Toby Young Toby Young

Status Anxiety | 21 June 2008

If I try to take Manhattan again, I’ll fail completely. Perfect!

If I try to take Manhattan again, I’ll fail completely. Perfect!

Well, my wife had the baby. I am now a father of four and, as such, have been doing some thinking about how I am going to support them all in the years to come. My problem is, I do not really have a profession. Or, rather, my chronic inability to shimmy up the greasy pole has become a kind of career in itself. I make my money from being a loser.

The trouble with being a professional failure is that my livelihood is dependent on not being able to earn a living. The moment I am perceived to be a success — even if it is just a successful failure — I can no longer plough this furrow. I have chosen a career in which I cannot, by definition, do well. In order to pay the mortgage, I have to remain unemployed.

The only solution is to keep setting myself more and more outlandish goals. For instance, I could write a book about my efforts to represent my country at the 2012 Olympics. Even if I chose a sport in which there are virtually no English competitors — softball, for instance — I would still fail. That way, in the unlikely event of the book becoming a bestseller I could still claim to be a Big Fat Loser.

In this vein, I have decided that my next big project will be to try and take Manhattan. I had a go at this in the mid-1990s when I went over there to work for Vanity Fair and was such an abysmal failure that I actually did get a bestselling book out of it. This time round, I will try to do it as a stand-up comedian.

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