What If the Plan Is to Have No Fixed Plan?

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The night is always the darkest just before dawn, they say. That period before the proverbial sun rises does come with a heavy and almost suffocating atmosphere.

You feel as if you're immersed in a dense silence that's pregnant with anticipation of how things will eventually pan out. But alas, it doesn't last much longer than you expect to endure it.

The sun eventually rises and a new day begins, a fresh start of sorts for those with a flimsy memory.

At this point in time, one of my main execution risks is not being able to perform up to the point of having my present visions become a tangible reality.

Here, execution risk means the potential for failure in translating a plan or vision into successful, tangible results.

I think it's a bit natural to not be sure on the precise "how" or "when" a grand vision will materialize. The real problem usually comes about when the "why" is also dragged into this "unsure territory."

We (a friend and I) were discussing flexible plans and not getting bogged down with the rigid details of a fixed outcome, both literal and non-literal.

Literal vs. Non-Literal Adaptation

In a literal sense, I think it's almost unavoidable that visions evolve as they encounter reality's constraints and also newer opportunities.


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Let's paint a picture here. You think at least a couple of years ahead. Have an arc from your current position that you're exploring. You realize that the time window between the years ahead and the exploration is closing in rapidly. Then you find yourself at a critical juncture, where the abstract future must confront the concrete present.

This moment, where the long-term arc meets the narrowing time window, is precisely when execution risk becomes an immediate challenge.

If I've been "thinking a couple of years ahead," then planning for a couple of years is more like a byproduct of maintaining strategic direction rather than the primary objective itself.

I just can't help it but keep strategizing even when I know that over-strategizing can become its own form of procrastination.

But as the "time window" starts to close (maybe market conditions are changing or simply an internal sense of urgency grows) the abstract vision must distill into actionable steps.

Given that the future is inherently unpredictable, any actionable steps taken are best viewed as experiments for further learning and adaptation.

Uncertainty as Skill

In a non-literal sense, I wouldn't want to commit fully to a singular, inflexible path that closes off all other emerging possibilities.

Taking steps that preserve optionality while building momentum toward the larger arc is only simple on paper because there are many other variables at play that demand continuous recalibration.

I did read somewhere that being okay with uncertainty is the most important skill to develop in this 21st century.

I don't even know where to start with developing this skill but I do agree that it's fundamental to thriving in a world that's in a constant flux.


Thanks for reading!! Share your thoughts below on the comments.



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