Juggling your accounts and your business is a tricky endeavour. It's why so many people get it badly wrong, and why our service is all about simplifying the process.

Some self-employed workers leave everything to the last minute and make a complete hash of their bookkeeping. Others think they can cheat the system and attempt to avoid paying the tax they owe.

All of them are destined for trouble, be it an all-nighter the day before the Self Assessment deadline (31st January, write it down!), or at worst, a few years behind bars. Welcome to the tax rogue Hall of Shame!

Jimmy Carr

"I've made a terrible error of judgement". An offshore 'wealth management' scheme made headlines in 2012 when it was revealed that comedian Jimmy Carr was a prominent beneficiary.

The report claimed that the popular stand-up and TV presenter was sheltering £3.3 million annually and paying as little as 1% tax using the K2 scheme, which channelled salaries through Jersey-based shell corporations.

While the scheme was a case of tax avoidance rather than evasion (and therefore not illegal at the time), it drew sharp criticism, with then-Prime Minister David Cameron calling it "morally wrong".

The professional funnyman was hardly a tax expert, and Carr understandably found himself wooed by the scheme:

"I met with a financial advisor and he said to me 'Do you want to pay less tax? It's totally legal'. I said 'Yes'."

What he did wrong:

Carr soon found out that sometimes things are too good to be true. After a public outcry, he apologised, pulled out of the scheme, and faced a reported £600,000 tax bill in 2014. HMRC has since cracked down hard on these types of arrangements, even winning a major legal case in 2019 against a promoter of a similar scheme.

Despite the scandal, Carr has since spoken out against tax loopholes and appears to be on the straight and narrow, with his company reportedly paying £1.2 million in tax and social security in 2025.

Alan Partridge

"I don't avoid tax , I evade it. Or is it the other way around? Shut up!"

Steve Coogan's egotistical TV host turned radio-DJ encountered a tandem of tax inspectors in the second series of 'I'm Alan Partridge'.

Norwich's favourite son responds by going into a total meltdown, offering out alcoholic drinks and performing an impromptu puppet show to stall for time, eventually just hot-footing it and leaving his long-suffering assistant Lynn to explain his transgressions.

What he did wrong:

The main cause for concern for Alan are the personal receipts he has filed under business expenses.

No matter what the excuse, anyone would have a hard time convincing HMRC that a cinema ticket for one to Shrek ("research!"), a pair of shoes ("you can't go and see Shrek without any shoes!") and a dressing gown are "wholly, exclusively and necessarily" for business use.

In his panic, he also blurts out that he is relieved he can pay the contractors working on his new house cash-in-hand, which of course is a big no-no.

Alan's plight perfectly illustrates the horror of a tax audit should you be on the wrong side of the law. Just don't risk it - separate your business and personal expenses at all costs.

Check out our related article "Business Lessons from Alan Partridge".

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Vince Cable

"An honest mistake was made" In 2011, the then-Business Secretary failed to inform HMRC when his income exceeded the VAT threshold.

Media appearances and a book deal had reportedly increased the former Lib Dem leader's earnings to a tidy £192,000 on top of his annual MP's salary.

If your turnover exceeds the VAT registration threshold (which is £90,000 as of April 2024), the rules state that you must register within 30 days. At the time of Cable's error, the threshold was £73,000.

Cable was billed for a figure of "less than £15,000" and was let off with a penalty of £500, reduced from £1,000. His spokeswoman said in a statement: "All Vince's tax affairs are above board, and he went out of his way to settle this quickly."

What he did wrong:

Cable, or at least his advisors, were alert enough to notice the mistake before it became a huge problem, but this could (and should) have been avoided by contacting HMRC as soon as the threshold was reached.

The £500 fine was dutifully paid, but this mishap was quite the egg on the face of a high-ranking parliamentarian who has repeatedly spoken out in public against tax evasion.

Gary Barlow

The multimillionaire Take That singer was exposed in 2014 as taking part in an 'aggressive tax avoidance scheme', leading to calls for him to have his OBE removed.

According to reports, the singer (as well as bandmates Howard Donald and Mark Owen and band manager Jonathan Wild) invested £66 million into the 'Icebreaker' scheme, which was designed to generate tax relief by appearing to invest in the music industry.

A judge ruled it was primarily a tax avoidance scheme, and by 2016, HMRC had ordered them to repay over £20 million.

What he did wrong:

"I have to take the full blame – I signed the documents. I knew what the investments were designed to do and I simply didn't ask enough questions about them," he wrote in his autobiography.

"I pay someone, a lot of people, a lot of money to take care of these things and keep me out of trouble… Bank accounts, tax returns, pensions, mortgages, expenses, inheritance planning, family trusts… they were all things that showed up in front of me, completed, and waiting for me to put a signature on them."

Barlow publicly apologised for the controversy in 2014, and the matter is now considered resolved. It's a stark reminder: always read the small print when you're handing over your financial responsibilities.

