Fifteen years in business: lessons learned on my entrepreneurial journey

It seems a bit hard to believe, but it’s been 15 years since I embarked on my entrepreneurial journey, first as a sole proprietor and now as the founder and CEO of one of Canada’s largest communications agencies.

To say I have learned a lot over the years is a gross understatement. It’s been a constant path of learning, relearning, and adapting as I go. I have come to love, and frankly live for, the excitement of the unknown and the challenge that comes with having to think differently or challenge your existing beliefs. 

You develop a great sense of humility in understanding the breadth of what you know, and more importantly, what you don’t. Below are some lessons I’ve learned over the years that I hope you’ll find helpful, regardless of what sector you work in:

1. Just start — let go of perfectionism

One of the most significant barriers to entrepreneurship is the pursuit of perfection. I’ve seen it happen to so many colleagues and friends: the fear of imperfection can paralyze individuals from taking that crucial first step or getting a project over the finish line.

Over the past 15 years, I’ve learned that it’s a must to embrace imperfections and just start. Waiting for the perfect moment or a flawless plan can lead to missed opportunities. The key is to learn, adapt, and refine your approach as you go.

2. Don’t be happy with the status quo

Entrepreneurship is about innovation and constant improvement. In a rapidly evolving business world, complacency is a silent killer. Instead of settling for the status quo, think like an entrepreneur. Continually challenge yourself and your business to evolve, explore new possibilities, and stay ahead of the sector you’re in. Innovation is the lifeblood of successful entrepreneurship. Push yourself to do better, be better, and ask for forgiveness later. Just start. (See a connection to the above point?) 

3. Surround yourself with support — choose your own board of directors

Building a strong support system is essential for any entrepreneur. Surround yourself with a  network of mentors, advisors, and like-minded individuals who can serve as your personal “board of directors.” These individuals can provide valuable insights, guidance, and constructive feedback. The collective wisdom of your chosen support system can be a powerful asset as you navigate the challenges of entrepreneurship. And, as author Adam Grant famously said, always be open to “think again.”

Use your personal board of directors as not only a sounding board, but a challenge team. Let them challenge your ideas, encourage you to think again, and let go of ego.

This group doesn’t have to be big. It can be as small as one or two people you trust and who have your best interests at heart.

4. Always be guided by integrity

Integrity is the foundation of long-term success in business. Over the years, I’ve witnessed the impact of honest and transparent business practices on reputation and relationships (as well as the opposite). Upholding ethical standards not only builds trust with customers and partners but also fosters a positive work culture within your organization. Always make decisions that align with your values, even if it means sacrificing short-term gains for long-term integrity.

5. Don’t feel guilty if you don’t achieve work-life balance

The myth of achieving perfect work-life balance stirs up unnecessary guilt and stress for entrepreneurs. Recognize that the entrepreneurial journey is demanding, and there will be times when work takes first priority. Instead of striving for an elusive balance, focus on integrating work and life in a way that aligns with your priorities and values. Embrace flexibility and find a rhythm that works for you, allowing you to be present in both your professional and personal life.

6. Give back to your community and approach your relationships authentically

Success in business goes beyond your profit and loss statement; it involves contributing positively to your community and building authentic relationships that transcend a business deal. As an entrepreneur, consider how your business can make a meaningful impact on society. Approach your professional and personal relationships with authenticity and sincerity. Genuine connections can lead to lasting partnerships and a more fulfilling entrepreneurial journey.

7. Learn to compartmentalize your life

I saved my biggest lesson for last. The BIGGEST lesson I have learned is compartmentalization of my life. When I am at work, that’s where my head is at. I’m thinking about our clients, my team, and our future. When I am home, I’m home. I’m zoned in on my kids, whatever chaos is happening, and I’m not fretting about work or letting it seep in.

This has been a very conscious and deliberate effort in teaching my brain to be present where it is. With so much on my plate, I don’t think I’d survive if I didn’t adopt this strategy. It’s been the biggest foundation for my success as a businessperson and a mom. It’s a learned trait, and one that I couldn’t live without now.

Reaching the 15-year mark in business honestly feels like I’m just getting started. I’ve built a bank of lessons through just doing and iterating as I go. I can refreshingly say I have a more open mind now at 40 than I did at 25, largely in part because of these experiences and valuable lessons learned. So, let’s bring on the next 15 years of growth, failure, and lessons. Isn’t that what life’s all about anyway?

by Jennifer Stewart

Co-founder of The Honest Talk. President and Founder of Syntax Strategic. She is one of the Ottawa Business Journal’s ‘Top Forty Under 40′, and was a finalist for Ottawa’s ‘Female Entrepreneur of the Year.’

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