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Career Profile: Lawyer by Day, Accountant by Night

Key Takeaways

How does someone go from earning an accounting degree to becoming a securities lawyer? Catherine and Steve are joined by Alan J. Wilson, JD, CPA, of the law firm WilmerHale to discover what led him down a career path where law and accounting intersect—and what secrets are hidden in such an intersection! 

Steve: Hello, and welcome to Off the Books, where we surf the uncharted waters of accounting, finance, risk, and wherever else the waves take us. This episode is brought to you by Workiva, the risk, reporting, and compliance platform that simplifies your complex work and helps keep you on that beach-ready fitness routine. Check it out at My name is Steve Soter, accounting enthusiast and Diet Coke aficionado. I'm looking forward to debiting a great conversation today, and I'm very glad to have you hanging ten with us. I'm also very happy to have Catherine Tsai joining me. Catherine, can you please tell the fine folks who you are?

Catherine: I'm not an accountant or Diet Coke aficionado, but I like asking questions and learning new things and writing about them later. So I'm here to learn. Steve, what can you tell us about today's episode?

Steve: Well, Catherine, in our last Q4 SEC Pro Group meeting, we had a terrific panel that included Alan Wilson, who is counsel at the well-known law firm WilmerHale, who, among other things, does substantial work in securities, meaning that they help do things like an IPO or help a company with their reporting to the SEC. And besides being a genuinely great person, Alan has a really interesting background that includes his experience practicing law, his CPA license, and actually some time as an auditor with KPMG. I'm actually reminded that at one time, my dad encouraged me to take such a career path. I largely ignored his advice, and Alan is now my gateway to figure out what I've been missing all these years.

Catherine: Steve, you rebel. If it makes you feel better, I ignored my parents' advice to eat all my vegetables, and I've regretted it ever since. Hopefully, you haven't missed out on as much as I have. Let's get to our conversation with Alan.

Steve: Alan, I mentioned in the intro a little bit about your background as both a licensed CPA and attorney, but can you give us a little more detail to get us started and maybe tell us what made you decide to pursue this career?

Alan: Sure, absolutely. And thanks for having me. So I have a bit of a nontraditional career path. I started out in business school as a college undergraduate, pursuing an accounting degree, and my initial career plan really focused on becoming a partner in a Big Four accounting firm. I figured I would go into the audit practice as many accountants do at the early stages of their career and progress that way. And of course, as most accountants know, in order to be a licensed CPA, you need to have 150 credit hours in almost every jurisdiction to become licensed. And the fork in the road that I encountered was that with my basic undergraduate degree, I didn't have the requisite credit hours to be fully licensed. And so it occurred to me that law school was another choice that was one that was not terribly explored very frequently by many, but would have worked for both satisfying the CPA requirements, but also would have given me a leverageable background and another career avenue should I wish to leave public accounting. What I found, of course, is after three years of law school, I actually enjoyed the practice of law and more so because I was able to leverage the accounting background. I'm really now a public company securities lawyer advising Fortune 500 companies on a daily basis as it relates to their accounting and other SEC disclosure obligations. So it's truly been a career path of evolution and really not the most linear path, but one based upon diversity and getting new experiences and growing with different opportunities that presented themselves.

Catherine: So you studied accounting as an undergrad.

Alan: Correct, yes, studied accounting as an undergrad, clearly didn't become the doctor that my parents thought I should have been and ultimately became a lawyer.

Steve: Clearly, you're the child that my parents never had, because the path that you laid out was exactly what my dad suggested. JD, CPA, study tax, you'll make a ton of money, and you'll have a great career.

Alan: Yeah, yeah, that's exactly, that was the path that I didn't know that I wanted to follow and that kind of fell into my lap. And you know, I'm a member of the American Academy of Attorney-CPAs, which is kind of an interesting little group of folks that have this dual JD, CPA, background, and most of them are tax. I'll say I'm even more of an outlier, given that I don't do tax and I'm on the security side of things, even though, of course, I still have a soft spot in my heart for tax and took about every tax class I could in law school thinking that I'd ultimately end up in that type of practice environment. So certainly a very lucrative and popular path.

Steve: Sounds like a really exciting group. What are those holiday parties like when you all get together?

Alan: Oh, scintillating. Section 179 deductions, accelerated depreciation schedules, really, really fascinating stuff

Catherine: That's riveting.

Alan: The accountants in the room are all excited looking to get JDs so they can join these fun holiday parties, I am sure.

Catherine: So you had a professional career then, too, before you went into law school?

