294. Sure Bets and Wildcards

26-01-2023 • 10 min

Which would you rather have? Mild success, or wild success? Most of us would prefer wild success. But we pursue mild success. And you can’t have one when you’re going for the other.

The struggle of an aspiring novelist

A more specific version of the scenario I mentioned in episode 253: Imagine you’re working at Starbucks during the day, and at night you’re writing novels – not just any novels, but your favorite kind. You call it Care Bear Fanfic Urban Fantasy. As far as you know, you’re the only person who writes Care Bear Fanfic Urban Fantasy. Judging by your sales, you’re also the only person who reads it. You’ve written three novels in this genre you’ve created, and there have been hardly any sales, aside from the handful of copies you’ve sold to your mom and close friends.

After a couple years writing and promoting your Care-Bear novels, you decide it’s time for a change. You told yourself when you started writing that as soon as you made as much as your Starbucks job, you’d quit and write full-time. You’re not even close. Your hourly Starbucks wage isn’t great, but you’ve actually lost money writing your three novels, after investing in cover designs and some ads.

A new opportunity

Fortunately, one of your friends is a pretty successful author. She makes a middle-class living writing in a genre called Sweet Romance – mostly read by retired women, some of whom read a new Sweet Romance novel every day. You buy your friend a coffee – or rather steal it from work – sit her down, and drill her to tell you all about writing and selling Sweet Romance novels. She’s super helpful, and tells you everything you need to know about the story structure readers expect, what tropes each novel has to hit, and even what keywords to advertise under.

Armed with your knowledge of the Sweet Romance genre, you get to work. It’s not your favorite, but it would beat serving coffee, you figure. The first couple novels are a challenge, but once you get it down, you’re cranking out a new one every several weeks. You’ve got it down to a whole system: You change the character names, the locations, and a few scenarios from your last novel, and they practically write themselves.

Making it, as a middle-class novelist

Three years later, you, like your friend, are a middle-class Sweet Romance novelist. You’ve written eighteen novels, in three series, and in the past year have profited $70k. You quit your job at Starbucks a couple years ago, and you were right: Writing Sweet Romance is way more fun than serving coffee.

Still, something is missing. You’re getting tired of writing the same stories over and over. New ideas for Care Bear Fanfic Urban Fantasy stories keep coming to you. But you keep pushing them down. Why would you bother writing another Care Bear novel, when you’re sure you’ll sell none? Why would you not write another Sweet Romance novel, when you’re sure you’ll sell some. Besides, you’ve upgraded your life: You now have a mortgage and a car payment, and your dog eats Purina instead of the off-brand stuff from Aldi. These novels don’t sell forever. If you don’t keep the Sweet Romance machine going, you’ll make less and less money.

A missed opportunity

But, one day, you discover something that changes everything you thought you knew about the business of being an author. As you’re tallying up your earnings at the end of the month, you realize that your Care Bear Fanfic Urban Fantasy series has started selling. In fact, you’ve sold a hundred copies in the past month! That’s more copies than you’ve sold in all the previous years.

You dig a little deeper, and discover another author, writing under the name Brave Heart Brian, has written seven Care Bear Fanfic Urban Fantasy novels. You’re filled with excitement, confusion, and envy. You’re excited to have some Care Bear novels to read, confused as to how Brave Heart Brian seems to have popped up out of nowhere, and envious that – judging from the Amazon ranks of his books – he’s making more money than you are!

You take a deep breath and wash away the envy – it is fanfic after all, it’s not like you invented Care Bears. You email Brian to congratulate him on his success, and ask him how it all happened. It turns out Brian stumbled upon your Care Bear series last year. He loved it, and wanted to read more Care Bear Fanfic Urban Fantasy, but since you clearly weren’t active anymore, he decided if he wanted to read more, he’d have to write the novels himself. Not only has he built up a nice following of readers, he just sold film rights for his series, for millions of dollars!

The good news is, Care Bear Fanfic Urban Fantasy is quickly becoming a popular genre. The bad new is, you’re not the author who will reap most of the benefits.

Where did you go wrong?

You wonder, Where did I go wrong? You tried writing Care Bear Fanfic Urban Fantasy for years, and the writing was on the wall: Nobody cared.

The problem was, Sweet Romance was a sure bet – or at least one of the surer bets writing novels could be. You expected writing in Care Bear Fanfic Urban Fantasy to behave like a sure bet, but it was not a sure bet. The Care Bear novels were a wildcard. You didn’t distinguish your sure bets from your wildcards, so you gave up on your wildcards too soon.

Sure bets for mild success, wildcards for wild success

We’re used to playing sure bets. You didn’t show up to your job at Starbucks for the small chance of making a lot of money. You instead had a high chance – a guarantee, in fact – to make a little money. You knew how much you’d get paid every hour you worked.

Sure bets have a good chance of mild success. Even when you fail at a sure bet, you succeed somewhat – if you slack off at Starbucks, you still get paid, so long as you don’t get fired. If your next Sweet Romance novel isn’t your best, you still make some sales.

Sure bets have a good chance of mild success, but wildcards have a small chance of wild success. When a wildcard fails, all your effort goes to waste. You get nothing. But when a wildcard succeeds, the sky is the limit.

In my second interview with Seth Godin, on episode 177, he told me this:

Your last book was really juicy. Your last book did not sell a million copies. Those things aren’t completely related. But it’s very important that your next book not be something that you think fits into a juicy slot – not be something that is searched for from an SEO point of view…. That’s how you become a second-rate romance novelist. It’s not how you write The Martian.

What Seth was telling me, essentially, was to not play sure bets – don’t write something just because you know some people are searching for it. Instead, play wildcards, to write what was interesting to me, and take the risk that it might not work.

Don’t rate your wildcards as if they were sure bets

Essentially, when you’ve played a wildcard, don’t evaluate its performance as if it were a sure bet. The number of sales you get on one book is not a direct reflection of the quality of that book. As Seth had told me in my first interview with him on episode 77, and as I explored on episode 286, nobody knows anything.

As I talked about on episode 251, if you keep playing wildcards forever, eventually ergodicity will take effect, and one of them will hit. But you can’t play wildcards forever. Your life is only so long, and there’s only so much time in the day to generate wildcards. If you had kept writing Care Bear novels, there’s no telling how long it would have taken to quit your job at Starbucks – or if you would have ever succeeded at all.

The security of sure bets + the success of wildcards

You don’t have to choose between playing sure bets and wildcards. As I talked about on episode 256, you can play the barbell strategy. Have the security of mediocristan, with the excitement of extremistan. If, instead of going all in on Sweet Romance novels, you had written, say, one Care Bear novel for every three Romance novels, you’d’ve greatly increased your chances of being the breakout Care Bear Fanfic Urban Fantasy writer, at the expense of a small pay-cut in the short-term.

You can play all sure bets, you can play all wildcards, or you can do a mix of both. But be clear with yourself when you’re playing one or the other. The quality of the decisions you make with your creative career depends on it.

Image: Mountain Village (Autumnal), Paul Klee