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Wi-Fi isn’t Working
“I’m getting deep on a plane” —Dierks Buenzli
I’m sitting in the window seat, on a plane, on my way to Houston. And I just won the lottery.
No, it’s not because I have a 5-month old baby sitting next to me, who happens to be exceptionally un-fussy.
Then, why?
Because the Wi-Fi isn’t working.
In a past life, this would’ve been a YUGE source of stress. I had emails to reply to. I had financial models to build. I had people who relied on me. An abundance of important work to do.
And now what? No connectivity? No ability to DM my colleagues? What am I supposed to do? Just watch a movie?
In this past life, amidst the Anxiety, I would feel stuck. Stuck in a tin can that was hurtling through the atmosphere without a way to contact the still-bustling world below me. I was miserable, as my means of being productive were left behind in the departing terminal.
In this past life, unable to bear the anticipatory shame of my bosses’ likely future criticism of my Slacking — even though we were a Teams-based organization — I pulled out my phone and started writing. It felt like I had no other choice. I was too caffeinated to sleep. I couldn’t wear the self-imposed “lazy” descriptor that accompanied watching a movie. I was too burned out to make conversation with the people who sat right next to me. So, I dove into my Notes app to try to create a home for the thoughts that were swimming inside of me.
Frustration. Anger. Preemptive excuse-making. I needed to release the emotions I was feeling, now that the Wi-Fi wasn’t working. Properly Excessively caffeinated, I just kept going… and going… and going.
In this past life, as I flowed freely, I realized something: the fact that the Wi-Fi wasn’t working was a gift to me. I now had no choice but to get proximate & present.
Sure, I could organize & re-organize my To-Do list. But after doing that for a couple of minutes, I realized that this exercise wasn’t doing me any good. It’s not like I was checking off these tasks. I was just reshuffling ‘em. Moving them around in the name of productivity. But, in Truth, it was just pointless, unnecessary busyness.
In this past life, as I started a conversation with myself in the private confines of my Notes app, I realized that I’d won the lottery. I’d won back both time & space (or maybe, it was just the first time I realized that these were always there in the first place).
As I sat there, hopelessly on Airplane Mode, jamming away with no means of escape, I jotted down what was living in my head. I took a look at what wanted to be said. I created the space for what wanted to be released.
In this past life, with no meaningful way to be productive, I was gifted a valid excuse to get introspective.
At first, I addressed some simple reflections:
What’s happening in my life?
What just happened on my last trip? How do I feel about it?
How am I feeling about where I’m heading? What’s my intention when I touch down in this new destination?
After all, if I’m sitting on a plane, then I’m inevitably closing one chapter, while simultaneously starting a new one. A new chapter, full of possibility, overflowing with potential. Whether it was a quick business trip or an extended vacation, I knew I was about to find myself in a different setting. Even if I was Returning Home, by the time I arrived, I’d be different than the person who left.
So, conducting these reflections gave me an opportunity to get centered. To choose how I wanted to approach these uncertain beginnings with my newly-discovered learnings. I got a chance to start again. I was gifted an opportunity to set new intentions.
As a wise man once said spoke:
When elementary school ended, a chapter in our life story closed. It was finished having been written. We came to Rolling Hills having no idea what was ahead of us. However, another chapter in our life story had just begun… starting with a blank page.
Throughout our 3 years here, we filled up that blank page full of memories, as we continued along our middle school journey.
…
So, as we head on to high school, we’ll have the opportunity for another fresh start. And we’ll have another blank page to fill up, full of memories to come.
But for now, the chapter in our life story that started 3 years ago is filled up and is finished being written. The chapter titled, “Rolling Hills Middle School”.
In this past life, a life full of emails & models & managers, I didn’t self-identify as a “writer.” I just wrote. Because I had nothing better to do. Because the Wi-Fi wasn’t working.
Now, back to the proximate present, I’m on a plane to Houston. A quick layover before making my way south of the border. A journey to what I’m told is the 7th biggest city in the world.
I’ve finished my daily tasks of reading & writing. I have a plethora of movies downloaded: Lincoln, Apocalypse Now, and the next set of Marvel-ous movies (as my LOML and I attempt to experience the Universe in chronological order). Downloaded, because I wanted to have options in case the Wi-Fi wasn’t working.
But, I don’t feel called to watch any of these movies in this moment.
First off, I wouldn’t dare commit the most egregious sin of a loving relationship: watching the next episode of a series without the person with whom I started it. But I’ve also come to appreciate the invitation for introspection offered by a Wi-Fi-less, distraction-less space.
I’m not as interested in watching someone else’s story unfold. I want to reflect on and prepare to write my own.
So, I’ll make an attempt to answer my own questions, out in the open:
What’s happening in my life?
I’m traveling. I’m exploring. I’m wrapping up the process of reflecting on my past, as I prepare for this exciting, yet immensely uncertain, future.
What just happened on my last trip? How do I feel about it?
I’m departing from Boston Logan airport after spending the week with my LOML’s family. The loss of a loved one brought the whole family back together. The loss of a loved one served up a heavy dose of Memento Mori.
We spent the week celebrating a man who lived his life as a Giver. He gave to his family. He gave to his community. He served as a sage advisor. He welcomed a conversation with anyone who came to him.
I’m departing from Boston Logan airport with an energy-inducing, inspiration injection.
How am I feeling about where I’m heading? What’s my intention when I touch down in this new destination?
I’m excited. I have no idea what’s about to happen in this new city. But, I have one of my best friends in the world waiting to greet me. I’ll be awaiting the arrival of my LOML, who’s coming to meet me. We’ll continue this adventure altogether. I can’t wait to start this next chapter with a couple members of my Chosen Family.
My intention remains the same as it’s been for the entire back half of this year:
Family
Go Pro in Creativity
I intend to balance:
Investing free time in some of my most important relationships
Continue making progress on high-priority creative projects
I intend to let these intentions guide my daily decision-making.
However, I also know that an intention is most effective when paired with a daily action.
So, here are the habits I plan to implement:
Go on 1 morning coffee walk or share 1 evening dinner together
Read & categorize at least 1 day’s worth of previously-handwritten journal entries
I know that I might not be perfect at adhering to these habits. (After all, #1 relies on the opt-in of another human. Although I guess if nobody’s around, then I could take my Inner Artist out on a date.) But, perfection isn’t the goal when setting a new intention + habit. The purpose of the practice is to create the structure for a successful practice.
I also know that I don’t have to commit to these habits forever. I’m only making the commitment for the tenure of this next adventure. Once we decide to book our next one-way ticket out of here, I will, once again, find myself on a plane. Reflecting. Introspecting. Intention-setting for the next chapter that’s awaiting.
On that future plane ride, I can only hope that the Wi-Fi won’t be working. But, I don’t want to be greedy. I don’t know if I’ll be lucky enough to, once again, win the lottery.

Time to spread my wings & soar. Life won’t be the same as it was before.
P.S. — I published this piece on my connecting flight because the Wi-Fi was working on this one. And yes, I do appreciate the productivity-related irony.

Window seat both ways baby! No need to fly private when you’ve got this level of luxury.
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