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. It was as if the normal rules of life that force the rest of us to compromise in all sorts of boring little ways didn’t apply to him. He drove a fancy car, lived at a fashionable address and took his family on exotic holidays. I began to think my Protestant habits of financial prudence and delayed gratification might not be so sensible after all.

But it all caught up with him in the end. His wife divorced him, his journalistic output has dwindled to one article a year and he now lives in a rented cottage in the countryside — a far cry from his glory days in the Groucho Club. Occasionally, I receive emails from him asking if I’d be willing to serve as a guarantor of a loan he wants to take out from a website called something like onebornevery-minute.com.

You probably detect an element of schadenfreude in this account of Philip’s misfortune — and you may be right. But I prefer to think I take no pleasure in his reduced circumstances in spite of being irritated by his Teflon-like ability to avoid any comeuppance for years. This is largely because, in all sorts of ways, he’s a great guy. He’s generous to a fault — whenever he has money he spends it as freely on other people as he does himself — not to mention charming, funny and compassionate. He’s a fantastic father, much better than me, and was a faithful and devoted husband. Indeed, the fact that he’s such an exemplary human being in so many other respects is one of the reasons he got away with mismanaging his own financial affairs for so long. He’s never been short of friends willing to help him out.

There’s also a mitigating circum-stance. Philip had a terrible role model in the form of his father. Like him, his father was a lovely man, but so bad with money he was forced to declare bankruptcy when Philip was a child and, as a result, his marriage to Philip’s mother collapsed.

Whenever I review the circumstances of Philip’s life, it seems a textbook example of Nietzsche’s concept of amor fati — the idea that a person is doomed by what they perceive to be their tragic fate and their blithe acceptance of this curse. At some level deep within his unconscious, Philip believes he cannot help but repeat the same mistakes his father made.

Could he behave any differently? Maybe, but I and many others have tried everything to get him to change his ways to no avail. Being in thrall to his father’s misfortune to such an extent that he wants to replay it in his own life is part of Philip’s character — and character, as Heraclitus said, is destiny.