Alan: Yeah. So I was interning at KPMG, and as part of the program, I was being onboarded so I could effectively join as a full time associate while pursuing a college degree to get the credits needed for the CPA. Then of course, became a full-time law student so quit KPMG, all the while thinking, at least during my first and even my second year of law school, that I would return to KPMG and join the tax department because there was a path there. I saw a lot of tax attorneys practicing at the firm and thought at the time that that would be a natural fit because I already had connections and I liked the work that they were doing. The other thing too, for context, is, of course, when I was in law school, we were still coming out of the financial crisis. And so jobs for lawyers were more scarce. The finance industry was changing rapidly. And so as I was thinking about job security and other things, you know, accounting is often touted as the bellwether for job security. And in the back of my mind, I always thought at the end of the day, I still have this accounting degree I can leverage, and tax and audit are always services that folks will need. And so as I think about it as a practical matter, that option always seemed to be the most viable, regardless of the economic territory we faced.

Steve: So I recognize we're already talking about a somewhat nontraditional career path, but we've talked a little bit about tax and of course, the natural go-between of law and accountancy. Of course you're practicing securities law. But what does typical career progression look like for somebody with your background? I mean, if you fast forward five or even 10 years, is it likely you'd be doing one or the other and probably not tax since you've already started to build out a career, of course, within securities law?

Alan: Yeah, that's right. And so I mean, I would say, obviously there's always the ability to change, right? And I encourage people to really think about that if they're in a profession or a career path that really isn't satisfying. And because of the background I have, that's all the more available because of the different experiences that I've had over the course of my career. That said, I've made significant investments to become a securities lawyer and really specializing in the securities corporate governance space. And so as I continue to build on that path over the next five, 10 years, the progression really is to become more expert in that field, work, become the partner at a big law firm, or even to go in-house. You know, those are the common options that are typically available and that are most available. But at the end of the day, law school teaches you how to think, and it's that critical thinking skill that opens you up to opportunities in boardrooms and other executive suites where you can really adapt. And so just because the natural path as I think about it is really going to become partner and really building a bigger corporate governance security practice for myself, there are a ton of other avenues available once you've got those experiences that you can leverage, particularly with a critical thinking ability. And really the way in which I've seen and advised public companies and other businesses, it truly is an opportunity to leverage those strategic experiences in any number of ways.

Catherine: I have a degree in journalism, and there are a lot of kids in journalism school who also cross over and go to law school. There's research and interview skills that crossover. What sorts of skills did you find crossed over from accounting into law?

Alan: Yeah. So for me, I will say my first year of law school was terrifying because I was the outlier with an accounting degree. And I thought because I didn't have a political science degree, I didn't spend my four years in undergrad writing nonstop that I was really going to be at a disadvantage.

Steve: Alan, let me assure you, you were the cool kid. You may not have known it, but you were the cool kid.

Alan: I was cool before I knew it, for sure, but I'd say the skill that translated, other than the fact that I worked on the writing and everything in law school, it was the formulaic way in which I was taught in business school because in business school, there's a lot of formulas and accounting, particularly things foot, they tie out. Audits have processes and procedures, and there's a lot of focus on the detail and going through those processes. And it's that attention to detail and that formulaic approach to thinking that actually benefited me in law school because I had to break down case law or statutes or regulations and really parse them into each of their individual component parts. Because a lot of the law, of course, is detail oriented. And those skill sets really were beneficial to me and still are to this day as I practice, because everything we do is incredibly nuanced and it's the focus on the nuance and being able to distill it quickly that really separates those in practice.

Catherine: Steve, as we were talking to Alan, I wondered if you would have made the same connection between accounting and law school.

Steve: You know, it's really funny that you would bring that up because honestly, I was having that exact same conversation with an old friend of mine who, not too different from Alan, actually studied physics as an undergrad, then completed his master's in electrical engineering, and then went to law school. Today, he practices as a patent attorney and I actually asked him if accounting would have made me enjoy law school because of the need to dissect case law or regulations. Well, he actually thought I was crazy to think that anybody would enjoy case law and told me that that part of law school was without a doubt the worst, most tedious and painful part of his education, and that the only thing he found interesting during his time studying case law was a situation where I guess a patient was standing up while his doctor was putting in a catheter, and the patient passed out backwards, with the resulting case law somehow making its way into a law school textbook.

Catherine: Thanks, Steve, for that mental image. Remind me never to ask you a question again. All right, let's get back to Alan. So I guess what is a typical day like for you in your job today?

