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A decade ago, I left the corporate world for that of entrepreneurship. I was joining RIGHTSLEEVE, a promotional products agency, as a co-owner. The business had been started five years before, meaning there was plenty of pre-existing knowledge and expertise that I could learn from.

Five years into my time at RIGHTSTLEEVE, we decided to commercialize software that we had built in house, spinning out a new startup called commonsku. All of a sudden I found myself in the position of being a tech co-founder, having to build and lead a team in an industry I knew nothing about.

There are few things I miss about the corporate world, but—and this might sound funny coming from someone who is now a staunch believer in the benefits of running one’s own business—one of them is having a boss. There’s a certain comfort level that comes with knowing that there is someone else you can turn to for help and learn from, with whom the buck stops, and who will ultimately make necessary decisions in tough situations.

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In the early days of a business, the entrepreneur is the one who always needs to have the answers. It’s exhausting, and lonely. You are constantly operating outside your comfort zone, and every day brings something new you have never done before. It’s hugely exciting and challenging to ride that massive learning curve, but—and entreprenuers often fail to acknowledge this—it’s also terrifying. Much of the time you feel like you have no idea what you’re doing, and it feels like you’re doing it all on your own.

Eventually, the fear and imposter syndrome lessen. You start to build deep knowledge in areas you knew nothing about before. As your company grows, you hire people who know more than you in specific areas and can bring expertise to the table. Soon you’re surrounded by a team that can provide support and lessen the burden of leadership.

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Looking back on my entrepreneurial career, there are two things I wish I had done sooner. The first is leveraging my network more for support. It can often feel like you’re the only one struggling, but the reality is many startup founders and business owners feel the same way every day. There’s a belief that you need to put on a face: Everything is going great. If the veneer cracks, it means the word will get out that you are struggling and you won’t get funded. But the reality is that most smart VCs know there is a high degree of BS out there, and that the reality behind closed doors is very different. If I’d been more open about how hard those first few years were, I might have gotten some perspective or good advice from other founders.

The second thing I wish I had done sooner was to push decision making down into the organization. As we transitioned RIGHTSLEEVE to being run by a management team, there were still far too many things that depended on me to make up my mind. That was my own fault—our original structure was so top heavy that nobody had the opportunity to develop management skills. To avoid that mistake, you need to build your bench strength early on by surrounding yourself with smart people and letting them run their own areas of the business. This not only reduces the risk to your business if something happens to you, but also positions the company for growth.

If you’re at a stage in your business where you have accumulated a few battle scars and learned some lessons along the way, take the time to be a mentor. Create a space where it’s okay for others to share how hard a time they’ve had getting their businesses off the ground. Sharing how lonely entrepreneurship has sometimes been for you just might make it a bit less lonely for somebody else.

Catherine Graham is the CEO of commonsku and the President of RIGHTSLEEVE. Prior to her current adventure, she worked in banking, management consulting and at eBay Canada when it was still a start-up. On the home front she has three kids and spends a lot of time at the hockey rink, both playing and coaching. She is passionate about fostering entrepreneurship, particularly in the tech space, and is involved in mentoring through a number of organizations.


Is entrepreneurship an inherently lonely occupation? What did/do you do to feel less on your own? Let us know by commenting below. 

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