Planning to Fail

“If you do not change direction, you may end up where you are heading.”

Lao Tzu

Whenever I’m feeling stressed or overwhelmed, it’s usually because either A) I’m trying too many things at once, B) I’ve said ‘yes’ to something I should have said ‘no’ to, C) My intention/direction is vague and-or D) All the above.

A. Doing too many things at once is something I’m constantly rebalancing. Curiosity can lead you down to thousands of wonderful (and occasionally bizarre) places. This can spark a countless number of ideas and opportunities, but if you let curiosity run on a rampage all the time, you’ll wake up a week later after being lost in a deep Reddit or YouTube rabbit hole.

The important thing is to have a firm grasp on the few major things that are important to you, so you can pare back when you become aware that you’re a few hundred pounds over your elevator capacity, so to speak.

B. This one is similar to A. Saying yes is easy. It’s nice when someone asks you to do something for you. But too many of these, and you’ll end up doing everyone’s work except your own. It’s hard to say no, but it’s essential if you want to still have the time and energy to focus on what’s most important to you.

C. If there’s a centralized theme to this observation, it’s that only having a vague idea of what you want can easily lead you off into a direction you may or may not have wanted to go.

Sometimes vagueness is what you want. You want the surprise and spontaneity that an unknown direction will bring. Traveling (remember traveling?) to a new place, for example. It’s a delight when you can discover an unknown (to you) restaurant that is divine in a city you’ve never been to before. Movie spoilers is another one. If there’s a movie or tv show I’m interested in seeing, I don’t want to know anything about it. Don’t give me the plot. I don’t want any details. I want to be surprised (and hopefully delighted) which I wouldn’t be if I knew what was going to happen beforehand.

But what about when you’ve got a problem you need to fix or when hazy ideas are holding you back?

When in doubt, make a plan.

The method can be simple. Grab some paper and a pen and start writing. Make a todo list. Ask yourself questions. Get specific. Dig. Come up with some potential action steps.

The true benefit of planning is clarity. We’ll rarely actually reach the exact goal we set out to achieve, but taking time to understand our next steps will move us in the right direction.

If we only have a vague sense of what we’re after, how can we possibly know what we can do to get there?

Planning gives us specific actions to take. No—it gives the next action we need to take. Our destination might be completely different after we finish that action, but by then we are ready for the next one.

Planning is about playing the chessboard. The next move is critical, but only when combined with the next several moves and countermoves in the future. The idea isn’t just to have one fixed thing we’re after. We’re thinking about all the potential outcomes—worst-case and best-case scenarios. We’re trying to nudge the outcome in a particular direction, but if it doesn’t work at least we have an idea of what a bad scenario looks like and what we can do to handle it.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1013

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