What a travel mishap taught an AI consultant about who owns the outcome
AlignIQ has just made it to two years as an AI training consultancy. A few months after we’d started, our target client hit its most sector-wide crisis. A few months after that, it went from LLC to BV at a completely different address. A housing shortage, major market research projects, pivots, tax confusion, language classes–among many other crises–ensued. For all these things to have worked out as well as they have two years on, we have the assistance of high-powered AI to thank at least as much as our entrepreneurship beginner’s luck (and hard work).
We deserved a vacation.
And we got one. And the goal was to select one as hands-off as possible: an all-inclusive resort in a relatively sunny clime was the way to go. Otherwise, it ends up being more AI taking over the job of being our own tour guides, because, let’s face it, AI performs pretty well at this task. It’s primarily AI we needed to take a break from.
If you’re Dan, you’ve lost your travel lifeline before in Central America, and you’re lucky that your Instagram handle is so similar to what’s printed on your passport, because a lovely Costa Rican will search you up and tell you where to meet them to get it back. See, the algorithm does some good.
Listen, I buy it. The research is on track. At least as my own individual case study, AI has slowed my cognition. I’m not going to blame AI or anyone else for the comedy of errors that took place within an hour of deplaning at our paradisiac destination, though. After all, haven’t I lost two expensive cameras while trekking in Europe, and broken one in Africa? I don’t need the insidiousness of large language overlords to make fatal travel errors.

Now that we’ve got that ado out of the way… my second person narrative of lessons learned:
First, make very sure to contact the tour operator about a 1.5 hour transfer from the airport to your hotel that will happen after midnight. They’ll assure you there’s a check-in kiosk right outside the airport exit.
Make extra sure to say the WHOLE NAME of the hotel to the folks at the kiosk. Repeat this name through deplaning, passport control, and the chaotic baggage hall. There are at least four versions of the hotel to be sent to, and some are actually sort of far from each other.
Remember to finally turn on your phone while you’re riding the bus. You might find out the tour operator had sent you the number of the bus you were supposed to board.
When you’re on the bus, take time to admire your new passport stamps. DON’T PUT THE PASSPORT IN THE SEATBACK POCKET IN FRONT OF YOU.
Once you get to the wrong hotel, note the number of the next bus they send to your actual destination.
When you finally arrive at 2AM, ransack all your luggage to see if your passport is there.
If it’s not, document everything possible the next day. Contact the tour company, alert the hotel aide who speaks your language. Beg to go on the bus to retrieve the missing passport. They’ll forbid you from doing so and assure you that they’re doing everything they can.
Find out they’ve checked the bus, the kiosk, and the airport lost and found and haven’t seen it yet. Have you really checked your luggage thoroughly?
It’s been 24 hours, so now it’s time to accept your fate of basically being passportless. Time for some paperwork.
See if the hotel’s P.R. officer can help with the foreign language at the police station for the report you’ll have to file. Bonus points if the country you’re in is famous for its prisons.
File for an emergency passport whilst learning the consulate of the country you’re visiting is seven hours away. Rent a car, since you can’t exactly hop on a flight.
Check with the passport control and consulate of the country you reside in, but aren’t a passport holder of. Find out an emergency passport and an untranslated police report won’t help unless you’re returning to the country that issued your passport. Make an appointment for passport reinstatement where you *do* live.
Got all these details? Great, you won’t need AI then, I guess!
Meantime, milk every service the all-inclusive tour company includes. Seriously, eat and imbibe like a true opportunistic omnivore. Watch the nightly hokey entertainment. Make the most of the car rental you can’t cancel and explore the area, unbidden by the tour operators who’ve seemingly wronged you, but really haven’t, and many of whom have no passports of their own to guard with their lives.
The day before you fly home, find out your passport has finally been found by a hotel transfer bus driver. No one will tell you which bus in particular.
Print everything. Send instructions to the airport personnel. Explain clearly to the scary people with guns that no, your passport will not pass the laser scan. Await word from higher-ups at both passport control stations.
Look out for the tour operator’s alert that your lost-and-found case is closed. The official report says they *didn’t* find the missing item? File a complaint about their horrible internal communications.
Get two passport photos to your home country’s bizarrely non-metric size and brightness specs. Don’t miss your reinstatement appointment!
There, you learn you can apparently revalidate a passport after having canceled it, but it makes more sense to replace it anyway since you’re four months from needing to renew. NB: If you don’t report your passport as having been found after being lost, you have to fully surrender it. No special little hole-punched record of the countries you passed through in the course of 10 years mailed back to you with the shiny new one holding so much potential.
Maybe you’ve sensed a pattern here: Don’t be like Caroline. Take good care of your passport.
Most of this post is for a larf. Part my living out loud is having had the privilege to exist in a bureaucratic holding pattern in multiple second world countries with beautiful beaches. Both beach joy and effective statelessness are wonderful opportunities to decenter our modern existence. It’s an honor, truly, to have experienced this. The most recent occasion had 10 different forms of baklava and halva pudding, so I almost felt I transcended this Kafkaesque coil for good.

Dan got his passport back because a stranger had a clever tool to find him. Mine took six days because everyone who touched the problem held a fragment of it, and the paperwork closed the case as “not found” while the passport mouldered on a tour bus.
That’s the failure I look out for in AI work: a dozen tools, with colleagues each holding them piecemeal, and a log that says “done” despite never being reviewed by a human. So the first question I ask clients about any workflow is the one nobody asked on that bus. Who owns the whole thing, and who verifies whether the case is closed?
Look at who failed in my case: the kiosk, the bus, the hotel, the tour operators on chat, whatever/whoever manages the missing item caseload, and chiefly, myself. Now back at the grindstone (with no foreign travel in sight), I see that my overarching role in an AI training consultancy is to take responsibility where the machine will not.
AI towers over my existence like a monolith, a goliath, a Babel. Nevertheless, it isn’t indispensable for travel. It definitely has its uses: checklist creator, strongly worded letter arbiter, cheap flight and accommodations polestar. But in this world, sometimes you have to be your own polestar.
For more on how we’ve managed the diceyness of travel, read Dan’s series on using AI for early integration as an expat:
- https://aligniq.ai/living-in-beta-ai-for-everyday-expat-life-part-1/
- https://aligniq.ai/living-in-beta-ai-for-everyday-expat-life-part-2/
- https://aligniq.ai/living-in-beta-ai-for-everyday-expat-life-part-3/
[In this post, we used AI for polish, not purpose.]


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