that was practicing at the highest level of my degree or whatever people say.

I wasn't selling legal services, I was doing stuff that mattered to me and it felt incredibly self-indulgent at the time but in retrospect, I'm glad I leaned into it and then added the discipline of turning it into a real business.

Sarah Cottrell: Yeah. This is a conversation that we have on the podcast a lot. I would love for you to talk a little bit more about that shame piece because I think that what you're describing exists for so many lawyers in different ways, especially because of the fact that the profession, there's just this idea of, “Well, this is the right way to do it. This is the best way to do it. If you're not doing it this way, then you probably are basically worthless.”

That's just the message that people get and even that's the message that people get in law school. Can you talk a little bit more about your experience with that, then just the group that you formed, and that whole trajectory?

Mike Whelan: Sure. I think it's significant that when people ask us what we do for work, we don't answer with the to-do verb, we answer with the to-be verb I am a lawyer. But if you look in the history of legal education in the early 1900s, things really shifted to the point where being a lawyer was no longer the old gentleman lawyer idea, the nature of how you think, it became highly regulated. It became highly regulated and rooted in legal services. “You are a lawyer if you do X.”

Now the X, the “you're writing a contract, you're showing up in court,” whatever those things are, the cause and effect switched. Only lawyers can do this list of things and therefore being a lawyer means you do this list of things. Therefore, if you don't love doing this list of things, you hate being a lawyer. They became deeply intertwined to the point that now if you ask somebody what it means to be a lawyer, most of the time, they'll point to tasks.

Significantly, they will point to tasks that probably won't be ours anymore pretty soon. Between regulatory changes and technology changes, a lot of these task-oriented mindsets, you're not a lawyer anymore. Now all these lawyers are having this crisis of identity of, “Okay, well, if I stop doing those tasks either because the job gets taken away from me because of technology or regulation or because I just don't want to do this job anymore, I don't want to look at documents like this anymore, now we've killed the to-be verb, we've taken away the identity.”

You didn't just take away the tasks. You took away the self and that's really destructive and something that I think we need to work through. What I did with the Future Solo/Small Firm Club at UT, which by the way nobody came, we would have pizza. We had pizza and students would still not come. Texas is an enormous law school. At the time that I was there, I think there were 400 students per class so there were 1,200, 1,300 students at this school.

I would host these events through the career services office and say, “Hey, come learn how to run your own firm. We'll give you pizza.” It was well publicized and we'd have like four people show up because all of these students thought, “Oh, no, no. I'm going to get the big firm job.” You're like, “Yeah, but data.”

Sarah Cottrell: Statistically speaking is unlikely.

Mike Whelan: Yeah. You can't all be the top five percent. That's just not how math works. But we were so rooted in this identity, in this illusion and so nobody would show up. I ran this thing for a while. It was mostly for my benefit. I came out. I had great connections in the community. I had referral sources because I was inviting local practitioners to come talk to us about their practice and I'm playing host. I'm the impresario, I'm playing host so everybody knew who I was.

I was showing up at local bar association events, which is unusual in itself for a student but also I was playing host so people knew me. It worked really well for me. But then former students started calling me and asking me for advice, “Okay, I wasn't able to get a job, what do I do next? What do I do now?”

So now I started teaching and it really is feeding me in the background, I'm running a law firm but I don't love running a law firm, I'm loving helping these former students, students that I went to law school with, these peers, I'm helping them move to this next thing in their life in running a law practice.

Then I started an event, I started Lawyer Forward, which was a live event that we did about my view of the legal supply chain, which is a concept I talk about in the book and the idea that if each of us is doing our freak flag thing, cooperation, collaboration is how we make that a business model rather than a thing we feel crap about. What the book is really about is me working through this idea of how you do you but in a way that's business viable. Does that make sense?

Sarah Cottrell: It absolutely does. I'm sure that this is part of what you are responding to or addressing in the book, I'm sure that there are lawyers who are listening who are just thinking, “What? How does that work?” because it's so different from how we are taught/indoctrinated when we are being trained to be lawyers. Can you talk a little bit more about that?

Mike Whelan: Yeah. I'll start by saying I'm one of those weirdos that thinks thinking like a lawyer is a real thing. There's this call now with law schools for them to create practice-ready lawyers. What practice-ready means is can you do the task that we're going to give you when you graduate? Even more task-oriented than it currently is.

