Scott – From Law, to Silk Screen Printing, to Small Business Consulting

Good morning, good afternoon or good evening, you're listening to career crossroads. And if you're new here, welcome. And if you're not new, welcome back. I'm Jonathan Collaton. And this is the podcast where I talk to one person each week about all the decisions that led them to their current career path. This week, I talked to Scott Mason in New York City, about his multiple career pivots on the way into realizing that he was meant to help people. There's a little bit of audio clipping In this episode, but it's not too bad. So I hope you stick around to the end, where we will chat a bit about what we can learn from Scott. Scott, welcome to career crossroads. How are you doing?

I am excellent. It's good to be here.

I'm so excited that you're here. I'm usually excited about every guest, though. So that's not unusual for me. So you're in New York City. Is that right?

Indeed I am.

So what's New York? Like right now is? Is it mass celebration? Is it What's the weather like? You know, what's the general vibe?

You know, it is I'm coming back. And it's been a gradual step back. I will say that, you know, a little under a year ago, 910 months ago, it felt like, stepping out of the house was entering an episode of The Walking Dead. Yeah, it does not feel that way anymore. And yes, due to events that I'm sure history will record that way. There have been periods of celebration and a sense of maybe optimism, that there might not have been for a while, not the least of which is based on the fact that people are beginning to get vaccinated. And pretty much everyone is beginning to know folks who are receiving vaccines, and there's talks about things like schools reopening. So that's all positive. And you know, New York is a very resilient place. It's what I love about living here. But boy, we really needed that resilience. The past year.

Yeah I, I suspect so. So I didn't mention this to you before we started coding. But New York is like one of my absolute favorite cities outside of Toronto, if my wife and I've tried to figure out a way that we could come and live there for like six months, my sister did it one time, and we came to visit and we've been back a couple times since love the city. So I want to know, is that where you grew up? And if so, or if not, tell me about what it was like when you were growing up. And usually I try to pinpoint around the age of 16. Really Tell me what you were like, because I think that's when people really start thinking about their future. And given that this is a career podcast, that's the direction we're gonna head in today.

Yeah. So I was actually born in London, England, but I was adopted by two Americans who were in the United States Air Force, and stationed there, they brought me to Kansas where I grew up. And that's where I was when I was about 16. The area of Kansas that I grew up in was a semi rural area. during times when I was younger, maybe in my early teens, mid teens before 16. You know, there were literally fields right in my backyard where horses would be. And even when I was 16, one of the things that I would love to do was go out jogging, there were wheat fields and cornfields. As far as you could see, I would jog five, seven miles, and see no one except maybe an isolated tractor. Then behind my house, even as they began to put up new houses and what had been that farm area, there was a creek, and there was a forest around that Creek, and I would go back there and splash around in it. And I would count the crawdads. And I would find baby turtles and then I'd take them into my backyard and they'd be my pet for the day. They always somehow managed to escape. They hated me. But that's what it was like. And then at night, I would look up at the stars. And I would dream about a life that was different for me. Because as serene and pastoral as the experience was growing up in Kansas. You know, I'm a biracial man that was adopted by two African Americans. There was not a social meal you that really existed for me. I was skinny, kind of homely, with big, thick glasses and braces and bookish. That was not cool. In Kansas when you were 16 years old. Thank goodness, I knew how to defend myself. And you know, and the other thing about it was I was different, which, you know, I later realized was being LGBT. And so it really wasn't isolated. depressing and hard place to be as a teenager. And, you know, I am the first to admit, I love disco. And I would look at those disco albums, and they would always have these big cities with bright lights in them. And I knew when I looked up at the stars at night that the place that I had to be, was somewhere like on those album covers. Look where I ended up.

Okay, perfect. Because I was going to say, what were you dreaming about when you were dreaming, looking up at the stars. But that's an interesting story, the way you tell that to because it sounds at first very much like what an idyllic lifestyle to grow up in that you can just go jogging by the wheatfields. And look at look at the stars, and how great is everything right? But that very much shows how there's two sides to everything and how not everything is going to be that perfect small country town lifestyle all the time. So I really I like the way you explain that. So when you look up at the stars, and you saw these bright lights, these disco cities, was New York, disco city was New York, the one that that you thought of? And you thought like that's the place or were you pretty open to a few different. It seems like muttrah Metropolis is where you were headed

A metropolis. So I ended up applying to go to college, at a school near Minneapolis. And I don't tell everyone this, I pretend a lot of times that it was because of the academic reputation of that school. But that's a lie. Excuse me. It really was about was back to this theme of disco. Prince and Purple Rain were popular from Minneapolis. So I needed to go there.

It was that simple. That's a prince is one of those phenomenons that like I sort of I, I sort of get it, but I don't at the same time because my parents never listened to Prince or anything. So I was never raised on that. So I remember when Prince performed at the Super Bowl, whatever year that was, I don't know, 10 years ago or eight years ago, and I watched that I was like, Okay, I think I get it now. But up until then I never really got it with Prince. So I. So I sort of understand where you're coming from, though. Prince was the catalyst for you to go to Minnesota.

Exactly.

All right. And what did you decide you were going to try and study in university.

I ended up studying language. I though pretty quickly figured out that I had an interest in urban and public policy. I was an area that I saw was ripe for social change. And you're having grown up in the middle you that I did with sort of the identity challenges that I faced, I understood the urgency of those sorts of changes, and really empathize with people that I you know, I felt were outsiders and maybe not benefiting from a lot of the goodies that society had to offer. And so that's where I ended up focusing. And that's how I ended up ultimately leaving the Minneapolis area from New York City.

Okay, so touching a little bit on that university experience. Was it very much an academic journey for you? Or was there a lot of other involvement in things like extracurriculars? Did you ever doubt the program you were taking at any point in time? Or was it very much like, here's what I'm going to study straight shot through, and you came out the other side? And that's when things really started?

