Toby Young Toby Young

Lessons from a friend with a tragic flaw

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issue 24 August 2013

Character is destiny, according to Heraclitus, and that becomes increasingly clear as you get older and chart the ups and downs of your friends.

Take the fate of one of my oldest acquaintances, who I’ll call ‘Philip’. Up until his mid-forties, Philip had a pretty spectacular career as a journalist and broadcaster. He won awards, and was invited to speak at international conferences. His personal life was equally successful. He married a beautiful, intelligent woman and had two lovely children.

But Philip has a tragic flaw: he’s hopeless with money. In all the time I’ve known him, I don’t think he’s ever paid a tax bill on time. He’s VAT-registered, and has been for 15 years, but when I asked him how he paid his quarterly VAT bills he gave me a puzzled look and admitted he didn’t know what I was talking about. That could be because whenever he receives a letter from HMRC he shoves it in a drawer where it sits alongside hundreds of others, all of them unopened.

You might think that isn’t a flaw at all, simply an attempt to put off paying his taxes. But his hopelessness extends way beyond this. I’ve known him borrow £1,000 from a payday loan company and, in an attempt to pay off all his debts in one fell swoop, put it on a horse. He doesn’t currently have a phone because he sold his mobile for beer money. When I discovered this, I ‘lent’ him my old iPhone, but he promptly sold that too — not very sensible for someone who is still, notionally, a working journalist.

For years, he got away with this. It didn’t appear to affect his life one jot. And as someone who is reasonably careful with money, I resented that.

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