Every year for the past 10 years starting in 2008 I have set myself a goal to do something I thought was impossible. Each challenge took me out of my comfort zone and either developed a new habit, stopped a bad habit or developed me personally in new ways I never imagined. 

One. Quit watching rugby 24/7

I guess I started out easy although I was rather rugby obsessed. To go cold turkey was a big deal for a rugby nut.

Quit being a consumer for a year

I bought nothing new other than essentials of life. If I broke something I cared about I would fix it. I still have a set of garden chairs I repaired 8 years ago.

Three. Cycle the length of New Zealand.

To make it harder I did it uphill from Stewart Island to Cape Reinga! 2 months and I lost 20kg in the process. (it’s not anymore uphill going from south to north but you would be surprised by how many people thought it was).

Four. Start a $100m venture in the middle of the GFC

I founded Vend during the GFC when many were claiming the sky was falling and it would never be the same ever again. I thought that’s just BS. Vend quickly grew to be NZ’s fastest growing startup and is now sailing towards a $1b valuation.

Five. Quit reading or watching the news media

Life instantly became more positive without my daily dose of pessimism. I worried I would be less informed, but instead the opposite happened. I had more time to contemplate the bigger issues when I wasn’t constantly distracted by daily gossip. 

Six. Quit drinking for a year

This was harder than I expected. When you are at industry events two nights a week and the “norm” is that you drink. I had many unsolicited apologies from people thinking I was a recovering alcoholic. I had to explain it was just a choice.

Seven. Run 1,000km

I hadn’t run 2 km in one go but I figured I could run 1,000,000 meters in the space of a year. It worked out to be 3 km every day. EVERYDAY. Miss a few days then you run a quarter marathon to catch up.

Eight. Get a paid gig to sing in front of 100 people

This was to take me well out of my comfort zone, and I would be judged by people. 100 of them. To make it worse, I crowdsourced the setlist 48 hours before the gig. 

Nine. Found a charity to make a difference

I set up the Pam Fergusson Charitable Trust with the purpose to change the lives of New Zealanders who needed it. My mum, Pam, was a paraplegic solo parent of three boys and she did impossible things every day. It was for her I really did all these impossible things. She passed away 7 years ago so never saw the benefits of all this crazy shit, and so I thought I would add her name to a bunch of them. The first initiative the trust started was OMGTech! And we have taught thousands and thousands of kids from all backgrounds how to program, design and invent with future technology. And it’s getting bigger and bigger every month.

Ten. Cycle around the world in 80 days

I charted a path around the southern hemisphere I could circumnavigate the globe in a straight line, and started in Cape Town and cycled east to Buenos Aires covering South Africa, Australia, New Zealand, Chile and Argentina as I went. To top it off I then entered an elite cycling event mountain biking over the Southern Alps where I almost lost my feet.

If you want a summary of the first 7 years of my challenges see my TEDx talk.

What's next?

I am working on my next impossible challenge, and it will be somewhat bigger.