Kerry Katona

"I don't even know when I've got a debt or when my tax is due or anything."

The former Atomic Kitten was first declared bankrupt in August 2008 for failing to make final payments of a £417,000 tax bill. She was declared bankrupt for a second time in 2013.

"We had this accountant called David McHugh who was a fraud," she told the Telegraph. "I asked David, have I got enough money for my tax? He said yes; the next thing you know I got a phone call saying I might be made bankrupt. But it was my own fault for letting it happen."

What she did wrong:

In her own words: "I was like, 'I don't understand this', but at the same time I was taking a lot of coke and a lot of that period is a blur."

While McHugh is the real villain in this scenario, Kerry's story is a good example of why you should maintain regular contact with your accountant. Thankfully, after a tough period, there's no public record of her being under bankruptcy restrictions as of 2025, and she remains professionally active.

Bernard Black

"What is your mother's maiden name?" What's her first name? I just knew her as "Ma"! That'll have to do."

In the first episode of Black Books, the misanthropic shopkeeper has done such a terrible job of his bookkeeping that it has come back to bite him.

When faced with the prospect of doing a year's accounts all at once, Bernard (Dylan Moran) puts off the task with every excuse possible. He invites a pair of Jehovah's Witnesses in for a lengthy chat, turns his receipts into a 'rather smart casual jacket' and gets intentionally beaten up by a gang of skinheads.

What he did wrong:

Bernard did have the forethought to hire an accountant, but unfortunately, the alleged professional ends up going on the run from the police, leaving his client high and dry. Black is left with only his hopeless filing system consisting of 'Recent' and 'Not so recent' receipts, scrunched up in his pocket.

This is a textbook example of the stress that can occur if you don't stay on top of your paperwork. Fortunately, this was back in 2000; business owners nowadays have no excuse not to be far more equipped with digital ways of keeping records organised and up to date.

Wesley Snipes

"Why'd you get locked away?" "Tax Evasion." Fiction aped reality in the above 'Expendables 3' quote. The Blade star was released from prison in April 2013 after serving more than two years for tax offences.

Prosecutors said he had earned more than $38m since 1999 but had failed to file any tax returns for years.

What he did wrong:

Snipes' advisors were high-profile anti-tax protesters who convinced him to use the "861 argument" – a theory, repeatedly thrown out by courts, that claims US citizens' income is not legally taxable. In 2008, he was convicted on three counts of willful failure to file federal income tax returns.

But prison wasn't the end of it. As of 2018, Snipes was still facing a federal tax liability of $23.5 million. His attempt to settle the debt for just $842,061 was rejected by the IRS, proving that these problems don't just disappear when you've done the time.

Shakira

The hips don't lie, but Spanish tax authorities alleged Shakira's tax returns did. The global superstar has been embroiled in a long and costly battle over her tax residency.

In November 2023, she reached a last-minute settlement to avoid trial over accusations she failed to pay €14.5 million in tax between 2012 and 2014. She agreed to pay a fine of €7.3 million and accept a suspended three-year prison sentence, stating she did it for the sake of her children.

What she did wrong:

The dispute centred on where she was living. Prosecutors claimed she was a resident of Spain, while she argued her official residence was in the Bahamas. In a separate case, a second investigation into her 2018 income was dropped in May 2024 due to insufficient evidence.

Shakira later accused the Spanish Tax Agency of acting with "sexist prejudices" and manipulating facts, claiming her "Spanish decade" was financially lost to the legal battles. It's a cautionary tale of how complex and draining international tax disputes can be.

Lionel Messi

Even one of the world's greatest footballers couldn't dribble his way around the taxman. In 2016, Lionel Messi and his father, Jorge, were found guilty of defrauding Spain of €4.1 million in taxes related to his image rights between 2007 and 2009.

Both were sentenced to 21 months in prison. Under Spanish law, the sentences were suspended as they were for less than two years and it was a first offence.

What he did wrong:

The court found they had used a network of shell companies in Belize and Uruguay to shield earnings from image rights. Messi argued he "knew nothing" about his finances and just "played football".

The argument didn't wash. While he avoided jail, his prison sentence was later converted into a €252,000 fine, on top of millions already paid in back taxes and other penalties. It shows that pleading ignorance is no defence, and even a "suspended" sentence can be incredibly costly.

HMRC is watching - don't get caught out

As we've seen, you don't have to be actively trying to dodge tax to get yourself in hot water. And if you think HMRC is too busy to notice a few mistakes, think again.

The UK government is investing £1.4 billion to recruit 5,000 additional HMRC compliance staff to crack down on tax avoidance and fraud. They're also launching new measures to shut down promoters of tax avoidance schemes.

Using online accounting software means you'll always be aware of what tax you owe and the real-time state of your finances. You'll save yourself time, money, and the stress of a dreaded brown envelope.

Check out our article to find out more benefits of using a cloud accounting service. We also have plenty of expert tax guides, including legal ways to reduce your Corporation Tax Bill and a full section on tax reliefs available.

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