The Surprising Stress of “Time Freedom”

I used to be a very busy boy.

Jacked up on Dunkin’ Donuts Hazelnut coffee and a mini-fridge full of Diet Coke, I would plow through jam-packed days.

I dug up an old calendar.

5:30 am wake up. Double breakfast. A hard Crossfit workout on 6 hours of sleep.

Meetings galore. And usually a work-related dinner.

Rinse. Lather. And repeat.

I’m exhausted just looking at that schedule.

Thankfully, things have changed.

I’ve had full time freedom since 2015.

But it’s not all that it’s cracked up to be.

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The tyranny of unstructured time

I’ll cut to the chase.

I know a decent amount of folks with Time Freedom.

Most are self-employed. Some have FIRE’d. And others (like yours truly) are semi-retired.

Yet for some reason, they can’t enjoy their Time Freedom.

They struggle to work out in the middle of the day:

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They feel guilty taking a walk at 10 am.

And they can’t watch their favorite TV show between 9-to-5 on a weekday.

Yeah, for some strange reason, I can only watch TV in the evenings. Even though it doesn’t f*cking matter one bit. (Oh, and I have ZERO issue working on a weekend)

So we need a new phrase.

There’s True Time Freedom.

And it’s flimsier counterpart: Faux Time Freedom.

Are you psychologically free?

With Faux Time Freedom you control your calendar.

You leave your mornings open for Deep Work.

You carve out time for kids’ pick ups.

You take a late afternoon walk with your boo.

However, you’re still racked with guilt.

Guilt that you didn’t do enough. Shame that you’re falling behind your peers. Or insecurity that this life of freedom’s gonna come crashing down.

Conversely, with True Time Freedom you bounce from one lily pad of joy to another.

You’re unshackled from the pernicious expectation that “I should be doing THIS instead.”

You are NOT your output

What’s going on here?

For me Time Freedom has not cured me of a struggle that has persisted deep in my soul for years.

Deep in my subconscious, I still feel that my ultimate worth as a human is measured by my “productive activities.”

Thankfully, I have the Time Freedom (True or Faux) to go inwards.

And I’m pretty sure psychological freedom lies on the other side.


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