No, I didn't really doubt I mean, I ended up majoring in English. And that was a match of my skills and talents with, like I said, an extra curricular and sort of additional study interest, including some off campus programs with regards to these public policy issues that we talked about a minute ago. In terms of weather, I look, I respected the academics, but I honestly didn't find them that challenging. It's a good school that I went to. It's a liberal arts college that did have a selective process for admittance. But, you know, it just it really wasn't, it wasn't that it was boring, or ridiculous or anything, I just felt it was very easy. And the reason I mentioned that is because that gave me plenty of time to do the other things that I had come to the Minneapolis area for, like going to see Prince in every single club in Minneapolis every weekend, or to get involved in other social justice or community activism related activities, as well as just have a lot of fun with my friends and Heaven knows, I always had a lot of friends and a lot of fun.

Yeah, perfect. No, I totally accept and like, not accept that's the wrong word. I totally. I feel you on that because I had a similar experience where the academics were just happening, but it was everything else I was doing that was really sort of for me. Important. I don't have a better way to put it than that. But like school, I was going to graduate and get my degree but everything else I was doing was what mattered. And so, yeah, I got through, same way. So when you're done, though, you mentioned you mentioned New York pretty quick there. So was it like straight shot in New York. That's where you were headed.

Yes, I applied to law school, I applied and looked at them purely based on whether they were near a major urban area and their ranking. And so the school that met all of those criteria that was the, you know, that I got into was Columbia University's law school. And it was in New York, and I was there. New York and me, fell in love at first sight. Columbia Law School and me. That's a different story.

Okay, interesting. So it's, so you find this place that you think is the perfect fit, and it's in the city, which turns out to be the perfect fit. But what was it about the law school that wasn't the perfect fit right away? Was it the the difficulty level of it or your were you just not as interested as you thought you might be in what you were studying?

What a tremendous and perceptive question. Three things, first of all, you You're absolutely right. It was not as interesting as I thought it would be. Law School. And the practice of law, generally, particularly, I probably for the first five to 10 years of almost all attorneys is highly technocratic in its approach. I loved in my imagination, the things about law school that I would be able to do with it be out there and involved in some sort of public policy sphere, making change, doing exciting, interesting projects that had major social impact, not sitting around, you know, debating the, you know, the impact of a comma in a multi page contract.

Yeah, you wouldn't be an activist, not a lawyer.

You busted me. I know. Yeah. And the other thing, there are a couple of other things, too, it was a huge shift in the academic level, which was a bit of a shock. But it was a shift that didn't necessarily play to my strengths. Because I am, by my nature, I'm more of a big picture thinker. I am more of a visionary thinker, I am more of a strategic thinker. I'm not particularly drawn again, I can pay attention to detail. And I learned to pay attention to detail. But there's a threshold beneath which my mind shuts off, you know, except for maybe a few seconds. So that was very, very difficult. I found a lot of the conversations I had with my colleagues to be extremely boring, they would talk about, you know, the details of such and such case versus such. And such case, 100 years ago, I honestly could not get myself to care. I honestly couldn't, I tried, but the love just wasn't there. And finally, Columbia University, like many, especially at the law school level, like many elite institutions, loves having people from outside a traditional elite background there. But to operate in that world, was indescribably challenging for me, I learned. But it was very difficult for me, as someone who always had a lot of friends always understood social cues got along with everyone loved to being the, you know, love being the life of every party, to suddenly find myself with people. You know, the example the way that people spoke in class, or even outside of classes, the language that was used in casual conversation, I called it beat up words, if I'd used that sort of language going up, my rear end would have been mud, rolled the gravel. Yeah, it just, it would have been the end of my of any hope of a social life that I ever had. And so I really had to develop social brokerage skills in that environment, to be able to pass. It is a way of speaking and communicating and presenting in the world, by the way that I carried with me for a few years. But Jonathan, I dropped it as fast as I could, because it was utterly and completely inauthentic. And I never looked back.

You know, this is why I like to start and talk about people's upbringing, because where you grew up really affects things like this, for example, right? Like you grew up in this small town in the country, with wheat fields nearby. And you're going to school with a bunch of people who grow up around the Kennedys and talk like they go to the dinner parties with the Kennedys. And it's it's a different upbringing, and you just have a different expectation of what life is going to be like, and what you sort of need to do to get by. And so I see what exactly you're talking about. And it's great that you were able to adapt to make yourself fit in in the way that you needed to. But it also sounds like you were doing that very purposefully. Like that was not you are transitioning to be that person you were doing this because that's what you needed to do to get by.

Yeah, it's funny, you know, my father worked for the State Highway Patrol, my mother worked for a dog food factory. So when people would talk about What their parents did for a living. It was usually, you know, judges, professors on finance, ears, things like that, you know, saying mom worked for the dog food factory didn't quite carry the same cachet. Yeah. And and

They're like sorry do you mean she owned the factory?

No. Yeah. Right, that would have been a different story. But you know, it's funny, the whole experience was encapsulated by another friend of mine. First year, I totally related to this guy, he walked in weather wearing, you know, leather motorcycle jackets. He had maybe an earring in his ear. He was like a total cool kid. And, you know, he had we wore glasses that were shaded, and I was like, oh, man, okay, this is someone I can relate to finally. And then, after our first year internship, I saw him on the street. And I said, Oh, how are you? I hadn't haven't seen you in a while. And he said, I'm great. I've learned to play golf. And then he gave this really wide tooth, broad grand, what I call almost like a Rictus sort of smile. And I realized this was someone actually who was adapting far more quickly. And I hope for his sake more successfully. I never could sell my soul so much that I would actually have a pretense of being interested in golf. And no, you no disrespect to those who do. But to me, like that was where the that was the line that simply could just could not cross.

Yeah, everybody's got a limit. And for you, that was that was the limit. So being that you touched on kind of your, what your parents were doing, and I imagine Columbia Law School is quite expensive. Did you? Did you have a scholarship? Or was it? I always wonder about people? Okay, so was there ever this like pressure that you felt to get through and finish it because of the cost you were incurring?

