It’s not supposed to go according to plan

Planning is always a good idea. The adage goes, “If you fail to plan, you plan to fail.” There’s another saying, attributed to Peter Thiel, “A bad plan is better than no plan.”

Things get weird when our plans create a byproduct: expectations. It’s like we forget that our plans are just guesses; it can feel like our plan became a labor of love, like a piece of IKEA furniture, and now we’re emotionally more attached to it than we should be. We see what we expect to see, and we lose our ability to become flexible.

Plans are also often restricted to our worldviews. We see the possible futures and choose between them, and we fail to notice there are other futures we didn’t even see. I love this diagram from Norman and Stephanie of Between the Lines:

The reality is, for most of us, finding a life purpose and sticking to a plan probably is not the best idea

Planning is valuable as an autotelic activity; it’s not meant to be followed to the tee.

It’s good to have an idea of where you want to be in five years; it’s great to hold it loosely, and to be flexible. You’ll see more opportunities right where you are if you stopped, relaxed, and breathed for a sec. Let go of the labels you’ve put on yourself—entrepreneur, employee, artist, etc.—and consider breaking out of your comfort zone.

A salient example: If you’d asked me five years ago, I would’ve told you I liked New York City so much I want to visit every season (and I did, two or three times!). Last week, I just moved here. I had no idea it would work out like this. Before I moved here, I lived in Hong Kong for a year and a half—this was even less expected, and I loved it. (I didn’t write much about it yet, except this brief diatribe on T-shirts, I’m still processing the trip!)

It’s okay that nothing went according to plan. In one aspect, I practiced Taoism and surrendered. In another aspect, I also started leaning into other inclinations (values, dare I say?) more; creativity, craft, health, curiosity, travel, generosity, and discovery.

If you wonder how the hell you ended up where you are—just know that this can always bend towards a positive. No matter how you feel about the outcomes or the present, it’s worth appreciating your open-mindedness, resourcefulness, and flexibility that brought you here. 

This piece feels like a first in exploration; I definitely wrote this one to think, and I’m sure it’ll reveal itself as I keep writing.

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