If you’re going to try . . .

J Clay
The Startup
Published in
6 min readJan 25, 2020

I watched the movie Factotum a couple of months ago. It’s based on a Charles Bukowski novel. Matt Dillon does a surprisingly good job of playing a young Henry Chinaski, Bukowski’s alter ego, as he goes job to job, trying to make it through life while attempting to build a writing career. The film ends off with the famous Bukowski quote about sticking to your dream through thick and thin.

“If you’re going to try, go all the way. Otherwise, don’t even start. This could mean losing girlfriends, wives, relatives and maybe even your mind. It could mean not eating for three or four days. It could mean freezing on a park bench. It could mean jail. It could mean derision. It could mean mockery — isolation. Isolation is the gift. All the others are a test of your endurance, of how much you really want to do it. And, you’ll do it, despite rejection and the worst odds. And it will be better than anything else you can imagine. If you’re going to try, go all the way. There is no other feeling like that. You will be alone with the gods, and the nights will flame with fire. You will ride life straight to perfect laughter. It’s the only good fight there is.”

These lines seem to have stuck with me since then. Maybe because I’ve slowly come to understand the power of playing the ‘long game’. Or maybe it made me think of myself. Here I am, stuck in career that no longer really appeals to me. Often I think back on the last ten years, wondering why I hadn’t just started pursuing a different, more enjoyable direction in life sooner. Something like writing, for example. If I did I might have found myself in a much more favourable position right now. Perhaps even on the verge of doing it for a living.

But life doesn’t work in hindsight. It works in the moment. And when you stack multitudes of moments on top of each other, you find life’s moved on and you haven’t. Well, not exactly as much as you wanted to.

While I can’t encourage the lack of eating for three or four days, or sleeping on a park bench, there’s a vital lesson in these words for any young person. Any person at all, for that matter. Or any company.

About ten years ago I became friends with a young guy who had started as a creative intern at the ad agency I worked for. By this time he’d established himself as a rising star in the creative and design department. I liked his sense of humour, and we knew how to have a good time.

But what always stood out about him was his sheer passion for advertising. He lived and breathed it. He spent endless hours on websites that exhibited great advertising. He knew the ins and outs of the industry. He devoured content around advertising awards shows. He loved it all.

By the time I left the ad agency a couple of years later he was at creative director level. I moved cities and we lost touch completely. Through friends, Twitter and LinkedIn I stayed loosely informed of his career path, which seemed to just grow and grow. From humble Port Elizabeth in South Africa, to creative director in large UK agencies. The last I heard about a month ago, he had just started at a world famous agency in New York City as a creative director.

I was happy for him. When I heard the news I couldn’t help but reflect that when he started at the ad agency we met at years before, I was considerably more senior to him. Yet in the space of a decade he’d surpassed me. He’s massively talented, yes. But at the heart of it I knew there was something deeper. He loved what he did. He had a clear picture in his head of what he wanted to achieve. Of this I have no doubt. From day one back in the agency a decade ago, he had a long game.

It’s worth telling another story of a friend of mine back in Johannesburg, South Africa. His wife has a high level executive job, which affords him the chance to work for himself. Here’s the thing . . . he’s good at everything. Well, almost everything. I’m not exaggerating either.

He cooks majestically. He can make a gourmet meal out of nothing. He could probably fix any electrical issue in your house. He’s a master of sound and speaker installations. He’s an excellent sound engineer, and even plays instruments fairly well. He knows carpentry, and could probably put together pretty much anything you wanted. In addition to this he knows how to fish, how to hunt, how to boat. He could skin an animal and cure the meat better than a butcher.

He’s dabbled in business in some of these areas. Yet for all his expertise, nothing has ever taken off. Often something he was heavily into would be forgotten six months later. He drifts from one thing to the next, all of which he is very capable, hoping something sticks. Hoping for a magic moment, when the money starts pouring in.

It never does. His situation hasn’t really changed from when we met him back in 2012. It’s a pity because I like him, and he’s good at so much. But he’s never played the long game.

Then there’s the story of the company I joined when I left the agency I spoke of. They ran a group of colleges around the country. No company is perfect, and neither were they, but I loved working for them. They were decent, down to earth people. They gave me a healthy dose of accountability, and I generally had fun while there. I badly wanted the company to ‘win’ and grow exponentially. But it never happened. We never grew anywhere near as much as I wanted us to, and at times we struggled. After five years I felt I’d outgrown much of the company and left for a bigger name.

Looking back now I sometimes wonder what held us back. Why couldn’t we grow like we wanted to? We had small budgets, yes. But we had a decent footprint and access to a large market. Our product was well developed and very relevant. Our campuses were well equipped and clean.

But we never stuck to anything. And because we never stuck to anything, we weren’t known for anything. Every year we seemed to latch onto a new direction in terms of what we stood for. One year it revolved around technology, then it revolved around delivery model. Then rested on appealing to a corporate market. There was never a defined sense of “This is who we are and this is what we’ll be known for” — that ingrained vision that you stand by, even in the face of one or two flat years while you build. It always seemed to be a moveable feast. No long game.

How many other companies fall into this trap? My guess is many. Company strategy is essentially an incredibly simple thing. Decide on a direction that makes market sense and that is in line with company strengths, and stick to it. Yet this seems incredibly difficult for many companies. Playing the long game doesn’t come naturally to us humans. New managers come in and want to make their mark. They want something visible to justify themselves, so the long game is often the casualty.

The most successful companies generally played the long game . . . and won.

Anyone who knows Bukowski’s story knows why that quote of his has so much relevance. Essentially Bukowski played the ultimate long game. For decades he suffered through life, trying to make it as a writer. Through hardships, poverty, failed jobs and bad living, he never stopped writing. Finally he got his break in the depths of middle age, and went on to be of the most famous American poets of the 20th century. He truly fought the long fight for his passion.

I myself sit at 35, regretting that I haven’t played the long game. I too am guilty of starting things and never progressing. Yet here I am. It’s not too late. It never its. But I know now more than ever that for people and companies alike: if you’re going to try . . . go all the way.

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