Ever since my ambition-charged teen years, I’ve sought a higher degree of freedom. The idea of doing “what I wanted, where I wanted, when I wanted” (my personal definition of freedom for many years) enthralled me.

This is not unusual. Most people share a similar goal.

What was unusual, however, is that when I finally achieved a heightened degree of “freedom” I was … well, quite miserable.

I went from scheduling every second of my life to finally accomplishing the unshackling of almost all scheduling. And yet, I felt like a hostage in an invisible prison.  For a while I couldn’t quite put my finger on why I felt this sense of unease. Worse, I experienced guilt for not feeling more grateful to have the freedom I earned.

It’s a scary moment to have accomplished a personally significant goal and simultaneously to feel the opposite of what you expected.

Danger a-head

I quickly learned that freedom can be a dangerous and unassuming trap. It’s a message too seldom discussed. In fact, the common message is the exact opposite.

With that said, I do believe the concept of freedom is a beautiful thing. For most it’s a source of inspiration and deep expression. I would also propose that humanity’s potential is magnified by the number of quality options they have.

So what’s the issue? For a start, we assume that having the ability to do what we want, when we want, where we want is inherently attached to happiness. I’ve since learned that fulfillment does not quite work that way.

Add car chase here

Like many entrepreneurs, I locked onto a target (freedom in this case) — like a dog rabidly chasing a car. But as the specter of logic suggests, the car, once in my clutches, was merely a superyacht in the desert. Beautiful, but meaningless.

And that was the problem. The meaning; it was missing. The definition; it was wrong. It wasn’t the car I needed, it was the car chase.

So then, what is freedom?

Ask anyone to define it.

First, you’ll most likely find there isn’t a shared definition — at least on a personal level.

Second, most people struggle to usefully define it for themselves. And even if they do, it will likely be vague and idealistic. Those two descriptors are important.

Vague: Not well defined in concrete and/or measureable terms.

Idealistic: Terrific sounding, but lacking meaningful substance and purpose. It’s probably most effective to say that an idealistic definition is missing the “Why?” More specifically, “Why will this make me happy?”

With this framework, let’s revisit my old personal definition for a moment: “Doing what I want, where I want, when I want.” It sounds attractive (it was certainly motivating). It was somewhat measurable. But it was cunningly idealistic.

As stated earlier, this definition is propped up fully on the very common assumption that freedom to choose equals happiness. In reality, “freedom to choose” is a fancy way of saying “flexibility in a void.”

And in my experience, many definitions of freedom lead to a similar void — a gap between nothing and some other meaningful activity. But the segue between the two is rarely smooth and almost never immediate. Cue, the restlessness.

The pursuit and the freedom

Adding to the disorder is a large helping of irony. Those most attracted by the pursuit of “freedom” have a genetic disposition that is more engrossed by the “pursuit” than the “freedom.” The glamour, in other words, is filling the void, not working to create one.

In the head of an ambitious, life-loving, Type-A, go-getter, freedom includes visions of filling this void with something “cool,” “fun” or “exciting” (intentionally vague words to indicate unintentionally vague planning). Visions of travel, cocktails on a beach, hiking, surfing, etc. But such visions are not freedom — they’re merely a completely different set of goals. That is a small, but incredibly important distinction.

Alas, it seems to me that although freedom can have many faces to many people, for the active personality (most readers of this blog), it may just be freedom to set more goals.

Once again, the commonly accepted concept of freedom can be seen as a very ineffective, widely-cast net — a quick and easy fallback resolution for purposeless action. But freedom ill-defined becomes its opposite — a confusing and consuming maze of unpredictability, as I personally experienced.

What is your current definition?

I don’t pursue freedom anymore. For my disposition and personality, it’s not the right carrot. It’s too esoteric to be useful. Regardless of how I’ve tried to define it, it continues to sound and feel forced — as though I am attempting to unsuccessfully sculpt a current goal into a single word. It feels like an exercise in frivolity.

So instead, I simply set goals — large and small — and set out to invest a set amount of time, energy, and money to it within a given period. I know when I’m on course and off course. There are no awkward segues and perilous voids. I know exactly what my future looks like — and it’s both exciting and fulfilling.

This same approach may not be what works best for you. But if you are still pursuing freedom, I hope you exercise your freedom of thought to design the concept with some profound analysis.

Stay uncommon,

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