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Posted on 5th Apr, 2023 in Travel

As some of you might have heard, I was on "vacation" on and off for what amounts to the better part of the month of March. Truly the dream, right? As luxurious as it sounds, it was anything but. It was a hard fought battle to ensure the tour actually happened, so I'll be chronicling what went in to it here.

Murphy's Law

"Anything that can go wrong, will go wrong."

There is a a lot of wisdom to be gained from taking this postulate to heart. So with the expectation of the unexpected in mind, I built in some safeguards to my wildly ambitious, highly optimized, continent-spanning journey. For starters all of my hotel accommodations (with the exception of the one in Los Angeles) are flexible bookings. They'll only charge me at check-in and I can cancel my bookings right up until the check-in date. I was trying to hedge against the risk of my train getting caught behind a 3 mile long freight train on the verge of derailment.

Yet the kinds of unforeseen problems I was prepared for were nothing like the actual problems I encountered. The week before I was set to depart my boss scheduled weekly "Super Important Training Sessions"™ for the entire team. Simultaneously, one of my coworkers was about to take paternity leave. In the interest of being a good team player, I rearranged my schedule so that I could attend the trainings remotely and still not miss any of my trip. I smugly praised the conveniences of the modern era. However, it was these same conveniences that would betray me.

The changes to my itinerary didn't satisfy my boss but instead drew scrutiny to my previously unscrutinized plans. It would seem that my boss, who despite having approved my time off over a month in advance, never actually read through what they were approving. With only 3 days remaining before my departure, my boss was now forced to confront the scope and scale of my trip. They opted to immediately reject my modified time off request (which also rejected the originally approved time off request because our HR software is of questionable quality at best). They insisted that I failed to communicate my plans to them and that working from a train is explicitly banned by HR policy. That's a startlingly bold claim to make to someone who actually read through every single HR policy when they were hired because I have trust issues from my previous job.

The Negotiator

Now I was in a difficult position. My boss wanted me to push my trip back by a month and to take the entire time off all at once. This proposition would defeat one of the core goals of the trip, celebrating St. Patrick's Day with my friends in San Francisco and would burn twice as many vacation days as I had intended to use this early in the year. On top of that, I've been working here for less than a year so I had to consider whether this is the hill I would die on or if I should save it for a more meaningful occasion.

To add to my mounting problems, I was stricken by plague. The currently infamous "winter vomiting disease", norovirus, paid my household a visit that week. At first I thought that the stress of the situation was catching up with me, or that perhaps I had contracted food poisoning, but soon everyone else was showing the same symptoms. I was out of commission for at about a day and a half.

It was now Friday morning. This was the last day left in the work week and only 3 days before I was due at the opening stop on my tour. After frantically trying to negotiate a compromise with my boss, we came to a tentative agreement. I would be able to take the Upstate New York segments of my trip as scheduled if I return to the office immediately afterwards. Then I could take the West Coast segment without working remotely before having to return to the office yet again. I'd be giving up the scenic long haul train route west to Portland, Oregon, along with my stop in Chicago (which is a shame because even at the time of writing I've never been). I'd also lose the scenic ride from Los Angeles back east, which costs me a return to New Orleans (which is disappointing given how wonderful the food, drink, and music is there).

Scheduling Shuffle
Revised Solid Rail Tour Itinerary
The results of my negotiations protected the majority of my itinerary.

After a busy afternoon of rearranging my train tickets, booking flights to replace the long haul routes, and cancelling hotel stays, I was ready to depart (both this job and for my "vacation"). I was worried that the flights would destroy the budget of my trip however, just as I was about to give up on finding a cheap flight from NYC to Portland, OR, I saw an offer for a blind box flight. They only details available before you buy it is where it generally (NYC has 3 major airports) departs from, where it would arrive (PDX), a price, and an 8 hour time span in which it would depart. I decided to roll the dice and came away with the perfect flight. Its wasn't too early or too late. It would arrive in Portland slightly earlier than my train would have and most importantly the price was a steal. After all the changes to my itinerary, I broke even on the costs.

What a way to kick off vacation! With the prologue out of the way, my next entries will cover my adventures across the nation.


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