Yes. But that was because the cost was utterly and completely on me. My parents were in no position to provide any support at all. And actually, that was a big issue. Because as you can imagine, the overwhelming majority of the students did not pay for law school out of their own pocket. Yeah, I would think. And not only that, but I was having grown up in that sort of working class background, it never occurred to me in order to get spending money, I had to work. Now, they did not allow you to work your first year, but I got a summer job. They loved me. And they kept me on. And I actually worked part time during the entire remainder of my law school years. During that time, I only met one other person who was working full time, or I'm sorry, part time during law school. And he was someone that was a New Yorker like me, but unlike me, but he was someone who liked me, had sort of come from a tough, you know, Italian working class background and just did not have spending money otherwise. So that was a real, real challenge. And it was, again, sort of another eye opener and differentiator as to what it was like for me day to day.

Hmm. All right. So with with all of these, this very different experience, likely from a lot of the other people you were in school with, as you as you were going through the program, I don't imagine law schools a short amount of time, it's probably a lot of expertise, you have to learn in order to become a lawyer. So as you were doing that, were you just thinking about, okay, when I get through, when I graduate, this is what I'm going to do next? Or were you just focused on kind of graduating? Or were you really prepared for what was next.

As I mentioned, this school, I paid for my own education, basically, through loans. The school did not offer scholarships, they told us right up front, we expect you to go work for a huge firm, and you'll make enough money that you'll be able to pay us back. So don't expect scholarships. I work for a big law firm, my between my first and second year, it was a very poor personality match. There's simply no other way to describe it. And I think that although it hurt me at the time, they were fair in their decision not to ask me to come back for the following summer, which happened, you know, that was the case with most but not all of the people that worked at that law firm. It just they recognized full well that I was not going to fit well into that atmosphere. And I just took me a little while to accept that reality about myself. So I think that there was financial pressure that, on the one hand, guided my thinking about what I would be doing afterwards sort of saying, Okay, I need to find a big law job, but the school did have a public service, sort of loan forgiveness program. Once I learned about that, and realize that I could probably scrape together enough money in a public interest job to live, then I was able to return to what I believe to be my principal interest and purpose being there, which was getting involved in public policy. And so I actually got the job of my dreams, which was as an attorney with the City of New York itself, which I viewed as a great way to enter into the world of public policy. And really the alphabet. I'm the alpha city in North America, if not the entire planet.

Hmm, yeah. And so that was like, right out of right out of the program, you got that that dream job, as you saw it?

Yeah.

That's a really quick turnaround. And so I always ask people, whenever something like this comes up in these conversations, so at that point, were you looking at your life and thinking, Okay, here's the next 45 years of my life, I got the dream job I've, I've got, I can I can live off the salary, life's good. Here we go, let's just go and experience what I've prepared for or was there some moment at some point where you realize, okay, maybe this isn't exactly what I thought it was going to be? Or did you sort of hit a ceiling where you thought, I need to move on to something else to push myself for? What was the thing that made you not stay in that role forever, is really what I'm asking, because I know that you didn't?

Yeah, um, initially, in law school itself, I was ecstatic when I got the job, I thought, this is going to be the perfect match, it's going to be fun, it'll be interesting, I won't be bored, I won't be treated. Like I am just some, you know, piece of equipment in some grinding Money Making Machine. And I will have the ability to get promotions and develop a real sphere of influence. And that, to me truly was exciting. It quickly turned into something else. One of the things I had not appreciated was the dynamics of large organizational life within a massive bureaucratic organization like the city of New York. Now, it wasn't so bad that I left it immediately, I had positions in five different government agencies and moved up and up and up. Over time, though, the dissatisfaction became greater and greater and greater to the point where I ultimately ended up after nearly 20 years, utterly and completely unbearable. And that's when I decided to make a switch in my life.

That's, that's while 20 years building your way up, but over time, just realizing more and more that you were, while I'm sure there's those little successes, right, as you move up, every time you get something new and exciting, and maybe more pay and a better title, it's, I'm sure there's excitement. But ultimately, you feel this just overall level of unhappiness, rising with what you're doing, that's got to be a hard thing to kind of come up against when on the outside, everything looks great. But then on the inside, you know, it just doesn't feel right.

I would say it wasn't just a general sense of dissatisfaction. By the end, it was a profound existential sense of dissatisfaction. I worked on some amazing projects. I was a building safety regulator on 911. I was one of the key people involved in skyscraper safety legislation, worked on that project for years after 911 to make sure that if such a catastrophe ever happens in the city again, 1000s of lives will be saved. After that, I worked on institutional reforms that completely changed how the city of New York handled the many homeless families that entered its shelter system. I was the project lead on a complete rejiggering of New York City funded Meals on Wheels programs. And I was second in command of the city's entire Administrative Tribunal system. And so these were projects that even in my worst days, I could not say were anything other than consequential and enjoyable and exciting. However, as you mentioned earlier, there was another side of the coin. First of all, as amazing and exciting and prestigious as these projects were, I was not connected to my ultimate purpose. And there were times when as wonderful as the project might be and as like you were saying a few minutes ago as exciting and glamorous as it might have looked from the outside, inside. I felt utterly incomplete. turmoil. I felt like a deflated raft and tossed around the ocean against rocks. And the low point came, I will never forget this Jonathan ever. I was at work for a few hours very early in the morning for some meetings. And then I went to get some breakfast. And when I went to get breakfast, I stepped outside and cross the street. And on the curb, on the street, where my office was, there was a coffee cart, and a man was selling coffee there for 75 cents a cup. And I looked at that coffee card. And I looked at that man. And in that moment, I was overwhelmed with rage, that I was not living his life, I would have done anything, anything to be the man on the coffee cart on that curb, selling coffee for 75 cents. The other thing too, is that government is not known for its emphasis on strong leadership and management development. Because there's no profit incentive, or there's no financials that can show a relationship between poor management and leadership and the bottom line. And so the level of verbal abuse that city employees often dealt with, even at the executive level, was so extraordinary, that even if I had felt connected to my purpose, I would have eventually left the city of New York was the only place where I was told in front of my colleagues, and my staff, by a supervisor by an agency head that when I talk, I sound so stupid, that I should consider buying a gun, putting it in my mouth and just shooting. I've never heard of such a thing said in any other environment. And the sad thing was, people were like, Oh, well, okay, back to work, just another incident. So those combinations of things made it ultimately unbearable. A lot of folks who work in these environments, value security or live in such a state of perpetual fear about their careers or their paychecks, that they will endure anything. I found that, especially having come from Kansas, worked so hard to leave those cornfields and make a better life for myself, settling for something like that to be an an utter and complete non starter

