Can you believe it? 2024 is coming to a close, and for many business owners, that means…(drumroll).. tax season is right around the corner. OMG! Cue the stress, anxiety, and that little pang of tax-time dread.
“I’ll just put it off for another week or so” you think, and hey, it’s not your fault if the dog ate your financial papers, right? After all, taxes can be rough… There’s a lot on the line, and sometimes the thought of sorting through all that stuff can feel overwhelming.
We’ve all been there. Tax season sneaks up, and suddenly, you’re desperately shoving receipts into bags and wishing you had a time machine. And if we’re honest, there’s that little pang of dread — did I forget anything? Did I save enough for taxes? Did I file my HST? “Isn’t there some receipt for that thing I bought last June?” The truth is, preparing to file taxes can be loaded with a lot of guilt, second-guessing and worse, a lot of anxiety.
Luckily, we can take a little pressure off by…blaming the dog! After all, he’s been known to chew through homework, right? Why not tax docs?
Or how about we make tax prep… dare we say… fun? Or at least a bit easier just to minimize errors and problems along the way? In that case, let’s dive into some common tax-prep hurdles (like disappearing receipts) with a humorous twist and share a few tricks for overcoming them!
The Case of the Disappearing Receipts
You know how it goes. You had everything together…once. It was all neat and tidy, colour-coded, and stapled in labeled folders. But then life happened. Between juggling client calls, managing inventory, and simply keeping up with day-to-day business tasks, staying on top of every receipt can feel impossible. In the hustle of running a business, it’s easy for receipts to get shuffled around, forgotten in the car, or left at the bottom of a purse or laptop bag.
By the time April rolls around, those once-organized receipts are nowhere to be found — especially the one for that big purchase that was 100% deductible.
But c’mon! It really was the dog! That innocent little face and wagging tail might say otherwise, but while you were at work, he was pulling out receipts like a pro, ripping them to shreds, and leaving an unfixable mess trailed around the house. All those old takeout receipts, business expenses, and crumpled gas station slips — gone!
Or so we thought…
Bank Statements – Did The Dog Eat Those Too?
Let’s not forget our old pal, the bank statement — a document that can make or break your deductions. You used to have a crisp pile of them (or maybe an organized digital file… somewhere), but now? Well, would you believe it if I told you that the dog got creative? You try to tape the shredded statements back together, but it ends up looking like a kindergartener’s art project. So, you tell yourself you’ll find them online… later. And yet, “later” keeps stretching on as you imagine explaining to the CRA Auditor that, yes, you’re aware your dog hates taxes too!
Somehow, he sniffed out just the ones you needed, and poof — they’re shredded beyond repair, just like the receipts. But the truth is, it’s not always the dog’s fault. As a small business owner, you’re constantly moving between tasks, accounts, and meetings. It’s easy to misplace a statement or overlook downloading one each month.
And with digital banking, statements often end up scattered across emails or cloud drives, mixed in with other personal and business documents. By the time tax season arrives, finding everything feels like piecing together a mystery.
The Missing Mileage Log
How about your mileage log? Remember that New Year’s resolution to log every mile for work? The one that lasted approximately two weeks?
Tracking mileage always starts out strong, but as business gets busy, it’s one of the first things to fall through the cracks. Between meetings, supply runs, and client visits, finding time to log each trip can feel like an impossible extra task. Not to mention, that notebook you swore you’d keep in the car somehow always ends up somewhere else — in the office, at home, or lost under a pile of files.
But of course, we blame it on the dog. After all, he loves chewing on notebooks, too! And guess what he got his paws on just last week?
Suddenly, you’re piecing together trips with a combination of Google Maps, memory, and sheer guesswork. Was that drive really 15 kilometers? Could it have been 20? You figure “close enough” is the new accurate. Maybe the tax gods will understand — after all, it’s not like you wanted to lose your log. If only the dog hadn’t mistaken it for a chew toy…
Procrastination Station: The Final Frontier
But let’s face it, while we keep putting the blame on others – like our dog — there’s also the small matter of procrastination. The truth is, your dog isn’t the only culprit here. There’s something about tax prep that makes us all experts at delaying the process and avoiding the inevitable. There was always one more day to organize everything, one last episode of The Dog Whisperer to watch on TV before facing the numbers.
