Would you Rather Write a Big Cheque to your Favourite Charity or the Government?

would you rather

I remember reading my kids the book “Would You Rather” when they were young. The book’s premise is that if given a choice, which would you choose. It would have two fantastical scenarios, and you had to select your preference. An example might be, “Would you rather be able to slide down rainbows or jump on clouds?” As business owners, we are faced with our real-life version of “Would You Rather” when selling our business. If we are successful at selling our business or investment property, we are faced with a choice, write a cheque to a charity or write a cheque to the government. As my kids would’ve said, “Duh!”. It is a bit of a no-brainer, yet many business owners continue to write big cheques to the government, even though things could be a complete wash between the two choices if they’re getting the proper guidance.

Is Legacy Important to You?

When you think about your legacy, what comes to mind? For some people, leaving a legacy is about leaving behind a tangible item, such as a piece of art or a family heirloom. But for others, it’s about leaving behind something more intangible, like a positive impact on the world. Regardless of how you define it, your legacy is important to who you are and how you’ll be remembered.

Why Should you Care About Your Legacy? 

 First and foremost, it’s a reflection of your values. What you leave behind will directly reflect what you care about in life. If you want to be remembered as someone who made a difference, for example, then leaving behind a legacy of kindness and compassion is essential. Secondly, your legacy is something that will live on long after you’re gone. It’s a way of leaving your mark on the world and ensuring that your memory lives.

Leaving a Legacy to a Charity

There are many reasons why you might choose to leave your legacy with a charity rather than the government. For one thing, charity organizations are often better equipped to put your money to good use. They typically have lower overhead costs and more efficient donation-distribution processes, meaning that more of your money will go directly to those who need it. In addition, charity organizations often better understand the issues they are trying to address and can better target their assistance accordingly. Finally, by supporting a charity, you can help to build a stronger community and create a lasting change. Your legacy will live on in the lives of those who benefit from the charity’s work.  

Additionally, you can leave an ongoing contribution in the form of an annuity to a charity which will help to ensure the long-term viability of the organization you are supporting. You may be honoured by a plaque or the naming of a building or park, so your legacy will continue. This may or may not be something important to you. One thing I can assure you of, regardless of how big a cheque you write to the government, you will not be granted a plaque, statue or namesake of a building.

Making the Most Impact on your Charity

There are a few things to consider if you want to ensure that your donation will have the most significant charitable impact:

  1. Research the organization and ensure their work aligns with your charitable goals.
  2. Consider the size of your donation. A large donation to a small organization can have a much more significant impact than a small donation to a large one.
  3. Think about how you want your donation to be used.

You may want to earmark it for a specific program or project, or you may want to give the organization flexibility to use it where it is needed most. By taking the time to consider these factors, you can be confident that your donation will have the greatest charitable impact.

Understanding the Efficiency of How You Donate

Sometimes how you give is more important than how much you give. For example, providing cash, debit and credit card is the least efficient way to contribute to a charity. You can donate marketable securities or a life insurance policy to help you donate a considerable amount more at a fraction of the cost. Donating corporately versus personally can yield a much greater tax credit. Not only is it better for the donor but also for the benefitting charity. Sometimes as much as twenty times the benefit of donating cash. So, when some claim they can’t make a meaningful difference to a charity, they are probably donating in the wrong manner.


Capital gains taxes are only going in one direction. Over the last couple of years, there have been rumblings of bumping the capital gain levels from 50% to 75%. This bump would translate into a 50% capital gain tax increase (for those who can’t do the math). If you’re looking to sell your business, investment properties, cottage or unregistered securities in the following years, you may want to investigate the various ways of contributing to charitable organizations. You will immensely benefit philanthropic organizations, build a meaningful legacy and benefit financially. Look at converting capital gains into charitable giving. So, would you rather write a big cheque to your favourite charity or the government?


Chris’ Bio

To say Chris is passionate about youth mental health is an understatement. Ever since he lost his 14-year-old daughter, Maddie, to suicide, he’s been trying to coach parents with similar struggles with their kids. He’s talked to hundreds of parents with struggling kids. In many cases, these parents are barely holding it together too. He knows because he was one of those parents. He is relentless in ensuring another family doesn’t experience the loss his family has endured. 

He is Co-Executive Director of How Are You Feeling, an online, scientifically-based teaching program that makes kids understand their emotions and how to properly deal with them before they become “big feelings.”  

Chris has been an entrepreneur for most of his career. He also runs a financial services company called The Finish Line Group, where he helps support the entrepreneur’s financial, philanthropic, and emotional journey.  

Chris has written extensively about his experiences with his daughter and has been featured in numerous print and online publications and radio and television media. He has been a keynote speaker at several entrepreneurs and mental health conferences.  

His personal “Why Statement” is “To openly communicate the lessons learned from his past so that others will thrive in their lives, minimize their setbacks and leave a positive and lasting legacy.”