I had a class reunion the other day and I got to talk to one of my classmates who completed his national service as a commissioned officer. If I had met him while we were both in uniform, I’d be obliged to salute him and address him as ‘Sir.” He was essentially the same guy, yet he was a little different- a bit wiser, a bit more worldly, a bit more mature. His words were placed better, and he had an aura of assured confidence about him- the kind that you get from being strong rather than looking it. It occurred to me there and then- something that I had thought about and observed several times before- that he had grown far more as a leader in his two years of National Service than I have. Naturally. He went to Officer Cadet School, and he had the real-world experience of leading, commanding and being responsible for many other men, some older than him.

I think back to my Signals course. My course sergeant was my age, yet I never thought of him that way. I admired him deeply- he was calmly confident and just the right amount of assertive. He knew his stuff inside out, and earned the respect of his men, his peers and his superiors. He could be counted on to get things done. He could conduct lessons with flair- better than most teachers I’d encountered in school. I was always conscious of the disparity between me and him- it was clear to me that he possessed a unique skill-set that I desired, but never truly developed. Somewhere along the line, he had overtaken me. I realize this often when wading through Facebook. When you’re in primary school, you get a sense of infinite possibility- everybody can be anything. But as you get older, you realize that people start to specialize. It’s highly unlikely now that I’m ever going to be a doctor, lawyer or fighter pilot- I blockaded the main paths I have to those destinations, without realizing it.

I could make excuses. I enlisted as a storeman because I was suspected to have a health condition that I do not have, and as a consequence of that I didn’t have the  chance to go to command school- be it SISPEC or OCS. I never got the opportunity to have my ass kicked, to be scrubbed raw against the asphalt. (I got a slight taste of it in BMT, and to be honest, I loved it. I felt so alive, because I was constantly being pushed slightly out of my comfort zone.)

But I don’t buy that. Life is  of infinite opportunity. There are all kinds of opportunities for leadership. Some people are cell group leaders at church. Others play sports, or even lead large teams in World of Warcraft. I’ve heard several times from military men the compelling argument that there’s no other organization where an individual has to be responsible for so many others at such a personal level (life and death, in some cases) at such a young age. That’s true. If you’re looking to join a pre-existing organization, the military is a pretty great place.

But I think about men I admire- Warren Buffett, Steve Jobs, Seth Godin, Steve Vai, Richard Branson- all of them are highly accomplished men in their respective fields. Read anything written or said by these men, watch them give speeches and pay attention to the way they manage their empires- and you get the sense that all of them would make great teachers and military officers (or ‘terrible’ ones- because they would have the guts to think for themselves, which is what the military needs, but tends to unintentionally discourage). Management wisdom- not just managing companies or careers, but everything- your relationships, your finances, your life.

So I ask myself- If I wanted to be a great leader, sometimes it seems like signing on to the military would be a good idea. But if I could be something like the other men I’ve mentioned, without having to go through the military route (or any other established institution), would I? Absolutely. That’s the dream. It’s just pretty damn frightening, that’s all.

“My interest in life comes from setting myself huge, apparently unachievable challenges and trying to rise above them- from the perspective of wanting to live life to the full, I felt that I had to attempt it.” – Richard Branson

Maybe that’s what it boils down to. Surmounting challenges, and growing as an individual as a process. That’s the difference between me and my peers who went through command school. Experiences. You have to have great experiences, and reflect on them, and then use the knowledge you get from that to create something meaningful. In Officer Cadet School, or at Harvard, or any other institution that seems like a great idea, these challenges are presented to you. It’s fairly straightforward, and a lot of the pathfinding is done for you.

But check out where the real fun is at- Steve Jobs going to an Ashram in India, doing LSD, practicing Zen, sitting in on typography and design lectures. Warren Buffett going door to door selling chewing gum, Coca-Cola and weekly magazines, delivering newspapers, detailing cars and owning several pinball machines in different barbershops. Steve Vai mailing Frank Zappa a transcription of Zappa’s “The Black Page” and a tape with some of Vai’s guitar playing-which got him the ‘break’ he needed. Richard Branson starting a magazine and an audio record mail-order business at 16.

Does it not become clear then that all the greatest magic happens when you get off the beaten path and pursue something that nobody else is doing? Do that, and the skills you get along the way are going to be far more fungible, transferable, relevant, useful. God damn, I need to do things. Outside my comfort zone. Constantly.

TL:DR;

“It’s better to be a pirate than to join the Navy.” – Steve Jobs