October 16, 2019

4 Things I Wish I Knew Before Starting My Small Business

I’m Jessica and I’m a money expert, speaker, Accredited Financial Counsellor Canada®, host of the More Money Podcast, and am currently writing my first book with HarperCollins Canada (2025).
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I've been self-employed for 3 years now, and I've made a TON of mistakes. Here are 4 things I wish I knew before quitting my day job about running a business.Is their such a thing as work-life balance when you’re self-employed or run a small business? If you would have asked me 3 years ago, when I’d just transitioned my side hustle into my full-time business, my answer would have been “Balance? What’s that?”

That first year I can honestly say was the hardest year of my career. It was all about growth, but there was zero balance or time for much of a personal life. I worked every weekend, I worked well into the night every night, and there were no vacations besides visiting family in Vancouver for the holidays. And sadly, this is a very common story. As per a new CIBC SmartBanking™ for Business Survey, it was discovered that 39% of Canadian business owners from across the country have taken little or no vacation time in 2019, with life becoming more stressful due to lack of leisure time.

But that was the first year of my business. I really didn’t know what I was doing. I didn’t have a business plan (or business background) and I learned what to do and what not to do by making a ton of mistakes and burning myself out.

In 2018, I did not want a repeat of that first year. I am all about the hustle and grinding it out to get results, but working yourself to the bone isn’t sustainable long-term. The only way to maintain that drive and energy to continue to grow and improve your business is by taking care of yourself first. But how can you do that if you feel like there’s no spare time to go away for a week, or even take the weekend off to take a nap and binge Netflix?

You find time by working smarter, not harder. And that’s what I did in 2018 and continued doing this year too. I actually shared this during my talk at FinCon 2019 this year, and I got a lot of questions from people in the audience about what I meant. Well, working smart, not harder has a lot to do with creating systems to make your business more efficient.

This now leads me to share the 4 things I wish I knew before starting a business, that I learned the hard way (but you don’t have to!).

1. Don’t Do Everything Yourself

You may think this is strange for me to say because I am technically a company of just one. But, that doesn’t mean I do everything myself. When I run my Millennial Money Meetup events, I hire staff to help me the day of so things run smoothly. When I’m working on a big project like hosting a Twitter Chat with a brand, I hire a contractor to handle all the back-end analytics reporting so I can focus on the content and promotion of the chat. When I need new headshots to make my brand look more polished, I hire a hair and makeup artist and get a professional to take all my photos. And when it’s time to file my taxes, I hire a tax accountant to handle all the heavy lifting.

As my business continues to grow, I plan on outsourcing more of my work so I can focus on the parts of my business only I can do like creating original content, public speaking and doing media.

This is a big way I’ve been able to prevent burnout, so if you’re doing everything yourself, think about investing in some help.

2. Invest in Software to Automate Your Work

Aside from outsourcing work to people, there are some amazing online programs to make your business more efficient too. This is actually the key to my success in working for myself. I invest in a ton of software to help me do things faster, such as:

  1. Accounting software
  2. Social media scheduler
  3. Image editing software
  4. Video editing software
  5. To-do list software
  6. Email list software
  7. Landing page creation software

Another way to automate things is to get your software programs to talk to each other. For instance, if you have a business bank account with CIBC, you can use their CIBC SmartBanking for Business Platform. It’s a free platform that integrates your business bank accounts with QuickBooks® OnlineXero, and Ceridian Powerpay Plus together so you can see everything in one dashboard, giving you a full view of your business’s cash flow, payroll, payables, and receivables and more in one place.

3. Don’t Say Yes to Everything

At the beginning of my business, I said yes to every opportunity. I felt guilty if I even thought about saying no to something because I thought that meant I was effectively saying no to money or exposure, which could hinder my business in the future. Although it’s good to be open to opportunities, if something is not the right fit, don’t feel bad for saying no! Because if you say yes to everything, you won’t leave any space to say yes to opportunities that either really excites you or pay you really well.

So whenever an opportunity comes your way, ask yourself these three questions before making a decision:

  1. Does this fit with my brand and personal values?
  2. Does this project excite me?
  3. Does this project pay me my worth?

And if all of those are a yes, do it! If you say yes to only 2 of them, it might be a sign you should say no and move on.

4. Force Yourself to Take Time off to Avoid Burnout

And lastly, force yourself to take time off. I am never more efficient in my business than when I know I have a vacation to get ready for. What that signals to me is I do actually have enough time to go away and unplug. And that also means that I don’t need to work weekends or evenings to have a successful business. I just need to use my work time more wisely.

That’s something we can all do. Because without you, there is no business. So make sure to take time off to decompress, recharge and enjoy life! That’s why you’re running your own business anyway, isn’t it? So you can earn money to enjoy your life? So…what are you waiting for?

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add a comment

  1. Jessica says:

    Hi Jessica.
    Do you have suggestions when it comes to accounting software for freelancers? I’m thinking about Wave software but was wondering if you had other recommendations.

    • I think most of them have free trials, so I’d test out a few to see which one suits your needs best. I’d also watch a few YouTube video tutorials to get a sense of how each works. For me personally, I’ve been using Freshbooks for years and have generally been happy. There are a few things I wish were different, but otherwise it works for me. Quickbooks is also good. I’ve tested it out and thought it was comparable to Freshbooks. I haven’t tried out Wave but I hear it’s also good.

  2. Chris says:

    I’m interested to know what To-do list software you have tried and which one you settled on as your preferred option – definitely something I need!

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