You know, when you first mentioned the coffee cart story, I was thinking, Okay, I'm gonna I'm gonna ask you to explain that. But I feel like now I already get it I, I can understand how what you're talking about would would lead you to think just like, well, look how simple this is. Wouldn't that be great and easy, and I wouldn't have to deal with people are happy when you give them coffee. It's the total opposite of what you were dealing with. Exactly. Yeah. Wow. Exactly. So that leads you to after almost 20 years, or around 20 years, you mentioned, decide that that's not the right fit for you anymore. And I imagine that's one of those really big moments where you have to consider, like, What now? Because there isn't that just general level of progression anymore, where you know, you're working for the city as a lawyer, and you can move around within different departments in the city. And there's always something that you're kind of connected to that you can you can see a path in front of you. But when you decided to leave, was it one of those, like, I just have to quit and then I'll figure out what to do next? Or did you already have your next kind of move in mind?

It was totally the former, I had no idea what I would do next. And it was perhaps not the smartest time in the world to make that little decision. The one thing that triggered it and made me feel comfortable doing it was that two weeks before I submitted my resignation, I had a vested pension. So I knew that once I was a very old man, I wouldn't be eating dog food. And in the meantime, I might be eating some puppy Chow, but at least in my golden years, I wouldn't be eating dog food.

You know, I really I like that because that's the first time something like that has come up when I've talked to anybody that there are those sort of like, it's almost like a ticking time bomb where you just gotta you gotta hit that moment. And then everything, even if it's not going to be great. You know what's better, because you've hit that moment where, as you said, it was vested and your your pensions good to go. And it probably really takes the pressure off when you realize that if I move, I'll figure it out.

Right. Right. And fortunately, I've always lived below my means and so I had money to live on for I budgeted for about a year and So I did not know though what I was going to do next. It was the tail end of the Great Recession, around 2011. And the unemployment rate, at least here in New York City was still high. Newspapers and magazines were full of what was called unemployment porn. And they involve stories, usually of middle aged men, like me, even though I look like I'm only 22 right now. And they don't bust me as a liar, please. And they,

No one heard it on mic, I did not laugh.

But these newspaper stories that you will see over and over, were about, you know, these high paid executives who were going to three years without a job, were possibly entering the ranks of the permanently unemployed, and they were having problems finding job as, you know, check out guys or stock boys at Target, after having made hundreds of 1000s of dollars every year. And I went to a career coach, because I was freaking out. And I knew I shouldn't be reading this stuff yet. Where was I going at the beginning of every morning, straight to the newspaper site to see what unemployment horror story I would read. Next, he looked at my resume the other counselor and he said, Scott, with your skills and experience, you'll have a job in three months. But Jonathan, that did not happen. Hundreds of resumes went out. I hadn't really learned how to network that well, because I'd never needed to when I worked for the city, I got jobs based on reputation, competence, and work ethic. Those things don't matter. I had naively thought that they did. They don't, what mattered and what ultimately enabled me to find my next step, were the people that you knew who would get behind you and advocate for you. But it was a year before that person that was really my advocate was able to find a job for me and, you know, support my application for it. And that ultimately ended up being for the best. In the meantime, I began to do some consulting work with some entrepreneurs. That ended up changing my life, I initially just viewed it as a way to keep my skills sharp, and to ensure that money kept coming in. But I quickly realized that in front of me, every day, all around me every day, had been people doing interesting and exciting stuff for businesses that they owned, that I somehow couldn't see, because I was so trapped within that, that career bubble. I couldn't, I couldn't even imagine that there was anything else. So I began to do consulting work around things like operations, infrastructure, compliance. And I even kept doing that after I got the next job. The next job I got was after more than a year of unemployment. It was after one of the lowest points in my life, when I really after that year pass, and there are still no prospects. I really thought maybe this was it. Maybe I will never work again as possible, which was devastating. And but I've kept doing that consulting work, even like I said, once that job materialized, and ultimately, that's what led to the next set of career changes after I was in that not for profit sector position.

Okay, so that seems like there's the cue not for profit sector. So what was the role? And it seems like, as you mentioned, you had an advocate, a friend who was helping you, and they either did they find the role? Or did they know someone who is hiring and suggested you have that workout?

Yep. He, the person who was my advocate, I had known as an attorney working for the city many, many years before he had since left the city and gone and done some other things, including being the general counsel for a major nonprofit. And the person that ended up being the CEO of the nonprofit that I worked for, had been friends with him at that other nonprofit. And so the person that I ultimately ended up working for apparently was either interested in my friend as a general counsel, or asked him if he knew someone that was a viable General Counsel. And my friend recommended me immediately. I heard later that the minute I stepped into that room, I was the first person they interviewed, that they thought we found our person. And they, they love me, and I loved them, and they had to sort of force themselves to forge through the rest of the search. But it was a it was a it was a great experience. And I quickly was promoted to oversee operations for this nonprofit. And that was the operations part ended up being you know, two thirds, three quarters of my job. And it but it was a it was a great organization and is a great organization. And although it ultimately ultimately It ended up not being the right path for me. I can't say I have any regrets working there.

