Anything worth doing might not work. You might fail. You might announce your project to the world and then have to admit that it did not work.

All the rewards, all the satisfaction, all the interesting things that happen in life go to those who are willing to play in the unknown, who are willing to do things that may or may not work.

At some level, “this might not work” is at the heart of all important projects, of everything new and worth doing. And it can paralyse us into inaction, into watering down our art and into failing to do important work, work that matters.

If all I’m doing is pursuing ideas, projects, and tasks that are guaranteed to work, then I’m doing it wrong. Creative and innovative work entails the risk of things that might not work. Breakthroughs, meaningful work, and genuine connections come from acknowledging the reality that they might not work.

In doing projects and work that matters, I have learned to be comfortable with “this might not work” mindset.

This is really the idea that risks and rewards are linked. If you create something really out of the ordinary, you increase the chances that people will ridicule or reject your work, but you also increase the chances that your work is massively celebrated.

Of course, trying to control what other people think is a trap.  Not only is it exhausting, it is counterproductive. Sales (of concepts, of services, of goods) don’t get made because you have spent a sleepless night working on your adverts. They truly happen because you have made something worth buying, because you have outlined something worth believing in.

Entrepreneurs and other people who do interesting projects and deliver products to the world are usually very aware of the fact that their hard work may or may not have the impact they want. But the best entrepreneurs don’t let that uncertainty water down their ambitions or scale back their designs to something they “know” will work.

If you are sure it is going work, where is the tension. Doing work that matters, doing work that might not work is where vulnerability comes from, and the fascination.

“This might work” is the twin sister of “This might not work.” They look alike, they dress alike and they are always together.

Of course we want what we do to be successful, but the only real way to be successful in the long run is to do things you are not sure will be successful, over and over again.

“This might not work” is either a curse, something that you struggle with, or it’s a blessing, a chance to fly and do work you never thought possible.

It turns out that I don’t just write my blog or book(s) just for you. It turns out I also write to remind myself of what I’m hoping to become as well. Hearing myself, months later, reading something I didn’t remember writing or reading, I shed a few tears. Yes, this is work worth doing. Yes, being out on a limb is exactly where I want to be.

That is where we are needed… out on a limb, out of our comfort zones, doing work that might or might not work.

I looking at the manuscript of my second book and I’m thinking to myself this might not work…. but…. that’s okay, I will do it anyway.


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