This Is Not How It’s Supposed to Work

The start of a new year has a way of making us reflective. We look back, we look ahead, or if not that, then we just think about life in some way or the other, even if that’s only for a few moments.

Has it ever occurred to you that usually the things you care about most don’t make sense the way you expect them to? I mean, the things we thought would make life simpler rarely did. All of us have experienced something when the harder we chased certain things, the further they drifted; the more we tried to control a moment, the more it resisted us. Meanwhile, the things that arrived naturally tend to do so when we weren’t looking for them at all.

These things—or let’s just say some of the most meaningful things—are paradoxical in nature. And this is not a paradox to be solved; rather, it is something to be understood. Some of history’s greatest personalities have observed this contradiction. Their observations can be a bit unsettling at first, but when we fully grasp them, it’s liberating and makes sense.

Learning from opposites

Lebanese-American poet Kahlil Gibran captured this strange tension with characteristic gentleness and poetic style. In Sand and Foam, he writes:

Here, Gibran is describing that his mentors were the negative experiences (or rather the opposites). The core idea is that we often learn most deeply from resistance, and not from exemplars.

When reflecting on this, I can immediately think of two opposites from which I learned:
i) It is from boredom I learned that what excites me. When I got bored, I had to force myself to think or find something that would excite me.
ii) And it was loneliness that taught me what connection and intimacy mean. When I was with my family and friends, I took things for granted, and I hardly realised what it all meant. But when I was away from them for years, then only I realised what connection is all about.

Let’s go back to Gibran’s quote—notice how he admits his ungratefulness to things from which he learned his lessons. He recognises that these teachers gave him something invaluable, yet he can't quite bring himself to thank them. So, why is it so? I think the reason is very human: it’s because the lesson required him to suffer first and get wounded before gaining any wisdom.

The paradox doubles back on itself: we need difficult people to become better, but we resent needing them. We grow from what hurts us, which means growth and pain aren't opposites; they're partners.

What we know that isn’t so

Knowledge is the thing we rely on to make sense of the world and all the happenings, but it carries its own trap. There’s a famous quote which is usually attributed to Socrates/Aristotle/Einstein:

There’s another one that is attributed to Mark Twain:

These two quotes challenge our basic idea of what certainty is. We assume confidence comes from knowing, and doubt comes from a lack of knowledge. But the most dangerous position is false certainty because it is when one is so sure of something incorrect that one never questions it.

The paradox of knowledge tells us to be intellectually humble. Because Ignorance that knows itself is wiser than knowledge that doesn't know its limits. True knowledge requires holding space for doubt.

The cages that liberate

Now, consider freedom, a word we use as if its meaning were obvious. But is it so? Eliud Kipchoge, one of the greatest marathon runners in history, once said:

This may sound backwards at first because we think that discipline is meant to constrain us, and freedom is something that will free us. Looking closely, however, we will realise that the undisciplined person is not freer; they're at the mercy of whatever impulse feels strongest in the moment (or slave to their moods and passions in Kipchoge’s words).

The paradox of freedom suggests that we have to be caged in the right cages. Because structure and system, when chosen consciously, clear the path and give us authority over our own lives.

The law of subtraction

We usually think of focus as paying all our attention to what we're doing. But there’s another quiet contradiction here. In WWDC’97, Steve Jobs famously said that focus is about saying no. He understood the law of subtraction: You become focused by ruthlessly eliminating everything except what matters most.

Even Albert Camus understood that. In his novel The Stranger, he wrote: 

The sentiment is similar: of subtraction.

The speed of slowness

You might’ve heard of a classic advice that is attributed to Abraham Lincoln:

Rushing introduces friction. Anything that’s rushed is prone to errors, tension, or wasted efforts. But slowing down builds precision, and precision compounds. Anyone who has realised this paradox is unhurried, and in being so, they are economical and precise. It may appear slow, but it’s smooth, and smoothness—the elimination of wasted effort—creates speed as a natural consequence.

To put that in Brazilian-Japanese martial arts legend Mitsuyo Maeda’s words: "Slow is smooth, smooth is fast."

What we chase runs away

Alan Watts called it the "backwards law": the idea that the more you pursue feeling better all the time, the less satisfied you become. Watts’ idea is that happiness isn't a destination we can aim for directly. It's a byproduct of doing things for their own sake. 

So, why does life work this way? Why are many meaningful things paradoxical? Why can't the path to freedom be more freedom, or the path to happiness be pursuing happiness directly?

Well, here's one way to think about it: things that matter exist in relationship. Freedom means nothing without constraint to define it; happiness requires unhappiness to give it shape and meaning; focus needs distraction as its opposite to be coherent as a concept; and similarly, knowledge needs ignorance as its boundary.

When we encounter a paradox, we often think we've found a problem to solve or a contradiction to eliminate. But sometimes paradoxes should be acknowledged and accepted. Doing that may or may not make life easier, but it certainly makes it richer. And maybe that’s the point.

When we stop demanding neat answers, we become better equipped to live with the complex reality that was always there—quietly shaping us, whether we noticed it or not.

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