Life Changers: Single Mom Success Stories


When we hear the term “single mom”, it often conjures up less than stellar stereotypes of young mothers who are a strain on social resources and financially dependent on our overburdened social systems. Very rarely are single moms ever depicted as successful, self-sufficient, productive, contributing members of society. However, there are many such moms who have defied these stereotypes and in many ways turned them upside down, achieving levels of success by far surpassing their coupled counterparts.

Re-Framing the Stereotype

In Canada, single mom success stories include women like Arlene Dickenson, Ettie Rutherford and Marilyn Denis. Internationally, J.K. Rowlings has not only defied the odds, but literally re-wrote the script. But what about your average everyday single moms who become successful entrepreneurs, what are their stories?

On the website Company of Women which is a networking organization for women entrepreneurs, in the Resource section, they feature 18 successful women entrepreneurs from across Canada. Of the 18, three highlighted the fact that they are single moms: Cora Tsouflidou, Cathy Boytos and Sherry Colbourne.

Although each path was unique, the outcome is the same: persistence equals success. On their path to success, each faced many of the typical challenges that most single mothers face – not having enough time or money and working under stressful circumstances. But despite the odds, they not only flourished, they thrived.

For me the journey has just begun.

I also chose to raise my children on my own and I can identify with many of the obstacles and challenges they described, as well as the lessons that they have learned along the way. Being a single parent was for me a far better alternative to staying in an emotionally, mentally and financially abusive marriage which I promptly left two and a half years in when the abuse became physical.

My situation was compounded by the fact that we both worked for the same employer, in the same building and for a short period in the same department. I stuck it out for a year and a half after returning from Mat Leave. But the combination of wanting to protect my two sons and working in a toxic, unsafe environment prompted me to resign and later use my severance to start my business.

At that time, my infant son had a condition called Encopresis (typically cause by lack of fibre, but in his case it was brought on by the stress of being shuffled between two households), which required frequent visits with the Pediatrician and resulted in severe discomfort and many, many waking’s throughout the night. I needed to have flexibility in my schedule, but my employer was not very accommodating, despite the fact that I had only two absences in the past seven years. This was further motivation to look at other alternatives.

Employee vs. Entrepreneur – What are the Challenges

Like these women, my main concern was the well-being of my children. Like most mothers single or otherwise with preschool children, I also had to decide whether I wanted to work for someone else only to see 50% or more of my pay go to childcare or work on my own and have the flexibility to work my own hours and still be able to participate in their activities while making a living. The primary reasons why many single moms choose entrepreneurship over a 9-5 job seems to be to care for their children; to have more flexibility; to have better allocation of financial resources and to have better earning potential. And simply because finding a job that not only pays well but is also flexible AND where there’s a family-friendly environment can be like looking for a needle in a haystack.

Many of us are looking for balance.

Cathy Boytos shared that when she was faced with the financial challenges of raising her 3yr old daughter on her own, “she struggled with finding ways to provide a good and balanced life for the two of them.” She found that the corporate job that she had held for the previous 20 years, left her with little time or energy for her daughter.

Sherry Colbourne’s challenges were different, but still contained elements of trying to find balance. In her case, she pondered the dilemma of how parents could teach their young adult children how to be responsible social drinkers, hence striking a balance between over consumption and not drinking at all. Balance is a priority not only for single moms, it’s a concern for most moms and dads alike, single or not. Although having a steady income from an employer means added security, a higher pay usually equates to longer working hours and therefore less time with your family. For a single parent, that means less quality time with your child(ren) – which is not a desirable option for many.

The other challenge I and many single moms face is making ends meet financially. Entrepreneurship when successful can net a much more lucrative income than being an employee, but this path is also rife with risk. For most entrepreneurs, financial risk is a main ingredient, particularly in the beginning. For single moms, the risk is magnified many times over because typically, there is no second income to fall back on. This means diligent planning, tight budgeting and accurate forecasting and for many women, dipping into personal resources.

Sherry Colbourne managed to shop her business plan to investors who agreed to fund her venture. However, for Cathy Boytos, she had to think out of the box. She resorted to borrowing from what little equity she had in her home. This is an all too common scenario for women entrepreneurs who commonly use equity, personal investments or retirement savings to fund their businesses.

For many, this is their only option.

But Cathy was very creative and industrious. In addition to this, she also used a number of very creative marketing tactics to generate sales, including sending letters to local Realtors who would potentially pass her information on to their clients. For both women, the risks they took paid off and their businesses are now very successful

Words of Advice

The journeys of Cora, Cathy and Sherry are not unique, but they are all inspiring and filled with life lessons. For Cora, there were two main lessons. The first was “surrender to life and let things happen…everything will come in its own time”. And two, don’t plan and don’t worry. According to her, “everything will turn out okay whether she worries or not”.

Cathy in describing her lessons learned said “you need to trust your gut feelings…listen to that inner voice”. These are all philosophies that I share and have grown to embrace more and more as I experience life and all it has to offer. I am very much a planner at heart (I would liken it to being prepared versus not preparing at all), but I completely understand the concept of not worrying.

All three women are shining examples of the struggles and doubts that one faces when choosing to become an entrepreneur and how that choice can be even more complicated, challenging and risky for single moms. They are also exemplary women who have defied the odds, confronted their fears head on and challenged the narrow definitions of single motherhood that society and Hollywood has cast on them. They have not only overcome those challenges and obstacles, they have far surpassed even their own expectations.

You go girl! Way to change the game!


AUTHOR: Kara is an entrepreneur and Principal Consultant and Owner of PlanIt! Outsourcing Solutions. She is a Certified Project Manager with over 11 years project management experience in progressively challenging roles leading corporate projects as well as an Administrative Specialist with over 20 years’ experience in Sr. Admin and Exec Admin roles in both the public and private sector.