Of course, the problem with that is that assumes that those tasks are going to be around which we don't know. We don't know that those tasks are actually going to be available to us. Law schools are doing this weird thing where they're like, “But we're not a trade school, we are a thinking school, we're an academic institution.” But they're also half-assing that because nobody knows what thinking like a lawyer is.

Everybody has a totally different answer about what the strategic work is. What I tried to define in Lawyer Forward was this idea that if you look out—I had a logistics background pre-law—and if you look out in most businesses, it is actually really rare that one person controls the entire supply chain. From the relationship before a purchase to the purchase to the fulfillment of that purchase, that just doesn't happen, there are very few business models where that works.

There are some expert-based consultancies where that's true where they create the relationship, they do the product delivery, they maintain the relationship afterwards but that's a model that I talk about in the book, that's an expertise model. It's very different from a service-oriented consumer directed specifically that I talk about. But even businesses, it's really rare that these companies will own the whole process.

What I talk about in the book is if you imagine a supply chain, if you imagine you go to Walmart, you get a doll, Walmart does not walk outside, manufacture a doll, and then bring it back to you. That's not how it works. There's nobody who calls the company in China and says, “Hey, guy in China who works for Walmart, send me that doll,” these are all separate companies that work along a supply chain to deliver to the end.

What I encourage lawyers to do in the book is to look across that supply chain and say, “Consumers don't care how you got them the doll. It doesn't matter to them. What they care about is “Were their expectations met?” and they have expectations for deep expertise and for accessibility. They want deep expertise to apply to their particular situation.

The great harm to the way we practice law is that we tell lawyers you have to be both, especially in solo small practices, we're telling them you have to be accessible if your client texts you, you better be available, you better answer them right away. But also, you need to be in a basement reading books, being a super nerd, and writing books because what they want is deep expertise.

I refer to that in the book as the Churn, it's the bad guy at the book because it's impossible, it is literally impossible to be the deep expert and constantly available. When we tell these lawyers to do that, what we're telling them is you have to live in this impossibility that we know is emotionally destructive to you. We know that telling you to do the emotional labor of giving a crap about somebody that you don't give a crap about, you don't care about this client, you are paid to care about this client.

You are paid to manufacture an emotion to represent this client, to care about their outcome. When you have no tribal connection to this person, it's all manufactured, it's all fake, it's emotional labor. There are a lot of studies on how flight attendants have to do this where they have to pretend like everything's safe for our benefit even though they feel like, “Good God, we're all going to die.” The plane's about to crash but they have to fake like everything's okay.

We do the same thing as lawyers where we have to manufacture this give a crap about somebody we don't give a crap about and also go be in a basement and deeply care about the nerd stuff. Anyway, the core thing in the book that I say is there are these two polls: this expert freelancer and this audience-building solopreneur who creates the supply chain, who connects these experts to clients.

Go find your place in the supply chain. Stop thinking of it as “I am the whole supply chain.” This is especially true for solos, “I am the whole supply chain.” go create and take parts in supply chains because the argument that I think is well validated right now is that we are all solos. We are all independent contractors even if we work inside a company.

Those companies do not care about you. If that firm is going to die, they will lose you. They don't care because you are replaceable. Why? Because you have task-based training. As soon as they can replace that task with somebody cheaper, they're going to do it. They don't care if you are solo and we are becoming increasingly solo. A lot of the changes in the pandemic just amplified stuff that was going on before which was we're becoming more and more solo. We see more and more of the American economy turning into independent workers who are connected.

Law is just super behind this and so what I talk about in the book is how to do that, how to create the connectedness that makes it so this increasingly solo environment is okay that we can all make money and do our best work doing that.

Sarah Cottrell: Yeah. A couple of things came to mind as you were sharing. One of the things is that I think you're right, it basically asks people to be superhuman, to not actually be human. On the flip side in a lot of cases where you have a client that you don't necessarily feel any particular concern for outside of the fact that you have this contractual arrangement you care, I think there's the flip side of people who practice in certain areas where they do genuinely carry these great amounts of emotional concern for their clients to the point where it's debilitating in a different way but asking people to be able to cope with superhuman levels of stress, duress, and all of these other things.

