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  • Jenny | President, 6&UP

Your Business Pants Are The Problem

One of my very first clients was a Google engineer who wanted to be a film director.


It was close to 2 AM, and I decided to hop on Craigslist to see if anyone had posted anything interesting. I wasn’t working. I was just eatin’ string cheese, seeing what the world was up to in the middle of the night.


In his post, he didn’t mention Google (I would learn that info later) but he did mention that he was looking for someone who was funny (check), could write dialogue (check), and wasn’t offended by fart jokes (hellooo, earth sign 👋).


I wrote back to him and said that if he was looking for someone that could out-fart-joke a ten year old boy — I was clearly the expert for the job.


Immediately my inbox pinged and we spent the next 30 minutes emailing back and forth. He hired me on the spot. Sent money to my PayPal at 3 AM.


The next day I wrote a few fart jokes and then went to Nordstrom.


I was in business.


It was an absolute high. It was my first realization that I could just connect to anyone, and that I could go from eating 12 string cheeses in the middle of the night, to working with a Google employee on his Hollywood dreams the next day. I never knew who I was going to talk to next, or what they’d be interested in.


Every day, I would check the Internet with this kind of insatiable curiosity, but really no expectations. And because I just followed whatever I was into at the moment, and was never shy to talk about what biography I was reading, or what weird nature show I was into…there always seemed to be a cool connection to be made.


I didn’t struggle to connect those things because I hadn’t yet separated business Jenny from weirdo Jenny.


I hadn’t yet put on my business pants.


If you don’t know about “business pants,” it’s likely that you’re wearing them. If you’re kinda moody, and a bit boring and you refuse to do things you like because of “business” - you’ve got ‘em on.


Business pants look and feel like success, they’re shiny and they suck in any self-esteem issues like Spanx for your insecurities. Suddenly, you’re important, and busy, with things to do and money to make, and an ego that is thrilled you’ve finally realized how important it is.




You start to look at things like scaling, and goals, and you start to get hard on yourself. And when your mom is like “all you think about is business” you take offense and then refuse to go to the Cuyahoga County Fair with her.


(Spoiler alert: I ended up going - I’m not a total asshole.)


Part of what makes you susceptible to being strangled to death by your own business pants — is taking everything way too seriously, but also taking outside advice. I feel, generally speaking, that I’m less susceptible to outside advice than a lot of people — but when you want to grow and do BIG things and make BIG money (all perfectly amazing goals FYI) you tend to start judging the “small things” you did that actually f*cking worked for you. And instead of looking at them with an expanded awareness - you abandon them all together.


All in the name of scaling. And sustainability.


I told you, it’s sneaky shit.


Here’s what I know. Yesterday I had a sales call with a random guy from the Internet. Turned out to be someone I’d love to work with via Pink Shark. He also happened to be a WWII buff, and when I shared with him that when I’m stressed I say to myself “If Churchill could defeat Hitler, I can run this company” — he busted out laughing.


He said, “I say the same thing to myself, and I have NEVER heard anyone else say that.”


He’s now referring to me as FCF (Fellow Churchill Fan) in all our correspondence.


I’m working on a proposal for him today.


Look. I like responding to randoms on the Internet. In the last two days I’ve talked to the founder of an app that has to be prescribed by a doctor, an economist and best-selling thriller author, and an ex-advertising executive who has conspiracy theories coming out of his ears about TV and film. And you know what? I think he’s right - so he’s getting a proposal too.


My process isn’t clean, it’s not pretty, and it’s sure as shit not cohesive. But it’s mine. And after a few years of trying to grow, and scale the “business” way. I’m just thrilled to be doing it 100% MY way - because that is the only thing that ever works (for all of us).


What does taking off your business pants mean for you and your business? What would you do more of? What would you do less of?


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