Skip to content
Join our Newsletter

Ask Ellie: Find new purpose in philanthropy after lottery win

You have the financial means to do some wonderful life-altering things for people in need

Dear Lisi: My wife won the lottery, enough for us both to retire and then some. We didn’t tell anyone. When the timing seemed inconspicuous, she retired. No one really asked any questions.

I chose to continue to work because I owned my own business and put a lot of energy and love into it. Now I’ve sold it and made an absolute fortune. It’s public knowledge, so now we know people think we’re affluent due to the sale. We never wanted anyone to know about the lottery.

We feel very fortunate and don’t take it for granted. My wife has lots of fun ideas, including lots of travel. I love to travel, but I’m not ready to retire and do nothing.

I don’t want to stop working. We’re only in our late 40s, and I’m afraid I’ll be bored silly. I have years and years ahead of me to sleep in, read, lie on the beach and waste away the days. But right now, I have too many ideas in my head, things I want to do, etc.

But I also don’t want to stop my wife from living her best life. I want her to have the freedom to do whatever she wants to do without any restrictions.

What do I do?

Bulging Bank Account

Though you’ve tried to be low-key about your stress-free financial situation, your sign-off taints your humility. So many people live under the poverty line, homeless, with no idea where their next meal will come from.

I appreciate that part of your financial gain was solely based on luck. And you should be very proud that you created a business that was so successful it also turned quite lucrative.

Perhaps you and your wife could find something philanthropic that interests you both; perhaps you could find some charitable work that gives you both a sense of purpose. I recognize that you want her to live her best life, but isn’t it selfish to not want to help others live theirs?

I’m not suggesting you walk around handing out $100 dollar bills, but you have the financial means to do some wonderful life-altering things for people in need.

Enjoy your hard-earned windfall — you deserve it. But think about helping others with what fell into your lap. You don’t seem to need it. And a little can make a huge difference to someone in need.

Reader’s Commentary regarding the mom worried for her child who keeps switching schools (Sept. 14):

“In the letter, it does not specify the reason for changing.

Without more information, it’s hard to know what happened. However, it seems to me that there is an issue that is not being addressed.

“How many more schools do they need to ‘try out?’ Is the issue with the child, bullying, or the curriculum? If it’s bullying, how can the child learn to handle it? Why is he being picked on (in three schools)?

“In any case, I think the issue will keep happening until it’s resolved. Deal with the issue.”

Lisi – As I mentioned in my original answer, I edited out a lot of specifics from the original question to protect the anonymity of the letter writer and her child. Her reasons for leaving all three schools sounded completely legitimate to me. As she said, none was for a social reason. She never mentioned bullying.

Sometimes, things just don’t “fit” the way you’d like them to for various reasons. I believe the mom is dealing with each issue that arose appropriately. I wish her the best of luck in finding the right fit for her child.

FEEDBACK regarding the dad who didn’t want to buy his still-growing son expensive shoes (Sept. 20):

“I just wanted to comment on your advice given to the ‘cool dad’ who was being pressured by his son to buy him an expensive pair of sneakers. I had the same situation years ago when our daughter also wanted an expensive pair of sneakers in Grade Eight. I solved this problem by saying I will give her the cost of a pair that I would usually by, but she needed to come up with the difference. Not only did she save all the money she needed, but she took excellent care of her sneakers once she finally bought them!

“A very important lifelong lesson was learned that day!”

Lisi – Brilliant idea! You definitely taught her life lessons about value, cost, want vs. need and financial literacy. She’s lucky to have such a smart mom.

Ellie Tesher and Lisi Tesher are advice columnists for the Star and based in Toronto. Send your relationship questions via email: