I know firsthand how busy life can get with family, work, and volunteer commitments, and how easy it can be to postpone certain to-dos you’ve been meaning to cross off the list for weeks, months, or even years. For many, one of those to-dos is to make a Will and Powers of Attorney or to update existing ones. As a lawyer who practices in the areas of estate planning, estate administration, and charity law, I also know firsthand how important these documents are and how difficult it can be for your loved ones should you become incapacitated or pass away without them.

In my experience, estate planning is an opportunity to consider and document your intentions relating to your assets, your family, and your care, in the event of your incapacity and death, and typically involves making or updating a Will (or more than one Will, if you are a business owner), a Power of Attorney for Property, and a Power of Attorney for Personal Care.

In Ontario, if you die without a Will (intestate), your estate is administered under the province’s intestacy laws rather than in accordance with your wishes. Not only can dying intestate result in very unintended and costly consequences, such as your common law spouse being excluded as a beneficiary (as common law spouses do not have the same rights as married spouses under these laws) or a loved one having to apply to the court to be appointed your executor/estate trustee, but also missed opportunities for trust planning, tax planning, insurance planning, succession planning, and legacy giving.

As May is Leave a Legacy Month, let’s focus on the last one: legacy giving.

Regardless of a client’s age, when discussing their estate planning objectives and helping them to make their Will(s), an important question I ask is whether they would like to include a charitable gift or gifts, and if so, what charity(ies) and causes they wish to support. Some of my clients have already thought about this carefully, have had discussions with their charity(ies) of choice, and/or have set up their own family fund or foundation to steward their donations. Conversely, for some of my clients, this is the first time they have ever considered or seriously considered leaving a legacy gift in their Will; not because they are not charitable, but because they have never been asked, have felt confused about how or when to incorporate charitable donations into their estate plan, and/or have falsely assumed their estate will be “too small” to leave an impactful gift.

These conversations are always meaningful and open the door for my clients to further consider legacy giving and to discuss their intentions and the benefits of same with me and their other trusted advisors, including their accountants, investment advisors, and financial planners.
I would encourage you to discuss estate planning and legacy giving with your trusted advisors as well – we are here to help.

Jessica Williams
Associate – Wills/Estates
HARRISON PENSA LLP

Briefly describe your work journey that led to where you are today?

Banking is my second career – I used to be a professional horse back rider and coach!

In equestrian sport, I loved helping people grow in the sport and achieve goals whether it be by training, or at times, navigating the sale/purchase of horse.  After a time, I realized I needed a job where a “bad day at the office” didn’t involve a concussion.

So after some great conversations with my clients, I saw a path forward and went back to school for an MBA in finance.  At the bank I learned that those things that I loved in sport were the same things I loved in financial services: helping people grow and achieve goals, whether that be for a business owner or an individual. Plus I get to help my own team grow in their capabilities and career goals while helping others, so it’s been super fulfilling.

Knowing JA’s three pillars of financial health, work readiness, and entrepreneurship, how do you think being involved in JA learning experiences in your own schooling would have made a difference in your career?

Absolutely! Had I understood more about personal finances from a younger age, it would have been much, much, MUCH easier setting up my own business in my 20’s.  It’s nicer to learn in school than from the school of hard knocks!

What do you think has been the key to your success?

I try to lean into curiosity.  How can we help this business?  What’s really important to this team member?  How can we do better?

If you could do one thing differently in your career, what would it have been and why?

I would have been kinder to myself.  Perfectionism is not a sustainable path, and offering yourself some of the same grace that you offer others around you is an important type of self-care.

What advice would you give young people starting out in business (your industry or any other)?

Remember that soft skills are just as important as hard skills; doing a good job is important, but doing that while making others around you feel good is even better!  And early in your career, particularly in banking, is the best time to explore lateral paths; not every step needs to be a promotion.  Lean into curiosity to build a broad experiential base so as to identify exactly what gives you joy in the workplace, and then you can pursue it at a higher level in time.

What do you think a young person’s biggest opportunity is at this time?

The world’s your oyster!  AI has the potential to bring about huge changes in the economy in a short time, so why not explore how that changes opportunities in any field that you love?  Regardless of computer changes, people will still need places to live, electricity and water, so the trades represent a pretty neat path to entrepreneurship too.

What do you think the biggest obstacle is for a young person today? How could they overcome this?