But now, tax time has officially arrived, and instead of a neat and tidy file, you have a pile of dog-chewed evidence that only a forensic accountant can make heads or tails of.
Yet even now, procrastination rears its head. Plus, the dog looks ready for a walk, and those taxes can wait… right?
It’s Never Too Late To Do Your Tax Prep
Even though the dog has “helped” you avoid tax prep for yet another year, let’s be real: there’s no reason to feel guilty about it. Life is busy, and taxes are hard! And guess what? If you haven’t kept everything together, you’re not alone!
The good news? You can still get everything in order without feeling ashamed. Blame the dog as much as you want (I won’t tell), but taking a few steps to organize, even last minute, can save you from headaches. And if it all feels overwhelming, remember: there are people to help, and no one’s judging you.
How To Stay Organized (With or Without the Dog’s Help)
So, what’s the game plan?
Set Up a Designated Spot for Tax Documents
Create a dedicated space for all things tax-related—whether it’s a small filing drawer, box, or folder. This is where you can store receipts, invoices, tax forms, and any other important documents throughout the year. By keeping everything in one spot (and out of reach of curious paws), you won’t have to scramble at the last minute to find things when tax season arrives. Plus, it’ll make your life a lot easier during the prep process, knowing exactly where to go when it’s time to organize and file.
Use Digital Tools for Receipts and Expenses
Tracking expenses and managing receipts doesn’t have to be a messy, paper-filled task. With today’s digital tools and apps, you can snap a picture of your receipts, upload them to the cloud, and categorize your spending as you go. Not only does this eliminate the clutter, but it also makes your financial records more accessible. Many apps also offer reporting features, so you can quickly pull up summaries at any time. With everything digitized, you can review your finances easily and avoid the panic of last-minute scrambling when tax season rolls around.
Schedule a “Tax Prep Day” Each Month
Don’t wait until the last minute to organize your finances. Set aside one day each month to review and organize your financial records. This can include sorting receipts, reconciling accounts, and categorizing expenses. By staying on top of it, you’ll prevent the dreaded end-of-year overwhelm. Plus, it’ll make tax season feel more like a quick check-in than a major undertaking. A little regular upkeep can go a long way in reducing stress and keeping everything running smoothly throughout the year.
Work With a Professional Bookkeeper
If you’re facing a mountain of tax documents and financial confusion, a professional bookkeeper can be your best friend. Bookkeepers are experts at organizing and managing financial records, and they can help you get everything in order, especially if you’ve let things pile up. They can assist with sorting out discrepancies, ensure you’re maximizing your deductions, and help avoid costly mistakes that could trigger audits or penalties. With a bookkeeper on your team, you’ll save time, reduce stress, and be in a better position to tackle tax season with confidence.
When the dog finally lets you sit down to work, staying organized will make the whole process feel much more manageable. And who knows? You might even start feeling tax-time confident with a little help along the way.
Wrapping It Up (Dog-Free!)
Taxes don’t have to be stressful or shame-inducing. Blame the dog if it helps (we all need a scapegoat!), but don’t let tax time catch you off guard. With a bit of structure, a dash of humour, and maybe a helpful bookkeeper like me, you can keep things smooth and stress-free — even with a mischievous pup around.
And remember, if you’re feeling overwhelmed, there’s always a way to get help (without the dog’s assistance this time!). So go ahead and book that call — no judgment here, just a little less tax-time chaos.
Did you like this article? You may also like:
What the Heck is Bookkeeping…Really??
The Money Habits of Highly Successful Women
From Worrier to Warrior: Conquer Financial Fears with Life Insurance