Alan: That's a fabulous question and one for which I think the answer's probably universal: there is never a perfectly typical day. I would say there are themes, right? So a lot of the work I do, of course, is SEC reporting, which occurs on a cyclical basis. So you have quarterly and annual reporting. And so there are busy cycles there as you're gearing up for 10-Q, 10-K, and proxy statements and those reporting cycles throughout the year. And accountants are familiar with those from the accounting side as it relates to the financial statements. A lot of what I do is counseling. And so days vary. There are many days where I do nothing but sit on the phone and talk with clients about challenging questions that they're encountering, whether it's financial statement requirements in an M&A transaction or any disclosure issue or the sale of a business or an accounting comment letter from the SEC staff and how best to posture the company's responses. A lot of what we're talking about now are investor demands too, and trends. So diversity, equity, and inclusion, climate change, and other things that historically have not been well within the purview of a securities lawyer or an accountant are well within both. And so we're rapidly learning and advising on those issues. Other days, of course, are spent reviewing documents and filings. Other areas, I would say, that are less predictable and why it's hard to have a typical day are the natural fire drills, as I call them, throughout the day, where clients get into emergency situations, there's bad press, the market does something funky, a new event occurs that nobody knew about, there's a disclosure issue, some other public crisis or the media storm is coming after a company, and I am often on the team that advises companies and helps navigate through those situations. And so that's a far less predictable path. But certainly one of the more exciting elements of the job is being able to bring to bear the accounting experience, the SEC disclosure. And then the corporate governance experience, advising boards of directors on how to navigate strategic situations and really think through all the various avenues that come into play. And that's just an example of one of the things that you never walk into the office thinking you're going to have to deal with that day until you get the client email with the exclamation point that says we need to dial into a call immediately and it hijacks the day. And it's really a rewarding experience where you can help navigate, give them the answers they need quickly, and really leverage the capabilities that I have along with others here at the firm with the robust background of experience that we have here.

Catherine: While there's no typical day for Alan, there's definitely a typical commercial break in this podcast. We'll get to that and be right back.

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Steve: And we are back with Alan Wilson, securities counsel at WilmerHale, talking about his career.

Catherine: Yeah, you talked about getting emails with exclamation points. Do you have any juicy stories you can share?

Alan: Yeah, absolutely. You know, one of the more exciting matters I worked on was a large corporate advice matter where we were advising a board as it related to its options for a company sale. It was a storied institution that was undergoing an M&A transaction that would have really changed the entire dynamic of the company and was happening at lightning speed. And the board had that notion to raise its hand and ask, How are we thinking about this? And what does this really mean for the future? And it was rewarding because it offered an opportunity for us as a firm to show our capabilities because there were a number of regulatory and corporate securities and M&A elements involved, as well as some nonprofit tax. And in addition to the fact that it was headline grabbing and it was certainly going to be subject to scrutiny, so it was a good opportunity to bring our experience to bear and really add value for a board that was looking for independent insights. And it started, of course, with an innocent email asking about a general question which led to months and months of work and then assistance on the transaction. And you know, when you talk about kind of the exclamation point, the immediate ask was, "Oh my gosh, we're going into a meeting in two hours. Give me the quick and dirty as it relates to what I have to think about. What are the questions I should be asking? And can you join, and can you ask them?" And then, of course, that led to a much broader engagement with the company and ultimately its sale successfully to a buyer that everybody would know. And in a rather public and smooth transaction.

Steve: Alan, a follow up question that I have is when that phone call comes in, and I ask because I've, in a handful of instances made those panicked phone calls to counsel, when that phone call comes in and you've got a two-hour window, how much confidence do you have in your answer? Because again, having received the response from that, sometimes I have a lot of confidence in what my attorneys would tell me, and other times I scratch my head and think I'm not totally sure they really understand the issue here. I'm just wondering because I know you are first class and your firm obviously is first class, is there a lot of confidence going into that kind of a situation?

Alan: Yeah, I mean, I would say, obviously, there's always the natural caveat, within two hours, you're not necessarily going to be able to boil the ocean for answers. But one of the benefits of practicing at this level and at this firm is that I typically have access to resources and folks who have dealt with these issues before. And so in many instances, there's an existing playbook or a resource available. So while the answer still may be subject to caveat and further review and diligence as would be appropriate, given the unnecessarily short timeframe in a lot of these cases, there is generally speaking, a high degree of confidence of the advice we're giving in any of those instances because of the fact that we have experience in these areas, and we know the way in which the rules play out. So a lot of it, of course, is basic principle stuff that we're well familiar with and that we can give as a basic starting point. And our answers are usually drafted and presented in such a manner like, here's how our initial reaction is. We understand more work will probably be required. We'll work on that with you. But here's where you need to know as an initial starting point with what we have, we're very confident in the advice that we're giving.

Steve: Alan, when I was in SEC reporting, I often had terrific outside securities counsel. In fact, some of them I'm still friends with today, having been out of practice for quite a while, but almost universally, none of them had the accounting experience that you have. So when it came to complex accounting disclosure matters, we were generally working much closer with our outside auditors, as you would expect. But you do understand that. You do have that accounting background. I'm wondering, does that give you and your clients a decisive advantage on maybe a dicey accounting disclosure issue where it's not just the company kind of battling it out with their auditors, where you can kind of step in and have an active influence on those discussions?