I think it’s challenging for a young person to decide what they would like to pursue, regardless of era.  To help, think about what you like to do for fun, and how it might translate into responsibilities or work-patterns in a career.  Do you like to work solo, or in a team? Do you like to work on processes or relationships?  It’s hard to listen to your inner voice at times, so ask it some great questions to help find your path forward. 

What is one goal you have set for yourself that you have not yet achieved? What has prevented you from achieving it?

When I was younger, I wanted to go to the Olympics.  And while I have closed that window as an athlete, maybe I could explore it as a judge in the sport.  I’ve not pursued a higher judging designation because I’m having too much fun doing other things at the moment.

What is your biggest passion in life, outside of work?

I love classical music, the opera, and going to the Stratford Festival.  And I spend a great deal of time with family, friends, gardening, golfing, and judging horse shows.  

What three words would your family use to describe you? Are those three words the same or different that your employees would use? If different, what would your employees say?

My family would say I’m cheeky, ambitious, and clever… but not always in a good way 😉

I think my employees would say I’m energetic, competitive, and I hope, kind.   

If a young person reads this interview, what do you want them to take away from it?

Go for it!  When you don’t know exactly which direction to go, choose any direction and you’ll be right.  And if down that path it doesn’t feel good, then you can choose another.

Who has been your greatest inspiration/role model/mentor? Why? What did they teach you?

I’ve had so many mentors and role models in my life – I think of it like a board of directors!  From my parents I learned how important entrepreneurial drive is in business, but also how important it is to help your neighbours and community.

What is your earliest memory of philanthropy? Why do you believe being philanthropic is important personally and/or in your business?

As a child I remember volunteering in a soup kitchen with members of our church.  It was a vivid lesson as it was the first time I saw a different world from my own, how other lives were shaped, and to see that we have a duty to share with each other.

What is it about JA’s mission that makes you choose to support its efforts?

I’m drawn to JA’s support and encouragement of the next generation of entrepreneurs and business leaders.  It’s an inspiration to see firsthand the energy and creativity that they’re bringing to bear to make Canada and the world a better place.

Knowing JA’s three pillars of financial health, work readiness, and entrepreneurship, how do you think being involved in JA learning experiences in your own schooling would have made a difference in your career?

Having early exposure to financial literacy and entrepreneurship would have given us a head start on understanding money management and risk-taking. JA’s work readiness programs would have helped us build confidence in practical skills like interviewing, teamwork, and problem-solving much earlier on.

What do you think has been the key to your success?

The key to our success has been a willingness to keep learning. We believe in always being curious, staying adaptable, and learning from others. Mistakes are part of the process, and viewing them as opportunities to grow has made all the difference.

If you could do one thing differently in your career, what would it have been and why?

If we could change one thing, we would have sought out mentors earlier in our career. Learning directly from someone with experience can accelerate your growth and help you avoid common pitfalls. We learned this later on, and it’s been invaluable ever since.

What advice would you give young people starting out in business (your industry or any other)?

Be curious and proactive. Don’t be afraid to ask questions or explore new opportunities, even if they scare you. The more you learn and grow, the better prepared you’ll be for whatever comes your way. And always build strong relationships—people are the key to success in any industry.

What do you think a young person’s biggest opportunity is at this time?

Technology. Young people today have access to information and tools that previous generations couldn’t imagine. Whether you’re starting a business, learning a skill, or connecting with others globally, technology gives you the power to make things happen.

What do you think the biggest obstacle is for a young person today? How could they overcome this?

The biggest obstacle is information overload. With so much information available, it can be hard to know what to focus on. Our advice is to find a mentor, set clear goals, and prioritize what really matters—one step at a time.

What is your biggest passion in life, outside of work?

Our biggest passion outside of work is traveling. We love experiencing new cultures, meeting new people, and seeing how others live. It keeps us open-minded and constantly learning.

If a young person reads this interview, what do you want them to take away from it?

We want young people to realize that there is no single path to success—it’s about staying curious, being adaptable, and finding joy in learning. Take risks, don’t fear failure, and build strong relationships.

What is your earliest memory of philanthropy? Why do you believe being philanthropic is important personally and/or in your business?

