Dwelling in Possibility

   The ancient Masters were profound and subtle.
   Their wisdom was unfathomable.
   There is no way to describe it;
   all we can describe is their appearance.
   
   They were careful
   as someone crossing an iced-over stream.
   Alert as a warrior in enemy territory.
   Courteous as a guest.
   Fluid as melting ice.
   Shapable as a block of wood.
   Receptive as a valley.
   Clear as a glass of water.
   
   Do you have the patience to wait
   till your mud settles and the water is clear?
   Can you remain unmoving
   till the right action arises by itself?
   
   The Master doesn't seek fulfillment.
   Not seeking, not expecting,
   she is present, and can welcome all things.

-- Tao Te Ching, Stephen Mitchell translation. http://acc6.its.brooklyn.cuny.edu/~phalsall/texts/taote-v3.h...

I think this makes a lot of sense if you tilt your head a little and look at "business-ing" as a creative position. What the author describes sounds a lot like an ordinary iterative design process.

You have some idea of what you want to do/make, but you aren't completely clear on 100% of the nitty-gritty specifics. You don't necessarily know if every little bit of your plan will work from the get-go, but you'll learn more as you move forwards and ferret out those loose ends. If your original idea does turn out to be untenable, there are likely going to be changes that you can make in order to take things in a new, more plausible direction.

The author says that they have trouble thinking like this, but I wouldn't be surprised if they did so naturally with their hobbies; writing, learning to play an instrument, software projects, hardware hacking...you face the same sort of cycle of vague direction, experimentation, validation or failure, and repeat. Ultimately, it comes down to confidence in your ability to be able to find a path forward and keep moving when you do run into issues; I think that just sort of comes naturally when you're doing something for fun.

One of my favorite quotes springs to mind, by Bill Gates: "We always overestimate the change that will occur in the next two years and underestimate the change that will occur in the next ten. Don't let yourself be lulled into inaction."

>All of them share a view that the principled or systematic person — the person who believes in one truth according to one set of principles — is weaker or less spiritually advanced than the person who sees things through multiple points of view.

If your own principles and views are coherent, tied down to observations and causal mechanisms, then you can imagine counterfactuals. If you can't imagine counterfactuals, and what would draw other people to believe those counterfactuals hold in real life, you don't fully understand your own point of view.

>Is it possible to love something, or pursue something, without freaking out about it?

Ever been married? You can't stay married if you're freaking out about your spouse, nor if you can't acknowledge flaws. You don't keep your cool about your spouse. You commit to loving them as the person they really are, rather than as your fantasy of them.

>I’ve had occasions myself when I deliberately “took myself out of the picture” in order to hold space for others — and it worked pretty well, and was fun in its own way, and people responded well to it, but I had a strong intuition that this wasn’t what I wanted to spend the majority of my life doing. I have a self, and it’s not going to like being cooped up forever.

Yeaaaah... I've definitely been in this situation. It's kinda been boiling at the back of my mind whenever I have to do work with a strictly political group rather than a technical one, or with technical ones where I want to work on some other problem.

These kinds of things take long-term planning to fix. It's not just a matter of working "on your own": you need to get in the right environment where your self can come out.

Many people have a need to be right all the time. This leads to very low comfort with a risk. Moving up the chain requires facing greater uncertainty, ambiguity, and chance of failure.

A very easy test: How do you feel when you get something wrong or make a mistake?

If a car almost hits me and I feel scared, that's an understandable reaction. But if I'm scared by the idea of thinking a different way than I'm used to, or doing something differently than I've always done it, that's less likely to be an understandable reaction, therefore worth interrogating.

If we stop at "it makes me scared", without asking why, how can we grow? If we don't know what part of ourselves we are protecting by avoiding change, how do we change?