Now, when you mentioned you go from being general counsel to was IT manager of operations or director of operations, VP of operations, VP of operations? So was that something where it just seemed at the moment to be kind of a natural like, it was available? And you were working there, and you were interested in it? Or? And I wonder this because of having a year of not working, when that opportunity was kind of came to you however it did. Did you think like, If I don't take this, what happens? What like, what if it? What if I end up not having a job again? Was that a concern?

Nope. What a great career question though. I started out with the city, during the very beginning of my nearly 20 years there doing litigation. I hated it. So I quickly moved to an in house counsel position where I did, you know, number of more interesting projects, including some of that legislative work that I mentioned to you earlier, with regards to building safety. But after that, as that moved on, I began to realize I really felt that as an attorney, I was either purely acting in an advisory role, or cleaning up somebody else's mess of mess. I wanted to roll up my sleeves and be in the center of action. And so I realized I had to move into a more central management role. It might be operations, it might be policy might be any number of different things, but I had to sort of escape that support function and go into the core business area of whatever agency I was working for. And that was why I began to also get promotions. Because the law degree as tough as it was, did teach me some very valuable skills in general management, especially due to some of my dispositional issues that made the earlier practice of law and law school itself, something that I didn't like, I am highly strategic. If you're going to be in the central business area of any organization of any size, being strategic is essential. If you want to rise above a certain level, you can't just purely be a tactician. Number two, I had the ability to present in a way that was professional and credible, which is not always the case in government, and you know, entities. And then number three, I had the ability to think, and to think incisively, multi dimensionally, and in consideration of consequences. So I automatically stood out because of that. So operations begin to more and more become a part of my portfolio. When I was with the city, when I was second in command of that tribunal. system. Operations really was what I ran, I was the COO, they didn't have that title. Formally, within the city, it was a different title. But it was the exact same position. So I was able to, with the consulting work that I did leverage those skills with the small businesses and entrepreneurs I was working with to help support their own operations. And they once they figured that out, they were overjoyed. And so my skills were sharp during that period between jobs simply because of that. And then another thing that I did to help get promotions, when I was with the city was opportunity scan, because there was a nine to five mentality, because hard work, staying there for more than 30 seconds past five in the evening. Things like that were very rare. I viewed that as a huge, constant, ongoing opportunity to show off my dedication, my skills, my work ethic, all of that sort of thing. So I stood out because of that. And that habit of looking for opportunities. There were times where I literally got promotions, because there would be some function that needed to be filled, there was no budget line for it of any consequence. I would walk in and say no one else wants to do this. Give me a few $1,000 I'll do it. And they'd roll out the red carpet and give me the money happily. So when I was at the nonprofit, the original operations person had some challenges. And as it became apparent that her challenges were unresolvable, I happily volunteered to bring my operational background before it was also a facilities based nonprofit. Having worked with the buildings department really gave me an understanding of things like zoning and construction codes and things like that, that were relevant and the ability to speak the language of the facilities world. And so I volunteered for this extra work. They loved the work that I did, I made promises about what I could do. The CEO told me I will say this about you, Scott, you say you can do something you deliver you Don't exaggerate, just to sell yourself. And so they happily offered me that and I felt no pressure I felt. Of course, I felt like if I didn't take it my career there would be over. But I wanted to take it. It was exciting.

Gotcha. Now, something you just said, that reminds me of an old saying, one of my old managers had, which was under promise over deliver. And that way everyone will be thrilled with your results. So it's a great thing that I've always subscribed to. All right. So that operations role, it was something you sort of naturally fell into. Because if I can use the word in a positive way, you're an overachiever you had done all this overachieving at the city. And so you had the expertise to fall into this role and have it fit quite well, with with your skill sets. But was that when you were doing that? Now that you had a stable job after a year of not having a job we were talking about for about this sort of advocacy and these other things that you had that you really wanted to do? Did you find that the job you were in aligned with those values? Or was there something on the side where you were really interested still in pursuing something in that direction?

The nonprofit that I worked for provided shelters for domestic violence victims, as well as for homeless people. And it also ran group homes for adult people with developmental disabilities. I cannot say that there was a single day that I walked through the door there and did not feel as though I was contributing to the betterment of the world. I was everyone there was did it ultimately align with my purpose? That is how I really hear your question. And that's a different story. It did match my skills. It did feel good doing it. Once I had discovered though entrepreneurship, and the possibilities that that opened up for creating things that were new, were impacting people's lives, a lot of the interest in public policy actually began to go away. Really, what I began to do was think about, okay, what was the desire and the drive to be involved in public policy, really about? What was the thread between that and what I liked most about working for that nonprofit? And then, how did that tie into and why did it put me in a position where I had such strong feeling states of enjoyment around the support work that I was doing with the small businesses that were still had me on retainer on sort of a side hustle as a consultant, even when I was working for that nonprofit. And I, it took me years, Jonathan, before I really understood and was able to put all the pieces together. But I did, again begin to understand during my time with the nonprofit that that was a transitional job. It was not my ultimate destiny.

Okay, so not your ultimate destiny, but in good job that felt like you were doing good work. So that's, that's still, that's a pretty good place to be even even take away the fact that you hadn't been working prior to that, that's, that's a good spot for a lot of people to be in. Because there is, however many jobs in the world and however many people in the world and not everyone's going to have a job that, that they're, they're fulfilling their life's purpose. But if they can have a role where they feel like they're doing good work, and people are benefiting from it, that's a pretty good spot to be. So you had the benefit of already having that, but also starting to understand more where your purpose was gonna lead you. So how do you decide to make a jump? Is there some sort of kind of clear moment for you where like, this is where you decided that that leaving that transitional job was the right thing for you or did an opportunity to do show up at your door and that was the move.

