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How “best” is the best case? I find this question invaluable for uncovering my willingness to *truly* commit myself to a decision.

A few months ago, I wrote an essay about the converse question: “how bad is the worst worst case?” I found that exercise to be rather interesting, and surprisingly comforting. I definitely understand the limitations of that question – re: the worse case – and how I am certainly privileged with special circumstances (being born in the year 2018, in the United States of America, into a family with a household, etc.). 

Today, I balance that question with the aforementioned: “how best will the best case be?” Say I take the job, or say yes to the event…what could the outcome possibly be? Is there a scenario in which I win? By how much? And what do I win? I think both prompts are equally important in the sense that one is far less valuable without the other. I need both to best understand how to make decisions.

Understanding the “best outcome” is of course just a guess. Guesses, especially mine, are often incorrect – especially when time-horizons can be so so variable.

So why guess? Why think about the “best case in the first place?” 

Because I find if I am not excited by the very best outcome…I am often unable to get motivated by the short term? Another way of saying that is: the best best case must really excite me. There must be one great outcome – one that I can believe in. Otherwise, “the cost of doing business” will be a large deterrent. 

The exercise works like this: imagine you make a choice…you go to a party…you start a side project…etc.

Imagine everything goes perfectly well. In fact, things go exceedingly well! Your project takes off. You end up owning the space. 

Then what..?

Are you then happy? Are you then proud?

Sure, there is value in understanding the short run. Not every decision can or really should be made via this type of analysis…sometimes you really just have to go for it and fail if you fail. Action is the only real remedy I have found for sluggish-ness.

But once you find yourself in a cycle of motion…where the question is not “if you can do things” but rather “should you be doing things” or what you should be doing…these types of decisions become more and more important.

And such, I like to imagine the best case. The impossible case.

People tend to push back on this case. They say it is too unlikely. Or too risky. Or too scary. Sure. It probably is. But is there another lens worth dreaming about? Is there another mindset that would be better? 

The case that has a slim chance of happening but is just possible enough that I could be motivated by it – that is what I dream about. 

More practically, I have learned a lot about what I want to work on in the future via this exercise. I have started projects, only later to learn that I am not so so excited by the best best case outcome. 

I do not want to build a marketing tool for marketers. I do not want to build a chrome extension that boosts productivity. I do not want my full time job to be planning events for students. Etc. 

The best case…if it is not the best…is it worth dreaming of? I guess that is another thing that I come back to often, I want to dream large. I want a wide imagination. 

I think I have one. Society of course does not want me to on all sorts of levels. 

But why be childish, naive, and dream so big?

Because “legendary dreams” are my only remote chance of doing something remarkable. I am not necessarily motivated by “remark-ability,” but the opportunity is rare. And, it is more fun, for me to take small steps towards big leaps versus nothing whatsoever. 

 


Also published on Medium.