When a Successful Year Starts to Feel Like Punishment
As a self-employed person, this is probably a familiar experience. Clients are coming in, revenue looks strong, and you feel good about where things are heading.
Then tax time rolls around.
Suddenly that successful year doesn't feel so great anymore. Revenue was good, but taxes weren't set aside along the way — or not enough was. So when the bill lands, the whole year starts to feel like a curse instead of a win.
But the problem isn't the revenue. We like the revenue. We want more of it.
The issue is not having a structure in place for when money comes in. Without that structure, success and stress tend to show up together every spring.
"I should have known better."
This is something I hear a lot this time of year. Along with: "I feel embarrassed that I didn't plan for this."
The people saying these things are capable, thoughtful professionals who care deeply about their work and their clients. But when the financial side of the business feels murky, tax time has a way of turning into a moment of self-criticism.
Most of the time, though, the issue isn't capability or effort. It's simply that taxes were never built into the day-to-day management of money. When we start treating tax like a daily necessity rather than an annual surprise, tax time tends to feel a whole lot more predictable — and a whole lot less stressful.
So if you catch yourself thinking "I should have known better," try pausing on that thought. Replace it with: I'm learning as I go, and I'm taking steps to improve. Just noticing the thought and shifting it can reduce a surprising amount of guilt.
The email sitting in your inbox
Here's another thing I see all the time: an email from an accountant sitting unread. Maybe it's been there a few days. Maybe longer. Every time you see it, something comes up — a bit of dread, a vague sense of apprehension — so you scroll past it and tell yourself you'll deal with it later.
This isn't about being irresponsible. It's about not yet having a comfortable, familiar relationship with your numbers. When you don't feel confident about what's in those numbers, it makes sense that you'd rather not look at them.
But avoidance tends to make the anxiety worse, not better. And the good news is that building that familiarity is very doable — it just takes some intentional steps.
Where to start this week
First, open the email. Then block time in your calendar — even just one appointment with yourself — to pull together what your accountant needs. Once you've done that, send them a quick note to let them know what date they can expect to hear from you. They're too busy to judge you for being behind, and they will appreciate the heads up.
Second, start setting taxes aside going forward. Here's a simple way to do it:
Look at what the “tax man” wanted in income tax last year. Divide that by your total income to get a percentage.
Open a savings account specifically for income tax.
Each week, apply that percentage to whatever landed in your business bank account and move it over.
It will feel tight at first, and the percentage doesn't need to be perfect right away. Just getting started and doing it consistently is what matters.
