When you hear someone tell you what they’re working on, how their dream is to be a singer or a comedian, how they’re dropping out of college because they have the next big startup idea, the expectation is that you’ll be encouraging. Dare greatly! You are a badass! I believe in you! That’s what they want to hear.
You’re not supposed to say “That’s a terrible idea.” Even if it’s true. Even if that person is going to waste years of their life pursuing a bad, or broken dream that they’re very unlikely to achieve. You’re not even supposed to question it: “Are you sure that’s really what you want?” Even when their motives are clearly all twisted up.
When I do consulting sessions with authors, I am faced with this dilemma a lot. They’re typically paying me to discuss how to market their book, or how to sell it to publishers. What they don’t want to hear from me is how preposterously far they are from even needing to think about either of those things. That they’re much closer to square one than thinking about the finish line. It is typically less than great business to insult a client and I can see how easily these folks get misled by other enablers—consultants, ghostwriters, marketers, coaches who refuse to be honest because it will deprive them of a potential paycheck. (When I wrote this piece about why people shouldn’t start podcasts, you know who objected most? The people who sell courses to people starting podcasts.)
But I try. I try to push past the resistance and deliver the truth as I see it. As was done for me at several critical junctures in my own writing career and in my own life. (Robert Greene once politely told me I wasn’t ready to be a writer and needed to turn down the book deal I was very excited about.) As was done many times in many people’s lives, shaping them in positive, important ways, sometimes with words, sometimes with fists. (Lyndon Johnson famously got the crap kicked out of him by a cowboy in his small town and it’s what finally made him see that if he wanted to be seen as an important person, he’d need to leave that small town, go to college and do important things.)
In his book Black Privilege, Charlamagne Tha God talks about his early aspirations of being a rapper. He did some work in radio early on, but mostly as a way of furthering his music career. Finally, one day, his boss pulls him aside: “Listen, Charlamagne, I know your dream is to be a famous rapper, but fuck that dream. You’re just not that good.”
You’d think he’d have been crushed. But he wasn’t—quite the opposite. It was as if a weight was taken off him. Perhaps he knew deep down that he wasn’t that good, perhaps he felt that it was someone else’s dream he was chasing, perhaps he just needed some kind of certain, confident person to point him in any other direction than the one he was going. His boss had explained that he was talented at being a radio jock and that if he could come to terms with the futility of his rap career, Charlamagne would be free to actually pursue what he was talented at and has been extraordinarily successful at doing so.
I’ve long called these ‘Fight Club Moments.’ The moment when an outside person or force is required to deliver a painful fact at odds with someone’s identity. “Fuck Your Dreams” is maybe one of the harshest things you could possibly say to someone. But it is necessary—especially when those dreams are tainted with ego, self-deception, or misguided expectations.
Let’s not dance around the fact that a lot of dreams aren’t sacred, beautiful things. They are bullshit. The person who claims to want to be a writer, but doesn’t do any writing. The person who wants to be a singer but actually just wants to be famous. The person who sees other people making millions with a startup and assumes it’s easy. A lot of dreamers remind me of Casey Affleck’s character in The Assassination of Jesse James by the Coward Robert Ford: He believes that he’s destined to be a great man and since Jesse James is a great man, obviously Jesse will see that in him. But that’s about as far as a lot of people think. It’s not a dream, it’s fantasy.
There’s that Upton Sinclair line: “It’s very hard to get a man to understand something when his salary depends on him not understanding it.” The truth is it’s even harder to get someone to understand something when their unearned self-identity depends on them not hearing it. As harsh saying “Fuck your dreams” is to someone, it often needs to be that harsh precisely because people refused to listen to the polite feedback which preceded it. In Charlamagne’s case, there was all sorts of feedback that his rapping career wasn’t working. When I got that offer to do a book, I’d only been writing for 2-3 years, I had a tiny audience—why on earth did I think I deserved a book deal or that it would go well if I said yes? I wanted to be an author, but I wasn’t ready and I hadn’t done enough work yet. I shouldn’t have needed to have been told any of that—but I am grateful that I was. It saved me a lot of painful trial and error.
I like to think America got its Declaration of Independence because someone told Thomas Jefferson he was a terrible speaker and should focus on writing. Oprah was lucky that a producer told her she was unfit for television news, it’s what gave her an opportunity to do daytime television. Plenty of people had their lives switched this way—they thought they were heading in the right direction until someone showed them they weren’t even on the right road.
I don’t think this is just limited to career aspirations either. If you see something, say something. Especially when someone has given you the greenlight (even if they don’t mean it) by saying: What do you think? Is it any good? When my manuscripts come back covered in red ink, with large X’s through huge passages I’m supposed to delete, my first reaction is anger. How dare they? But I sit on it. A few days later, I tell myself, “I’ll just go through and accept the parts I agree with.” By the end of it, I have taken almost all their advice and my attitude has gone from anger to gratitude. Fuck my dreams of hearing “It’s perfect” on the first try. I need to hear “It can be a lot better.”
Criticism serves the same purpose as pain in the body, is how Churchill put it. It lets us know where we are unhealthy or weak. “If [criticism] is heeded in time,” he said, “danger may be averted; if it is suppressed, a fatal distemper may develop.”
Nobody grows by flattery. No one benefits from chasing down a flawed dream they are not suited for or can’t properly defend. Certainly the market is worse off when crap that should have been caught and prevented makes its way through. God knows there is plenty of great stuff out there that will never get seen because of all the noise.
And look, if you feel bad about being discouraging to someone, remember this: It’s actually impossible to discourage someone from their true calling. If they were meant to do it, if they can’t not pursue this calling, your rejection will be fuel. If they weren’t, they will thank you for releasing them from this self-made prison. And the world will be better off in both cases.
So fuck your fake dreams. Fuck your terrible ideas. Fuck your delusions of grandeur. They’re only holding you back from what you’re actually good at and how good you can actually be.