My 2014 impossible challenge: singing in a band - and getting paid for it

UPDATE: Feb 15, 2015: After a year's preparation, it's finally here. Enterepreneur Vaughan Rowsell will fulfill his 2015 "impossible challenge" by singing on stage and getting paid for it.

The gig will be March 1 at The Winchester in central Auckland, and tickets are now selling on PledgeMe from $60.

Chip in a couple of extra dollars, and you'll be able to choose a song from Vaughan's setlist, or even choose a track for him to howl (gentle now, remember one of his challenge criteria is to not get booed off stage).

Money raised from the concert will go to the OMG Tech! charity, co-founded by Rowsell, Michelle "Nanogirl" Dickinson and Rab Heath to support future inventors. Special guests are promised.

See Vaughan's original post on his challenge below - CK.

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Feb 14, 2014: Every year I do an impossible challenge. It’s a thing. Okay so obviously the things I attempt are not impossible, because impossible is impossible! Right? It’s funny how often we use the word impossible in life not really meaning what we think it means.

Impossible, impossible. We say it. But, really, is it?

In previous attempts, I have cycled solo from Steward Isl and to Cape Reinga. I told people and they laughed at me in my face, as I was a 100kg+ fat guy who hadn’t done anything physical ever, and hadn’t ridden a bike since I was 13.  I dropped to a trimer 80ish kg on the way.

I’ve quit drinking for a year, quit watching sports. I’ve quit reading, listening and watching any form of news media.  I have founded my own software startup. And I have run 1,000km including give half marathons.  Again, not bad for a recovering fat guy.

I am pleased to confirm that I have succeeded in every challenge so far. See, not impossible.

I’ve mainly been alternating between quitting things and doing crazy physical things. I figure this way I gradually remove all the things that make my life worse, like bad news and smoking and do lots of good things for my body that make my life better, like running and cycling crazy distances.

This year I am adding a new category to my impossible challenges. To learn a new skill. I’m not talking about learning to do woodworking, or pottery, or hand-gliding. I have to learn a new skill and reach expert level. Well perhaps not expert, but generally nail it in some epic way.

This year my challenge is to learn to sing, in a band.

Now, that alone sounds pretty doable. So to make it an impossible challenge, I need to learn how to sing (I am not a singer. Ask my kids) and get a paid gig singing in front of at least 100 people, for MONEY.

And not get booed off.

So not only do I have to learn to sing, but master a level so I am good enough that someone wants to pay me money and attract a crowd of 100 or more people.

I have to overcome all my horrible fears and demonstrate my new skill publicly in front of a bunch of really critical people, basically not my family.

Considering that any form of public speaking turns me into an incredible sweating twitching nervous wreck, singing is bound to give me a full nervous breakdown.

I think I can probably get half decent enough at the signing bit. It’s the public gig part that is the impossible bit for me.

But just as I felt a few years ago when I announced my bike ride of NZ to everyone, and quietly shat myself, I then overcame all my own doubts and I then went about doing it. One step at a time. Instead of focussing on what you have to do at the end, focus on each step that will get you there. One at a time.

That’s the bit I think that makes people think things are impossible. Self doubt. When you stop saying “I can’t” and then start saying “I’ll give it a go” you will find out there is a whole lot of things you can do. Amaze yourself at how impossible you are.

So I have the most part of a year to get a paid gig and nail this. In the meantime, DO NOT ask me to sing a song for you. I might punch you in the face. I am terrified of this challenge, and I need to slay some demons first before I can even consider humming a tune.

But I will invite you along to my gig, if you are happy to pay.

Vaughan Rowsell is the founder and CEO of Vend.

Follow @rowsell