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Red-Eye Redemption: A Farewell to Flying in the Dark

Passengers in a dimly lit airplane cabin wear headphones, two focus on tablets, with a view of the window. Calm mood.
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There comes a time in every traveler's life when they must ask themselves the hard questions.


Like: "Why did I think flying overnight was a good idea?"

And: "Has this seat always been made of concrete?"

And most importantly: "Is that child behind me practicing for the Olympic kick-boxing team?"


Let me paint you a picture: There I was, leaving paradise at midnight. Honolulu, 80 degrees, palm trees swaying in the breeze. The kind of weather that makes you wonder why humans ever chose to live anywhere else.


Fast forward six hours.


Colorado welcomes me with all the warmth of a vengeful ex – 5 degrees and a snowstorm that's apparently auditioning for a role in "The Day After Tomorrow."


As Steve Martin once said, "A day without sunshine is like, you know, night." Except this was night. And then more night. And then a really, really cold morning.


The Universe's Sense of Humor


You know what's funny about red-eye flights? Everything. Everything is funny when you haven't slept for 24 hours.


The way your neck keeps doing that thing where it drops and jerks back up, making you look like a malfunctioning robot.


The way you try to convince yourself that if you just position your travel pillow slightly  differently, you'll achieve perfect comfort. (Spoiler alert: You won't.)


The way you pack your "comfortable" clothes for the flight, only to discover that there is no such thing as comfortable at 35,000 feet at 3 AM.


The Wisdom of Age

Wayne Dyer once said, "Change the way you look at things, and the things you look at change."

Well, I've changed the way I look at red-eye flights. They've changed from "money-saving travel hack" to "voluntary torture session."


From "efficient use of time" to "why am I doing this to myself?"


From "I'll sleep on the plane" to "I'll lie to myself about sleeping on the plane."


The Temperature Tango


Here's something they don't prepare you for: The thermal whiplash.


Hawaii: "Here's a lei and 80 degrees of pure bliss!"

Colorado: "Hold my snow shovel."


The highway's closed, by the way. Because apparently, the weather gods thought, "You know what would be funny?"


The Seth Godin Moment


Here's the thing about red-eye flights: They're a perfect metaphor for all the other things we keep doing even though we know better.


We do them because:

- They're cheaper

- They seem efficient

- Everyone else is doing them

- We've always done them this way


But what if we stopped?

What if we admitted that some conveniences aren't worth the cost?

What if wisdom isn't just about knowing when to start things, but when to stop them?


The Awakening (Finally)


I did eventually sleep. In my own bed. For approximately the length of time bears hibernate.


And in that post-red-eye clarity (which feels suspiciously like a hangover without the fun memories), I made a decision:


This was my last red-eye flight.


Not because I'm too old.

Not because I can't handle it.

But because sometimes growing up means admitting that just because you can do something doesn't mean you should.


The Lesson


As Wayne Dyer might say (if he ever took a red-eye from Hawaii to a snowstorm): "Your reputation is in the hands of others. That's what the reputation is. You can't control that. The only thing you can control is your character."


And my character is telling me: "Book a daytime flight, you fool."


The Promise


To all future versions of myself looking at flight options:

When you see that midnight departure time...

When you think "It won't be that bad"...

When you do the math on how much money you'll save...


Remember this moment.

Remember the kick-boxing child.

Remember the concrete seat.

Remember the snow.


Because some lessons are best learned at 35,000 feet, in the dark, while watching everyone else somehow sleep peacefully while sitting perfectly upright.


And if you ever see me on another red-eye flight, feel free to quote Steve Martin: "Boy, those French. They have a different word for everything."


Because clearly, I've lost my mind.


Until then, I'll be booking my flights like a proper adult – during daylight hours, when humans were meant to be awake.


Aloha, red-eyes. It's not you, it's my circadian rhythm.


I'd love to hear your thoughts. Please contact me by clicking here.

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Purposeful Financial and Legacy Planning

Fee-Only Financial Planning

(970) 443-1873

3400 Rosestone Ct, Fort Collins, CO 80525

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