Simplify Your Why

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The Only Decision That Matters Is Your Next One

Where are you headed? Avoid the temptation to ignore such a simplistic question. It's one of the most valuable questions you can ask yourself. When you aren't sure what you want to do with your life or business, start here. Why? If you start with the wrong questions, then even the right answers will steer you wrong... eventually.

I worked a summer up at my uncle's farm when I was thirteen. Thinking back, it feels like a cheeseball Hallmark made-for-TV movie. Send a city kid to learn some much-needed life skills. Let's just say, my aunt still laughs at how little I was able to accomplish. My three-year-old cousin made me look like Billy Maddison going back to grade two to learn the fundamentals.

This was a time before phones. I had little to distract me, but as a teenager, you're a master of distraction. I was mesmerized by the number of flies that would pile up on window sills. It looked like I had stumbled upon a post-apocalyptic Mad Max scene where the world had been left for dead. Crawling into bed I watched the flies buzz around my room, knowing every last one of them would be dealt the same horrific fate. They'd search for light, head for the window and repeatedly smack themselves against the glass. I'd fall asleep to the soft buzz of life, knowing sunrise would start with a heap of lifeless bodies that never found their way.

When you don't know where you're headed, you follow what everyone else is doing. Here's the problem: How do you know that the person you're following (or society) is pushing you in the direction you want to go?

Seth Godin in a recent post reminded me why so many of us fall into this trap. We take the path of least resistance by asking, "Wouldn’t it be great if we always had a map? A set of step-by-step instructions on how to get from here to there, wherever we were and wherever we wanted to go…"

This is like the people who talk about wanting to try something new when they dine out, but default to chicken fingers and fries. They know it's a safe bet. It's so damn tempting because it feels like you can avoid the pain and discomfort of the unknown. But you're also missing out on taste-bud-melting deliciousness like the Cronut burger (food poisoning be damned).

Have you ever noticed yourself or others do this? You're highly motivated to change or try something new. But all the motivation in the world won't help if you keep trying the closed window like everyone else.

You've got to change your approach. The fly stands a chance only if it backs off and looks around for another exit.

What I mean by this is, you must take time to get clarity on where you are now. This lets you understand where you truly want to go, so you’re not just copying someone else’s idea of success.

Knowing where you are and understanding where you want to go is like being given a compass for life and business.

As Godin brilliantly put, "Happy endings come from an understanding of the compass, not the presence of a useful map."

It's too bad flies can't read. Steven Pressfield shared a magical story of one man who was able to find his way home despite facing a closed window. "A Ghurka rifleman escaped from a Japanese prison in south Burma and walked six hundred miles alone through the jungles to freedom. The journey took him five months, but he never asked the way and he never lost the way. For one thing he could not speak Burmese and for another he regarded all Burmese as traitors. He used a map and when he reached India he showed it to the Intelligence officers, who wanted to know all about his odyssey. Marked in pencil were all the turns he had taken, all the roads and trail forks he has passed, all the rivers he had crossed. It had served him well, that map. The Intelligence officers did not find it so useful. It was a street map of London."

A similar sentiment of self-discovery was expressed by the entrepreneur Sam Altman, who has helped thousands of startups over the years with his work at Y Combinator. When he was interviewed by Tyler Cowen for the Conversations with Tyler podcast he said:

“I think one thing that is a really important thing to strive for is being internally driven, being driven to compete with yourself, not with other people. If you compete with other people, you end up in this mimetic trap, and you sort of play this tournament, and if you win, you lose. But if you’re competing with yourself, and all you’re trying to do is — for your own self-satisfaction and also for the impact you have on the world and the duty you feel to do that — be the best possible version you can, there is no limit to how far that can drive someone to perform. And I think that is something you see — even though it looks like athletes are competing with each other — when you talk to a really great, absolute top-of-the-field athlete, it’s their own time they’re going against.”

Part of the realization that changed everything for me was when I understood what practicing gratitude really means. It's what you feel when you want what you already have. You don't need a map to tell you where to go. You were born with an internal compass to guide you in your life. But you were never taught how to use it. It's not some mystical woo-woo bullshit guided by The Secret. It comes from an unwillingness to ask questions that scare you. When you refuse to ask yourself empowering questions, you set yourself up to fail.

It’s your choice. Be grateful and free, or be imprisoned by your own fear. This is what leaves you waiting for the ideal path to appear. But it never does. In most cases, you find you’ve got the wrong map because you had let others (parents, teachers, friends, partners, a psychic who channeled the far nethers of space) decide where you should go.

This moment is a chance to sink into life just as it is presenting itself right now. Again, where are you headed? No matter what happens in life, your compass will get you home if you know how to use it.

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