So one of the clients that I had, with my small business, consulting side hustle was a family of martial arts schools. And part of my compensation was cash. But part of it was the ability to train with these jujitsu, dojos for free and let me tell you all, that was the best compensation ever, ever, ever, ever. I loved. My martial art skills weren't terrible, I thought. but I still had a good time going there night after night, meeting people learning new things, pretending I was bad as all that sort of stuff. And, you know, it was funny because although my skills were terrible, I still would have a good time rolling around with People now they might be beating me up. But I would be laughing my head off while I was getting crushed. And one of the people that would headlock me night after night was a man that owned a silkscreen printing company for apparel and accessories. And he left his prior company and wanted to start a new one that this new company had been started using equipment that he found in the basement of a dead man. And he had started in his mom's garage. And he had heard that I was providing business consulting services to the martial arts schools, I'll never forget this. He said, you know, the the owners of this martial art, these martial arts schools only drive Cadillacs. And that's what I want. So that's why I'm talking to you when you work with me. And after that, how can I say no. So he and I worked together on projects for years. And we, you know, we would literally beat each other up him mostly beat me up. And then we would go and work on projects and have a grand time doing it. And one night, after hours, or, you know, being head locked, and kicked and thrown to the floor and all that by this man. We stood outside talking and laughing. And I said, you know, we have been having a great time working on these projects with your business together, let's make this company into something specialists. Are you interested in, you know, building our relationship either even further, and he's like, dude, I'm ready to hop into bed right now. And so, you know, we signed our papers, within a couple of weeks, I gave that nonprofit a very long notice. I think it was close to six months, and was involved in the hiring of they split my job up, I was involved in the hiring of one of my replacements. They didn't have budget for another one. But you know, and they were when I went to that company, that silkscreen printing company, that nonprofit became a client of mine. And we have maintained a good relationship ever since.

Wow, that's great. So in terms of the practical side of of that company, it seems like to go, like what were the skills that you found you were using from these previous jobs that you had, because it's interesting when you hear law school, and then you hear silkscreen printing, I usually don't equate those together. And that's probably because usually, when I'm hanging out at a silkscreen printing place, I'm getting like my hockey team jerseys printed. And so I don't picture a bunch of lawyers walking around. So the type of stuff that you were doing there.

And you know, it's funny, because at one point, we grew quite quickly once I was there, and we had to get some new equipment, and including a big, big piece of machinery. And the owner of the company that manufactured this machinery wanted to investigate us, because before we purchased that machinery, because we did not fit the usual profile of companies that were ready to invest in that level of equipment. And so he met me, I gave him a tour of our of our first location. And we talked and when he asked about my professional background, and I said, I'm a lawyer, he, like just stopped and looked at me goes, Well, that's something you don't hear every day. And I told him, this is something else you don't hear every day. And then I started to run through all of our financials and our ratios and our margins, and all that sort of stuff. And he's like, you're right. And I heard that he went on from that meeting to the company that provides loans to businesses that are seeking to purchase this equipment, and call them up and said, I don't care what their credit rating is, or what any hesitations you have, get them that machinery. So it was something that was very different in that space, I viewed that as opportunity. My business partner was an excellent silkscreen printer, and he'd been doing that his whole life. But subject matter expertise is not the same as understanding how to run a business. Not only that, it's not the same as business development. So quickly, I moved into the business development role, as well as bringing all of in which by the way, I had had corporate finance experience being on the executive team of that nonprofit, I was familiar with financials there. And so I brought that skill set to the table, as well as the ability to understand again, things like compliance, or QA. As an attorney, I also realized I had developed a profound skill that can help the business and that was how to sell something. As an attorney, you sell an idea, not a product or a service, but you're selling something. And so really one of the best things that I brought to the table there, and one of the things I enjoyed the most was the ability to sell the lack of technocratic skills that had challenged me during law school, particularly in contrast with the skills that I had an abundance which were the ability which was the ability to talk to anybody, and have fun and be enjoyable to be around and not be shy in any situation and all of that sort of stuff. All of a sudden, were of massive consequence, I could relate to any client, whether it was a major organization or the local taqueria, and our business grew, we tripled in revenue. During the time I was there, we tripled in staff side size, we opened a location in another city. And that was due to that combination of skills being combined with the leadership skills.

So I'm pretty confident after uhhh...if I know anyone who is a silkscreen printer, after they hear this, they're gonna go hire a lawyer to work with them to help grow their business, that's probably what's gonna happen.

And you know, a lot of it's weird, because I went to a Christmas party of a bunch of lawyers that I've worked with in a prior job. And I remember feeling very nervous walking in there, I thought they all would laugh at me or make fun of me or look down on me, because of the career choice that I had made. But when I turn that knob and walked through the door, I saw an old friend of mine there, and I told her what I was doing. I said, I'm really nervous about being here. And she said, Scott, don't be nervous, you're going to be the belle of the ball, every one will be jealous of you.

Everybody else is doing the same old law and dealing with the same pressures and stresses. And this is me as an outsider, maybe I'm way off here, but but you've got this exciting, different job where you're getting to, to do very different things. And I'm sure that I imagine how that would make you like the most interesting person to talk to you at that party. Everyone else is talking about the case they're working on, and you're talking about something they don't know anything about.

And I loved it.

Oh, fantastic.

I loved it, too. I think they did.

Yeah, well, otherwise, they're probably good liars. Because I imagine that

well, they were lawyers so you know,

oh, that's a good point. It's a great point. Yeah. Okay, so, so this screen printing company, you mentioned first location, which makes me think you expand it to be multiple locations. Overall, your time at that company? Unless you're still there now? Seems like, successful from what what you're telling me so far? And because I don't think you're still there, Now, what was the step to go from that to something else? Yeah.

You know, I'm gonna get a little existential on you.

This is what this podcast is all about. Go for it. I love it.

