Why Simple Isn't Easy (And Why That's the Point)

Stop me if you’ve heard this one: An old man, let’s call him Lenny, brings his clay pot and a rope to a well for water each day. He slowly lowers the pot into the well with the rope, hand over hand, careful not to let it bump against the edge and crack; when it’s full, he slowly pulls the heavy pot back up. It’s hard work but simple. Chuck, a young man, tells Lenny, “You should use the pulley set up over the well instead, man. It’s more complicated but easier.”

Lenny agrees but tells Chuck, “No thanks. The water wouldn’t taste as good.”

In this cultural moment of simplification obsession, everything we believe about simplifying our lives is a paradox. First, the simple thing is most often the harder thing. Second, externally simplifying our lives without internally identifying our values and choosing to spend our time and energy to those ends makes us more anxious, less content.

So let’s talk about why this is — why simple is rarely easy, and why internal simplification is really the first and only step needed for all-around decluttering.

Why simple is rarely easy

If something is simple, it's uncomplicated—few parts or steps. If something is easy, it requires little effort. The simple things are rarely the easy things.

Take meditation. You just stop and observe your thoughts for a short time. Not easy. Why? Because it requires sustained attention and facing uncomfortable thoughts. Also, it can't be "hacked." You just have to do it (so we often don't).

Or washing clothes. You could wash them in the bathtub with a bar of soap. Simple but not easy. Instead, we use a washing machine. Easy but complicated. Do you know what a water inlet valve is? I don't. Could you build agitator paddles or a control panel? Me neither. But I need them all to wash my clothes.

Even Henry David Thoreau’s mother famously washed and mended her son’s clothes when he roughed it at Walden Pond.

Popular ways to live “simply”

Today's attempts at simplification often chase trends instead of changing how we live. Minimalism promises peace through fewer possessions. Homesteading promotes freedom by disconnecting from modern systems and reconnecting to our food (and the poop it makes before we can eat it).

But external solutions don't address internal complexity. We end up with empty closets but cluttered minds, fewer dependencies but constant work. Each still results in anxiety — about losing access to modern conveniences or failing to master the skills needed for self-reliance.

What's missing is knowing what we actually value. Without that, our attempts at simplification become another form of consumption. We buy organizing systems, follow influencers' advice on chicken coops, and chase the next trend in simple living.

Start with what matters

"In the long run, men hit only what they aim at," Thoreau said. What are you aiming at?

Start by identifying your core values. These values serve two functions: they point you toward what matters most, and they help you recognize what to let go.

This internal clarity naturally guides external choices. Knowing your values helps you distinguish between what supports your aims and what distracts from them. The result isn't just a simpler life, but a more meaningful one.

Meaning arises naturally

When your attention aligns with your values, meaning emerges on its own. You don't need to manufacture significance or chase purpose. They arise from being fully present to what matters most. This is the real gift of simplification: not the absence of complexity, but the presence of clarity.

The paradox resolves itself. The simple things might not be easy, but they become deeply satisfying when aligned with what you value.