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  • Sam MacDougall

From 1L to Articling: Demystifying the Path to a Securities Law Career

Hello! Please introduce yourself.

Hello! My name is Sam MacDougall. I am a current articling student at the Ontario Securities Commission in its Corporate Finance branch. I attended law school at Western University and graduated in 2023. 


At Western, I was a part of the Western Business Law Clinic. I also served as a Managing Editor for the Western Journal of Legal Studies and worked as a research assistant for a professor at the law school in the areas of securities, mergers & acquisitions, and corporate governance. 


I’m most interested in transactional securities/capital markets and corporate governance work. 


After finishing my undergraduate degree and beginning law school, I spent a year working at Citi in its Toronto office, where I was a part of its liquidity management and trade finance team. Interestingly, my work there did not make me as interested in banking/finance/lending law as I thought it would! While still very interesting, I found that I gravitated more towards capital markets work.


Outside of work, one of my biggest interests is music. In 1L, I started a music blog where I began writing and publishing my own reviews of what I deemed to be culturally significant or genre-defining albums. If I had to pick 1 album that everyone had to listen to at some point, it would be Marvin Gaye’s What’s Going On.




What motivated you to pursue a career in law?

Before law school, I obtained an undergraduate business degree from Western. I then took a year off to work. I was always fascinated by the role that lawyers play in the real world and the type of work that they do. I often reflect on what I feel was a highly formative experience from when I was 8 years old at Thanksgiving with my family; I remember my granddad asking my uncle (a labour lawyer) “Can I ask you a legal question?” and I quickly found myself hanging onto every word my uncle was saying. It was fascinating to see years and years of specialized training come out in a clear, easy-to-follow way. 


The law school application process was intimidating. I remember spending an inordinate amount of time writing, tweaking, and editing my personal statement. In hindsight, I think applicants get too caught up in the numbers. Your GPA and LSAT are obviously important, but so are your other, non-quantitative factors. On reflection, I am pleased that I took a lot of time to write a strong personal statement and asked past professors with whom I had positive relationships with for reference letters. 


My personal view is to apply to as many law schools as possible. I believe that you should always try to maximize the opportunities available to you. This requires more work given that each school generally has its own application components, but this extra effort is a small price to pay if it ends up scoring you an extra offer of admission. 


What was your experience like in law school?

My most memorable experience in law school came in my first week, when I volunteered an answer during class and my professor asked me a series of follow-up questions to test me and to see if they could get me to contradict myself. After my response to his final question, he paused and said, “that’s exactly right”. As a very fresh 1L, it did wonders for my confidence and made me much more comfortable speaking during class discussions. 


I only did one “real” moot in law school: the mandatory 1L moot. I also participated in a mock arbitration for a sports law class which was very fun. I tended to stay away from moots because I felt that my strengths lay in a more transactional area of law. I served as Western’s researcher for the 2023 Davies Corporate Securities Moot and really enjoyed my experience. Being involved in a moot as a researcher is a great way to get involved with litigation-type work without having to do the mooting. 


On getting involved in law school, I highly recommend getting involved in an extra-curricular activity that complements your area of interest. Hopefully, at the end of 1L you have a rough idea of what area of law you’re interested in; this way, you can try to get an extra-curricular position in that area. This helps show your interest in that area of law when you’re applying for jobs and also allows you to learn if you really do enjoy that area of law or not. 


My biggest piece of advice for success at law school is to build a strong support network for yourself. This means building friendships with your peers. I had an exceptionally wonderful group of friends during law school that made it all so much easier than it would have otherwise been. My friends and I would always take study breaks to get ice cream, play games, or just fool around. Law school is difficult, long, and isolating; good friends make it much, much easier. 


How did you find your articling position?

I was previously a summer student with the OSC’s Corporate Finance branch and received an articling offer through that position. 


Law school recruiting is notoriously stressful and it can be very demoralizing. The best way to prepare is to cast a wide net and maximize the opportunities available to you. It’s not uncommon for students to not apply to a certain firm/organization because they don’t feel they have the qualifications for it. To that, I would suggest applying anyway; a firm/organization could see something in you that you don’t see in yourself. 


On your first summer job, my best advice is to get the easy stuff right. The lawyers you work with do not expect you to find the perfect argument for them, to draft a document perfectly, or to do perfect research; what they do expect is that you spell things correctly, format properly, ask clarifying questions when you don’t understand something, meet deadlines, and show an interest in the work that you’re doing for them. Remember, when you’re given work, it’s work that the assigning lawyer doesn’t have time to do. You should treat it as your own file/project, and you should treat the assigning lawyer as your own client. You are responsible for your work product. 


If you could give one piece of advice to prospective or current law students to help them succeed, what would it be?

Always do your best, no matter what you’re doing. You never, ever want to be in a position where you look back/reflect on an experience 6 months after the fact and wish that you would’ve worked harder. The “what if” can be very dangerous. You always want to be able to look back on something and be satisfied that you tried your absolute best. 


What are your future career plans going forward, and how can our readers connect with you in the future?

I’m currently focused on building a well-rounded transactional securities law practice. After working in the area for the past few months, I’ve realized how much there is to learn; there is a lifetime of learning to look forward to. One of the most satisfying parts of becoming a lawyer is realizing that you have a special set of skills that other people rely on you to know, understand, and use to guide them toward their goals. 


In the long term, one of my main goals is to find a way to balance my passion for my career with my passion for community involvement. I’ve volunteered at a number of organizations in Toronto and I hope that in 10-15  years I am still able to regularly support those organizations. Being a lawyer is an immense privilege in society and I feel that they have a broader societal obligation to contribute to their communities in both legal and non-legal ways. 


I’m more than happy to connect and speak with prospective students about anything I’ve mentioned here. Please feel free to contact me at sammacdougall97@gmail.com.









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