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ContractorCalculator CEO takes the (192m) plunge for National Freelancers Day!

ContractorCalculator CEO Dave Chaplin makes the 192 metre 83 km/h jump from Auckland’s Sky Tower in New Zealand, the tallest building in the southern hemisphere, to celebrate National Freelancers Day and to encourage others to make the jump into contracting.

“When National Freelancers Day was announced by the Professional Contractors Group (PCG), I’d already booked my trip to New Zealand,” explains ContractorCalculator CEO Dave Chaplin. “I wanted to mark the occasion with something that would inspire others to take the plunge into contracting, so when I heard about the SkyJump it seemed the perfect opportunity.”

So was it scary? “You bet it was!” says the former IT contractor and author of the Contractors’ Handbook, “It was much more frightening than taking the leap from my permanent job into IT contracting in the City of London. But I knew I had a safety line, just as when I moved into contracting my safety line was knowing that I could always return to a permanent job. Fortunately, in both cases, that wasn’t necessary!”

Before they make the leap into contracting, Chaplin urges budding freelancers and contractors to plan and prepare. “Anyone thinking of going contracting has a huge amount of resources available to them to plan the transition,” he says. “PCG, the organisation behind National Freelancers Day, provides a wealth of information and support. Plus there are now easy-to-follow guides for first-time contractors and the more experienced contractor on There is also the Contractors’ Handbook, written so that others could benefit from my hard-won experience.”

Anyone thinking of going contracting has a huge amount of resources available to them to plan the transition.

Dave Chaplin, CEO ContractorCalculator

Chaplin believes many successful contractors make their jump into contracting prompted by ‘right, that’s it!’ moments, such as broken promises made by employers over promotions or pay rises. “You reach a point when the desire to make the jump outweighs the fear that makes you stay put,” continues Chaplin. “When I was approaching the edge of SkyJump, there came a point when there was no way I was going to ask to be untied and left to go down in the lift, because I’d spend the rest of my life wondering what it would have been like!”

Chaplin’s advice to anyone who wonders what freelancing is like is to make the jump and give contracting a go: “I spent six months thinking about becoming a contractor and, once I’d made the jump, I wondered what all the fuss was about and haven’t looked back!”

Published: 23 November 2009

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