Career Planning and the Dao

You’ll swim fastest if you go with the current. You’ll accomplish more in life if you work with the flow of things rather than against it.

The ancient Chinese called this the Dao. The ineffable becoming of things to which we are all linked. The height of wisdom, they believed, was to work with this Way, not struggling against it.

At first, this idea may seem to be simple passivity. That to “go with the flow” means to surrender control and let the forces of nature steer you randomly. Worried about becoming a swimmer crashed on the rocks downstream, this idea troubled me.

But a better understanding is leverage. That an almost invisible action, applied at the right moment, can subtly guide the becoming of things to do almost all the work for you.

There is a story about Duke Huan of Qi who had a secret meeting to invade a state that was becoming rebellious. A servent, seeing the conversation between the king and the general, although not hearing it, inferred this plan and shared the secret. By sharing the secret, the general could no longer launch a surprise attack, losing the advantage and thus avoiding starting a war altogether.

Wu wei

This concept is called wu wei in Chinese, sometimes translated as non-doing or effortless action. The principle being that wisdom means taking barely perceptible actions when things can be easily altered instead of trying to brute force a large change when it is too late.

This concept has had a lot of influence in how I plan my career and my life.

I don’t set long-term goals. If I ever needed to do a job interview, it would be hard for me to answer the question of where I see myself in five years, because I have no idea.

Instead, I try to go with the flow. Not being passive, but trying to apply small, minimal effort in key places to create shifts in direction downstream. Instead of demanding a certain outcome, being open to subtle opportunities to shift directions with smaller effort.

This approach doesn’t mean that there is no work involved. That’s also a misunderstanding. Instead the effort flows naturally out of the flow of tiny actions made earlier.

This is where the swimming analogy breaks down. Because in it, there is a difference between the flow of water and your body. But in an appreciation of wu wei, there is no separation. Your actions also flow in the same way, and just as a small push in the stream can pull you into a different fork of the river, so can a small push create different currents within yourself.

A good example is an elegantly designed habit. If designed well, it fits nearly effortlessly in your life. As it gets repeated, it creates its own current of behavior so that it becomes self-sustaining. If designed poorly, it requires constant willpower to sustain as you struggle against yourself.

Career Moves and the Dao

I think people underestimate how much successful people implicitly use this principle of wu wei in their careers and businesses.

Derek Sivers, who built CD baby into a multi-million dollar giant, originally started when the service he was providing for himself as a musician became popular with some of his friends. While its growth and success depended on Derek, the original idea was pulled along by the environment.

Although I believe it’s incorrect to view successful people as simply being lucky, it’s I think also incorrect to assume that success is caused by a force of will. Instead it comes from recognizing where the water is flowing, and making small adjustments that result in big differences downstream.

Applying this idea can be hard. After all, it is certainly more difficult to find ways to solve problems with tiny actions than major ones. The first idea is often the one of brute force. It takes considerable wisdom to spot the solutions of wu wei.

But I think that presents the first step. Knowing that you are looking for actions which will work with the flow of things in elegant ways makes more more sensitive to those opportunities. They also attune you to areas where you are not working with a flow—where you catch yourself trying to aggressively swim upstream. Spotting these moments can force reflection on whether there might be other alternatives.


The neo-Confuscian scholar Wang Yangming points out, “When blessings and calamities comes, even a sage cannot avoid them.” Thus, suggesting that our abilities to struggle against the flow of things are often in vain. Instead, he suggests a sage should concern himself with the “incipient activating forces in things” and handle everything in accordance with that.

The insight here, I believe, is that often our great strugglings don’t work. Trying to force a business idea to become successful will not make it so. Instead, it is by recognizing subtle points of contact, the “incipient activating forces in things”, that we can make progress.

The most powerful insight of productivity isn’t the self-help bromide that we can accomplish anything we set our minds to, but rather that our willpowers are incredibly weak. But in recognizing that weakness also admits a strength. Because if thrashing around trying to make progress won’t work, then you must instead look for small changes that can have big ripples downstream.