My Mother the Entrepreneur

My Mother the Entrepreneur

A student once asked me, “What is it that makes you who you are?”
“It must be your mother”, another replied.
I smiled and remembered my mother – the Entrepreneur

My Mother spoke about money like it had a life with a pulse and a heart beat. She had very strong feelings about money and several other things. I thought I’d share a few of the things she was passionate about.

She believed that a woman should always have a career, her own money, her own bank account, keep her father’s name after marriage, wear slacks when travelling and make sure to always cast her vote (since women were beaten by their husbands, fathers, and brothers), not to attend the suffrage movement which gave women the right to vote and that your wallet or purse should always be tidy.

She knew at all times how much money she had and how much she owed. Her money was placed in her wallet with the faces up and if she had a wrinkled bill she would iron it out until it was smooth. She believed that if you took care of money that money would love to be with you, therefore, you would always have money and increase your wealth.
To always be in debt, she believed, was a sign that you are not managing your money properly or that you are living beyond your means.

I grew up listening and observing her. She never ever left her bedroom without being made up and was always ready to face the day. The moment she stepped out, whether it was to her bakery, her grocery store or to communicate with her employees, she was on stage.

She gave her full attention to whatever project she had for the day. She spoke to us often about our behaviour and decorum, instructing us to walk with heads up high, no slouching, looking at people in the eye when speaking with them, that there were no stupid questions and to always remember that if you do not know the answer then you can only learn it by asking the question.

Her Entrepreneurship started after her marriage to our father. She began by making eggnog and topping it with the whites of eggs that had been beaten into a peak and sprinkled with cinnamon. In those days it was okay to consume as many eggs as one wanted and she began selling them every day at the factory owned by our father’s family. Eventually she included cakes made out of coconut and other special baked goods. On Fridays just before the men lined up to be paid, she would be back at the factory to collect her money – a minimum of five shillings just for 5 glasses of eggnog from each of the men and the cakes were extra.

The baking took off and my father built her a tiny oven. This eventually grew to a very large bakery where all of us children had to do our part. Some of us would get up at three am to wake the baker and drive him to the bakery, while others counted or delivered the bread to the shops and customers. From the bakery she opened a grocery store and a bar. Above the store was the dance hall where dances were held every Friday and Saturday nights. The businesses were very successful and she was able to share this experience with the community by employing families in the neighborhood.

My mother always saved 15% of her sales to build and develop her business ventures. Quite early in her career she decided she wanted to purchase land. This was in the late forties when women were still housewives, but not her. She was out there competing and pushing her plans. She spoke often about the time when she attended an event (the only woman, no less) where a parcel of land was being auctioned and she won. She said, “I had my money and I was prepared. I knew who the other bidders would be and they were shocked to see a woman there amongst all the men. I wanted the land more than they did. Then, I found out that I had more money to bid than they had. I came to win and was completely prepared to win that land. No one was going to out bid me.”

My mother continued increasing her net worth throughout her life. What was even more fascinating about her was that she also encouraged others to follow her lead. I often heard her telling the people who were renting homes from her, how they too could own their own home and went so far as to take them to the Credit Union to begin their savings plan.

Many people, when told that my mother was only 5’ 2” tall, were quite surprised. “She seemed so much taller!” they said. She was a formidable woman who always took the time to study her opponents and her plans. When she executed a plan it was well thought out. Her behaviour and attitude made you believe that she was tall and powerful.

She was a strong woman and amazing planner who was always writing, reading and thinking. She woke up early just so she could have time for herself and her thoughts. At 5am, she said, the world is still calm enough that you are able to think without being disturbed. She also believed that if you made a decision and the outcome was not what you expected, or wanted, that you should look at the experience and continue on the journey without looking back since you are not able to affect the situation any longer.

The businesses she started all those years ago are still thriving today – the plantation is running and the houses are being rented. She was a real pioneer who never stopped planning and developing new ideas which often came to fruition. The day before she died she was still giving orders to my brother telling him what should be done, when, who should do it, and how much should be paid.

Once when she was visiting Canada she told me that this place was a gold mine and with a little planning and some thinking – anyone could make it here.

Having had my mother share her life experiences with me made it possible to make the choices that I have made in my financial life. There are no regrets – just lessons learned and I am constantly learning and growing.

The young man from the beginning of this story, who questioned what, makes a person who they are, made me stop and think about who I am and what I have accomplished. I realized that it all comes from being the daughter of a woman of substance.

I spoke with my siblings about what the young man said to me that day. They all fell silent until one of my brothers said, his voice full of emotion, “She was, wasn’t she?

