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November 23rd, 2022

Things that are fulfilling can be fun. But not all fun things are fulfilling, and oddly, the litmus test is:


Most “fun” things ultimately resolve into expressions of convenience: going out to dinner, for example. It’s really convenient when a stranger prepares your food. Even something like travel: someone else built the plane, flies it, set up the systems that allow planes to fly to distant points on the globe, and despite how uncomfortable long flights can be, all of this is enormously convenient when compared to the alternative… driving, or taking a ship across an ocean. And these two conveniences basically compromise the top of the list for things people like to do for fun in many well-developed societies.

But take for instance something that is fun but has no relevance to convenience: playing chess with a loved one, for example. There’s no question of “convenience” or “inconvenience” involved in such a thing, and so it’s something that fits in the overlapping sliver of the Venn diagram that conjoins fun and fulfilling. Strangely, such a wholesome activity has a lot of counter-intuitive and inconvenient roommates in that little home in the center of that Venn diagram. Wholesome activities may be the only category where fun, fulfilling and convenient overlap. When we regard the rest of life, things diverge in very strange ways:

Let’s examine the relationship of fun and fulfillment from the other side: what is fulfilling often isn’t fun! Working hard on a personal project, for example. When it’s finally all done, the feeling of relief is amazing, and the fruits of that work can provide a sense of fulfillment… forever! But such fulfillment is often gained from hardship.. which isn’t usually fun.

The point of juxtaposing fun and fulfilling is to point out the fairly robust idea that a fulfilling life generally means taking the more inconvenient route. This completely contrasts with the usual paths of life which are directed at optimizing and collecting convenience. Getting a steady and stable job, an apartment or house and replicating the usual relationships common to such an existence are far more convenient than say, trying to bootstrap a business with nothing but an idea and a little relentlessness. The former will be seen as normal - which is also very convenient - but risks living a life that almost certainly lacks the potential to experience much greater levels of fulfillment that are possible during one’s short time alive. The bootstrapper will almost certainly be seen by others as weird, and probably lost and wayward. And when compared against the “normal” person, the bootstrapper can easily look like a loser for not having the normal conveniences of life at their disposal. So why does the bootstrapper take such an inconvenient path? Well for one it’s likely to be more fulfilling, but that’s not the full answer. We should probably ask if the bootstrapper even has achoice about following such a path, but that question broaches the murky topic of free will, and that obnoxious realm of discourse is probably better left inside Pandora’s Box. So perhaps it’s best to take a step back and say the bootstrapper regards the more inconvenient path as the more fulfilling one.

The trade off is a simple one:

Would you rather have more comfort and convenience?


Would you rather have a more fulfilling life?

The two aren't mutually exclusive. But it's a definition of degree: more fulfillment likely requires less convenience. Unless of course the inconvenient route taken by the bootstrapper leads to an outsized pay off which can then provide all those missing conveniences. But this is not guaranteed, of course, and that uncertainty is part of the price of admission to such a life.

This opens up a deeper question about the connection between convenience and uncertainty.

Those who can afford more luxury (convenience) are in effect eliminating uncertainty from their lives more and more. Convenience correlates to predictability. Conveniences are reliable, and this reliability helps tame an uncertain future into a familiar shape. The convenience of getting Starbucks on the way to the office helps determine a predictable shape for tomorrow. In contrast, the inconvenient route can be symmetrically defined as a willingness to engage with uncertainty. The bootstrapper may not know where they are sleeping tomorrow, which is.. well - very inconvenient. Few things are potentially more inconvenient and uncertain than being effectively homeless.

But, it’s all about how you look at it. The bootstrapper who sees such an issue as “where am I going to sleep tomorrow?” as part of an adventure with a larger mission is going to experience practically no stress (and maybe even a little thrill!) compared to the convenience-addict who is faced with the same circumstance and sees it as daunting.

In fact, that parenthetical comment in that last paragraph is really the key to all of this. If a person can train their mind to see the difficult, inconvenient path as thrilling… as fun…. Then they really have a golden ticket to the rest of their life.

This has a very strong basis in neurology regarding the dopamine-fueled reward system. Enjoying the struggle is how you crack the code and “have your cake and eat it too.” These sort of sneaky tweaks are generally regarded as unrealistic, and impossible, kind of like cultural myths that everyone likes to ignore and deny. But it is possible to enjoy things that many if not most others see as horribly unenjoyable.

Just as many people shudder at the prospect of uncertainty, others see uncertainty as ripe with options, like an able painter smiling at a blank canvas, or a writer seeing the blank page as a gold mine, pick-ax in hand, lips licked, and boiling with an eagerness to get started. Others are terrified by such open-endedness. Not knowing where you are going to sleep tomorrow can be seen like a blank canvas. The absence of options can be seen as an abundance of options if the muscle of resourcefulness is well maintained and powerful.

The divergence in such life paths among people likely has to do with confusing fun and convenience at the expense of fulfillment.

Children are guided by fun, and given their cognitive development and familiarity with the world, life is quite literally a giant uncertainty that they have fun exploring.*

At some point, people slowly trade in the fun of exploring the unknown for the convenience of comfort. This process is also defined as a shift away from uncertainty as a potential source of fun options towards uncertainty as something to fear - something that directly contradicts convenience because convenience correlates to predictability.

Fun is replaced with convenience.

Fulfillment is replaced with a sense of certainty and safety.

But the thing is, no one is ever completely safe nor secure, and because of this it’s always a false sense of certainty. And that’s all certainty is - a feeling. An emotion. And as convincing, solid and persuasive as it feels, feelings can be incorrect in just the same way a thought based on flawed data can be incorrect. Anyone who revels in their sense of certainty is fooling themselves.

Remember what Feynman wrote: The first principle is that you must not fool yourself, and you are the easiest person to fool.

When uncertainty inevitably forces its way into a person’s life - which it is guaranteed to do given enough time - who is going to have the mental composition to deal with the situation more effectively? The one who collects a life of conveniences? Or the bootstrapper who has become an adept navigator of the inconvenient and uncertain path?

Again, the more inconvenient path proves to be the more useful since the inconvenient path requires a person to exercise the muscle of resourcefulness more often and more deeply than the one caged by convenience.

So will life be fun or fulfilling?

Those who are shrewd and ruthless about what they want out of life can end up with both!

While those who don’t take the time to carefully investigate the distinctions here can be lulled into a life that has… neither: a life that not only lacks fun and fulfillment but which is also fragile to the risk of crumbling beneath the weight of some challenging uncertainty that lurks somewhere in the future, waiting for its inevitable opportunity to become the present.

*Note: we should not confuse conveniences with necessities. A child who has necessities provided for by parents can explore the uncertainty of life and have a ton of fun doing it. Facing the uncertainty of being short on necessities is another matter - one that might be fun for a scrappy adult bootstrapper, but only because there’s a huge difference between the child and the adult bootstrapped when it comes to agency and the ability to make things happen and get things done.

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