Our earliest memory of philanthropy was participating in fund raising activities at school. We would carry small coin boxes to collect money for Unicef traveling door to door at Halloween. It was a simple initiative, but it made a lasting impression on us about the power of community action. We learned that even small contributions could collectively make a big difference. Being philanthropic is important because it creates a positive impact in society, fosters a sense of responsibility, and helps bridge gaps in our communities. It’s a value that we’ve carried into our business practices by creating the Blue Door Initiative that supports local nonprofit organizations in our community. We’ve supported everything from animal rescue shelters to local theatre groups to up-and-coming musical talents.

What is it about JA’s mission that makes you choose to support its efforts?

We support JA’s mission because we believe in empowering young people to take control of their futures. Financial literacy, work readiness, and entrepreneurship are skills that can open doors and change lives, and JA is giving young people the tools they need to succeed.

Briefly describe your work journey that led to where you are today?

My professional journey began with 18 months in farm sales, where I gained valuable experience selling grain, fertilizer, and seed. This initial role allowed me to develop a strong understanding of agricultural commodities and their market dynamics. However, I eventually decided to pursue other interests that would lead me to greater challenges.

I then became the youngest commodity broker in North America, dedicating the next 8 to 10 years trading commodities primarily with hedging client’s financial risks. I managed several portfolios, thriving in the fast-paced and high-pressure environment that the commodities market demands. My career started at Merrill Lynch, where I honed my trading skills and learned the intricacies of the financial markets.

Recognizing the need for a shift, I transitioned to a retail-focused role, as I realized the life expectancy of business relationships in the commodities sector is often short-lived and leads to a lack of fulfillment. Seeking a better work-life balance, I moved into the parent company part of sales and focused on building a retail business. By 1996, I had fully transitioned away from commodities, concentrating on expanding my client base and establishing long-term business relationships with individual investors.

Throughout my career, I have remained passionate about the markets and genuinely enjoy working with people to help them achieve their financial goals.  I believe in simplifying the investment process and creating tailored strategies that align with my clients’ objectives . This approach has allowed me to build a successful retail business while fostering meaningful client connections.

Knowing JA’s three pillars of financial health, work readiness, and entrepreneurship, how do you think being involved in JA learning experiences in your own schooling would have made a difference in your career?

If I’d had been involved with JA in high school it would have exposed me to areas of business that I had no experience with at that age.  Coming from a family tobacco farm it was the path I assumed I would continue. However, after taking specific business classes (financial statements, marketing etc.) and taking a trip to the Toronto Stock Exchange, I was inspired to start in the financial industry. Exposure = education.

What do you think has been the key to your success?

What my father taught me!  Set a target – work hard.

One of the most important lessons my father taught me is the value of hard work. He always emphasized that nothing worthwhile comes easy, and the key to achieving a goal is to dedicate yourself fully to the task at hand. My father instilled in me the importance of setting clear targets and working diligently toward them.  Whenever I face challenges, I remind myself to focus on my goals and make the necessary effort to reach them. This mindset has been instrumental in my journey, shaping my approach in both my professional and personal life. By working hard and staying committed to my targets, I have learned that perseverance and determination can lead to success in whatever I choose to pursue.

If you could do one thing differently in your career, what would it have been and why?

I would not change anything in my career as all the ebbs and flows in this industry have brought me to where I am today.

What advice would you give young people starting out in business?

Pressure is a privilege!  Starting off in any career will not be a 9 to 5 position should you want to excel and succeed. Roll up your sleeves and jump in. Having and keeping connected to multiple mentors is a necessity. Realize that stress is a part of life.

What do you think a young person’s biggest opportunity is at this time? 

You can always work harder than your competition.

What do you think the biggest obstacle is for a young person today? How could they overcome this?

I was born with an extremely busy brain so I had professionals and consultants help me learn that it was a gift, not a curse.  They all played a critical part in helping me overcome and learn to focus, hence being more efficient with my time and organizational skills.  Having a great assistant and staff that have been loyal and part of the team for over 30 years were key factors in my success.

Having clear cut vision and written goals (1 yr, 5 yr and 15 yr plans).  Learning work ethic and going above and beyond. Being patient with the process and learning as much as they can from everyone. Remember: Integrity follows you for life.

What is one goal you have set for yourself that you have not yet achieved? What has prevented you from achieving it?

So many great community leaders have been nominated to the Business Hall of Fame.  It would be an honor to be named to the Business Hall of Fame but because I am not technically an independent business person, I don’t qualify.

What is your biggest passion in life, outside of work?