One of the phrases that came to mind as you were talking was setting people up to fail, asking people to do a task that is a series of things that is essentially impossible for one person to hold, and then of course, lawyers, I'm sure you have talked to lawyers who talk about this, I talk to many lawyers who feel like it's their fault, there's something wrong with them, they can't hack it, this is how it's supposed to be but they haven't figured out the magic life hack that makes it all doable.

I think one of the things that you're saying, if I'm hearing you correctly, is that it's not that you haven't figured out the magic life hack, it's that it's actually an unsustainable system.

Mike Whelan: Absolutely. Is it possible? Sure. But we have enough data in the legal ecosystem that says lawyers are miserable, that we can look, step back, and say, “Man, even if you can do this, should you? Is this healthy?”

I remember a study that I read recently, Sofia Yakren, where she talked about the emotional labor of lawyers, how we are supposed to care about other people's stuff. Basically, what the research found was that there are two approaches to that: either we lean in and we care and then we experience emotional burnout because we're owning other people's problems. They stack up to the point that we're dealing with the emotional labor of caring about all these people and we just can't handle it. It gets beyond what we can handle.

Or we have to emotionally detach ourselves and say, “Well, I'm just not going to care about anybody.” I practiced family law, I can tell you of plenty of lawyers who that's their coping mechanisms. They have to get to the point where they just don't care. They just see people as cogs and they just get them through, which has obviously downsides in the other way.

But what she talked about in that study was cause lawyering, that emotionally, the only way for lawyers to really deal with that emotional dissonance is to seek stuff that they care about and to only take the kinds of cases that it's not just emotionally fulfilling to the client for you to care about their situation, it's emotionally fulfilling for you to care about it.

Of course, she points out this is risky because now you're dealing with, for example, criminal defendants that you might hate. If we say it's a requirement for lawyers to give a crap internally about all of these situations, we're dealing with all kinds of corporate law that really nobody cares, none of this matters, but we need lawyers to care. There are downsides but what that study really drives home is that we are expending ourselves for the benefit of clients and there are costs to that.

Sarah Cottrell: Yeah. I think for the people who listen to this podcast, often part of the problem is that they're expending themselves in ways that aren't really consistent with their values and also feel like they shouldn't feel burnt out, exhausted, or overwhelmed, all of these things which are actually products of the work environment and the way that we have structured the work.

Mike, when you graduated from law school, you weren't like, “I think I'm going to love every moment of being a lawyer,” it sounds like you had this sense of there are certain things that you like and certain things that you're not as interested in. You can correct me if I'm wrong but it doesn't sound like you had some huge moment of “I think I'm going to love every moment of this. Oh, wait I actually don't like it.” But rather that the way that your career evolved, it just brought in all of these different strands.

Can you talk a little bit about the timeline and talk about how you ended up doing what you're doing now?

Mike Whelan: Sure. The background of the book is this story of me coming to terms with the business model issues that you talked about with law and the way that we work in law and what it really means to be a lawyer. As an aside, not to pick a fight but I hate the term former lawyer, I do not consider myself a former lawyer.

Sarah Cottrell: There are no former lawyers, you're a lawyer for life.

Mike Whelan: I mean, I'm a former lawyer in the sense that I no longer sell legal services, but one of the core issues with this industry is that we've deeply associated the lawyer identity with delivering legal services like we talked about. I still consider myself a lawyer.

One of the things that you talked with Laura Evans about in your episode with her is she uses her lawyering to do what she does now as an environmental planner and specifically the skill that we learn as lawyers, I'm working on a book called The Big Picture Department that asks the question once legal operations work in these in-house environments, what do lawyers do after?

My answer is they do systems thinking. They do what systems thinkers call emergence, which is I can play out scenarios and see what's coming. That's what lawyers do. That's what thinking like a lawyer is. Nobody told me this when I was in law school but apparently, there's a cliche that if you know the rules you get to C, if you can apply the rules you get a B, if you can see a future state and imagine rules that might be true then you get an A, that's emergence. That is being able to see things played out. That is the skill that lawyers have.

When I looked at my own career, I was looking across the ecosystem, the legal ecosystem, and saying, “Where do I fit? What is my thing?” I did that activity, that thinking like a lawyer activity of imagining what is the future state. Where are we going as an industry? What are the trends that are likely to continue? What are the pressures on us? What's likely to continue about my own life?

