What successful people know: Sean Stanleigh on prioritizing and scheduling

Sean Stanleigh has already spent his career proving his versatility, but balancing roles as both an employee and an entrepreneur has forced him to become equally adept at maximizing every possible moment.

Starting out in traditional journalism, Stanleigh was working for one of Canadian media’s most prestigious publications: Canada’s national newspaper, The Globe and Mail. As editor of the Small Business section (and later its digital presence), Stanleigh could have stayed in his lane. Like many of those who come to Course Compare, however, Stanleigh felt an itch to do something more, which is why he founded The Entrepreneurship Society, an events business that brings together founders from some of the country’s most promising startups together for education and peer relationship-building.

Getting those mid-stage, high-growth entrepreneurs together at exclusive, invite-only events would enable them to network and gain knowledge from each other, rather than exclusively providing the advice,” Stanleigh explains. “The big issues for me? I knew the events business was notoriously difficult to scale, and I loved my day job and didn’t want to give it up.”

Much like Erin Bury, who helped us kick off this series, Stanleigh is often juggling several things at once. Which is why we asked him:

“What’s a time management tip you’d offer to someone trying to carve out enough time to pursue a learning opportunity amid an already busy life?”

Instead of resigning, Stanleigh has continued to stretch himself professionally. He now serves as Managing Editor for Globe Edge Content Studio, which produces high-quality, editorial-style stories for some of Canada’s biggest brands. He’s also continued to grow The Entrepreneurship Society, which recently produced an event about artificial intelligence with Northeastern University, Rogers, BMO & BDC. That means he fully understands the challenges of someone who wants to build their skill set via a workshop, part-time course or bootcamp.  

Here’s my advice to people with busy lives who want to fit more in: It’s easy to finish your day, go home, put your feet up and spend the night on your device, or watching TV or a movie,” he says. “While that’s enjoyable, and something I also like to do, it’s not particularly productive.”

Think of it the same way you’d approach a weekly yoga class, Thursday nights out with workmates, or regular volunteer work, for example, Stanleigh says. Mark the chosen dates in your calendar as a series. Keep your weekends free whenever possible, he advises; those will be your days to recharge.

Don’t just stop at prioritizing, however. Stanleigh suggests making deliberate scheduling decisions, combined with motivation, will make a big difference.”

“Choose two or three specific weeknights and set them aside over the long term for a passion project, whether it’s a learning opportunity or a side hustle, something you really want to do,” he says. “That last part’s important. You have to want it, or you’ll find excuses not to do it.”

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