Work to live, not live to work!  Spending time with family and friends. Sports (skiing, hockey, golf, fishing, motorcycle, boating, woodworking and adventure/extreme travel)

What three words would your family use to describe you? Are those three words the same or different that your employees would use? If different, what would your employees say?

Driven, compassionately committed and boundless energy.

If a young person reads this interview, what do you want them to take away from it?

Success is achieved by those who go get it. Be focused, driven, and not afraid to stand out from your peers. Be open to volunteering and helping in the community and those around you.  Do not fear failure as failure is a part of success.

Who has been your greatest inspiration/role model/mentor? Why? What did they teach you?

My father and mother played a vital part in my success, passing on their work ethic, values and reiterating that challenges are what make you grow.  Another couple, who I admire and have inspired me through their philanthropy, are people with great integrity and incredible values. I believe having people like this in my life reinforces my own values.

I have clients who are professional athletes and have always been in awe of their dedication to their goals. It takes grit, perseverance and mental stamina to succeed as a professional athlete.

What is your earliest memory of philanthropy? Why do you believe being philanthropic is important personally and/or in your business?

A six-year-old boy who did not have a father present in his life was a child that I took under my wing and in a sense, adopted. To this day I am like a father to him and a grandfather to his children. This young boy ended up getting a Master’s in Education, is a great son, father and husband. He is family and I consider him my son.

I have always chosen specific organizations to support with my time and money. It started with the United Way where I spent 22 years on fundraising campaigns and helped raise a significant amount of money.  I have been on numerous Boards and volunteered with many worthwhile causes, over the years.  I’ve watched closely and learned from the philanthropic efforts of past and present community leaders such as those who have been honoured in the Business Hall of Fame .  All have the same mindset; it is each of our responsibilities to give back.  Giving back is high on my priority list and part of my Christian beliefs.

What is it about JA’s mission that makes you choose to support its efforts?

I have supported JA for over 30 years and fully support the JA mission. JA offers students hands-on learning, teaching economics, networking, the importance of community involvement and so much more. Students flourish when they are involved with JA. They are exposed to great mentors and people they can aspire to be.  These students are our future leaders.

Briefly describe your work journey that led to where you are today?

I founded Next Dimension 27 years ago with two business partners, starting out in a customer’s warehouse on Hawthorne Blvd. Back then, we had just one client, our personal PCs, and a mission to deliver outstanding IT support to businesses in the city. We didn’t have all the answers at the time, but we knew that if we provided exceptional service and built strong relationships, our business would grow. Those early years meant 80-hour work weeks and sacrificing time with family and friends to establish a customer base large enough to expand our team. While the range of services we offer has evolved over the years, our commitment to building lasting client relationships has remained unchanged.

Knowing JA’s three pillars of financial health, work readiness, and entrepreneurship, how do you think being involved in JA learning experiences in your own schooling would have made a difference in your career?

I strongly believe in teaching financial health to young people. Like many young Canadians, I didn’t fully grasp the importance of saving or how to make my money work for me. I used to think that if I could afford the payments, it was okay to make the purchase. If I had understood the benefits of saving and investing earlier, I would have saved more and taken advantage of compound interest, achieving financial freedom much sooner

What do you think has been the key to your success?

Having a plan and never giving up is key. It’s about deciding what you want, figuring out how to achieve it, and then putting in the blood, sweat, tears, and most importantly time to make it a reality.

If you could do one thing differently in your career, what would it have been and why?

I would have sought out a mentor in a similar business to gain guidance, rather than constantly learning things the hard way. While making mistakes and experiencing failure can be valuable, it’s often better to learn from someone else’s missteps and have a sounding board to talk through challenges.

What advice would you give young people starting out in business (your industry or any other)?

When starting out in business, my biggest piece of advice is to never give up. The journey will be filled with obstacles, setbacks, and moments of doubt. It’s easy to get discouraged, especially when things don’t go as planned. However, success in any industry requires perseverance and resilience.

Challenges and failures are part of the process, and each setback is an opportunity to learn and grow. Keep your vision in mind and push through those tough times. Remember, every successful businessperson has faced failure at some point. What sets them apart is their unwavering determination to keep moving forward, learn from their experiences, and adapt.

So, stay persistent, keep refining your skills, and don’t let temporary failures define your path. The most rewarding achievements come from pushing through the hardest moments.

What do you think a young person’s biggest opportunity is at this time?

