Lessons in Entrepreneurship

Jessica Rose

This is a Guest Blog from Jessica Rose, a writer, editor, and strategic communications professional in the not-for-profit and arts sectors. She is also a former Hamilton HIVE Public Relations Chair. Leading up to the STEEL Conference, we'll have a guest blogger write us a piece about each of the Pillars of the conference. Enjoy the following blog about Entrepreneurship, and find out more about the conference here.


Five years ago, give or take a week, I accepted the role of Hamilton HIVE’s Public Relations Subcommittee Chair. At the time, I had just left my first career in publishing, determined that I was done with the burnout of unwavering hours and a long commute. I’d landed a part-time job for a local not-for-profit and built my own writing, editing, and communications business on the side. I spent my year at HIVE meeting and admiring entrepreneurs and full-time freelancers, wondering if I could ever make it on my own, too. 

Fast forward to early 2020, I unexpectedly lost that part-time job and found myself solely in business for myself—during a global pandemic. It was terrifying, but it forced me to recall the wisdom and advice I’ve acquired in the past five years, reading about entrepreneurship, engaging with the young professional community, and maintaining a side hustle. 

Part of entrepreneurship is learning while you go. I can’t claim to know it all, but here is some of the valuable knowledge I’ve grown to trust. 

Fill a Gap

You offer something that nobody else does. You just have to figure out what it is. The first step is to ask yourself what sets you apart. For me, I knew there were many communications professionals in Hamilton. What’s been helpful (and profitable) has been to specialize in areas I know well—locally rooted not-for-profits and the arts (particularly literary arts) sector. When you specialize, your pool of potential clients or gigs might shrink; however, those seeking your expertise and skill set will appreciate your deep knowledge and experience. 

Your Connections Matter (So Much More than Your Resume) 

I spend a lot of time trying to secure contracts with new clients, submitting proposals and resumes. Yet, most of my clients are referred to me by someone I know. Many of my long-term contracts are from organizations I’ve worked with in the past or are led by people I’ve known for a long time. You never know when making a positive connection will prove to be beneficial to you in the future.

That means you have to network. You’re reading a Hamilton HIVE blog post, so you probably know that already. But networking doesn’t always have to mean attending events with the sole purpose of handing out as many business cards as you can. (And let’s face it, that’s pretty much impossible right now). It can also mean volunteering your time to a board or committee, attending panel discussions, or engaging with people you admire online. If your woman-identified, join online communities like Women Who Freelance or Fempreneurs. 

Being connected to and active in your community isn’t only beneficial because it might add to your client list. Here’s a quote I love from The Conscious Creative: Practical Ethics for Purposeful Work, a book by Kelly Small. “Ensuring we understand community needs from the inside is an amazing way to ensure we’re not developing projects with a hierarchical, exclusive mentality. Attend community meetings. Stay informed and active in local politics. Volunteer. Have more conversations including with people with whom you suspect you don’t agree. Ask people what matters to them. Every chat is an opportunity to better understand the hopes and needs of the people we call neighbours and will invariably inform our collective creative output.” 

Know Your Worth

Don’t buy the garbage that the 9-5 is your only option. There are other sorts of purposeful work, too. Entrepreneurship, freelancing, and contract work are valid. 

However, those options mean your out-of-pocket expenses are likely higher. You’re not getting paid to wade through your inbox, spend an afternoon invoicing, or attend conferences or other professional development opportunities. Make sure this time is built into your fees or costs, whether that means the product you're selling through your small business is priced slightly higher or your hourly rate for the clients you consult is more than what you would charge working for someone else. 

Have awkward money conversations with yourself. Some months, working for yourself is hard. Payments are late. Gigs are wrapping up. If you can, pay yourself a wage so that your budget doesn’t have to fluctuate too much. However, if that isn’t possible, just know that some months you’re going to have to cut out the take-out or skip your trips to the local coffee shop. 

Bring Your Personal Values to Work With You

We’ve all been in that position where we’re working for someone else and we’re asked to do something that just doesn’t feel right. This could mean working retail and selling a product you don’t truly believe in or working for a large corporation that doesn’t have sustainability in mind. Working for yourself gives you the opportunity to bring your personal values to the work you do. 

Here’s another quote from Kelly Small: “It’s measurably proven that public companies that show their ethical stance regarding factors such as climate change, labour rights, and public health are actually more stable and profitable than those whose visible focus rests solely on the bottom line.” 

Once you establish yourself as an entrepreneur or freelancer, you’ll have the privilege of choosing who you work with. You’ll also control your own messaging and how you’re viewed in the wider community. Ask yourself “How can I amplify things that are important to me through my work?” This could mean amplifying the social media messages of causes and organizations you support or leading a rallying cry in support of small businesses, locally owned businesses, or businesses led by oppressed groups. 

Collaborate! Seek out others with your shared values and look for opportunities to work with other entrepreneurs, freelancers, and contract workers, especially locally. 



Turning what you're passionate about into marketable skills is possible, but it takes a lot of work and planning. So, to get you started, I’ll end with another favourite quote from another favourite book about working for yourself:

“Figuring out what you don’t want can be one of the most helpful tools in figuring out what you do want.” — Careergasm: Find Your Way to Feel-Good Work by Sarah Vermunt.