Serial ‘job hopper’ changed his job 41 times

Gary Waldon has been a bank teller, teacher, bouncer, topless waiter and more. Here’s what being a serial “job hopper” taught him.

From his first after-school job as a milkman to a teacher, small business owner and everything in between, Gary Waldon has seen it all during his unorthodox career.

The Queenslander has racked up more than 41 different gigs since his teen years, and has now spent decades as a serial “job hopper”.

In fact, he gave up his teaching career after just three years in the role despite years of study when he came to the realisation his dream job wasn’t for him after all.

“Teaching is one of those truly noble professions but it was not a perfect fit for me – I had more of a commerce drive and I quickly realised I was not able to give as much to the role as it deserved,” he said.

He then launched a retail business but picked up “multiple” jobs on the side to boost cash flow, including working as a topless waiter, actor, model and presenter.

But he said the competitive nature of the entertainment industry also made him feel “uncomfortable” and like a “failure”, and that it demanded a “level of resilience I didn’t have at the time”.

He told news.com.au he had taken on a string of roles over the years for many different reasons, and now he has also added author to his long CV after publishing Sort Your Sh*t Out, a guide to help others thrive during tough times based on his own experiences and lessons learnt along the way.

He’s also managed to turn his lifelong job-hopping habit into a fresh career of its own, advising CEOs and companies as a “transformational change specialist”.

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Gary Waldon has had more than 41 jobs. Picture: Supplied

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Mr Waldon said he’d taken on some jobs over the years purely because they already interested him and he figured he “may as well get paid”, while he took on others out of necessity, such as when his fashion business was no longer viable.

For Mr Waldon, one of the most important lessons he’s learnt is not to tie your identity too closely to your job title.

“One of the biggest things for me was when I realised your identity doesn’t necessarily have to be about the things you are doing at the time – it’s more about being inquisitive,” he said.

And he added that every job taught skills which could be transferable into other, even unrelated, industries.

“For example, being a labourer is all about accuracy and attention to detail, and being a topless waiter taught me to take things with good humour and not get offended,” he said.

“I wouldn’t be who I am today without all those experiences and they each taught me different things.”

But it hasn’t always been smooth sailing.

“One job that didn’t fit as well was when I worked as a bank teller – that gig was very operational, in the back of the office and I’m a bit of a talker so it didn’t feel like the right job for me,” Mr Waldon said.

“Another one that didn’t last long was when I worked as a kitchen hand in the middle of summer – it was sweaty and hot … and I lasted two weeks before I realised at 16 I didn’t want to be playing that game.”

“I have a brain that doesn’t like to stop too often – I’d think, ‘Let’s give it a try and see how it feels.’ Change is where I get my biggest buzz.”

He said another benefit from job hopping was the resilience that came with it.

Originally published as Serial ‘job hopper’ changed his job 41 times