Self-Employed Insurance Guide: Key Coverage For Entrepreneurs

That’s one of the first things we hear, and the answer is, yes, you can indeed, in many cases. If the insurance helps for your work as a self-employed professional, such as liability or business overhead coverage, it generally counts as a deductible business expense. Even health plans can count at times, particularly if you have a Health Spending Account. Make sure you go over it with a tax advisor before filing, but yes, there is typically a way to get your insurance to work for you at tax time.

If you’re on the move — whether it’s between provinces or beyond Canada — you’ll want to think bigger than basic health plans. The last thing you want to be worried about is unexpected medical bills if something goes wrong on the road. And if you’re hauling gear like cameras or tools, consider insuring that as well. We’ve assisted in crafting ”plans for the road,” and clients are covered whether they are in Toronto, Vancouver, or on location in Portugal.

Yes — just because you’re part-time doesn’t mean the risks disappear. If you depend on that income, a health issue covering only a short period could cause you disruption. The good news? You can size coverage to your condition. We have created insurance plans for self-employed clients who work weekends or after 5 pm. It’s not about how many hours — it’s about how much risk you are carrying completely unsupported.

You’ve got options. If you move to full-time employment with benefits, you can often end or suspend the private coverage. Just be certain that the employer plan will cover all you need. Some people even retain a piece of their private insurance, such as critical illness or life coverage, or both, that is not very good on the employer plan. We have guided many clients through such a transition smoothly, without having to pay twice or without losing coverage.

Indeed, very few people are aware of this. If you are a member of a professional association, union, co-op, or the like, those organizations might provide group rates that lower costs for you. And if we don’t, we are sometimes able to assist clients in joining a group-style plan through our networks. It’s a question worth asking — group coverage is no longer only for large employers.

That depends on the type of insurance, but usually, yes, you still have some choices. Some plans include medical questions, and others don’t. It may factor into your Health Insurance premiums or produce exclusions, but I can tell you we’ve had several clients who thought for sure they would never qualify, and they did. The key is to have that out front so that we can make sure that we’re matching you with the right provider and that we’re not wasting your time.

Not necessarily. Some plans allow scaling down or putting payments on hold temporarily rather than cancelling outright. If you cancel altogether, you might miss out on a good rate or need to reapply with fresh health questions in the future. We typically suggest hanging on to some kind of basic coverage — health, life, whatever — so you’re not starting completely from scratch the next time you’re at it. Every situation is different, but let’s talk it through first.

Yes, it can. A graphic designer and a roofer will not pay the same premiums. Insurance companies consider the risk level of what you do, how often you do it, and where you do it. But that doesn’t mean your job is “uninsurable.” We have a few to choose from, so we can always find one who understands what you do and won’t gouge you on the price.