When I worked for the city, I was not only not a spiritual person, I was militantly and aggressively, anti spiritual. I was very much like there is nothing in this world beyond us. And what we imagine the only reality, the only meaning there is, is what we choose to make it. No one cares. The universe certainly doesn't care. So what I want, I will opportunity scan for I will find a way to take it. And that's that I did not particularly sometimes, you know, I wasn't a ruthless evil person. But I was someone who was concerned with my own advancement and my own agenda. And if you were in my way, or if you were opposing me, well, it sucks to be you. And I didn't care about the consequences of that from any sort of metaphysical or existential perspective, because I viewed there as being none whatsoever. That gradually began to shift. Once I left that behind. As I moved deeper and deeper into these additional career paths, things inside of me, began to emerge. And I think some of that was as I began to feel a little bit more passion or a little bit more connection to purpose that the entrepreneurial work on that I had been exposed to demonstrated, visibly the owners. By the time I was with that company, I had more fully embraced it. I had begun to really get a sense that there was a reason why I had had this diversity of experience, experiences, why I had faced the challenges that I had faced, that there were gifts that I was given, that I had underutilized or in some cases over utilized not in the best sort of way and I really began to also say to myself an entrepreneurial ism and the small business community, particularly the networking community, open this door. Am I really interacting with the world in a way? That's reflecting abundance? Or is it reflecting pure, personal, ego driven concerns? The reason why I mentioned all of that is because as the time went on with the silkscreen printing company, as much as I loved it, two things occurred. First of all, my business partner and I began to have different visions for that company's future, I love growing and scaling and would have taken it, you know, we did open another location in another city, I was ready to open begin to move to open locations in at least two other cities, maybe even three. And I was gung ho about it, my business partner, it was one thing to plan and dream about it, it was another thing to live it. And so we had conflicting visions. And we ultimately decided to split because of that, on the surface. But I had also begun to feel that Providence, just how I began to frame this connection to purpose, or this drive that I had to be to make something of the gifts I've been given and the experiences I've had had begun to also pull me against my will somewhere else. And I recognize that. And so the split was also a matter almost an ethical matter, I had to follow where I felt this force from outside of me was pulling me.

So where did you feel like that force was pulling you?

So the first thing I had to do was let go of the idea that wherever it was going to pull me was where I wanted it to be. And to say to myself, Scott, how can I best be of service? And then how can I let the drive that I felt Providence was pushing me in point to where my service should be directed. And so with that, a lot of pieces began to come into play. You know, thinking about my next step from a service perspective, changed the nature of the conversations I had with people, when I would talk to them, how can I help you out. And so I began to, again, get small businesses that were seeking to have the benefit of my expertise. In fact, I had small businesses, right before COVID went down that word on that were asking me to do work before I even had a company in place, or a bank account to charge or an invoicing system to charge. So that was a rare good position to be in, but then also, people. Again, perhaps it was because of the nature of the conversations I was having, or the energy that I was putting out, or the force of, of whatever external projections that I was having. People literally began to appear in my life, saying things like, Scott, have you thought about this, this this, and it would be exactly what I needed to hear. You're smiling, I suspect you can relate to that.

I no, it's n t that I can relate to that. B t I did. One of the other p ople I've interviewed Episode S ven, Brendon has a very s milar path to what you're t lking about right now. And h 's now studying to be a p iest. And he had. So I've h ard, obviously, it's a d fferent story. But I've heard s mething like this before, w ere these things just kind of a pear in front of you. And so I u derstand what you're talking a out, even though I think t at's what I'm looking for, for m right now, actually. And so I m waiting for those things to h ppen. And in a perfect world, t is podcast leads to those t ings, but we'll have to see. B t that's, that's for the end f r me to sum it all up. But l t's get back to you. So. So t ese, these things just started a pearing and pulling you in c rtain directions.

Or people would say, let's have a meeting. Out of the blue, I haven't seen you in a while. And they would say you should be doing this, this that and let me help you for no reason. A common denominator began to circle around my voice, my ability to present and the level of experience the gravitas that that brought to the table, and the ability to inspire people, particularly those that were lost, or in transition, or feeling hopeless. And by the way, as a certain negative set of public health events, during the past year or so has demonstrated all of this began to happen and pick up speed as that went down. People were looking everywhere I went for someone to just some extent provide the sort of support to help Small businesses stay alive. And that sort of work has sustained me. But it's also looking for someone that could talk to them about the shifting paradigm that the changed world that we're living in, presents someone who's been resilient, who survived, people who felt like my career suddenly over, I'm not making my businesses dead, my careers I got laid off, I don't have anywhere to go, I'm depressed because I can't leave a house. All these sorts of things. Non Stop, began to appear in my life. And I was able to provide them and have been able to provide them with hope, with inspiration, with the ability to feel charged about the future. And that to me, you know, podcasting itself, another way to bring out my voice that plays to a similar strength that you have, that you're demonstrating during this interview, the ability to communicate the ability to rate the ability to connect with people, and get their stories out there, and then drive that story to meaning. These are all skills of enormous power. And john, I'll tell you, this being really personal. The past year and a half, have been brutal, none of us would deny that. But I think that the future is very uncertain. We're walking through a forest where the end is at an uncertain location, and the trees are blocking any view of what might be on the other side. And then when we finally leave it, people are going to be traumatized. The other thing that I'll just say, is that the pandemic has been, in my opinion, point zero, for a lot of choices, that as a culture in North America, we have made cultural choices, personal choices, ethical choices, social choices, were lost. People who are in the space that I am, am in are going to need strength, hope, resilience, the ability to work through what all of this means. That's how we're gonna make it through the other side. That's how people whose employment lives, their own connection to purpose, who and what they are in this world. They're gonna need this, to fully step into it. That's the beauty of what's happened to is it presents different opportunities, as you yourself are living.