My mother taught me at a very early age about setting goals, making plans and working diligently to acquire them.

What kind of impression have you made on your children when it comes to managing money?

What are you doing to help your children set goals, work towards them and to stay focus on those goals?

Tessa- Marie Shillingford is the author of Controlling the Debt Monster. She is Personal Financial Planner, with a designation from the Institute of Canadian Bankers, and a Financial Counselor certified by the institute of Canadian Banker. She is presently a Program Facilitator of Financial Literacy at JVS Toronto. Tessa- Marie was employed by TD Canada Trust for twenty years in the retail section of the bank. During her tenure at TD Canada Trust she held various positions interacting with customers of the bank. As a Financial Advisor and Manager of Financial Services she led a group of Financial Advisors in helping customers of TD Canada Trust successfully manage their finances. Details of her book… Controlling the Debt Monster, can be found at

14 thoughts on “My Mother the Entrepreneur

  1. What a great example your mother has set for you and by writing about her, she is also now an example for us. Thank you for so much your generosity in sharing your ideas and stories to help people improve their financial health. I have learned a lot.


    1. Thanks Allen, One never knows who will trigger wonderful memories, I will never forget these two young men they made me remember the words of:
      T.S. Eliot “We shall not cease from exploration, And the end of all our exploring, Will be to arrive where we started, And know the place for the first time.”

  2. We need to have these conversations with our youth. We speak with our youth about bullies, self esteem, and sexual reproduction but, very rarely, do parents have formal or consious conversations about financial viability. We need our parents to equip us with the where- with-all, to maneuver this mess we call “financial freedom” for those who are financially illiterate (like me…lol).

    1. Hi Zola, You are definitely right we concentrate on all the other things that are also important when talking with our children, but when it comes to money we all whisper around them or wait untill they are in bed or at school to get down and dirty about the true picture of the family finances. Our children are smarter than we give them credit for. They do not have to know all the nittiy gritty details but surely with a little bit of planning and calmness we can surely find something to let the children know what is going on and perhaps based on their ages ask them for their feed back in so doing we are teaching them how to manage money long before they have money and commitments of their own.

  3. Thanks for sharing your mother’s story with us Tessa-Marie. I am a firm believer that our mothers, if they are working or if they are running a house, they always run it by following the principles of a successful business and everything is accounted for. Once again thanks for this wonderful article.


    1. Hi Sagid You got it, to be successfully more families should follow the business plans of great successfully companies. They cut back, the lay their staff off, they strealine their functions and then they ask the remainder of the staff to go a little further to help the company meet its target. The same principle can be applied within our family. we need to let the members know how things are going and if we keep going that way we will not succeed as a family unit.

  4. Very interesting blog.. really makes me think about my mother and the little tid bits she has instilled in me regarding money management. As a new comer to Canada, single parent of 3, she worked did domestic work to pay for nursing school and after completing this worked 16 hrs a day for 35 years (2 full time jobs) and ran her own cleaning business on the weekends for 10 of those years. In so doing, we never had our lights turned off, we always had food in the fridge, dinner on the stove and more importantly knew the value of hard work and how to manage life… such a wonderful person.

    Thanks for inspiring me to re-remember :-)!


    1. Monique, This is an inspiring story about your mom, after reading the note I realize why you are who you are, being raise by a woman who never gives up has only made you a woman whose children will also write and talk about you like you do about your mom. Keep it up and please let her know how her behaviour has impacted your life.

  5. Your mother was a very wise and independent woman. The knowledge that she gave you has touched everyone that you come in contact with. I am very grateful of the knowledge that you have shared because it inspires and motivates me to want more and accomplish more. I want to thank you and your mother for helping me to manage my money and know that all goals are attainable when you have a plan and follow it.

    1. Hi Psachal Great insight, yes my mother was a very wise and independent woman. I remember my cousin telling her that she was working while her husband attended university,
      my mother said “thats great and when are you going to university?” My cousin said” when she told me that I knew for sure I had to educate myself also.” Her answers were always provoking, she made you think, not that she wanted an answer but she just made you think of what you were doing or not doing. She was an absolutely amazing woman.

  6. No wonder you’re a strong black woman just like your mother. You took her back bone and built yourself into a hard working, motivating woman. Nurturing other women with big dreams as far as your beautiful eyes can see for them. May God Bless you and continue to do so.

    1. Hi Sandy, Yes my mother was an amazing woman, way before her time, I therefore had no choice and whenever the going got tough I just had to keep going because I wanted to get out of tough and the only way was to work myself out of it. If I could dream a dream for someone it would be to be successfull in managing their finances.

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