Why a Cautious Leap Can Be the Smartest Way to Start a Business
- Roger Pierce
- Apr 11
- 2 min read
Thinking of starting a business but not ready to jump all in?
Emily Baillie gets it.
On a recent episode of The Unsure Entrepreneur Podcast, Emily shares how she built her marketing business Compass Content Marketing without burning the bridges of a steady paycheque. Today, her company is nominated for a Canadian SME Small Business Award and she teaches AI and social media marketing at McMaster University and Humber College.
But her success didn’t come from big risks or bold leaps.
📌 Don’t underestimate the power of a cautious start.
Emily held onto her 9-to-5 job while building her business on evenings, weekends, and lunch breaks. “I didn’t have family money to fall back on. I wasn’t a big risk taker,” she said. “So I built slowly.”
It's incredibly smart to keep your full-time employment and launch your business part-time. “What I did was I kept my nine to five job, and then I started taking clients on the side. So when I officially started my business, I wasn’t starting at zero,” explains Emily.
Her approach is refreshingly honest — and rare in a world that celebrates overnight success. In the interview, Emily stresses that entrepreneurs shouldn’t be afraid to take a slower, more secure path. She gave herself a one-year deadline to test the waters and it worked.
📌 AI won’t replace you. But it can help you run a better business.
In the podcast, we talk about her business focus on helping entrepreneurs to embrace artificial intelligence by teaching them how to use tools like ChatGPT and Perplexity to save time and make better decisions. Through training and workshops (she's currently criss-crossing the country doing sessions) Emily shows how small businesses can use AI to speed up content creation, respond to customers, prep for meetings, and more.
She emphasizes experimenting with low-risk tasks to start. “Ask it to help with a recipe or a quick content idea. Get a feel for it,” she advises.
According to recent research from the Business Data Lab at the Canadian Chamber of Commerce, 73% of Canadian businesses are yet to try AI in their operations.
Emily wants to introduce more entrepreneurs to AI and its benefits. “I believe technology, especially AI, shouldn't feel out of reach. It has the power to transform businesses, careers and industries, but only if we make it accessible and create welcoming spaces to learn.”
3 key takeaways from our interview
Start your business slowly. Hold onto your job while building.
Focus on marketing. It takes time and consistency.
Try AI for small tasks first. Build confidence through practice.
When asked about the "truths" of being an entrepreneur, Emily’s advice is simple: don’t fall for the highlight reels you see online. Talk to real business owners. Ask real questions. Learn what it really takes.
“There’s a lot of hype around entrepreneurship and AI. But behind the scenes, there’s just real people trying to make it work.”
Have a listen to the full podcast episode on your favourite streaming platform.
Resources
CompassContent.ca website
Prompting Productivity: Generative AI Adoption by Canadian Businesses (Report from the Chamber's Business Data Lab)
[Photo credit: Emily Baillie]
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