Planes, trains and real estate deals | corporate attorney

Matt Newell
I think I worked as a junior associate for two years before my wife demanded that I take time off for a vacation. Probably said something to the effect of, "You will die, not by my hands, but just from overwork if you don't take some time off.”

Dave Weich
Hi, I'm Dave Weich, and you're listening to Work-Shaped Life. 

Your coworkers’ spouses—another whole category of characters in your life. They’re like work in-laws, colleagues a degree removed. They could be anyone, and then all of a sudden they start showing up for dinner.

In the early 2000s, Matt married a coworker of mine. Those being the years that inspired Portlandia, we wound up on a kickball team together. For six seasons. 

Did I know what he does for work before this conversation? I knew what his job was called, does that count? Think about it: You’re familiar with a lot of job titles, right? Do you know what those jobs entail? 

I knew that he worked a lot. I’ve heard stories. He’s had a bunch of different jobs since we met. But I have work friends, and Matt’s not one of them. This recording aside, most of the time, we talk about other things. 

[1:33]
Matt
I'm a partner at a small law firm. My practice is split evenly between a broad corporate practice…so I form companies, I help companies with different governance issues, I review contracts, I buy and sell businesses—in the legal world, that's generally what corporate means. And then the other half of my practice is commercial real estate transactions, so buying, selling, leasing real estate.

Dave
How would you describe your clients? Who are they typically? What kind of organizations or people hire you?

Matt
Kind of a mixed bag right now. My three partners are estate planning attorneys.  I get some of my work from them. Those tend to be families that have companies that are largely owned in a trust and oftentimes are going through generational change, trying to figure out how to transition from the founder to the children. So closely-held, family-run companies are one area of focus. And then a lot of the bigger transactional work are corporations largely based in the Pacific Northwest. 

And then the other main bucket is individuals that also tend to be ultra-high-net-worth and have a lot of assets that they own. I work with them in an advisory capacity to help them manage all of these things that they have.

Dave
I happen to know that you majored in philosophy.

Matt
Yes. 

Dave
Why?

Matt
I was actually thinking of doing computer science, but then I had a conversation with my father, who was an engineer early in his career, and then went to business school. Very, very smart person. 

[3:35]
I was just talking to him and said, "Yeah, I'm thinking of going into computer science." He said, "Well, have you ever considered philosophy?" I said, "No, I haven't ever considered philosophy. Why would you suggest that?" He said, "Well, I think that you can learn a trade at any point in your life, but you have few opportunities to learn to be a critical thinker. I really believe that a liberal arts education is one of the best things you can do in college." So I took an Intro to Philosophy course and actually really enjoyed it, thought it was very interesting.

I didn't learn until after the fact… This is one of my favorite stories. My father, he started college at Cornell and declared a double major in theater and business. Why a college-age father decided that he wanted to double major in theater is… I never got a chance to ask him that.

But he had very overbearing parents, and so came home from Ithaca for the summer to the Chicago suburbs and did his thing over the summer. When it was time to go back to school in the fall, he said, "Okay, Mom, Dad, I'm going to go back to Ithaca next week." My grandfather said, "No, you're not." And he said, "What?" 

My grandfather didn't approve of his choices that he'd made his freshman year in his first major. And so he forged his transfer paperwork—

Dave
Oh, my God.

Matt 
—and told him that he would be going to the University of Illinois instead, where he had been enrolled in the College of Engineering, and he was going to get a real degree. 

[5:37]
So my father's advice to me, as it so often is in our lives, our views and our recommendations to others are based on our own personal experience. His recommendation that I study philosophy was a direct response to his experience with his father being so heavy-handed and telling him that he was going to be an engineer.

Dave
Wow, and he did. He completed the program. He got an engineering degree?

Matt
Yes.

Dave
It's not the craziest part, but it's almost the most unbelievable. "Okay, I'll just get an engineering degree then," as if anyone could just do that.

Matt
Yeah. He was an incredibly intelligent person, so it doesn't surprise me that he was like, "Okay, I'll be an engineer and then do well at it." The kind of math he did after he went to business school and then started trading in derivatives, that was the family business. My brother ended up doing it, too. I could never quite wrap my head around what they were doing.

Dave
You were the child who was not going to head in that direction, and that was perhaps clear.

Matt
Yes.

Dave
It's funny because I remember the course that I often think about as being, in some ways, the most useful to me, the most practical, was in the Department of Philosophy. But it was Logic. I think about it all the time. The ability to actually think through any number of problems—obviously, not math, not philosophical arguments, but just life questions, and apply a more logical framework to it. 

[7:24]
I met you more than 20 years ago. At the time, you were working at Starbucks. 

Matt
Yes. When I graduated with a Philosophy degree and my now-wife and I moved out to Portland, I had no idea what I was going to do with my life. The first job I got to pay rent was a barista at Starbucks. 

On my breaks, I would sit outside with my coffee and journal. I just freeform thought, "Well, what am I going to do with my life? What am I good at? What do I enjoy doing in a professional capacity?" 

