Shannon Lee Simmons celebrated her 5th anniversary as a business owner last September. After working in the Bay Street world and for one of the big banks she quit and set off on her own in 2010. With her schedule booked months in advance as a financial advisor and the rest of her time devoted to building her online DIY finance courses, she’s making personal finance accessible to everyone, not only those with extra cash to invest in mutual funds. 

When I interviewed Shannon last month in the article ” 5 Tips to Make 2016 the Most Successful Year Yet”  we talked about what she’s learned over the last five years and she shared five of her top lessons:

1. Find your community

Over the last five years of owning a business, the biggest thing Shannon’s learned is that, it’s very important to have a go-to community, like an online hubs or Facebook group, where you can ask questions, find resources, and get referrals. “When you’re starting out it’s easy to think “I can do all this, I’m on top of this, I’m on top of that,” but really, knowing where to go to get good, reliable information, can save you so much time, so much energy, from making so many mistakes…and from googling 10,000 things. I think time is our most precious resource.”

2. Invest in yourself

If you spend most of your time trying to fulfill all the roles for your business – being your own web developer, bookkeeper, marketer, writer, administrator- you may not leave yourself enough time do the things that will grow your business. Shannon told me that she when she first started out she was “totally operating in the scarcity mindset. I was scared to spend money on anything.” She tried to do everything herself and “ended up working 16 hour days.” The thing she learned from this is, “Invest in yourself and your business. Within reason.” If you can afford to, hire experts to take on the things that you’re wasting the most time on and getting little return.

3. If you can’t outsource or delegate a task find a way to get faster at it

Not everyone is in the position to hire experts or delegate the most arduous tasks. If that’s the case, Shannon suggests that you think about the thing that is taking the most time and find a way to learn the skill so you can get faster at it. For example, “if you’re going to do your own web stuff, rather than you just sitting for hours poking at your WordPress site trying to figure it out, see if there someone you can pay, for one hour, to teach you how to do it and then you can actually do it yourself indefinitely. That would be a small investment for a big pay out, right? When it comes to those types of skills, figuring it out yourself takes forever…spend the afternoon to learn how to do it and then you never have to pay someone again but you’ll be so much faster and you won’t waste so much time.”

4. Don’t be afraid to barter

Another way to get what you need without having to put forward a big financial outlay is bartering. Try reaching out to other business owners to see if you can do an exchange of skills or products. As an entrepreneur, Shannon doesn’t have benefits but because she sits at a desk all day she finds she needs regular massages to keep her healthy and her body moving. So she does taxes in exchange for RMT (registered massage therapy), “That’s something that I started to do years ago before I could afford it and it’s something I continue to do.”

5. Everyone wrestles with self-doubt

Shannon sees hundreds and hundreds of female entrepreneurs every year and the one thing we all have in common – no matter how successful our businesses are – is that we all sometimes feel that we can’t do this. Or that it’s overwhelming and scary. “We all are super women, every single one of us is trying to be a good parent, a good wife or partner, a good friend, a good family member, a good all the things, and still be hot. And so the crushing weight of all this is a bit much. When you start your own business if everything doesn’t go perfectly right away or if you feel like it’s a constant struggle, it’s important for you to know that so does everyone else.” 

Shannon says that one of the reasons many of us feel this way is because we’re so busy multitasking. So make sure to follow the first few tips and don’t do everything yourself. Your business and your confidence will thank you for it! 

What have you learned as a woman in business that might help others? Tell us on our Facebook page.


See Shannon Lee Simmons Speak at the The Thrive Summit!

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Join us at The Thrive Summit on April 4, 2016 at the Centre for Health and Safety Innovation in Mississauga for The Thrive Summit. Focusing on our four pillars  to Success: Learning & Leadership, Fun & Financial Well-Being, Healthy Living & Spirituality and Community & Compassion, top experts will take you through interactive and engaging sessions where you will learn to prioritize the thrive in your life. Learn more at