I'm a complex system inside a complex system. My career is complex inside complexity and so let's play that out. Through the book, through the conference, and through a lot of these activities that I was doing, I did that. I played it out by saying, “Well, in 10 years, I want to be somebody who is writing, speaking, being on podcasts, and teaching. That's where I want my energy to be spent. What can I focus on? Well, I can focus on this on what it means to be a lawyer into the future, what that social role is, detaching it from legal services, and playing that out.”

The book changed my life in that sense. At the beginning of the book, I give this story about a moment when there was this guy in court, I was living in Rockport, Texas at the time which is a rural area, I was running around as you do when you're a rural lawyer to five different counties, and I saw this other lawyer who was miserable. He was older. He was detached. He was just running through. He was in the churn. He's just doing the next case and the next thing. He can't remember his clients. He doesn't care because he can't.

I realized he was like my anti-OB1, he was who I did not want to become. He taught me that I don't want to become this life. The book is this journey of me going, “Okay, well, the one thing I want to do is teach. Where is a place that I can teach in this ecosystem?” The question that kept coming up is how does language lead to collaboration? How does the way we talk to each other make people connect and work together who would otherwise not connect?

The book is about the legal supply chain, which is a version of that, but that was the through question. I decided to just get obsessed with that question. Now I'm in legal marketing which is marketing to lawyers. I don't help law firms because again that's just not a question that's interesting to me, but I help legal technology companies move lawyers forward for reasons I can explain, I deeply care about what happens to lawyers, and so now that's what I do every day.

I use language to help lawyers collaborate in ways that help them, that move the industry forward. My days now are spent thinking about the future, thinking about the nature of work, thinking about law in general, law practice, and lawyers and how we help them to be better. That's my day now.

Sarah Cottrell: It's so interesting because I think as lawyers, often we have been trained to think in very black-and-white terms. Either it's like everything about the legal profession is terrible or everything about it is great. Burn everything down, let's keep it the same way it's been forever. I think part of this conversation that you and I are having right now is recognizing that there are lots of other alternatives and paths forward, which for people who are listening to the podcast, I think it's important to think about that and know that because you can also see that show up in individuals.

Often, you'll have an individual lawyer who sees their options as completely getting away from the law or becoming the person that they don't want to become that they're seeing. This comes up so often with people that they are looking at people who are more senior to them in the profession or in their particular firm and they're saying, “I don't want that life.” What do you think about that?

Mike Whelan: Yeah. To the work that you do, I think that black-and-white thinking and that risk obsession is a B-paper. That is the B on the exam because you're not using your greatest strength. I think as people listen to this podcast and the work that you do to help lawyers figure out what's next, I think the big question that we have to ask ourselves is what's the A version of what we learned? Can we go back and say, “How do I get that emergence ability? How do I get that systems-thinking ability?”

There's a book called Sensemaking that talks about a lot of how you keep the liberal arts mentality in future companies that in fact most of the most successful companies, they're not technical wizardry, most of them are social systems wizardry. They figure out how people work, how people make decisions, and how to make decisions in a world where Google wins and Facebook wins.

I think about for marketing now, and what I do, a lot of legal tech companies just to give an example are former lawyers who went and founded something and they are B-thinkers, they are writing B-papers because they're obsessed with a task and they're saying, “I'm going to scratch my own itch and I'm going to go create this company. I'm going to do product first and put it out there and people are going to buy it because it's so dang good.”

They think that's product-led marketing. That's a B-paper. It's not even successful and that's why you see so many technology companies, in general, are very risky, but legal tech companies flail because they don't look at the systems, they don't use their lawyer brains to understand the bigger picture and say, “How can I play this out?”

An A paper would say, “You know what, instead of keeping on building a product that solves for what I think needs to happen in the legal industry, let me solve for what people are searching for. Because I know in 2022 I can't succeed as a technology company unless I can win Google. Let me go match the distribution. Let me go look at how this company is going to be distributed, how are people going to run into us.

“Instead of just solving problems for this idealized black-and-white situation, let me solve problems for where people are at. Let me see them in a search and move this lawyer not from where they are to where they should be, but from where they are to where they can be. What's the realistic next step? Let me just nudge them along.”

