Money & Leisure: Do You Deserve Permission?

I’m lucky to have had an empty house to escape to over the past couple months. It’s about an hour and a half north of Atlanta, nestled near the beginning of the Appalachian trail.

Though only six miles of empty road, it takes me 15 minutes to drive the winding final stretch before reaching the driveway.

With no other homes in sight, it’s just me, the house, and the rustle of a squirrel-filled wood.

Muted echoes of footsteps on the front porch, a key in the door, and an opening to expansive mountain views behind floor-to-ceiling windows. My heart rate slows.

Having been unoccupied and for sale, the house is tidy and pristine, as though brought to life from the pages of Southern Living magazine.

No occupants also means no internet. Nor does the network reach my phone.

north georgia mountain view

But the discomfort of no email access fades and is replaced by the comfort of accepting I’m unreachable. Of knowing that for the next night or two, it’s just me … and me. And maybe (if my ears don’t deceive) a nook-dwelling chimney mouse.

I awake to birds and sleep in silence. My mind rings with the silence of natural sound, and somewhere therein is revived.

Whether I leave having gotten work done or only having only read, cooked, and gone for long walks, departure nearly always comes with a sense of fulfillment.

And almost immediately after, a question:

“Am I allowed to escape to leisure? What do I possibly have to show for it?

The question lingers during the drive home and through the days that follow. It robs me of my experience.


The Shadow World of Permission

This idea of Permission keeps popping up in life, and it’s clear I’m not good at giving it to myself—especially when it comes to taking time off from work.

Look, it ain’t like I’m living on the streets. Though minimal, I have financial wiggle room, and philosophically, I think it’s important to wiggle in it. Life is short.

Yet despite my meta-philosophy that says I should enjoy the life and opportunity I’ve been given, a day-to-day shadow philosophy tells me I need more money, more wiggle room, before being “allowed” to enjoy my life.

If my core beliefs are the sun, the annoying thoughts of permission and undeservedness are rain clouds. They trick me in into forgetting the power that lies behind.

What is the difference between my present and future financial states? Perception.

The literal numbers might be different, but in truth: money is just a concept. It’s an idea. The stuff we trade back and forth is just a symbol for our perception of money.

You Venmo somebody forty bucks—did you trade anything more than a number in space?

(p.s. The This American Life episode on the invention of money is everything.)

I’m reminded of a quote from one of the first books I read on the road to self-discovery, Illusions: The Adventures of a Reluctant Messiah. I don’t know if the quote fully fits this theme, but I’m going to leave it here anyway:

“Look at the sky,” he said, and it was such a quick subject-change that I looked at the sky. There was some broken cirrus, way up high, the first bit of moonlight silvering the edges.

“Pretty sky,” I said.

“It is a perfect sky?”

“Well, it’s always a perfect sky, Don.”

“Are you telling me that even though it’s changing every second, the sky is always a perfect sky?”


I perceive financial problems just like I perceive rain clouds—they’re temporarily covering up a larger truth.

Bottom line:

If I [objectively] have enough money now to survive after a few days of leisure, and if I will also have enough in the future, perception is what causes my current strife, and lack of permission is what keeps me from moving past it.

rain clouds blocking the sun

I’ve known people who go years without a vacation because they want to give everything to their career. They wear this absence of permission like a badge of honor, and it’s both terrifying and awe-inspiring.

Could I stand to have more of that in myself? YES. But in truth, it’s not the life I want.

I prefer balance. I prefer semi-retirement (not later, but now … and forever, damnit!).


Why You Don’t [think you] Deserve It

Here’s the thing:

There’s a good chance that you get a perverse sense of comfort from withholding permission, from dwelling in the realm of “I don’t deserve great things.” Why? Because it’s the realm in which you’ve spent the most time.

The record beneath the needle is the record that plays.

You keep saying you’re not worthy? You keep denying yourself permission?

Repetition breeds reality.

Early on, factors outside your control began outlining the story that said “You aren’t enough.”

The dad who was always late to get home, the kids who bullied you, the teacher who sighed while handing back your homework.

Because you were probably still struggling to learn how to poop by yourself, you almost certainly didn’t know how to analyze the formation of your subconscious beliefs.

Feelings and thoughts you internalized as a youngster became your personal narrative simply due to unchecked exposure.

We’re talkin’ years of repetition, yo. Years of reality construction that turns out to be—you guessed it—false.

Because if we really dig into it, there is no reality. There is just story. There is just sky, ever-changing, boundless and without rules (look, that quote fits after all!).

coffee and relaxing mountain view


Feel Gratitude, Give Permission

How do you fix it? You rewrite the story.

You commit it not just to memory, but to waking consciousness.

Personal stories aren’t just things we visit when we feel like it—they quietly influence everything we do.

Sometimes, the best way to get a song out of your head is with another song.

Want to give yourself more permission? Train your permission muscle.

(There will be growing pains.)

And when feelings of self-loathing, imposter syndrome, and rejection overwhelm, incorporate a little bonus gratitude training:

The only feeling that can exist when you focus on gratitude is gratitude.

Try it—seriously. Take a moment and focus on something for which you’re grateful.

( … go!)

Didn’t that feel good? Didn’t it take over? Even if for a moment?

Gratitude training is one of the strongest tools in overcoming negative mental stories.

Give yourself permission. Focus on gratitude.

When you want to switch it up, focus on your accomplishments, your greatness, your inspirations. They’re all sides of the same coin.

I’m talking about a many-sided coin here. I want that coin!


And now, with a looming weekend and a lengthy to-do list, I’m going to work, then give myself permission to relax.

I hope you do the same.

Your thoughts? I’d love to hear ’em below. And get an email when I post something new!

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