As the nights draw in and the pumpkins appear, we thought we’d share some true tales from the darker side of accountancy - stories of missed deadlines, muddled numbers and misunderstandings that turned into financial nightmares.
Don’t worry - the names (and some of the details) have been changed to protect the guilty. But every one of these stories is based on something that’s really happened. So gather round the campfire… and remember, there’s always a happy ending if you ask for help early.
The Landlord’s 20-Year Secret
Our first tale begins with a landlord who’d been quietly renting out a property for twenty years without ever declaring the income. He thought it didn’t really matter - after all, it was “just a bit of extra cash”.
But with HMRC now cross-checking data from banks, letting agents and online platforms, the truth was bound to surface eventually. When the realisation hit, he came to us for help.
We gathered twenty years of rental records, calculated the tax properly and made a voluntary disclosure through HMRC’s Let Property Campaign. The result? Significantly reduced penalties and a clean slate.
Lesson: HMRC would always rather you come forward than wait to be caught. The earlier you act, the less frightening it gets.
The Phantom Receipt Dropper
One morning, a mysterious stack of crumpled receipts appeared on our reception desk. No cover letter, no envelope, no name. Just a heap of paper.
We puzzled over it for days, trying to work out whose they were - until a client rang to ask how their bookkeeping was coming along.
“Oh,” they said, “I dropped everything off last week!”
Mystery solved - but it could have been avoided entirely.
Lesson: Good bookkeeping doesn’t need to be supernatural. Label your records, or better yet, send them digitally through tools like Apron or Xero. You’ll save your accountant a séance.
The Client Who Drained the Coffers
This one still gives us chills. A business owner delivering professional courses took deposits totalling over £150,000. The problem? The courses hadn’t yet run - the money wasn’t technically hers to spend.
Despite our warnings, she withdrew every penny for personal use. When refunds were requested and bills came due, there was nothing left. The business went into liquidation, followed by personal bankruptcy.
Lesson: Company money isn’t your money until it’s properly earned. Spending ahead of delivery might feel harmless, but the ghosts of cashflow will always come calling.
The DIY Accountant
Determined to save on fees, one client decided to prepare their own accounts and VAT returns for three years. “It can’t be that hard,” they said.
By the time they called us, they were drowning in spreadsheets and sleepless nights. VAT had been claimed on everything (even items that weren’t eligible), and tax had been miscalculated across multiple returns.
We had to resubmit two sets of accounts, redo the corporation tax, and correct all the VAT - resulting in thousands owed to HMRC.
In the end, our fee to fix everything was higher than it would’ve been to do it properly from the start.
Lesson: DIY accounting might look like a money-saver, but it rarely is. Getting it right the first time costs far less than cleaning up the mess later.
The CIS Catastrophe
And finally, the story of a well-meaning gardener. While landscaping a client’s garden, he hired a subcontractor to build a brick retaining wall. The subcontractor invoiced, was paid in full - and the gardener thought nothing more of it.
Until HMRC came knocking.
Because the work involved construction, the gardener was technically a contractor under the Construction Industry Scheme (CIS). He should have registered, deducted CIS tax from the subcontractor’s payment, and filed monthly CIS returns.
By missing this, HMRC not only demanded the tax but also added penalties for every late or missing return going back years - a bill running into thousands.
Lesson: Just because your business isn’t in “construction” doesn’t mean HMRC sees it that way. If in doubt, check before you pay. It’s cheaper than explaining it later.
The Moral of the Story
These stories might raise a smile - but each one shows how easy it is for everyday financial mistakes to snowball into real problems. The good news? Every one of them could have been prevented (or fixed) with the right advice and a little honesty.
At Donaldson Ross & Co, we’ve seen it all - and helped clients find their way back from every kind of financial fright.
If you’ve got a story starting to sound like one of these, don’t wait for the sequel. Get in touch today, and we’ll make sure yours has a much happier ending.