I 100% agree with pretty much everything you said there, the the walking through a forest part is something that I thought about a lot that there are people that are sort of getting by right now, because what else are you going to do? But then I think once things become more available, accessible, once there's more choice, I think, I think life's gonna be hard for a lot of people like it's not that it's not hard. Now, I think it's just going to be a different type of hard for a lot of people. And I've, I'm one of the people who I've been very lucky during what's gone on in the last year and a half that my job's been quite safe. And yet I've found myself I've had approximately three to six total breakdowns, from being able from from being not free to live as I want to live. And the incredible amount of social change economic change over the last year year and a bit has been, there's going to be a fallout from that, I think is a way I would put it and so so people like you are here to try and help others through that. So talk to me about some of the specifics. I know you have a podcast you do public speaking, you're doing small business consulting, if you're the type of person that somebody listening to this wants to get in touch with, where are the places they can find you and and how can you help them?

Yep. So if you are looking for small business consulting services, and by the way, one of the things that I do in that package is provide leadership and management mentoring. Because a lot of small business people that are subject matter expertise, just like my experts, just like my ex business partner was, even if they have a basic understanding of operations and how to run something, they may not have the background or expertise to be able to lead. And so I can provide mentoring for people like that. And by the way, I view leadership very comprehensively, really at the end of the day, anytime our actions impact others, I believe we're acting as leaders. And so if any of those sorts of services are things that you're Interested in I'm reachable via my website, Scott Mason llc.com for inspirational speaking services for, you know, conversations with regards to things like purpose transitions in your life resilience. www speaker scott.com. And my podcast is at WWW dot purpose highway.com.

Fantastic. So I'll put all those links in the show notes as well. So if anyone's listening to this, just go to my website, and you'll be able to get those links directly. As well as any social media stuff that Scott gives me. I'll put that on there as well. So, Scott, this has been a lovely conversation. Thank you so much for coming

No than you, yo 're a

I very much appreciate hearing that. And I'm gonna, I'm going to take that compliment and ride off into the sunset tonight, have a beer, and just just bask in feeling good about myself now. So thank you. So one more time. Thank you so much. And I hope that some people listening to this, gather some inspiration from it, and it helps them move forward, beyond whatever is coming next.

Thank you.

All right. So that is Scott's journey so far. Now, I love that his journey includes one long career with one organization in the city of New York, but then also has periods where he didn't have a regular day job. And he was sustaining himself with a side hustle while trying to figure out where his career should take him next. So with everything we heard, what can we learn from Scott? Now I work at a university. So I see a lot of students who are very focused on pursuing that one thing that they're studying, they have a very specific goal in mind. But Scott is proof that if you end up not liking the one thing that you're studying for, you can take a less obvious path to utilize that education in that skill set. I've had a few people on this podcast who've talked about wanting to become courtroom lawyers, mostly because they saw law and order. And I'm sure many of you listening to this think of the courtroom when you hear the word lawyer. But Scott did not like litigation. As he told us, he liked advocacy. And it just so happened that being a lawyer provided a great skill set for him to do that kind of work. So let's examine Scott's career path for a second. Working for the city of New York, He had roles as an in house counsel, where he got to be part of a whole bunch of projects and initiatives that were very interesting to him, but also allowed him to utilize his law degree and be a very valuable contributor on those initiatives, things where he could really make a difference. He got to work as a building safety regulator, working on policy around housing and shelters, working on Meals on Wheels, those are all noble tasks that likely saved lives. And yes, there is elements of law intertwined in all those areas. But I imagine those aren't the first things that come to mind when you think of a lawyer, because they definitely were not for me. But it was his next career that really nailed the point that I'm trying to make. After 20 years working for the city of New York, he was able to use his education, his experience, and his natural talents to shift into a VP operations role with a nonprofit. Think about the things he said he's highly strategic, he had the ability to present in a credible way. And he had the ability to think with consequences. Those are those interchangeable skills that I'm sure he got practice utilizing as a lawyer, but they came in handy as this VP operations role, and it's why he was such a perfect fit for it. So a clear takeaway from that is that if you end up with a degree in a skill set in something you don't love, that's okay. Do a little bit of digging and figure out how you can utilize your education and your skill set to do something that you do want. Lesson number two from Scott is that you can never know where career opportunities will pop up. Think about when he was working on the side doing small business consulting, and he mentioned that he got paid in unlimited access to a dojo that he was working with on their business plan. So he goes there regularly and regularly gets beat up by a guy who ends up wanting to hire him. And then after so many projects together, they formalize their business relationship. And Scott ends up working full time at a silkscreen printing company expanding the business. That's one of those things that is just totally random and unplanned. And there's no way to know that that is going to happen to you. You just got to keep your eyes out and tell people what you're doing and opportunities will present themselves. And another way how that happened for Scott was just a change in his mindset and how he viewed things He went from having a mindset that could perhaps be described as mercenary. He said that he thought meaning is what we choose to make of it. And that if he wanted something, he would find a way to take it. He was very concerned about his own advancement and agenda. But then provenance, a word that he used and a word that I'm aware of, but I definitely had to go look it up to make sure that I knew exactly what he was talking about. And provenance means the beginning of something's existence. And Scott's start of something new, was a totally different mindset. It manifested itself as something pointing him to where his services should be directed. And he said he couldn't control it. It just, it just happened to him. He wanted to help people. And it ended up being that small business consulting was a big part of that, as well as the motivational speaking he does now. None of this was planned, it just happened. which just goes to show that people change over time and have new interests. You don't have to keep doing the same thing forever. But you might have to wait until someone throws you down at the dojo to figure out what you're going to do next. That is all for this week's episode of career crossroads. So I hope you enjoyed it. If you know someone who could benefit from hearing Scott's journey, I hope that you share this episode with them. And if you want to hear more interviews, go to career Crossroads podcast.com. You can also review the show while you're there, and subscribe to make sure you get notified about future episodes. Episodes like next week's interview with Chris who starte working at the age of 16 by 23 he left the corporate world behind to open his own skateboard shop