”Hah! This idiot’s social security number has “69” in it!”

Career I Quit Google to Follow My Dreams. You Can, Too.

By Joey Masterson

”Hah! This idiot’s social security number has “69” in it!”

 2 months in, I loved Google. It was practically a given that I’d be there for 15 years, at least. I was surrounded by brilliant engineers, all of whom had incredible conversational skills and didn’t just talk about crypto. I had access to the most powerful software, and would spend lunch breaks perusing private data and sending the funniest bits to my friends. 
”Hah! This idiot’s social security number has “69” in it!” 
Even in terms of the work, I was crushing it. My supervisor told me, “you seem to be picking things up nicely.” I was definitely on track to be a Senior Engineer, just like my father was until Google made him CTO 3 months ago. 
But then something changed. As I was nibbling on a free RxBar, my personal masseuse said something interesting to me: “Hey, looks like you dropped your wallet—is that Amex made of actual gold?” 
My jaw dropped. This is why it’s crucial to always listen, even when it’s a lowly peasant with thick, calloused hands doing the talking. I spent 7 semesters at Wharton learning this lesson in their “Economics of Conversation” course. 
“Yes, it is—now please stop talking to me.” I responded. 
I considered my options. I could stay at Google and bless them with my engineering prowess (by then, I’d spent over 3 hours on codeacademy.com), or I could do something greater. This masseuse made me realize: I have a unique skillset, and deserve greater opportunities because I worked hard all through prep school, Stanford, and Wharton, and now have an Amex Actual-Gold Card™ that I was given when I was 8. 
I could make my dreams reality. Maybe I’d do like, painting or something. I could start a non-profit to like build factories in Africa or whatever. I could make black-and-white short films and put them on YouTube. I could buy a bunch of real estate and sell it in 10 years. That can’t be too hard, right? 
Anyways—there’s an important lesson to be learned here. No matter what your career trajectory looks like, you can always make time for your entrepreneurial dreams. Just follow a few key steps: 
  1. Visualize exactly what you want to do. My friend Chaise L. took me to their art gallery once so I picked painting. But then I saw a homeless person playing guitar, so I could probably just do that. My uncle owns a recording studio and it can’t be that hard to learn a guitar.

  2.  Identify the first milestone. Whether it’s finish a painting, or record a studio-quality album.

  3. Determine how long it will take you to achieve that. This is the easiest bit—simply check the limit on whichever precious-metal Amex card you have. For me, it was $50,000, so I could easily just pay someone to finish a painting really quickly for me or hire studio musicians. I imagine it’s similar for all of you?

  4. You’re done! Go to Cabo.

Listen—it can be scary to leave your main source of income with only a trust fund to fall back on. You’ll find yourself questioning everything.  What if the economy turns, and we have to sell our vacation home in Cabo? What if I don’t feel like skiing, and don’t want to go to our Swiss Chalet? What if I leave the credit card at McSwiggans pub after the Delta Chi reunion? What if pursuing my dreams requires like, work or something?
You can’t let these questions keep you down. Entrepreneurial ambitions are a lot like Gulfstream G650 executive jets—you’ve got to let them soar and occasionally take them for a spin so the engine’s high pressure turbines don’t rust. So, next time you’re sitting in the executive dining room you have access to, covered in lobster crumbs and truffle slices, asking yourself “should I follow my dreams?”—stab that porcelain lobster fork straight into your potatoes dauphinoise and scream “Yes! I am daddy’s fancy boy, and I can do anything I want!”