I think the big picture thing that I've taken from my own journey is that I had to stop doing the black-and-white thinking. I had to stop thinking in terms of bests and thinking in terms of losses and risk and start thinking about my job in this world is to help some people.

The people who are going to show up at your funeral are probably your employees and your family members, not the clients you serve, not the bottom line that you changed on a spreadsheet. Most of your impact in this world is going to be the people who are close to you that you encounter frequently. How can you move them? How can you live a really interesting life out inside your work and then bring that to your work in a way that moves people along?

I really feel like that's all we can do and all you need to do with your work is find an economically viable way to do that. You don't have to find all your fulfillment from your job but if you can align your job so that it feeds your fulfillment, which comes from all these other relationships, I think that's the best you can do.

Sarah Cottrell: Yeah. I think that's so true and I also think that—and I know this is something that you talk about quite a bit—but a big part of it is developing an understanding of who you are, to go back to what you said earlier in the conversation about being a lawyer and the ways in which we often take that into ourselves to the degree to which we're like, “Well, this is who I am, and apart from this specific archetype, I don't know who I am.”

I think for many lawyers, that is a huge struggle because we haven't necessarily been taught how to actually see ourselves for who we truly are as opposed to the things we do. That I think is a lot of the work to get to the place that you're talking about in terms of being able to find something that does feed your fulfillment in whatever way.

Mike Whelan: Yeah. I agree. This is not who you are. Your job is not who you are. Your job is what you do. It's unfair in the American ecosystem because you do spend the vast majority of your time working on your job and so in terms of hours per day, your job is a big part of who you are but at best, your job is going to provide satisfaction, it is very unlikely to provide happiness. You just need to optimize for that.

I like to think of it as a board game. Remove it from yourself. Put it on a board and you're just maximizing assets. Maybe your asset that you have in abundance is time. Great, well, then build your game board strategy around time. Maybe you have money, maybe you're really smart, maybe you're really a good connector. Whatever it is, when you sit and play a board game, you start with these resources. Your strategy should come from your resources. Make your strengths your strength.

The thing that makes you weird is not the thing that makes you a failure in law, it makes you exactly what the law needs or whatever it is that you do next. Your freak flag is the thing that actually makes you valuable.

Sarah Cottrell: Yeah. One of the things I talk with my clients about a lot is if your strengths are not being treated as strengths or are not strengths in the environment you're in, then let's figure out where those strengths actually will be and are valued, and go there and do that instead of trying to be someone you're not and shame yourself for not being a certain type of person, whatever that type of person is that is particularly valued in your workplace.

Okay, Mike, as we wrap up our conversation, is there anything else that you'd like to share that we just haven't had a chance to talk through yet?

Mike Whelan: Yeah. The last thing is—and this is to pivot to sharing where people should go next to find me and whatnot so we'll just combine those—but I have pivoted in my work because I'm doing this work with legal technology companies, the way the economics work out is they pay me to pay creators.

The way one of my clients refers to me, he calls me the Ryan Seacrest because I have this perfect hair. When you guys see the profile picture, you'll get the joke. But I have really changed my work with lawyers from helping them do operational stuff because frankly, that was boring to me, and have really focused on helping lawyers become creators.

Because once you do that, once you be yourself loudly, once you create media and you are yourself out loud, and that freak flag is flying, that actually gives you a whole lot of leverage for whatever your next thing is. What I would encourage people who are listening to do, you can find my book Lawyer Forward on Amazon, you can go to lawyerforward.com and there's a link there.

But also I did a series on the Lawyer Forward Podcast called The 90-Day Known Expert Series and really what that turned into was a writing class to help lawyers look at and say, “How do I be myself loudly? How do I learn out loud in a way that gives me leverage later?” You are becoming a media company in that sense and it is a sustainable model that gives you a lot of power.

If I can help any of you to learn how you can teach, how you can become a media entity and be a creator out loud in this economy, it will be the thing that helps you pivot to your next thing. I would love to help you do that, just reach out to me. I'm just [email protected].

Sarah Cottrell: Awesome. Thank you so much, Mike, for joining me today and sharing your story.

Mike Whelan: Absolutely. Good to be with you.

Sarah Cottrell: Thanks so much for listening. I absolutely love getting to share this podcast with you. If you haven't yet, I invite you to download my free guide: First Steps to Leaving the Law at formerlawyer.com/first. Until next time, have a great week.