I’ve been a freelance writer for the better part of 10 years, and admittedly am still figuring out my own financial strategy.
This past tax season, that reality hit me harder than ever. I was on the phone with my tax preparer, who asked not to be identified because his employer doesn’t allow public media commentary. After reviewing my finances and explaining how he’d arrived at the figure, he finally revealed the number I’d been waiting for: the amount I owed in federal and provincial taxes.
My stomach dropped. I knew I’d owe money—that’s just part of being self-employed—but the number didn’t match how financially insecure I felt. I’d always tried to do the “right” thing, setting aside roughly 30% of my income for taxes. But like many freelancers, I’d occasionally dipped into that money during slower months or to cover unexpected expenses, assuming I’d earned enough later in the year to make up the difference. Apparently, I hadn’t.
My tax preparer suggested opening an FHSA to reduce my taxable income. It was solid advice on paper: contributions would lower my tax bill while helping me save toward a future home purchase.
The problem was that I wasn’t sure it fit my reality. I’m single and rent a one-bedroom apartment in Montreal for less than $1,000 a month, so homeownership isn’t a pressing goal. More importantly, my marginal tax rate was already approaching 30%, and the idea of locking away another significant portion of my income while also paying a large tax bill felt impossible.
Was I simply being undisciplined, or was traditional financial advice built around assumptions that didn’t reflect the realities of variable income?
To find out, I spoke with financial planners, a money psychologist, and freelancers to better understand what financial planning looks like when your income isn’t predictable.
Why irregular income changes the rules
One of the biggest challenges of being self-employed is managing uncertainty. When I worked in-house, it was much simpler to understand how much I had coming in each month, what my expenses were, and what was left over.
When you’re self-employed, those numbers aren’t as clear, and they’re also not necessarily guaranteed. Projects get put on hold. Budgets get frozen. But your bills still need to get paid, so you’re left scrambling to make up that income.
Conventional financial advice often assumes that income is predictable. Keep three to six months of expenses in an emergency fund. Avoid interest-bearing debt. Max out your RRSP, TFSA, and FHSA. But for freelancers, liquidity matters, too. The question isn’t whether your income will fluctuate, but how you’ll manage it when it does. How can freelancers build financial systems that account for that uncertainty without agonizing over every dollar?
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To answer that question, I spoke with financial planner Chris Enns, who specializes in helping artists and others navigate the realities of variable income.
Enns starts by asking every client the same question: “What is your money for?”
The answer helps him design a financial plan tailored to their goals, drawing from a range of tools and systems while recognizing that no single approach works for everyone.
That philosophy is shaped by his own experience. As a self-described “opera-singing financial-planning farmboy,” Enns spent the first 10 years of his career training in opera performance. During that time, he says, he ignored money as much as possible—a decision he now recognizes was a mistake. Today, he’s made it his mission to help artists and other people with variable income become more financially literate.
One thing Enns sees often is clients following conventional financial advice without stopping to ask whether it actually serves their goals. One of the most common examples? “I need to max out my RRSP.”
