Freelancing: Putting Yourself In the Way of Good Luck

I’m just going to put this out there at the start, because we’ve all been here: we work, and we work, and we work some more, and it is hard to see someone else enjoy success that we aren’t having. I don’t mean we’re all consumed with jealousy all the time – often, we are genuinely happy for these people – but that there are days, like the ones when the bread was moldy so there was no toast and you still haven’t found another freelancing job for next month and your royalties are down and your tummy doesn’t feel all that great and… And watching someone else have success through the roof is just hard, because you work a lot and why isn’t it you, dammit?

We have all been there. If it isn’t now, it was in the fifth grade when that one kid made the play you worked your ass off to memorize the speech for, or when your younger sibling seemed to just have opportunities fall into their lap after college while you were still working at a job that made you want to gouge your eyes out. It’s human, it happens to all of us.

Today, we’re going to talk about how to let it go…and turn it around.

In a book called The Black Swan, by Nassim Nicholas Taleb, the author describes a “black swan event” as…well, simply an unusual event. For today, we’re going to focus on positive black swan events, like you landing a crazy-cool, very high-paying project (most of us here are freelancers). Now, all things being equal, this event is going to happen one way or another – the client will create the project and look for freelancers who might win the contract. Given that there are several billion people on earth, your starting odds of getting the contract are remarkably slim.

You can totally get way closer with just a little effort, though. Let’s start with a few broad strokes: you can have a presence on freelancing websites and message boards that this person might post the contract on (try googling “find a freelance [your job here]” or “find the best freelance [your job here]” and see where that takes you); you can have a good reputation on that board because you worked like crazy to make previous clients happy; you can scan regularly for new jobs that have been posted; you can have a cover letter detailing your achievements already written and edited so it’s easy to submit applications. Look at that, doing just the things you were pretty much already doing, you’re in the running for this job. Excellent.

“I know that, Moira, I was looking to get ahead today.” Yes, yes, but what about the fact that we’ve now shown that you’ve already put yourself in the way of this black swan event? The odds are tilting ever more in your favor, and you don’t even have to participate in the Hunger Games.


So, now, I’d like you to grab a piece of scrap paper and write down a goal. I’ll go with you, with a goal of mine: write a critically-acclaimed, engaging, best-selling fantasy book. (You know, small stuff like that.)

Now, let’s work backwards. What’s the immediately-preceding thing that needs to happen for you to achieve your goal? In my case, I need a lot of people to buy my book, and I need both the regular readers and the critics who read it to enjoy it. Bestseller = people buying; critically acclaimed and engaging = people enjoying. Draw little arrows from your goal and write down each thing that needs to happen.

Select one of these, for example, “lots of people need to enjoy my book.” I’m going to have a few arrows going from this one to show the requisite factors: first, a lot of the people who buy the book need to read it, not just keep it on their ereader or bookshelf; second, I should try to get people to buy it who are going to like the types of books I write; third, I should make sure that the book is well-presented in cover, grammar, and formatting so that the experience of reading it does not detract from the reader’s enjoyment; and fourth, I should make sure that I have written the best book I could by creating an engaging story.

Now we’re getting into the tough stuff, with the exception of that third point. You’ll have your own equivalent of that one, and I’m going to tell you right now to take the time and make the effort. Presentation is not meaningless, but instead an important indicator of how you approach the world, and whether or not you respect people’s time. Occasionally, you will be tempted to rush a product to market. Learn from my mistakes in this area, and skip that.

Back to the tough stuff. We could continue, drilling further and further down, and I hope that you will do so with your own goal. The point, however, is this: there is a series of actions you can take, starting today, that will help you put yourself more and more in the way of positive black swan events. There is luck in this world. It would be pointless to pretend otherwise. But, to quote fellow author Boyd Craven, you can get to the point where you’re effectively taking a lightning rod and climbing to the top of a lone tree in the middle of a thunderstorm: you’ve effectively changed “if” to “when.”

And it’s odd – the funniest thing will happen as you do this: your resentment will largely disappear. You’ll look at someone’s success and you’ll feel the genuine happiness of watching a friend succeed, but where there might otherwise be a tangle of shame and jealousy, you will instead have the quiet confidence that you are working hard and smart, and that you are doing the most you can to put yourself in the way of success, too.

Some people say, “make your own luck.” I say, “put yourself in the way of good luck” instead, but the idea is the same, and it (quite literally) pays to remember it. Do the smart things, and let the rest go.


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