On Planning

Dear True Self,

How can I plan better for my life, both in short term and long term? I find myself making a lot of mistakes and feel like I’m taking steps backwards.

Sincerely,

Man With No Plan


Dear MWNP,

Planning is one of the greatest illusions of security that we cling to. We think that by planning properly, we can either guarantee an outcome or avoid unwanted outcomes. But the reality is, there are no guarantees, and there is no such thing as security in life.

The past can never predict the future. It doesn’t matter how many models and data you have, it is not a guarantee. Even if you bounce a ball 10,000 times, and each time it hits the floor and comes back to you, it doesn’t mean the next time it will do the same. It could go sideways, to the moon, turn into a snake and slither away…! You have no way of truly knowing.

Now of course, all this sounds far fetched. You’re not going to go jump off a rooftop thinking there’s a chance of flight based on this logic. Odds are overwhelmingly that you will fall to your demise.

So why am I talking such nonsense? I am merely attempting to point out to you the limitations of planning. If you think planning is somehow a guarantee in life, you have forgotten it’s limitations. When you forget the limitations of something and act as though it’s a sure thing, you are headed for suffering.

Never fool yourself into believing that you can pin down life and make it behave the way you want. When it comes to the external, you need the cooperation of so many variables to make things happen. Plan all you want, but in the end, things will land where they land. Life will not let you get away with forcing your ideas upon it.

If you rely too much on your planning, you will become extremely narrow minded. Constantly trying to jam the square peg into the round hole, unable to see the stupidity in it. If you make up your mind before something even happens, how will you ever be able to adapt?

You must always act as the situation demands. The situation is always changing, different moment to moment. If you have some 10 point plan and just try to barrel through executing it regardless of the cost, you will wind up causing a lot of damage in the process. In the end you still may fail miserably!

But if you instead learn to look at each situation on it’s own and act sensibly, you will see there are always countless opportunities. With a one track mind, you will see only obstacles – with an open one, you will see possibilities.

So don’t let planning overtake your sense. Don’t let it narrow your mind and your scope. The plan isn’t what’s important. What’s important is your trajectory.

Stay on target. If you cling too hard to your plans, even when they aren’t working, you will miss. If you throw away your plans at the first sign of trouble, you will never get there either.

It is important to have a steady focus and work towards it however the situation demands. You want a plan that will work in all situations – no such plan exists, for anything.

Whether it’s short term or long term, whatever your vision is, you must work intelligently, or at the very least, with intelligent people!

So maybe you’re confused. Should I have a plan or not?!

First, you must stay absolutely focused on where you are going. Keep your heading straight and true.

Then, be willing to get there however unexpected the journey becomes. As long as you keep focused on where you are going, no matter what life throws at you, you will use it for your vision.

Lastly, go in with some semblance of a plan if you wish – the more complex the vision, the more planning will be necessary. Just don’t be too attached to it. Be willing to rewrite it constantly, shift it, throw it out even!

What I am saying is, the only plan you need in life is this: whatever life gives me, I will use it.

If you make that the foundation of your action, then it doesn’t matter what you do. Plan or no plan, whatever happens you will make the most of it.

With gratitude,

Your True Self

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