Keeping Your Day Job While Starting Your Business is Really, Really Smart

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. 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. It worked.

📌 AI won’t replace you. But it can help you run a better business.

We talk about her business and her work focussed 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

• 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

LinkedIn Profile

AI Training

Prompting Productivity: Generative AI Adoption by Canadian Businesses (Report from the Chamber's Business Data Lab)

[Photo credit: Emily Baillie]