From Solo to Supported: Creating the Team You Need as a Sole Proprietor

I spent years working as a senior manager in local government, enjoying the perks of job security, benefits and support from IT, Finance and Human Resources teams. On top of that, I had access to paid professional development opportunities. But all of this disappeared when I took the leap to become a consultant. 

While I wouldn’t trade my freedom for a 9-5 job, adjusting to solo work wasn’t easy – especially when it came to getting the support I had once relied on with a quick (and free) phone call.  

It took some time, but I’ve managed to build an incredible team while remaining a sole proprietor. Since this is a common fear among my coaching clients who are considering leaving secure jobs, I wanted to share some tips on how to create your own team as sole proprietor. 

Know yourself 

Before you can look for supports, get clear on your strengths and stretches. What tasks do you excel at? Which ones do you struggle with? And, most importantly, what do you hate doing? 

For me, math has always been a challenge. This was my biggest fear when becoming self-employed. But instead of immediately hiring a bookkeeper and accountant, I took time to assess my needs. I asked myself – what bookkeeping tasks can I handle on my own and where do I need help?

I ended up using QuickBooks and Dext – both easy to use for tracking expenses, entering receipts, and creating invoices. I can handle that part myself. From there, my bookkeeper reconciles my accounts (which I definitely don’t understand) and sends a year-end summary for my accountant to file my taxes. 

Knowing where I can pitch in and where I need to hire out has saved a lot of time, money and frustration. 

Hire out your weaknesses

One of my coaching clients told me “Hire out your weaknesses,” and it’s a principle I love. It’s about taking a holistic view of your life and business, finding where it makes sense to bring in help.  

As a working mom of two kids, two dogs and six ducks, I hire someone to clean my house. This reduces my stress and gives me more time to spend with my family rather than spending weekends scrubbing toilets.  

I also hire out website updates and IT troubleshooting. While I’m comfortable uploading blogs and other small website changes, when it comes time to doing a website overhaul or I’m stumped by an IT, I call up my web support. 

Same goes for graphic design. Working in public relations, I’ve seen enough bad design to know I need a professional. All my promotional material – from e-books to handouts – are designed by a pro. 

The result? Clean, crisp and visually appealing content that represents my brand well.  

Trust your gut

My biggest advice when building your team? Work with people you like – people you genuinely enjoy interacting with. I have a friend who grumbles about their accountant and avoids dealing with them. The result – they get into pickles that could’ve been prevented by a conversation. 

While I might not be best friends with everyone I work with, I like and respect them. And I know the feeling is mutual. 

I take time to build a relationship, so it’s not all business. 

Trust your gut. Take things slow at first, paying attention to any red flags and know when to end the relationship. 

As a sole proprietor you have enough balls to juggle without having dead weight pulling you down. 

Grow your circle

As your business grows, so should your circle of support. Over the years I’ve added a personal trainer, business coach, counsellor, speaking agent and others to my team. 

If you want to grow your business you need to grow your team. It’s that simple.

My business coach has challenged me to reassess how I spend my time, encouraged me to pursue new revenue streams and asked tough questions that have helped me grow as a person and entrepreneur. He’s also reminded me that time is my most valuable resource. 

Growing your team is about maximizing your potential – spending time where you get the greatest return on investment and hiring others to do the rest. 

Let go of control

For many, one of the hardest parts of entrepreneurship is letting go of control. But I promise you, by trusting others with key tasks, you’ll reduce your stress and free up more time to focus on what truly matters. 

Many of us became sole proprietors to have more freedom in both work and life. I encourage you to reflect on what’s important to you and grow a team that helps you live your best life.