Entrepreneurship is not for the faint of heart, but can bring tremendous joy and satisfaction

Reflections on Women’s Entrepreneurship Day 2021. Running my own business has brought me some of my greatest highs and some of my lowest lows.

By Deb Day, CEO and Chief Strategist, Innovate By Day

Running my own business has brought me some of my greatest highs and some of my lowest lows. 11 years in, I am clearer about how I want to do business, what supports and structures I need, my strengths, my weaknesses and how to roll with the punches. And trust me, there are many humbling experiences.

I am clear about my commitment to living our company values. I regularly come back to our three core tenets: Listen - Engage - Respond. I set them when I started Innovate By Day, and they are as relevant today as a decade ago. The art of listening is a skill to be honed and refined. It is central to all that I do. Being heard is a fundamental need. Without listening and inquiry, we cannot know or understand what people need. Listening is the starting point of everything.

I began this entrepreneurial journey in search of more agency over my life, at the same time as recognizing a new opportunity to be fulfilled. I mapped out a reasonable business model and decided to go for it. And most of the time, it has worked. Over the years, it has evolved, as have our team, systems, and processes. It is a journey that continues to shift and change.

Entrepreneurship is not for the faint of heart. It has required me frequently to be pushed out of my comfort zone, to evolve, to try, to fail, to learn, to question, to improve, to explore, to grow, to collaborate, to innovate, to reevaluate, to communicate, to thrive. It can be relentless, cause sleepless nights, and involve risk; it can also offer tremendous joy, satisfaction and pride. And It can be isolating, especially over the last two years when the team has been required to work remotely.

In October, Innovate By Day was certified a women-owned business by the Women Business Enterprises Canada Council. I was able to attend the 2021 WBE Canada Annual Conference last week and meet with many women business owners. In spite of it being all virtual, connecting with other women business owners through speed networking, trivia games and in sessions was inspiring and hopeful.

Connecting with my fellow entrepreneurs like this has been essential. I’m a member of several groups that, like WBE Canada, align with my values. Where I can be supported, ask questions, and support other business owners. From The Pierce Group, CFC Media Lab’s Fifth Wave, SheEO<span">, and the Toronto Region Board of Trade’s Trade Accelerator Program (TAP). Having a network of leaders, mentors, and diverse business owners has been a game changer for me. It hasn’t always been easy for me to ask for support. I feel fortunate to live in a country where these programs are supported by our government.

If you have a fire burning in your belly to start your own company, test out the concept with some people you trust who will listen, ask the tough questions, and can help you shape your vision. Consider partnering, or teaming up with an existing complementary business or service. Identify networks that can support you as it will be quite the ride. Reach out, be in touch and go for it.


Deb Day is Innovate By Day’s Founder, CEO & Chief Strategist. 

Photo by Emily Adams on Unsplash

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