Winging it

I have nothing against people who like planning and following plans.

But all planning is ultimately your need to feel in control. It's a you-problem.

I say problem because being good at planning nurtures a bit of entitlement within you. You move ahead in life thinking - because plans work out 70% time, the other 30% fail because of an externality.

Excessive planning makes you arrogant about your capability. It's an identity you love to own and boast about.

After all, excessive planning definitely reaped immense material benefits in life. But you're incapacitated when struck by failure. The sudden loss of control keeps you stuck.

Contrast that to a person who freestyles their way through life.

Freestyling may come across as messy and unproductive. One might think of it as wasted potential initially.

But the freestyler is equipped enough to become a good planner too.

The freestyler is aware that one externality or another is always at play and won't try to optimise every little detail in life. They are ready to work things out without a plan too.

But don't think of freestyling as a justification for a sloppy life.

I think if you are someone who constantly feels inadequate, please know that most people are winging life, freestyling rather.

The planners do well at making it appear as if they have it together, and all the tools, and systems they design, make their ways seem elegant. But it could be a front.

Because regardless of if you freestyle or plan, the only thing that matters most is when you act. Only actions count.

You can keep planning and never get through the doing, or you can do something without excessive thought, leaving sense-making for later.