Getting Ahead: A Letter to Myself

All the pulses of the world,
Falling in they beat for us, with the Western movement beat,
Holding single or together, steady moving to the front, all for us,
Pioneers! O pioneers!

I moved to Silicon Valley the summer of 2006, as soon as I graduated from the University of Chicago. Two college friends, Ryo Chijiiwa and Isaac Wolkerstorfer (neé Wasileski), asked me to join their startup OpenHive, a "social" search engine for college campuses that allowed students to search each others' bookshelves. I had no expectations. In fact, before my plane landed in San Jose, I had never even set foot in California.

I was underprepared. I suppose everyone is, though. This is the letter I wish someone had written me that summer. Since nobody did, I'll have to write it to myself six years later.

Dear Jesse

Dear Jesse,

Hello from the future! You're about to move to California and help Yitz and Ryo with their startup. There's so much you're going to fuck up, but it's all worth it — honest. I want to help you get ahead.

The best thing about Silicon Valley is how friendly, open, and helpful everyone is. The chattering class can be cynical, but this is where the future is getting built if you look hard enough. Do look hard enough.

Here's the big secret: do valuable work and share it. People out here spend so much time talking about who's up, who's down, who's working with whom, who raised money and on what terms, who sold their company and for how much, etc. Twitter has nothing on the speed at which gossip travels in Silicon Valley. It's the work that earns you respect and credibility in the end, though.

Forget meetups, getting coffee, and "quick" phone calls. Doing valuable work and sharing it is the best way to build a network — it becomes your calling card. Idle meetings are the Silicon Valley equivalent of showing up empty-handed to a potluck. Everyone is happier if you bring something unique and delicious. Until you can do that, you're better off practicing your kitchen skills. You want to be able to point to something fantastic and say "I did that."

It's hard to know whether your work is valuable, particularly while you're in the middle of doing it. What if it's not good enough? What if people you respect think poorly of it? Being dissatisfied with your own work is what pushes you to improve, but don't give yourself too much credit. Most people won't think anything of it at all. You have to trust yourself that if you're thoughtful enough and prolific enough, something amazing will happen.

Small work can be valuable, too. When I was first learning Erlang there were no tutorials outside the official and very opaque documentation, so I took the time to write the tutorials I wish existed. If you think it's valuable someone else will, too. It might even be an opportunity to work with them. Don't be trapped by thinking that all your work has to be momentous. Seeds aren't momentous.

I know you can be independent and stubborn, but don't be afraid to ask for help in your work. You'll be surprised at how helpful people are, even people you've only met once or twice. The Midwesterner in you will say it's impolite to be a burden on other people's time. He's being overcautious (that's a polite way of saying he's full of shit). Ask for help especially when you're about to do something you've never done before.

Conversely, don't take everyone's advice to heart. You can get every possible piece of advice, if you want. Take the job, don't take the job. Work with him, don't work with him. Hire that guy, don't hire that guy. Take the money, don't take the money. You'll feel like a ping pong ball if you try to listen to it all.

Speaking of advice, someone will give you a copy of this poem when it really matters:

since feeling is first
who pays any attention
to the syntax of things
will never wholly kiss you;
wholly to be a fool
while Spring is in the world

It applies to everything. Life, love, work, business. You're great at being logical, mathematical, and methodical. If that's everything, though, you run the risk of being effective but uninspiring. Remember that poem and be more audacious (in everything). When it comes to inspiring people the Daniel Burnham quote — "Make no little plans. They have no magic to stir men's blood." — is absolutely true.

Finally, surround yourself with talented people you trust and respect. Keep them close, help them every chance you get, and make sure they know how much they matter. These are the people who will help you regardless of how much help you can offer in return, and will keep you grounded when you're about to do something really crazy.

I hope you don't find this letter too self-absorbed. I thought of ways to make it more clever, funnier, etc., but decided to opt for plain-spoken and sincere. If it annoys you, well: fuck off. ;)

Cheers,
Jesse

Acknowledgements

Thanks to David Cole, Joe Damato, Raph Lee, and David Kaye for reading earlier drafts of this essay.

Have your own letter you wish you'd received when you were just starting out in your career? Send me a link — I'd love to compile a list.

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