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Get to Know Your Exec: Mark Simon

June 11, 2026 | Tomiwa Ogundipe

  1. When did you first get involved with the OBA?

I engaged a bit with the OBA while I was in law school, but I only recently returned as a member of the OBA last year.

  1. What is your role on the OBA Business Law Section?

I am a Regional Representative. I assist the section executives by giving my perspective as a lawyer outside of the GTA. I specifically run my practice in a rural area and try to include some of the issues common to lawyers in rural settings when participating with the executives.

  1. What is/are your specific area(s) of practice?

I practice in a more generalized solicitor-type role common to regional lawyers. My practice specifically focuses on real estate; wills, estates and trusts; and business law. I take a somewhat holistic approach to providing services to my clients.

  1. What is the most challenging aspect of your job?

I would have to say the most challenging aspect of my job is keeping current on multiple areas of law. I want to provide high quality services to my clients, but the nature of the region that I practice in doesn’t permit me to specialize further, so there is a lot of time spent keeping up with all areas.

  1. What is the most interesting or fulfilling aspect of your job?

The most interesting or fulfilling aspect of my job is working on a multi-faceted plan for my clients. For example, I appreciate having the opportunity to develop a succession plan for a client’s business that incorporates each of the areas that I practice in.

  1. If you were not practicing in your current area of law, what other area(s) of law could you see yourself in and why?

I could see myself as having specialized in tax law, since I have an MBA with an accounting specialization; however, my career would have had to have gone a bit differently if that was the case. I also really enjoy constitutional law, so if a career focused on that or administrative law was an obvious option, I may have taken that route.

  1. What are you excited for as an executive member of the OBA Business Law Section?

I am particularly excited for an upcoming CPD that I am co-chairing. We have created it in tandem with the Trusts and Estates Law section and I think it reflects a situation that is common to regional solicitor practice lawyers. The title is Corporate Reorganizations in Estate Planning: A Practical Guide.

  1. What is the one thing you’d like to see the OBA Business Law Section do this year?

I would like to see the OBA Business Law Section do what it can to lay some groundwork for further lawyer community building. As I’ve heard many of my colleagues bemoan, there isn’t a lot of interaction between lawyers that goes on these days, especially outside of files. It would be nice to have more of a community to be a part of.

  1. Can you mention one exciting thing you have worked on recently?

The more exciting files I tend to work on are the purchase or sale of businesses. Assisting an entrepreneur navigate the process from business owner to retirement can lead to a lot of areas to discuss, particularly if they’ve built the business themselves. It can be both difficult and exciting for them. Similarly, buying a business for someone looking to be their own boss can be both a nerve-wracking and exciting prospect.

  1. Where did you go to law school?

The University of Windsor.

  1. What was the most helpful thing you learned in law school?

How to manage being competitive with my grades while developing friendships with the other students. Mostly learning that grades will only take you so far and relationships end up being much more important in the long run.

  1. What is the one piece of advice you wish someone had given you when you were still a student?

Aggressively seek out a good mentor. Unfortunately, good opportunities to be a mentee are few and far between, and I had to learn most of the practice with little to no real guidance. I think I would have saved myself a lot of difficulty if I had been able to find someone keen on teaching a young lawyer about the practice.

  1. What is your go-to mental health wellness activity?

Going to the gym. It sounds like just more effort expended, but if I put myself through a difficult workout, I need to focus on moving the weight and it forces me to be present; instead of continuing to think about work.

  1. What is your go-to coffee order?

Black. Good coffee will speak for itself.

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