Learn to Love Uncertainty

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Learn to love uncertainty.

That’s the best advice that I feel anyone can give. Especially today. Alright, so maybe not especially today since in a lot of ways today is more certain than days when you could get killed by the flu or pirates.

Yet, today is still precarious. While the uncertainties may be far more subtle than starving or getting mauled there may be a greater variety of them.

One such uncertainty is job security.

There are many popular voices today that upon seeing mass migrations, automation, and all sorts of economic shenanigans reflexively begin to espouse the virtues of entrepreneurship.

While I think that entrepreneurship is a fine thing, I also think that one of its core pillars is more important to highlight. That pillar being initiative.

Initiative is what will allow you to navigate uncertainty.

Before you can navigate uncertainty you have to want to navigate uncertainty. This means learning to love it.

Fortunately this loves come naturally, at least somewhat. Despite uncertainty’s membership in an acronym that marketers use to sum up difficult targets (FUD – Fear Uncertainty and Doubt) uncertainty is thrilling. Uncertainty is vital because a sure thing is generally a boring thing. The addicting nature of gambling bears testimony to our innate love of uncertainty.

The aptest analogy for uncertainty is probably the open sea or if you want to get a bit more modern open space. I think that it can be argued that gazing out at the ocean produces a fairly consistent reaction. That being excitement, wonder, and the desire to explore.

Yet, even in days and cultures where sailing was common and promoted as a great virtue not everyone sailed. Why?

Because not everyone learned to love the sea. Not everyone learned to love uncertainty. The infatuation with the idea and romance of seafaring is not the lived love of spreading actual sails, braving actual storms, and overcoming your aversion to such things.

This is where the point of this little essay comes in. Why would somebody have to learn something that comes naturally? What does any of this have to do with work and navigating modernity?

Because it is only the beginning of the thing that comes naturally. Because the world of today is as fluid as the ocean and our social institutions, means of relating to each other, professions, and technology require the deft navigation that you can only master by learning to love uncertainty.

Loving uncertainty will teach you the need for initiative. It is the expectation of challenge and the unknown that will drive you to make the adequate explorations and preparations needed to succeed in an uncertain world.

A favorite lesson that I learned from Alan Watts comes into play here. It is the lesson of the benefit of perspective. Of not seeing yourself as lost in a maelstrom of causality but as an integral component of the great happening. This perspective allows you to see that the hard ground is holding you up, that the hill that’s in your way is taking you higher, that your hunger and fatigue are keeping you alive by pulling you towards seeking out necessities and thus appreciating their satiation all the more.

Uncertainty is the firm ground that’s lifting you up, it is the rain that though at times cold will make that ground fertile, and learning to see it in this way is a psychological tactic that I believe is essential today.

It is essential because it teaches initiative and it teaches love. The whole reason that I pluck the word initiative from the entrepreneurship concept is because it is a principle.

Entrepreneurship you see is a practice, a very specific practice, and one whose successful execution requires a host of skills and realizations.

Principles are much simpler and more essential things which make entrepreneurship possible.

If you have the prefabricated notion that you must become an entrepreneur then you run into the problem of fitting into a mold. You are limiting yourself in the same way that you would by trying to squeeze into a pair of skinny jeans cause they’re hip.

Running a business, a website, programming a game, or opening up a Cafe are all entrepreneurial pursuits which may or may not be a good fit for you at any given time. Holding any one of them or even the more nebulous notion of entrepreneurship as concrete goals may be premature.

Before you begin any of these ventures you need to learn to love uncertainty and take initiative. Starting with a simple physical job while seriously pursuing a creative or academic project on the side is what I’ve found to be best. There is something in the instant feedback and relatively small number of variables of simple manual labor that is absolutely incredible for building the skeleton of timeliness, sequencing, and stamina. You of course still have to be seriously pursuing your creative or academic project.

By academic I do not mean college or university. While those institutions do have value I think it important to point out that one can do serious scholarly work on ones own. Especially with the tools and resources available today.

Staying out of the restricting mindset of becoming an entrepreneur, or needing this or that career, or this or that degree is exactly the sort of embrace of uncertainty that I’m trying to get across.

First learn the initiative of getting things done in a timely manner, of making sure that you are able to provide you and perhaps others with resources, and learning what you love and value.

Entrepreneurship, or a law practice, or a degree in anthropology will I think come more naturally and painlessly with this mindset.


This essay has been mulling about in the back of my head in various forms for a while, and is finally brought forth because I had a firsthand encounter with uncertainty just today.

I’ve taken on seasonal work to pay some bills. Today, there was a surplus of people and a lack of work for them to do. So a couple of us got the day off.

This got me to thinking. Suppose that this was my only idea of income, my only idea of how to make my way in the world, this would make me very nervous perhaps even a little panicked.

Sometimes seasonal work is all that’s available, sometimes law graduates work at cafes, I actually recently ran into a female programmer who is now waiting tables because she got laid off.

These things are testaments to the dangers of certainty and not taking initiative. I am not saying that people that got laid off don’t have initiative or got too comfortable. I’m saying that culturally it is altogether too common to rely on institutions and credentials as if they’re always going to provide us what we need.

I think that many of the folks that comprise these companies and institutions have excellent initiative and understanding of uncertainty but I think that we need to start to stress the need for yet greater initiative and understanding. We need to start to develop practices that foster flexibility and reflect the increasingly fluid nature of class and demographic dynamics.

I have not provided a concrete set of practices in this essay but I may make the attempt later and think that I at least made a decent crack at conveying the requisite ethos.

Some might think this to be dreamy, overly philosophical, and flowery. Perhaps in some ways it is. Perhaps some think that this was merely writing for the sake of writing. Yes, that is true, at least in part. I decided to sit here and type this out not only because I think it is useful and entertaining enough to be shared but because I need to practice writing. I think that this is a good example of living out the ethos of initiative since I could just as easily have watched 90 minutes of stand-up.

I hope this was helpful and thank you for reading.

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