In news that’s sure to send many a child of the early 1990s into a tailspin of existential panic – Mr Will Smith turns 50 today. That’s right. The Fresh Prince is now officially middle-aged, and if you’re old enough to remember the last time he referred to himself by that particular sobriquet, then so are you. Too bad.

No 50th birthday is complete without a good old-fashioned mid-life crisis. For his part, Mr Smith is celebrating reaching this milestone by throwing himself out of a helicopter into the Grand Canyon, an elasticated bungee cord the only thing holding him back from certain death. In a video posted to his YouTube channel, where he will stream the stunt live, he explains his motivations.

“I’ve had a whole lifetime of feeling squashed and squelched and controlled by fear,” he says, raising the question of just how much of an extrovert he would have been had he not been so cruelly afflicted. At the risk of stating the blindingly obvious, a man who named his debut album Big Willie Style doesn’t seem like the anxious type.

That’s the thing about fear, though. Those who go to the greatest lengths to overcome it are often the ones most affected by it. Some bungee jump out of a helicopter to conquer a fear of heights. Others perform at open mic nights to overcome stage fright. But living fearlessly doesn’t have to involve such bold gestures. It can be as simple as initiating a conversation with a colleague you’ve been sharing an office with for a year, but still haven’t met. Or dressing in a way that expresses your true sense of style in the face of what people might think.

In the latter example, Mr Smith again provides us with an object lesson. Throughout the early stages of his career, from channelling the best (and worst) of early 1990s style as the Fresh Prince of Bel Air – MC Hammer harem pants, highlighter-yellow snapbacks, tribal-print shirts and Air Jordans – to rocking outrageous suits to the Grammys in the late 1990s and early 2000s, he has never once shied away from making an impression. After an Oscar nomination for 2001’s Ali turned him into one of the most bankable stars in Hollywood, he developed a look that was 50 per cent leading-man power dressing and 50 per cent streetwear from the Sean John and Fubu heyday. Unlike his style from the Fresh Prince era, this early 2000s phase is arguably still a few years away from a positive re-evaluation, but that’s hardly the point. It’s the anarchic IDGAF attitude. It’s the swagger that matters.

And while his style today is a little more reserved – come on, the guy’s 50 – he has a natural heir in his son, Mr Jaden Smith, who is, by all accounts, even more of a risk-taker than his father. You can say what you like about an 18-year-old attending a ball brandishing his freshly shorn dreadlocks in his hand, as Mr Jaden Smith did at last year’s Met Gala, but ask yourself this: would you have the nerve to do something like that?

While you’re tuning in to Mr Smith’s livestream, then, and keeping your fingers crossed that his bungee cord does its job, why not take a moment to ponder your own worst fears, sartorial or otherwise, and consider what it would take for you to make your own leap of faith? It doesn’t have to be quite as literal as his.