On Planning

You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.” – Steve Jobs

The first 21 years of my life were planned. I had a blueprint. I had dots and I was hell-bent on connecting them. The last 2 have been an open canvas – more of a “see what happens” approach.

In 2012, I decided not to go to law school and told a buddy of my decision. His first response was ‘so what’s the plan then?” I didn’t have one and I told him as much. He looked at me and said ‘what do you mean, you always have a plan.’ He was right. At that point in my life I’d always had a plan. I was always scheming- not on my next move, but on the three moves past my next move. Up to that point, it had worked. I was going to a good college, on track to get into law school, which put me on the path of a prestigious career and (hopefully) making large chunks of cash. Tough to argue with where I was thanks to my ability to make plans and follow through.

But we all know things change. We change. These days few of my friends ask me about my long term plan. To them, it’s apparent that I don’t have one. Since graduation I’ve been going about my life differently than them. Different strokes for different folks as they say.  At times it’s hard. Part of me wants to turn off my desire for adventure and just stay in grind mode. Part of me wants to have tangible dots to connect. It almost feels like I’ve been suppressing my true “planning” nature. Have I’ve been hiding from my true self pretending to be this guy who just rolls with the punches going wherever life takes him? Lately, I’ve been wrestling with the question of which one is the real me? The guy who had plans A-Z or the guy with the “let’s see where this goes” mentality? Can we successfully fight our own nature? Will our nature win out in the end? If I make conscious decisions going against my “default mode” am I living a lie? Does the fact that I’m choosing a different way to live make that my real nature? Do our choices matter more than our natural disposition?

I’ve talked about finding your passion and chasing you dreams before. The only way to do it is to try new things. Sometimes that means deviating from your original plan. I’m moving to Australia next week which definitely deviates from my original plan. It’s not something I ever expected to do once I got back from Europe. I can’t explain why, but it just felt like something I had to do. An experience that I shouldn’t pass up. This is where I’ve been struggling the most with my “true nature”. The planner part of me hates that I’m moving down there with no job and no real plan. Dozens of people who I talk use the word “crazy.” But my adventure side is excited because of the endless possibilities this decision may bring. Which one should I listen to?

When I was younger I wouldn’t change my plan for anyone or anything. I had dreams. I had goals. If you weren’t part of them than I wasn’t interested. Then I started dating a girl and after a few years assumed it’d all work out for the long term. I decided to put law school on hold (wanting to go out of state) and stuck around in Nebraska for an extra year because she hadn’t graduated yet. I took a job I didn’t care for, in an industry I was indifferent to, merely to keep that relationship going. I sure I wasn’t the first person to let a relationship dictate my location or life circumstances and I know I won’t be the last.

Unsurprisingly, two months after taking the job we broke up. Through no fault except my own, I was stuck. I felt lost. I had given up my plan in the hopes of something else and it blew up in my face. Of all the things I had planned for (and I had planned years into the future) us breaking up wasn’t one of them. What do most people do when one plans falls apart? They build a new plan. Most never really realize that their inability to control the future means that the construction of their plan is like a sand castle built next to the ocean’s rising tide.

What is perhaps surprising is that this was the moment that I stopped trying to plan everything. Even though switching from my original plan had backfired it had also freed me.  I was no longer forced to follow a plan that I had long out grown.

No matter how much I planned I could never plan for everything. At 18, I never planned on meeting that girl, at 21 I never planned on us breaking up, and at 24 I never planned on living in Australia again. But while goals are important, having a concrete non-changing plan isn’t. After all, it only takes one wave to come in and destroy your sand castle.

Planning in life is like planning in chess. As you play you’re constantly thinking moves ahead. You have expectations of what will happen next. You expect your opponent to make a certain move and then you plan to counter and their response to your move and so on. The problem? What if your opponent makes one move different from what you planned? One simple move in a different direction ruins everything. Back to square one. What good did it do you to plan six moves ahead getting your hopes up for checkmate? None.

Life’s a lot like that. There’s no point in planning more than two or three moves ahead because on any given day, at any given moment, something can happen that completely shatters our perfect plan. For better or worse life is constantly changing. It’s constantly challenging us. Constantly exposes us to new things that we could never have seen coming and therefore never have planned for. What happens when you have an incredible opportunity (chance to travel the world, meet the perfect person, or an unexpected job arises) but it doesn’t fit into your plan? Do you have the courage deviate from what you you thought you wanted? Or will you ignore a life changing decision because you didn’t plan for it?

Mary Schmich wrote in a graduation speech a few years back:

“Don’t worry about the future. Or worry, but know that worrying is as effective as trying to solve an algebra equation by chewing bubble gum. The real troubles in your life are apt to be things that never crossed your worried mind, the kind that blindside you at 4 p.m. on some idle Tuesday.”

We spend an outrageous amount of time planning and worrying. The truth is that a vast majority of the things we plan for or spend time worrying about never happen.

The big moments in life can’t be anticipated. There’s no way of knowing what’s coming. But the not knowing is the most exciting part of life. It’s the reason to get up in the morning. Knowing that today could be the day that changes your life forever. When you look back today could be the dot that changes the trajectory of your life. If that doesn’t inspire you to get out of bed and seize every opportunity possible then I don’t know what will. When we have set plans we are seeking only one thing- the next milestone in our plan. The next dot. But that leads us to missing all the amazing opportunities around us.

In Hermann Hesse’s book Siddhartha he writes:

“When someone seeks,” said Siddhartha, “then it easily happens that his eyes see only the thing that he seeks, and he is able to find nothing, to take in nothing because he always thinks only about the thing he is seeking, because he has one goal, because he is obsessed with his goal. Seeking means: having a goal. But finding means: being free, being open, having no goal.”

As odd as it sounds, the key to finding what you want may very well be not seeking it. Instead, keeping yourself open to whatever may come your way and having the courage to pursue it. After all, you don’t have the see the end of the staircase to take the first step.

Thinking about my past and my future, I realized that I haven’t changed all that much. There’s no need for me to worry about which one is the “real” me. They both are. I’m both a planner and a spontaneous experience seeker. I’m not in inner conflict as much as I am learning to blend my desires and experiences to find what I would call a meaningful life.

I still plan, just not as far ahead as I once did. I still think about the future, but it’s more fluid like water not solid like stone. My plan has become not to seek a specific end goal but to seek as many different experiences as I can.  Because only through experiencing as much as possible can we truly ever know what we want.  You can’t truly know you want something until you’ve had options and chosen that thing.  Without options there can be no free will no real pleasure.

I’ve become increasingly more comfortable with not knowing where each dot is leading me. But in time I know that my collection of dots will have created a picture that has have never been seen before.

Stay Gold.

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