Steve Jobs

Like so many of us, my first computer was an Apple. An Apple //c, to be exact. It was then that I first learned about Steve Jobs.

In 1996, I was working as a dial-up tech support technician and junior Solaris administrator for a fledging dedicated server company called digitalNATION. Everyone there, from the CEO to the receptionist, had a NeXT workstation. NeXT was one of the companies that Steve Jobs founded after being ousted from Apple (the other being a company he bought from George Lucas, which became Pixar).

If you’ve never worked with a NeXT, it’s what computers would be like in 10 years. In 1996 I could drag and drop a file from a folder into an email, and it would auto-attach itself. Today, that’s old hat. But in 1996, NeXT was about the only operating system that could pull off that “drag and drop” seamlessness. Even though NeXTSTEP was based on BSD/Unix, you didn’t have to see the Unix parts if you didn’t want to.

The CEO of digitalNATION, Bruce Waldack (who passed away in 2007) was one of the earlier resellers of NeXT gear, and knew Jobs. Bruce told me that Jobs was vegan, which I initially didn’t believe (I’m vegan, and I thought he was taunting my fanboyism).

Bruce said “Don’t believe me? Email him. sjobs@next.com”. So I did. I composed quick email message: “Dear Steve. Are you vegan?”

Within the hour, I got a curt reply: “Yes -Steve”.

I’m sure I squealed like a school girl.

As the years progressed, I read every biography on Jobs and Apple I could get my hands on. He was a fascinating man. A geek gone good. Complicated, flawed, yet undeniably effective.

I think it’s somewhat telling that Steve Jobs, quite possibly the best CEO the business world has seen in 100 years, didn’t get an MBA or law degree, but instead spent his young adulthood as a stinky (literally) fruitarian who dropped acid and went to India. Seriously, Steve thought that because he was a fruititarian he didn’t need to bathe. The stories of his overpowering stench in the early days of Apple are legendary. While most Forutne 50 CEOs are insufferable douchebags with halitosis competing with other bad-breath in matters of golf and yaucts. Steve walked around in jeans and sneakers. His decisions were made for the long term, while other leaders fretted about the quarter. Under Jobs, Apple wasn’t afraid to eat its young (iPhone eating iPod sales, iPad eating MacBook sales). Few companies had the guts.

But it was more than his business successes or influence on technology that inspired me personally. It was the way he lived his life, it was his philosophy and his fearlessness. Many of you have heard of or seen his commencement speech at Standford in 2005. If you haven’t read it, it’s one of the most inspiring pieces of work I’ve ever read (and that’s no hyperbole). I’ve read it at least once a year since 2005, and I’ve never read it with a dry eye.

I’ll give you an example: Since I was a kid, I’ve dreamed of piloting a plane. In 2008, I moved from New York City to Portland, Oregon, and pursued that dream by training to get my pilots license.

But there was a problem: Even though I’d flown hundreds of thousands of miles on commercial airlines in the preceding three years, it turned out being at the controls of a small plane myself scared the absolute daylights out of me. During my first flight with my instructor, in a 2-seater Cessna 150 built the year before I was born, I held on to the control yoke for dear life so tightly, I worried the rental company was going to charge me extra for buffing out my fingerprints.

I would drive to my flying lessons, shaking with fear. I would almost turn around and head back home, with some excuse as to why I couldn’t make it. But I didn’t.

The antedate for that fear came from the words of Steve Jobs.

Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything — all external expectations, all pride, all fear of embarrassment or failure – these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.

Someday, I am going to die. I didn’t want to die before I could fly a plane. Dive with sharks. Run a marathon on every continent in the world. Talk to that girl. Help a stranger on the street. What might stop me? Fear of death, fear of loss, fear of failure, fear of embarrassment, fear of looking stupid.

We all fight fear in our daily lives. From the big decisions to the little ones, there’s always doubt and fear in the back of our mind. It’s amazing how fear of little things (rejection, embarrassment) end up causing us as much fear as the big things (death, loss). Big fear of small fear, they all hold us back.

Partly with Steve’s words in mind, I’ve been able to do this:

So it’s not the iPod, iPad, or MacBook Air that I’m writing this on that I will remember Steve Jobs by. It will be the memories of flying an airplane upside down, running a Marathon on the Great Wall of China, swimming with sharks, and facing the thousand little fears we all have every day.

Stay Fearless, stay foolish. Steve Jobs: Fuck yeah.