The mythical startup: mojito island

“Ridiculous yachts and private planes and big limousines don’t make people enjoy life more”
–Richard Branson, Virgin Group founder: his number one life lesson

“Humans are generally not built to derive sustainable happiness from sipping mojitos on a picturesque island somewhere in the Pacific. Once you’ve tasted the sweetness of a dedicated purpose, it’s near impossible to be content just sitting on the sidelines”
David Heinemeier Hansson, 37signals

“I wish I had not sold it to [Yahoo]. The cash and freedom do not even come close; I would rather work on a big, popular product”
Joshua Schachter, founder of

Rowan Simpson

Kiwi business people are often criticised for a lack of ambition—selling out once they have a bach, a boat and a BMW.

I agree we should all aim all aim higher than this, but I don’t think this means aiming for a private jet or super yacht instead.

If you measure yourself based on how many expensive toys you can buy, you’re never going to be satisfied.

This series of posts expands on ‘The Mythical Startup’ in Idealog #33

One Man Band
Inventor In A Shed
The Firehose
Pinch Me!
Mojito Island
All Together Now

It is also cross-posted on Rowan Simpson’s blog

The reason is simple: there is always another level above—a more expensive car, a bigger house, a longer race. As soon as you have achieved something, you quickly normalise it and start to take it for granted. Then you start to compare yourself to those who are slightly ahead of you. Your appetite is always slightly bigger than your wallet.

To make this worse, if you’re lucky enough to be part of something that is successful, the first thing people ask afterwards is, “What are you going to do next?” That can weigh you down, take my word for it!

So it pays to think about what you really enjoy.

Consider this formula, from hotelier Chip Conley’s TED Talk:

Happiness = Wanting What You Have
Having What You Want

How much time do you spend on each part of that equation? Those who understand how fractions work realise that the idea is to focus on increasing the numerator (on the top) not the denominator.

It’s hard to describe how much better it is to work on something that you care about, unless you’ve experienced it yourself. It’s not a factor of two or three times better, it’s more like 100 or 1,000 times. If you don’t understand this, go and work for a large corporate for a while.

Likewise, once you’ve been part of something as exciting as a startup that has momentum, and the rewards that come from that, sitting on the sidelines is going to feel like a step backwards. Even the biggest boat you can buy probably won’t compensate.

So, enjoy the walk. Think about why you’re doing all of this in the first place. If you’re lucky enough to work on a new venture and create your own job, appreciate the opportunity and try to enjoy it. Financial rewards are a way to keep score, but don’t get too hung up on them. Even if you do all of the above, it still may not work out the way you hope.