Hire Yourself

Tax season always brought the same question to mind: why is it still this stressful for so many people, when the software gets easier and cheaper every year?

I’ve seen the full range. Some people have everything to me the day filing opens, organized enough that I could practically just hit enter. Others I’d chase for years before finally filing a decade’s worth of returns in one sitting. In between, every shade of relief and dread you’d expect.

To be clear, I’m not talking about genuinely complicated returns; sometimes hiring a specialist is exactly the right call, so you can focus on what you’re actually good at. I mean the more ordinary case: employees, or people running a simple sole proprietorship, who still can’t bring themselves to sit down and do it.

Most of what stops people comes down to fear, in one form or another. Fear of making a mistake and facing penalties. Fear of having made too much money and owing a lot. Or, on the flip side, fear of discovering they made very little, and reading that as some kind of verdict on themselves rather than just a number. Easier to not look at all.

Then there’s the sheer volume of it. If you run your own business without a system for tracking money in and money out, facing a full year of receipts can feel enormous. I understood that fear well; some of my clients handed me a literal shoebox of receipts every year. Not my favourite kind of work, but it always helped to know I’d get paid for it.

All of that fear adds up to people avoiding a significant part of their financial lives. I’ve always believed that more information puts you in a better position to make good decisions, and burying your head in the sand tends to keep people stuck rather than protect them.

So what actually helps?

If it’s genuinely overwhelming, hiring someone is a reasonable option. Find someone you’re comfortable talking to, and ask them to walk you through what they’re doing as they go. It costs a bit more upfront, but it usually pays off, both in savings and in finally understanding your own numbers well enough to lose the fear around them.

I’m a firm believer in outsourcing what you genuinely can’t or don’t want to do yourself. That’s not a failure; it’s knowing your limits. But there’s a difference between outsourcing the task and outsourcing your understanding of your own financial situation. The first is fine. The second leaves you exactly as afraid of your own numbers as you were before, just with someone else quietly managing that fear for you instead of you managing it yourself.

My favourite suggestion, though: hire yourself. Decide what your own time is worth, sit down, and do the work. Once it’s done and you know what you’re owed, take that money and spend it on something that actually makes you happy. If saving it is what makes you happy, save it. But there’s a good case for putting at least some of it toward an experience you’ll actually remember.

Do that once, and next year’s taxes start looking less like a chore and more like an appointment with a bit of found money at the end of it.