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TurboTax spokesperson Jami Monte says there’s a lot of shame in the tax world. People who might benefit from the assistance of a tax professional often worry that their messy bookkeeping will be scoffed at.

But she says parsing through these complicated matters is part of the job, and tax professionals are ready to help you out no matter how bad a job you did keeping receipts.

“Your goal is to generate income, not keep track of your taxes,” said Ms. Monte.

The general rule here is that if anything about your work life is more complicated than having one regular employer, you could seriously benefit from the advice of a professional. Here are some of the folks that might need help the most.

Self-employed people, gig workers and business owners

The intricacies of bookkeeping and expensing are so much more complicated for people in these demographics, and it is all too easy to misunderstand the rules and make faulty expense claims. To get the most out of your tax return and to avoid a particularly painful auditing experience from the Canada Revenue Agency, it’s best to talk to an accountant or tax preparer, during tax season and when you start this form of work, to better understand bookkeeping.

People with foreign income

Taxation gets extremely complicated when you bring another country into the mix. You may have to file in two jurisdictions if you worked abroad or received income from a foreign job. There are tax credits to prevent you from paying an exorbitant amount of tax in this case, but it’s best to have a professional help you through this process.

Seven tax tips for newcomers to Canada


Filing taxes isn’t necessarily difficult in retirement. But strategizing to pay the least amount of tax through income sharing, different forms of savings accounts and other techniques can save you massive amounts of money. Retirement unlocks a whole treasure trove of tax strategies, and dealing with a professional even before you retire is the best way to maximize your money.

People who recently entered a marriage or common-law relationship

Estate planner Cindy David says couples can benefit from seeing a professional at least once to better understand how they can take advantage of opportunities to pool their expenses and lower their tax burden.

Contact the CRA’s helpline

If you’re still not sold on an accountant but want some free advice, CRA spokesperson Charles Drouin says the agency offers free and confidential helplines for people with questions about their taxes.

Are you a young Canadian with money on your mind? To set yourself up for success and steer clear of costly mistakes, listen to our award-winning Stress Test podcast.