When I look back at my teenage years, I think about how many opportunities I missed. Most of the time, I didn’t even hear about the opportunities or appreciate how important they were and how much they could change my life, so I didn’t develop my senses for it. The ones I did hear about, I’d learn more and immediately disqualify myself. I felt blocked by it. It’s almost like I heard a voice in my head, saying things like:
Who did I think I was, to apply for these opportunities? Why should I be so special? I’m just some kid.
It’s too late. Other people have a leg up and I discovered this opportunity too late, I’m going to get rejected. So why waste time?
My portfolio is trash compared to all of these other people. They are so good at what they do and I’m just some hack.
Looking back, none of these points were actually true, so there’s a sense of regret. I missed out on an enriched arts program (I could’ve developed my skills as a cartoonist!), a media program (too much commitment and ate too many credits!), journalism school (I’d probably be doing the same thing I’m doing now!), scholarships, and an enriched business school (I didn’t think they’d care about my application!), amongst many many many other things. It was a mental form of repression; I was holding myself back.
A small consolation: I love what I’m doing now, and there’s a really good chance that I’d probably be doing exactly the same thing. But damn, if I improved my drawing skills, that would only add to my skillset and enrich what I’m doing now by a mile.
There’s a common thread in a lot of interviews with people who have experienced some success: at some point, they faked it. For me, in my second year summer I was doing an internship and wanted to learn how to code. My friend, upon hearing this, told his uncle who approached me to see if I could build a new website for his business. I asked him how much he would pay, he said a few thousand bucks, and I never called him after that. The money and commitment scared me off—I barely knew how to style my own WordPress website!
Of course, looking back, I realized that that was already enough. I’d have something that I’d be able to show him. And he wasn’t dumb either, he knew he was hiring a college kid, and a website should cost way more than a few thousand bucks—but I didn’t trust him, I thought my friend and I had fooled him somehow. So I missed out on a chance to save him a ton of money, gain myself some valuable experience, and prove myself wrong about myself.
That was one of the last times I would miss an opportunity like that. I’m lucky that in college—I did go to a business school—one of the things I learned from peers and from applying to jobs was not to hold back anymore. Just go until you get the offer. You don’t get to decide whether you want it or not until then; just do it. You are free to quit the offer, and to quit the job, and to drop those things after you get it, but if you want it you need to go for it.
We’d call these Lamborghini problems; entrepreneurs were so busy figuring out what color they wanted their Lamborghini to be that they were not spending time focusing on their business and actually getting it. I’m not much of a sports car enthusiast, but that really resonated—don’t count your chickens before they hatch.
The lesson here is: Don’t get in your own way. Just try your best at that moment and sometimes it’ll be more than enough. You are more than enough. I am more than enough.
Lucky for me, along with the new insights I got in school, paradigms shifted, and institutional powers are fading. Instead, it’s cool to be able to do it yourself now. Almost everything I do now, I started off by myself, without institutional support—though I do think I’d be further with education and networking benefits that came from institutions. Like Derek Sivers writes in Your Music and Your People, it’s best to make two plans: one that relies on nobody else, and one that relies heavily on everybody else.
My first plan is to work in technology and write. My second plan is to work with publishers. I’m working on both at the same time. Check out my latest book, Creative Doing, with Holloway.