[8:05]
One of the things I really liked about philosophy was all of the thought experiments and the different kinds of reasoning and logic. And a lot of paper-writing in college is analyzing those arguments. Throughout college, I really developed an interest in writing. Writing in the sense, not—
I don't think of myself as creative. I'm not an author. I don't write things that people want to read, you know, books and things, but I really enjoy persuasive reasoning and enjoyed the process of structuring an argument and then building it. I like the iterative process of drafting, where you start with an idea and an outline, then you build out sentences and paragraphs.

So I realized that I really enjoyed writing in a technical sense. I like problem-solving. As I journaled about these experiences, I thought, "Okay. Well, this is something I enjoy doing. What is a lucrative career where I can employ these skills?" Oh, I guess I'm going to be a lawyer because that's what at least a lot of lawyers do. I spend a lot of time writing and solving problems. 

Dave
Are you happy with that choice?

Matt
That's a complicated question, or maybe the answer is complicated. There have been many times in my career where I have questioned whether it was the right choice. And as I tried to figure out what my options were, and when I told myself I needed change—how drastic was that change going to be?—one of the things I did is I went out and found a career coach, professional coach, and met with him over a couple of months. Talked about what I liked, what I didn't like. He had me do some skills assessments and personality assessments. 

The funny thing is that the results said that my personality traits and my skills, the highest correlation to a career with job satisfaction was computer science.

[10:40]
Dave
That's wild. 

Matt
I went, Oh, okay, maybe I made the wrong choice. Am I going to start over now? At this time, I had just had my first child. I had to worry about paying the bills, but I was still young in my career. 

I never fully explored the idea of just scrapping the legal profession and trying something different. 

[11:12]
Dave
The thing that I wanted to ask about: You worked for a company headquartered on the other side of the country.

Matt
Yes, so when I left the big law firm, and I went in-house, the client that I went in-house to— 

I paused for a moment because I've been reflecting a lot about my career progression lately, and I've been focusing on the five years that I was with this client because, with the benefit of hindsight, I think you can appreciate a time and place and how wonderful it was, even if you couldn't appreciate it at the time. 

For five years, I worked for the client that I went in-house with. It was a small management team. It was me, the CFO, and the CEO. It was the three of us. I was brought on to help execute an aggressive growth strategy. Over five years, we doubled the size of the company, and then ultimately sold it to a company that was based on the East Coast. 

That five-year period was really special because I worked with good people. I worked hard, but I had autonomy. And I had coworkers that respected my contributions. And so it was a really great period of time. 

Then, when we sold the company, we sold to an east coast group. Part of their reason for acquiring a west coast-based company and part of our reason for selecting them as the buyer was they were looking for an infusion of human capital, and so they actually saw value in our management team and our corporate headquarters here and wanted to integrate us into their operations, rather than just shut down our corporate office as unnecessary overhead.

So for seven years, I worked for an East Coast-based company. 

[13:22]
Dave
How did your life change? You were going back pretty often. I know, you'd be like, "Hey, I'm going to New Jersey, going to New Jersey."

Matt
When I think about that chapter of my life, both the five years before we sold it but then the seven years after the sale, yeah, for the seven years that I was working for a New Jersey-based company, with the exception of the pandemic and a break in between, I was generally on a flight to the East Coast every two to three weeks. When I reflect on that time of my life, I laugh now because, going to law school, I did not set out to be a road warrior.

Dave
Were there conversations at home at that point? How did your family feel about the fact that you were going to the—
Like you said, every couple of weeks, you were flying to the East Coast. 

[14:16]
Matt
Yes. We were in a phase of life where we were still both working full-time, and we had young kids,  and it was just put your head down and go. Looking back in those times now, we were worn really thin because I was gone a lot. My wife was single-parenting for weeks at a time.

Dave
With a demanding full-time job.

Matt
Yes, with her own full-time job. Because it sort of happened…because these jobs sort of happened, as opposed to me intentionally seeking them out, it was a frog-in-boiling-water situation. The travel picked up, and then we sold the company. Then it was like, "Well, oh, okay. Now, I've got to figure out what the culture is here and what the expectations are. Oh, okay, the expectations are that we're going to have lots of face-to-face meetings? That generally means that I'm flying to them. Oh, okay, that's a lot, and it's really hard." 

I got used to flying to the East Coast, getting an hour of sleep in a hotel, and then just being on from 7:00 AM until 10:00 PM for four days, and just hoping that one of those nights in between, I would get a decent night's sleep so that I was functioning. 

And then I would come home and I would just be completely discombobulated. It would take me a couple of days to recalibrate. Yeah, so it was intense and unpleasant, but the conversation at home, at first, it was just like, well, we're just both working hard and trying to make money and providing for our kids.

Over time, as the grind became greater and greater, and we were getting more and more tired, it became more of an urgent…kind of periodic, stress-induced conversations like, "This is hard, and this is not great. We can't keep doing this indefinitely. What are our options for course-correcting?"

[16:41]
Dave
I've been hiking with you. The joke is you put your head down and you go up the hill. God forbid, you pause for 10 seconds and look around. 
Are you just that way? You're describing... okay, it's very easy to see how going to New Jersey and spending all this time traveling and away from your family and not sleeping, a million reasons why that would build up and, essentially, you'd hit a wall. But you worked 90 hours coming out of the gate when you got your first job. 