Alan: Absolutely. And that's probably a sizable portion of my practice, in fact, answering those questions. Ultimately, a lot of times the auditors are the final arbiters in these things, given that they're the ones that control the release of the audit opinion as we think about it practically. But whenever you're working through the more complex issues, oftentimes the way that the clients will approach it is I'll go through an analysis with them, think about the issues, point out the areas where I think there's some flexibility, and then typically joining the calls with the auditors. Not necessarily in an adversarial way, of course, but in a facilitated discussion, having had the informed views and perspectives and the experience that I have to bear, which I think allows them to think about issues from different angles as opposed to the sometimes canned answer that you get, which is, this is how we think we have to do it. We don't see other views. We're not open to that. And whenever you get on a call with somebody that actually knows what they're talking about, you can engage in that deeper-level discussion. And a lot of the times the clients will be there already, but I often will act as that extra voice that raises the quote dumb questions, right? To make sure that everybody's thinking about the issue. And many times, it leads to a reassessment of the outcome where the audit firm actually comes around and says, you know, I think you're actually right. You know, we have been thinking about it wrong. We weren't aware of all the details of the facts, and it's my ability to communicate accounting and law interchangeably that really adds the value because I can communicate with the accountants on the accounting level, but then speak with some of the legal folks that are dealing with the legal disclosures and translate back and forth and ultimately get to the right outcome.

Steve: There's a lot of value in dumb questions, that's for sure.

Alan: Absolutely. I will say one of the things I wouldn't have thought about coming out of law school, but it's just having the courage to ask the questions and present them and frame them in a new way that gets people thinking and is really an undervalued skill I think in the current environment.

Steve: Well, along the lines of having the courage to ask the question, Catherine, do you have the courage to ask our closing question of the day?

Catherine: I suppose so. I'm an expert in asking dumb questions. So, Alan, I know you're well into a career at this point, but if you could choose a different career or maybe if you want to switch careers after this and money were not an object, what would it be?

Alan: This is a fabulous question. It would not be terribly different, but I would probably be a real estate developer, which of course, leverages the background in accounting and law but would be a different avenue to express those types of talents and blend the two functions.

Steve: I like that. I like that a lot.

Catherine: Also lucrative.

Steve: Yes. Yes. Very.

Alan: Maybe a side hustle. In my copious amounts of spare time

Steve: Between that and Dogecoin. No, I'm just kidding. I meant that as a joke. Catherine, how about you?

Catherine: Oh, well, we've talked about this. How as a kid, I wanted to be a zookeeper.

Steve: That's right. We have. We actually had a career podcast episode recently, Alan, where we asked the same question, but it just seemed so fitting to ask you the same thing. I do remember the zookeeper. And since I know, Catherine, you're going to ask me. I don't actually remember what I said last time, but in this moment, I'm back to a part-time accounting teacher at a high school, or maybe adjunct faculty at a community college talking about accounting. I think that's where my mind is at today.

Catherine: You went with altruistic. I thought you were going to say Diet Coke factory worker or taste tester.

Steve: No, because when I studied accounting, that was very formative to me. Actually, my eyes were opened, and I knew that's what I wanted to pursue. Not too different, Alan, I think actually from your experience as well. Clearly, you took maybe the higher road than I did and maybe had a little more effort.

Alan: No, no. I mean, but I will say that's the theme, right, is that I never really left accounting. I practice it in a different way, but that's always been the focus is to have that involved as part of the professional career that I have and making sure that it is involved because I think it was an incredibly special experience for me to really understand. And it just makes so much sense to me. I realize it's a challenging topic, but intuitively, the accounting profession really makes a ton of sense the way that you think about audits and accounting disclosure, it all really ties out. And I really like that, and I'm certainly attracted to the type of profession.

Steve: Well, if you can practice accounting without having to book journal entries or be buried in spreadsheets, you're doing something right. So kudos to you.

Alan: I wish I had more spreadsheets.

Steve: Said no one ever.

Catherine: That was a good one. After talking with Alan, do you still regret not taking your dad's advice and going to law school, Steve?

Steve: Honestly, no. I have no regrets about my career. It has been wonderful, and the cherry on top is that I never have to put in a catheter.

Catherine: Stop talking about catheters, please.

Steve: I'm sorry, I will stop with the catheters, and unfortunately we will stop with this episode. Very big thanks to Alan Wilson of WilmerHale for joining us today, and big thanks to you, dear listener, for surfing along with us. I'm Steve Soter. That was Catherine Tsai, and this has been Off the Books, presented by Workiva. Please subscribe. Leave a podcast review. Tell your buddies if you like the show, and feel free to drop us a line at Surf's up, and we'll see you on the next wave!

Off the Books season 3


24 minutes


Steve Soter, Catherine Tsai, Alan Wilson

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