4 Biggest Fears Contractors Have

contractor insurance fears
Jul 07 2021 3 min read

Working for yourself can be a beautiful thing, so most people think.

If you’re not self-employed you likely look at those who are and envy their ability to make their schedule or the fact that they don’t have a boss to answer to.

While this is true to an extent, small business owners tend to work more hours than most.

According to a 2005 Gallup poll, small business owners like contractors work an average of 52 hours per week (some up to 70 hours per week) and take fewer days off than most people as well. (1)

Why do small business owners put in so many hours?

A local general contractor, Myles Calvert of Myles Calvert and Son sums it up this way:

“It all stems from having a family to support. It’s always what’s driven me.”

We asked him what could potentially keep him up at night.

Below are the 4 most common reasons why a contractor may be lying awake, in no particular order.

Contractor Insurance


Not surprisingly, concerns of short and long term financial stability is a common concern for people running their own business, as is often the case for most people in general.

When it comes to contractors when they can work and generate revenue may be out of their control no matter how good of an operator they are.

Take seasonal businesses like landscape contracting for example. Landscapers operating in locations with long winters, as we have here in southern Ontario, usually deal with lean winters when there is little work activity happening and nonstop work in the summer when the getting is good.


A business is only as strong as its team. One of the most difficult aspects of running a contracting business is finding the right team members to join.

“Qualified help is on the list. Early on I was wearing all the hats because I couldn’t find many people I trusted enough.” Myles Calvert says.

If you’re running a business that is difficult or impossible to do on your own, worrying about not being able to find the right people to hire can be a major stress.


On a good day, certain quality building materials can be hard to find at all, let alone find at a good price. On other days, like during the summer of 2021, this can be a daunting task.

When Myles was asked about what impact the material situation in 2021 was having on his window installation business, he told us that he was dealing with a 43 business day lead time in July which means he and his customers were waiting 8+ weeks for windows to be delivered.

Customers were forced to make decisions quickly to get the pricing quoted and their parts ordered in time.

Patience is a necessity for both contractors and the property owners they service when there are material supply issues out of either of their control.

Dealing with spikes in material costs and the thought of having to re-schedule a project for next year due to material delays is enough to keep just about any business owner up at night.


Contracting work can be dangerous work.

Operating power tools from a ladder, carrying heavy equipment, working in tight spaces. All of this adds to the risk for contractors from both potential property damage and personal injury point of view.

According to Myles, having contractor insurance is a must.

“If there’s an issue or injury you may as well give up the keys to your house if you aren’t properly insured.”

And it’s certainly worth the cost for him.

“Insurance doesn’t cost a lot. It’s not a budget breaker.”

While he and many other contractors are fully insured, not all are.

There is a law in Ontario requiring electricians to have insurance but there is no such requirement for general contractors.

“It’s the wild west with no mandate,” says Myles, which is partly why he makes the fact that his business is fully insured a part of their advertising.

It’s an uncomfortable question for some homeowners to ask (whether or not a contractor is insured) but it should be one of the first they ask when deciding to hire a contractor. If they don’t, it’s not only their contractor who will be lying awake at night.

Being a contractor and running your own business is a labour of love. Sometimes that love hurts. If you’re looking for quality and affordable insurance, click here to get a contractor insurance quote.

Erie Mutual Insurance proudly serves the commercial insurance, farm insurance, home insurance and auto insurance needs of members throughout Southern Ontario including Haldimand, Niagara and Hamilton.

Please don’t hesitate to contact us with any questions you may have about this or any other topic related to your insurance.



1 – https://news.gallup.com/poll/18088/work-labor-love-smallbusiness-owners.aspx




Please contact us with any questions you may have about this or any other topic related to your insurance.

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