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The most underrated travel (life) tip Always worth Remembering

the most underrated travel tip
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Last month, I stayed in Boston for Christmas and wanted to do something fun for myself. 2018 was a very intense year for me with working and writing a book, etc. 

Traveling is no longer a priority in my life as I’m in a different place now, but that’s not to say I don’t miss it a lot. Although I was able to get away a couple of times in 2018, I felt the itch to get away towards December. The euphoria of checking into a hotel and checking out of reality is one of the best feelings. 

Boston has some pretty nice hotels, one of which is The Omni Parker House. Since moving to Boston in 2015, I always felt intrigued by this hotel. It has a lot of history, from Lincoln to JFK and Charles Dickens, all of whom used to call this place home. And it’s said that Stephen King was even inspired to write the book 1408 at this hotel. It exudes an alluring sort of character that’s always drawn me to it but I’ve never stayed there.

One day towards the end of December, I decided to book a Saturday night staycation when I got news of a promo rate which inspired me. I was super excited about this getaway to this historic 4-star hotel and having a nice space to get some work done in a relaxing place. 

Upon checking in, the front desk girl gave me a room with a full-sized bed. I agreed, not sure what that entailed, but I assumed that since this was a 4-star hotel, then the room would still be nice. After all, it was a busy weekend there and I thought maybe this was all that was left. 

I walked into the room and a massive wave of disappointment washed over me. This room was practically the size of a closet and worse, it was hideous. The mini desk was like 2 feet wide crammed into a corner. There was a re-patched hole in the wall and the lone tiny window opened up to an ugly view of a dirty concrete rooftop. 

The TV was like 10 inches. I couldn’t sit in this room, much less enjoy it. The room felt like a prison cell. What kind of staycation is this??! This felt like a cruel joke. This room was hardly even worth a 2-star rating, I wasn’t even aware that this hotel even had rooms like this! 

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At one point in my life, I think I would have accepted what I was given. After all, it was a busy weekend and I might have felt slightly bad for complaining. But how many times do we accept what we’re given and settle for less, all the while actually feeling miserable? It’s such a metaphor for life in general, as we often settle for less than happy and aren’t even aware we have the power to change things. 

Fortunately, that’s the opposite of who I am today. I couldn’t stay there, something had to change. Whether it was going back home (because I’d rather sleep in my own bed than in that room), I wasn’t staying there. I went back to the front and kindly asked if they had a larger room because this room was much too small. 

For no charge extra, the nice man gave me a larger room with a queen-sized bed. After my initial disappointment, I honestly wasn’t expecting too much better after that. But I went to my new room which was located on a corner of its own. I opened the door and my jaw dropped – it was a corner suite! A gorgeous suite. Now this is what I had in mind when I booked this hotel! 

This situation almost felt like a test and upon opening door number two, it was a powerful reminder how just a simple decision to act can effectively change everything. 

This room was nearly three times the size of my previous dungeon. And instead of a view of dirty concrete building rooftops, there were two large windows on each side, each opening up to the Boston skyline and a gorgeous view of City Hall. 

The desk in the room was gorgeous and very large. The TV was quite large and the room overall was large and stunning and worthy of a 4-star rating, unlike the previous room they put me in. 

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I ended up ordering some excellent room service from Ruth’s Chris across the street and I had a brilliantly productive night – one of the most productive nights I’ve had. It was the perfect night and the perfect end of 2018 for me. It was also actually one of the best travel experiences I can recall and an important lesson to remember – never settle.

But, this night could have gone completely different, the exact opposite. It makes you think about how simply asking for something better is really the difference between a dreadful experience and an incredibly memorable and fantastic experience. And I didn’t even have to pay for the upgrade. 

But often times, it’s not the asking that’s the hard part; it’s having the awareness to know when we aren’t happy and that it’s ok to do something about that. 

It was an important reminder that we don’t have to accept what we’re given if it’s disappointing. A lot of people, including my old self, would have found some reason to justify why I should be at least grateful for this staycation and would have tolerated this discomfort. But, actually, there’s nothing inherently good or right about settling for less. 

So moral of the story, never be afraid of asking for something better because you never know what you can possibly get. And, that it’s never ok to settle for less than happy when we have the power to do something about it. 

If you’re heading to Tokyo soon, I highly recommend my book Hidden Tokyo. It’s filled with tons of insights on a range of activities around Tokyo.  It also helps to explain this complex city better by dissecting 18 different major neighborhoods into chapters, with around 400 pages of pure Tokyo insight & recommendations. It lays out the city in such a way that any tourist can get to know it like a seasoned expat. 


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