There have been glorious triumphs and, I confess, some dismal defeats, in my 22 years as racing editor of this paper, tipping under the nom de plume Hyperion.
But when it comes to gambling with the happiness of my daughters (three of theatre-going age) I need to make sure the odds are stacked in my favour.
Tickets to see David Tennant – whose under-nourished body apparently holds some allure for teenage girls – as Hamlet in the London RSC production will apparently bring the required joy.
But this is a run of only 32 performances, the lion's share of tickets has been snapped up by RSC members and it is too late to sign up now. Having failed pathetically to get tickets for the Stratford run, I cannot disappoint them again. There are only 100 tickets per performance for the general public and all on sale from 10am yesterday.
There can be no messing about with net booking – the site is bound to crash. So, the box office it must be and a trip to the Novello Theatre. But only a fool would risk rolling up there at 10am. The obvious answer is to camp outside overnight.
When I make base camp at 9pm on Thursday there are already five determined folk ahead of me. Some have been there since 5pm; they're ready to party and the wine is flowing. The only problem is a lack of suitable drinking vessels. So a quick trip to Ladbrokes on the Strand where a tenner on Hyperion's selection in the 9.30pm at the Great Leighsall-weather track produces a double result of £60 profit and a stack of cups.
But will the serious gamble pay off? It is 5am before the queue begins to form properly. The comfort of a canvas chair on the pavement has been rejected for a shared tarpaulin in the theatre's doorway. New arrivals are politely redirected towards the tail-end, which is now a few hundred people away and disappearing round the next corner.
Morning has broken, and a member of the theatre's staff comes out to reassure us: "Don't worry, everyone here now will get a ticket. I wouldn't brave coming out if they weren't." So, 17 hours sitting on the pavement is going to bring the same reward that these showered and suited blow-ins are about to enjoy? "Not fair", as my daughters might have said if they hadn't spent the night snuggled under their duvets.
So waiting for Hamlet, was it worth it? The tangible reward is four tickets in the centre of Row D, well within spitting range of the great man. Then there is the undying affection of my girls (I haven't told them about King Lear and his daughters) and the three darlings might even let their old dad have the fourth ticket.
But what are the odds that Tennant gets laryngitis?