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How Your Plans for Success Can Become the Source of Your Failures

Do you spend most of your time planning your life as a fancy way to actually procrastinate living it? Or do you avoid planning anything altogether as your way of ignoring what’s truly important?


This master-student comparison serves to illustrate the true purpose of planning and why our actions are the key to gaining the information (unobtainable through planning) required to successfully navigate the un-walked path toward the fulfillment of our deepest desires.

The Master (Wisdom)

The master knows that a plan is nothing but a temporary substitute for his inexperience, ignorance, and incompetence relative to a desired outcome. Because he hasn’t done this before, he outlines what he knows, and resolves to do whatever it takes to uncover what he doesn’t.

This is the only purpose of a plan, map, or sign-post: to help you come up with the appropriate direction for your next best step toward your goal. Why only the next best step and not a distant milestone, or the entire journey for that matter?

Because as all masters know, a plan or map is only as useful as what it is accurate to the reality or terrain to which it points. And that the only way to know how accurate it is—or what is required to reach your outcome—is through objective evaluation of the step you’re taking right now.

This is the great secret. The master has realised that you gain/have the most reliable information only during the act of taking your next step, and not through guess-work prior to taking it. And it is this information, acquired only in this way, that leads to true progress.

The difference? The master is okay with not knowing what the next step will bring and learns how to deal with the inevitable cycles of order and chaos, certainty and uncertainty, as a prerequisite for conquering the challenges presented by the un-walked path.

So then the goal of the master is this: to turn all of her plans into replicable results-producing procedures instead of false guarantees and excuses to delay taking (w)holy action.

This is mastery. The ability to strike the perfect balance between staying clear of your outcome, adopting a temporary plan, taking daily action, and course correct as you go.

The Student (Extremes)

The student, who has not yet learnt how to strike this progressive balance, learns through extremes. On the one end, we have a student who spends most of his time developing the perfect plan but hardly gets anything done.

And on the other, we have a student who loses herself in the minutia of life by mindlessly acting without any direction.

The first student, paralysed with fear of making any mistakes, runs the risk of making the worst mistake of all: falling in love with a plan that has no direct relationship with reality. A course if left uncorrected, can only create a life where the present and future is driven by the past.

The second student, who confuses being busy with being effective, runs the risk of wasting years achieving nothing of real value for which a fulfilled life is dependent.

An extreme if gone unnoticed, can only lead to a meaningless, unfulfilled, and insignificant existence. A balance is required. The two students need to become one.

The Myths (What to Remember)

1. You absolutely need a plan and the more detailed your plan the better

Plans are useful. They give us a sense of direction and allow us to feel more confident and organised. But they also quickly become the source for fancy procrastination, misdirection, and attachment.

Plans should therefore be treated for what they really are: a paper-trail reflection of your best guess for moving forward. Guesses that should quickly be affirmed or disproven so as to avoid stagnation, inaction, and denial.

2. You don’t really need a plan, it’s all about the outcome anyway

You’re right. Plans aren’t a requirement. What is needed on the other hand, is vision, purpose, and direction. Because without these, nothing we do or achieve will seem to matter or have any real meaning.

We will always get more out from ourselves with a vision than we will without. But no outcome should ever be overvalued to the extent that it robs us of experiencing the joy, aliveness, and fulfilment exclusive to the present moment we call the journey.

Making it Practical (What to Do)

  1. Purpose: Get clear on what you want for your life. Remind yourself of why you do what you do so as not to lose yourself in the irrelevancies of things that don’t really matter.
  2. Planning: If you know what you want, write down (no more than one page) your best guesses as to how and roughly when you will be able to achieve your goals.
  3. Action: Once the guesswork is done it’s time to take action. Remember, the most reliable information upon which one can act is revealed through experience, not speculation.
  4. Adapting: Continuously re-evaluate your plan relative to the continuous flow of new information and personal experience so that you (and your plan) can adapt accordingly. Course correct instead of starting over each time.
  5. Joy/Life: The actions you are taking now are just as important (if not more) as the goal you are chasing. Indeed, the purpose of the goal is to enrich our present experiences.

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