A young person’s biggest opportunity right now is time. They have the luxury of time to explore, experiment, and figure out what truly excites them. With fewer obligations and more flexibility, they can afford to take risks, make mistakes, and learn from them without the pressure that often comes later in life.

This period is a chance to try different paths, build skills, and make adjustments as needed. It’s about investing time in understanding their passions, honing their craft, and developing a strong foundation for future success. The ability to spend this time learning, growing, and iterating is invaluable. By using this time wisely, young people can set themselves up for long-term success in whatever path they choose.

What do you think the biggest obstacle is for a young person today? How could they overcome this?

The biggest obstacle for a young person today is often raising the necessary capital and finding talented individuals who share their vision. Access to funding can be a major hurdle, as many young entrepreneurs may lack the track record or connections that attract investors. Additionally, building a team of talented individuals who are equally passionate about the vision can be challenging, especially when resources are limited.

To overcome these obstacles, young entrepreneurs need to start by building a strong network. Attend industry events, join entrepreneurial communities, and leverage social media to connect with potential investors, mentors, and collaborators. A well-crafted, compelling story behind their vision can also go a long way in attracting both investors and team members who believe in the mission.

What is one goal you have set for yourself that you have not yet achieved? What has prevented you from achieving it?

One goal I have set for myself that I have not yet achieved is continuing to grow the business by building and mentoring a strong team to help drive that growth. While I’ve made progress, I haven’t yet fully established a team that can independently take on key roles and responsibilities.

The main challenge has been finding the right talent—individuals who not only have the necessary skills but also share the vision and values of the business. Additionally, balancing the time between daily operations and dedicating enough time to mentor and develop the team has been difficult.

To overcome this, I am working on refining my hiring process to better identify candidates who align with the company’s mission and investing more time in training and mentorship. I believe that building this team is crucial to scaling the business and achieving long-term success.

What is your biggest passion in life, outside of work?

My biggest passion in life outside of work is spending quality time with my wife and family. We love to explore new places together, whether it’s traveling to exciting destinations or enjoying our favorite pastimes. Motorcycle riding in the mountains of Tennessee offers an exhilarating escape, while power boating on the Great Lakes and the North Channel provides a serene yet adventurous experience. Long drives on hot summer days in our convertible are also a cherished way for us to relax and enjoy each other’s company.

What three words would your family use to describe you? Are those three words the same or different that your employees would use? If different, what would your employees say?

Dedicated, Hardworking, Focused

If a young person reads this interview, what do you want them to take away from it?

If a young person reads this interview, I want them to take away the importance of hard work and perseverance. Success doesn’t come easily; it requires dedication, resilience, and a willingness to overcome challenges. By staying committed to their goals, putting in the effort, and never giving up, they can achieve anything they set their minds to. Remember, every obstacle is an opportunity to learn and grow, and with determination and persistence, the possibilities are endless.

Who has been your greatest inspiration/role model/mentor? Why? What did they teach you?

My greatest inspiration has been Bill Gates. His work with Microsoft, particularly the development of Windows, fundamentally transformed how the world works and interacts with technology. What impresses me most is how he didn’t just stop at creating groundbreaking products but also shifted his focus to philanthropy through the Bill & Melinda Gates Foundation.

Gates has taught me the importance of using one’s success and resources to make a positive impact on the world. His transition from technology to global health and education initiatives demonstrates that success can be leveraged for greater good, and it encourages me to think beyond personal achievements and consider how I can contribute to broader societal progress. His journey underscores the value of innovation, commitment to excellence, and the power of giving back.

What is your earliest memory of philanthropy? Why do you believe being philanthropic is important personally and/or in your business?

I’ve always felt that giving back is both the right thing to do and deeply rewarding. Over the years, I’ve made it a priority to support events, programs, and charities that benefit the youth in our community. Early on, shortly after starting our business 27 years ago, our initial sponsorships were directed towards the Teen Health Center in downtown Windsor.

What is it about JA’s mission that makes you choose to support its efforts?

What draws me to support Junior Achievement of Southwestern Ontario’s mission is their commitment to empowering our youth. I firmly believe that the young people of today are the leaders of tomorrow, and investing in their education and development is crucial for shaping a brighter future. Junior Achievement’s programs equip students with essential skills, knowledge, and confidence, preparing them to succeed in both their personal and professional lives. Supporting their efforts aligns with my belief that nurturing and guiding the next generation is one of the most impactful ways we can contribute to the future of our community and beyond.