Do you not work? Can you imagine yourself not working?

Matt
Yes, I can imagine it. Whether I would do well at it isn't— 

Dave
What's the longest you've ever gone without working hard?

Matt
I don't think ever since I went to college.

Dave
What's the longest vacation you've had?

Matt
Two and a half weeks.

Dave
In 30 years?

Matt
Yes, but we're in America. That's common. 

Dave
Is it? I don't know. 

I personally, the longest vacation I've had, aside from when I got laid off, is three weeks. I'm not coming to you as someone who's been sitting on a beach for four months at a time, going, "Hey, this is great. Everybody should do it." I'm not wired that way either. But do you ever talk about taking a long break? Can you imagine? Do you aspire to it at all, or is it two and a half weeks was great, and maybe you can get two, two and a half weeks again at some point?

Matt
I don't feel like my profession allows for a long break. 

In private practice, it's difficult because when you're on a big transaction, that transaction has a timeline and a sequence of events. It has milestones. Once that train starts moving, it doesn't stop for anybody.

It's an occupational hazard that when you're doing that kind of work, it gets in the way of vacations, important family events, because emergencies come up or there are deadlines. You can't just say, "Well, I'll pick this up in a week when I'm back. You either find somebody to fill in for you, which, at a big law firm, sometimes you can do that. Sometimes it's not efficient to do that. Certainly what I'm doing now, my partners don't do the kind of work that I do, so I don't have anybody to hand things off to.

But then the alternative, if I'm not dealing with one transaction that has a life of its own, I'm doing a lot of little things. I think the practice of law is similar to many other jobs that all involve sales in this regard, which is you can take a break, but when you stop having all the dialogues and the points of contact and the networking, and all of the busy work that you have to do to build and maintain relationships and put feelers out and come to mind when people need help with something, you want to be the person they call. 

If you stop all of that, then when you come back, you don't have anything to do. Then that one-month vacation, or two weeks, however long it is, there's also a tail to that where you're like, okay, now I've got to get the machine going again. 

Those two different kinds of work pressures are very different kinds of pressure, but they both make it difficult to take large amounts of time off.

[20:53]
Dave
Is there anything that you wish you knew then that you know now? Going back to maybe getting out of law school. 

Matt
Yes, there's lots that I wish I knew now, but I wish in law school somebody… that    there was curriculum or support in an institutional way to help students understand that the area of law that they go into affects their quality of life. 

I did not know that being a corporate attorney means that you're always working on big transactions that don't stop for anybody. Then when it's transaction, transaction, transaction, when do you fit in a break?

I think I worked as a junior associate for two years before my wife demanded that I take time off for a vacation. Probably said something to the effect of, "You will die, not by my hands, but just from overwork if you don't take some time off." I wish that law schools did a better job, and maybe they do today, I don't know, but helping students explore career potential, not just for the things that interest them, but also what the area of interest that they want to pursue actually looks like in terms of a practice and its demands on your personal life.

Another thing that I wish that I knew then that I know now is one of the things that's really challenging about the practice of law is… I mean, everybody knows the jokes and the stereotypes about lawyers. Nobody likes lawyers. People need lawyers, but they don't like lawyers. And that is reflected in a lot of my interactions with clients.

[22:44]
Dave
How do you mean that?

Matt
How to put this? There's a lot of people that just resent that they have to pay a lawyer to help them do something. There are companies where lawyers are highly respected and senior executives. Then their input is valued, and they drive decisions and drive a lot of policy. There's other corporate cultures where lawyers are a necessary evil and where people feel that they're a necessary evil.

Dave
They're an impediment to just doing what you want to do.

Matt
Yes, exactly. There are companies where the culture is, We're only going to invite them when we absolutely have to. We're going to do everything we can to not involve them in conversations because they're an impediment. 

I'm a transactional person. I help people finish something that's important to them, buying and selling a business or buying and selling real estate. That's an inherently positive thing. As I've been in different phases of my career, I have had different experiences with how people feel about what I do. So  I'm thankful, at least, that I can appreciate the benefit of really good clients who genuinely do appreciate what a lawyer can help them do.

[24:20]
Dave Weich
On the next episode of Work-Shaped Life:

Hannah Louise Poston
I am a professional social media influencer. And it is also at this point my husband's career. In 2026, with a mortgage and a kid and a two-person production studio, which is essentially what we run, and social media content as my full-time job, there is no way, no way to make it work other than starting from the knowledge of what will cause a video to do well in the algorithm.
 
[24:54]
Dave Weich
Subscribe on your favorite podcast platform to hear the episode when it drops. 

In the meantime, check out Work-Shaped Life on Substack, where this week our editor, Bailey Cain, had some words to share about my interview with her mom. That was  pisode six. 

Work-Shaped Life Life is produced by Sheepccot Creative. It's hosted by me, Dave Weich, edited by Bailey Cain and Michael Nipper.

Production support from Ben and Gottfried, Rosie Struve, Amelia Lucas, and Kate Sokoloff. 

We'll be back in two weeks with Hannah-Louise Poston. Thanks for listening.