When The System Breaks Down
What happens when your routines meet reality
I'm writing this as an apology.
Not the kind where I grovel or make excuses.
But the kind where I tell you exactly what happened and why your inbox went quiet for a few days.
Because if there's one thing I've learned from building systems and routines.
All the structure that's supposed to keep everything running smoothly.
It's that life doesn't give a shit about your Notion board.
Let me walk you through what a complete travel disaster looks like.
And what it teaches you about the difference between systems that help you and systems that pretend chaos doesn't exist.
The Plan That Wasn't
I had it all mapped out.
I was in Tampa for the Client Ascension event.
I'd written newsletters ahead of time, scheduled through Sunday.
Smart, right?
I'd even accounted for travel time.
I thought I'd have a window on the plane to write another one, keep the streak going, maintain the commitment I'd made to write every single day.
Then we got to Tampa airport.
First delay notification.
Our flight from Tampa to Atlanta got pushed back.
No problem, we still had an hour and 45 minutes to make our connection to Dublin.
Tight, but doable.
We grabbed coffee, tried not to stress.
Second delay notification.
Another 45 minutes.
Now we're looking at less than an hour between landing in Atlanta and our Dublin departure.
We're doing mental math, calculating gate distances, wondering if we should just start jogging the second the wheels touch down.
We board.
We sit.
The captain comes on.
All northbound flights canceled due to weather.
We're stuck on the tarmac for 45 minutes to an hour.
By this point, our Dublin flight has already left.
We're still sitting in Tampa, watching our connection take off without us.
And there's nothing we can do but wait for the plane to finally move.
Welcome To Friday Night Smackdown
We land in Atlanta and immediately sprint to the help desk.
And I mean the entire airport has had the same idea.
The scene looks like some weird corporate version of a riot.
People shouting.
Accusations of line-cutting.
One guy threatening to call his lawyer over a missed meeting.
The energy is pure desperation mixed with rage.
Here's something you learn quickly in these situations.
Being an asshole gets you nowhere.
Being calm and polite gets you to the front of the line.
I talk to a Delta representative.
She's nice, she's trying.
But she's also telling me the only available flight to Dublin is 7pm the next day.
Nearly 24 hours from now.
We take it.
We have no choice.
Now we need a hotel.
It's 7 or 8pm in Atlanta.
I deploy some company funds because at this point, nothing has gone right.
I am most definitely not about to add "sleeping on airport benches" to the list of experiences.
We get to the hotel.
I walk up to the desk.
"Hi, I've got two rooms booked."
The guy barely looks up.
"No, you've one room booked."
"No, I've two rooms booked."
"One room."
At this stage I’m about to threaten to fucking kill myself in a hotel lobby.
Twenty minutes of back-and-forth later, we finally get our two rooms.
We collapse.
We sleep.
We wake up and think:
“Okay, today HAS to be better.”
Spoiler: it wasn't.
The Bags That Weren't
When we'd originally checked in, I'd specifically asked the rebooking representative:
"Are you sure our bags will be put on the new flight? We don't need to collect them in Atlanta?"
"No, I am positive they will definitely be put on the plane."
Famous last words.
We land in Dublin.
My friend Lewis is in a full panic because he's got 40 minutes to make his connection to Edinburgh, then a two-hour train to Newcastle.
We're standing at the baggage carousel, watching bags circle, waiting for ours.
Then the beep. "Last bags have been delivered."
Ours aren't there.
We go to the baggage desk.
The lady checks the system.
"Oh yes, it seems your bags are still in Atlanta."
Of course they fucking are.
Lewis fills out an incident report and sprints for his gate.
My friend Stephen asks the lady:
“Just out of curiosity, what happened to our bags? Why weren’t they on the plane?”
She checks again.
"Let me see... yes, it appears they were actually loaded onto the plane… and then they were taken off again."
That sentence, right there, sums up the entire trip.
Loaded on.
Taken off.
No reason.
Baggage handlers saw our names and went “lmao fuck these guys.”
I think my bag is currently on a flight from Minneapolis to Dublin.
It’s meant to be delivered to my house.
It will probably end up launched into the ocean or something at this stage.
The Thing About Systems
So why am I telling you all this?
Because I promised to write a newsletter every day.
I built systems to make that happen.
I time-block.
I pre-schedule when I can.
I have templates and processes and all the productivity porn you're supposed to have.
And none of it mattered when I was stuck in an airport with no wifi, arguing with hotel clerks, and trying to figure out where the hell my luggage went.
There's no system for that.
About one in four flights in the U.S. gets delayed or canceled.
That's roughly 25% of all flights experiencing some kind of disruption.
The most common reasons are airline operational issues, late-arriving aircraft (which creates a domino effect), and air traffic system problems.
Weather accounts for less than 2% when you look at the official stats.
But it ripples through everything else, turning small delays into total breakdowns.
The average traveler hit with a major delay or cancellation spends around $500 to $2,700 dealing with it, depending on how bad it gets.
That's hotels, meals, rebooking fees.
All the shit that piles up when your plan falls apart.
But here's what's interesting.
The numbers don't capture the real cost.
The missed commitments.
The broken streaks.
The guilt that creeps in when you realize you can't do the thing you said you'd do.
Edge Cases and Real Life
I talk a lot about systems because systems work.
They reduce decision fatigue.
They keep you on track when motivation fades.
They turn goals into automatic behaviors.
But systems aren't magic.
They're tools.
And tools break when you apply enough pressure.
You can't systemize your way out of a flight delay.
You can't routine your way through a family emergency.
You can't time-block your way around a sudden crisis that demands your full attention.
What you can do is build systems that account for failure.
Not failure in the sense that you're planning to quit or give up.
But failure in the sense that life is messy and unpredictable and sometimes you're going to miss a day.
Or three days.
Or a week.
The question isn't whether you'll get knocked off track.
You will.
The question is how fast you get back on.
That's the real system.
The one that says: "Okay, this didn't go as planned. What do I do next?"
Not, "I failed, so I quit."
Not, "I missed three days, so the whole thing is ruined."
Just, "What's the next right move?"
Getting Back On
The Client Ascension event was incredible, by the way.
Worth every delayed flight and missing bag.
I learned a ton, met great people, came away with ideas I'm still processing.
(I think Eddie Maalouf inspired me to open a friend chicken store)
But the trip itself was a reminder that you can't control everything.
You can prepare.
You can plan.
You can build the best systems in the world.
And then Delta can take your bags off the plane for no reason, and you're standing in Dublin airport at 6am filling out an incident report.
The move isn't to blame yourself for not having a backup plan for your backup plan's backup plan.
The move is to accept that edge cases exist.
That catastrophes happen.
That the only thing you actually control is what you do next.
I missed a few newsletters.
I don't love that.
But I'm back now, writing this, because the system isn't about perfection.
It's about momentum.
You build routines not because they'll work 100% of the time.
But because they'll work most of the time.
And when they don't, you acknowledge it, adjust, and get back to work.
That's it.
That's the whole thing.
So if you're beating yourself up because you:
Missed a workout
Skipped a habit
Broke a streak you were proud of
STOP.
You didn't fail.
You hit an edge case.
Life got messy.
Something unexpected happened.
The only failure is staying down.
Until death, all defeat is psychological.
Get back up.
Write the next newsletter.
Do the next workout.
Make the next sales call.
The system isn't the streak.
The system is the comeback.