When I worked at Twilio, we had a 3-word saying that was incredibly important to us. It was so important to the company it’s still listed as one of the company’s core values, even now that they are a $4B+ public company.
And to most outsiders, these 3 words are total gibberish. But to any insider, it was as close to a rallying cry as we had.
“Draw the owl.”
The actual entirety of the phrase was “Draw the rest of the fucking owl.” Yes, the “fucking” was often said by the C-level executives. This was serious business.
This phrase is from a 2010 meme called “How to draw an owl”. The process of drawing an owl is simple.
Step 1: Draw some circles.
Step 2: Draw the rest of the fucking owl.
There, see how easy it is? 😂
I think about this phrase all the time, and it’s one of the big reasons I was drawn towards the culture at Twilio. There was a culture of “Just figure it out. There’s no playbook. You’re making the playbook. Draw the fucking owl.”
When I was 14, my best friend and I started booking DIY music shows around our hometown Louisville, KY. Thinking back, I can’t believe we had the balls to do what we did. Here were two freshmen in high school going around to music venues and convincing them to let us rent out their hall for a night, renting sound equipment, asking for ride favors from older friends to move that equipment, booking bands who were often in 20s and 30s, then paying out a few hundred bucks to those bands, and pocketing a bit for ourselves.
After we had been doing it for a few years, we went to rent a venue we’d already rented once before. It was a beautiful church hall, great sound and location. The priest was the guy with whom we’d make the deal. We’d hand over some cash, and then he’d hand back a key to the venue. They didn’t provide any staff onsite, they just gave two 15-year-olds keys to their venue and said “Good luck!”
This latest time we show up to meet the priest. We’re 16 now, and he doesn’t remember us. He asks for our IDs and realizes we’re under 18. We can’t rent the venue now, he says. He got in trouble a few months ago for renting it out to a few kids who were too young, and the church made him put some rules in place.
This is when I remembered that last time we rented it, he asked for an ID to scan so he could hand over the keys. Since I was 15, all I had was my high school ID. Name, photo, graduation class. No address, DOB, or anything. The fact that we’d ever been able to rent it in the first place was comical.
There was nobody around to guide us through booking a show, renting a venue, convincing touring and local bands to come, promoting the show, or everything else we had to do. And there was no playbook for how to rent a venue when you didn’t even have a driver’s license. We just drew the fucking owl and figured it out.
I love helping other people, especially talking through how to find jobs, negotiate salaries/rates, build their products, and more. But what invariably happens, people show up looking for advice on too grand of a scale.
“How do I get a job?”
“How do I do freelance work?”
“What should my product be?”
It’s nearly impossible to help when these questions are the starting point. They’re far too broad, and honestly, you’ve got to figure out most of the steps on your own. The more you lean on someone else to guide you and give you the answers, the more likely you are to never make real progress. At least not progress that you’ll actually take to heart.
Start figuring it out. Put some of the pieces together. When you truly get stuck, ask for pointed advice. Stuff like “What sort of salary should I be asking for at my experience for this type of job?” and “Do you think X marketing strategy is good for this type of product?”
Nobody else can lay out all the steps for you, because nobody else has been you or is in your situation.
You’ve just got to draw the owl.