Fear and Loathing in The Matrix Pt. 1
Business is a sparring program.
It’s similar to the reality of the rest of life. It has the same basic rules.
We need to learn that some of these rules can be bent, and others can be broken.
Learning which rules are which, or more accurately when which rules are which, is critical to success.
Sure you can bend and break rules, but sometimes you must.
Anybody who’s worked in entertainment long enough has been told to “ask for forgiveness, not for permission.” Newbies in any field have to find ways to differentiate themselves. They have to show they know not only what to do, but also that they can get it done. In hyper-competitive fields, oversaturated job markets, and glamor industries this frequently means having the gall to work above your rank, or do something outright not allowed.
Classic and oversimplified example:
You’re working your hell desk. You’ve been awake for 36 hours (and are somehow still behind on coverage) and you’re counting on the triple-dirty chai you really didn’t have the money for to get you through this day.
A reprieve! Your boss steps into what’s sure to be at least a 90-minute meeting that you’re instructed not to interrupt, no matter what. You’re settling into a nice glossy half-asleep state when a casting director calls with an emergency: Actor X fell out, they’ve got an opening that needed to be filled 30 minutes ago. Client A is perfect, and you know they need some love right now.
Great, except you’re newish to this company, very new to this desk, and explicitly not allowed to pitch your boss’ clients. By the time they’re out of this meeting, the opportunity will for sure be gone.
What do you do?
You break the rules. You promote yourself, and you pitch the client. If your boss gets upset, you ask for forgiveness. Getting clients work is your company’s raison d’etre, after all.
If you’d interrupted the meeting to ask for permission to pitch (0r worse, to ask them to handle it for you), you look unconfident, incompetent, and reveal an indecisiveness that undermines your entire career trajectory.
I’ve had more than one boss who thinks this way through the years. Higher-ups are constantly extrapolating indicators about your future career from the most minute decisions.

And the single worst indicator in a high-speed, high-intensity game is fear. You can’t afford to be afraid. You can’t even afford to be fearless. You need to be fuckless, as the LA Carpet Bagger recently put it.
One of my goals here is to highlight “Hollywood stuff” that gave me more trouble than they should have. In this way I hope to help the cohort below me.
In my earliest and most formative years in the business I was (with a few notable exceptions) surrounded by role models who imparted flawed lessons designed to keep me working under them.
The industry is hyper-competitive. Your assistant today could replace you tomorrow. Nobody doles out what few hacks they have. I’m guilty of this, too. I only started recently telling the assistants at my company one of my most closely-guarded productivity tricks. I’ll be dropping some other nuggets here and there. Enjoy — but enjoy knowing that most of my anecdotal advice is likely to get you fired.
While breaking rules is more fun, bending rules is definitely more common. Coming up, this too commonly takes the form of “the self-promotion.”
I don’t mean in the marketing sense — talking loudly about your web series in the break room, or taking out a billboard with your face on it over Sunset Boulevard. I mean that almost as soon as someone has been around long enough to warrant getting drinks with, they immediately promote themselves in conversation.
The one I despise most is the “pretty much promotion.” Here, your meeting will talk to you about work, acknowledge you hold positions equivalent in the hierarchy of your respective companies or departments, and then add, but they’re “pretty much an X,” or they “pretty much do Y,” with X and Y being job titles or responsibilities above their rank. Example:
Young Turk 1: Yeah so that’s enough about my office. It kind of sucks but I kind of love it.
Young Turk 2: Yeah I know. Just being so close to the action is cool. Plus I’m pretty much a CE so I’m doing all the work that comes with that, too.
No. If you were pretty much a CE, that’s what your business card would say. But you’re bending the rules to make yourself seem a little more important than you are. To get a little status, a little access to info, and a little edge in the game. You want to be wanted. It’s petty, understandable and in some offices even encouraged.
OR
Young Turk 2: Yeah I know. Just being so close to the action is cool. Plus I’m pretty much producing this web series my boss isn’t paying close enough attention to also.
No. Your boss (likely) isn’t ignoring their responsibilities and letting their assistant / CE do their job for them. They may be slacking a bit, and you may be covering for them. Sorry, but that’s still part of the job you currently have, too.
You know the person I’m talking about. They pretty much: run the office, represent one or more of their bosses clients, have taken on another job, are already hired at a new job, have already made a sale they haven’t yet made, do stuff they aren’t really doing.
People usually self-promote for one of two reasons:
- They are a True Knight of Hollywood Douchebaggery, and just have to do and say everything they think will impress you at every intersection. Usually this person is newer to the industry.
- They are being hard on themselves. They feel they are too old to be at their level, or have been their for too long. To compensate they lie more to avoid losing your respect for having not been promoted than to gain your respect by seeming important.
A good litmus test for when this is happening: People who are really doing two jobs, while getting the title, pay, respect, and benefits that go along with the lower of the two aren’t annoyed and/or cavalier about it. They are sometimes angry, always exhausted, and usually aggressively seeking new employment.
Other times, bending unspoken rules is a wise choice.
Take my good friend, Andy — a cool young guy who found himself on the fast track to becoming an unscripted producer.
I met Andy on his first day in Hollywood. We were not friends (yet). Not only were we not friends, as far as I was concerned, Andy and I didn’t exist on the same plane. (Oh yeah, I wasn’t really a nice guy in my earlier industry years).
Andy was the newest member to the slew of interns our then-sister company “employed.” Untrained, unpaid, unskilled, and unconnected, I had and needed nothing to do with Andy, as I was a mighty first assistant to a co-founder at the time.
So, on his first day, having been assigned some task and missing the assistants’ ritualistic lunchtime sprint for the elevator, Andy did something to inconceivably, laughably wrong:
He knocked on my boss’s (closed) office door. When let in, Andy asked him, a semi-infamous and extremely intense executive he did not know, to lunch.
He didn’t even so much ask him to lunch, as a newcomer does to a potential mentor, he more just asked him if he wanted to eat lunch with him.
This escalated Andy’s career instantly.
My boss thought he had chutzpah, and he respected that. He poached him from our sister company, promoted him, trained him, gave him my desk when I quit, then helped him find his next job after a time.
Today, Andy openly admits he simply did not know that interns (much less assistants), do not ask executives to lunch.
This is not to say Andy has not gone on to do fantastic work, and earned everything he has. He’s incredibly smart and has a fantastic knack for his corner of the business. He’s gotten where he is on merit. But knows this particular “mistake” worked out very much in his advantage.
Making people like you can be jet fuel for your career. This applies to any business, but is especially true in the tangled web of personal/professional relationships that make working with the glitteratti especially cult-like.
This goes doubly for the cult of internet fame. I operate in a world within a world. Neither of those realms are real in and of themselves, but they have tangible impacts on reality.
Not unlike how The Matrix is the front end of a system extracting real energy from humans. Content creators, and by extensions the brands that pay for their influence, leverage a digital existence to extract a tangible value.
This isn’t far different than how celebrity has always operated — distribution notwithstanding.
When it comes to work, don’t think you can — know you can. Learn to trust your instinct. Learn when to bend and when to break the rules.
But none of this will happen unless you hustle hard, do your homework, and internalize the lessons you pick up.
If you can do all this and stay sane, one day you’ll wake up and realize you know kung fu.