Draw The Owl
The owl—besides being my site's unofficial mascot and my dad’s favorite animal—has had a pretty big impact on my life. During my time at the Startup Institute of New York, we were given the exercise to "Draw an Owl." What seemed like a random task at the time ended up teaching me something that stuck with me for the rest of my life. Let’s talk about it.
A Little Backstory
Before I got into tech, I was a struggling musician. I worked at a music store while trying to land gigs that would pay enough to get better gear. I played live, did some recording, and gave it my best shot. Looking back, part of me wonders if I didn’t “make it” because I didn’t commit hard enough. I was always the guy who measured three times and then thought about cutting once. In other words, I hesitated a lot.
Eventually, after seeing how hard it was for musicians (myself included) to find gigs, I had an idea—what if there was an online platform where musicians could market themselves? The classic Field of Dreams product development approach: "If you build it..."
I believed in it so much that I quit my job, sold my gear, and started learning web development. That led me to building my first MVP, which eventually took me to New York, where I found the Startup Institute.
The Startup Institute was an eight-week career accelerator that helped people break into the startup world. Part training, part networking, and a crash course in what working at a startup was really like.
The Owl Exercise
The program split us into different tracks—Product Design, Marketing, Software, and (I think) Business Development. I was in the Product Design track. Most of our time was spent learning from people working in the industry, but sometimes we had group exercises.
One of those was “Draw The Owl.” If I remember correctly, it was the first exercise we did as a group. One of the organizers stood in front of us, put a marker on the whiteboard, and asked, “Who wants to come up?” For some reason, I either volunteered or got voluntold.
They gave me a simple instruction: “Draw an owl.”
Now, I’ve always been pretty good at drawing, but for some reason, I blanked on what an owl actually looked like. My mind went into overdrive. "What does this have to do with startups?" "What if I mess up?" "Is this a trick?" I was overthinking it, hard.
But I took a breath and just started drawing. I heard people whispering, “Do owls have ears?” “Oh wait, no, those are just feathers.” Eventually, I ended up with something that at least looked like an owl. Much to my surprise, the organizer was actually impressed—apparently, it was better than most of the owls she’d seen before. But what was the point of all this?
The Lesson
Turns out, the whole point was the overthinking.
It didn’t matter if I was good at drawing, if I remembered exactly what an owl looked like, or if I was worried about what people thought. The lesson was simple: commit.
If you Google "Draw the Owl," you’ll probably see an image showing a two-step process: Step One, draw some circles. Step Two, draw the rest of the f@#$ing owl. It’s a bit blunt, but it makes the point. It’s kind of like Nike’s "Just Do It," but I like this version better. With Nike, you usually have at least some idea of what you’re doing. With "Draw the Owl," there’s no roadmap—you just have to dive in and figure it out.
Why It Stuck With Me
This lesson has followed me throughout my career and life. I’ve lost count of how many times I’ve been thrown into complex situations with no clear plan. Sometimes you don’t have time to look things up. Sometimes you have no idea how things will turn out. Sometimes you’re not even sure if you’ll succeed or fail.
But you do it anyway. You commit. You follow through. You finish what you started.
Good or bad. Prepared or not.
Draw the owl.