
This image provides a basic outline of where I went on my fall road trip. I did end up deviating from this path a bit, but it still provides a good reference regarding the places I visited, and the length of time I was out of town- roughly two weeks when the time I spent in Chicago is factored in.
This was the kind of trip where all of the pieces of the puzzle came together quite nicely. I knew I wanted to take a road trip this fall. First of all, for those of us that live in Colorado and take advantage of the outdoor activities the state has to offer, it is the ideal time of year to take a road trip. The season for summer activities has come to an end, but the main ski season has not yet begun. So, basically leaving Colorado in the autumn (or the spring) has the lowest opportunity cost.
More importantly though, I knew I wanted to take advantage of the spare time I have right now while I have it. Life gets hectic sometimes, and when people get bogged down in day-to-day lives it becomes much more difficult to pull off a journey. I hear a lot of people discuss trips they would like to take “someday”, or “when the situation is right”. Unfortunately, sometimes years go by, with one situation after another coming up, and people lament the trip they never got to take. This is why I was actually quite thrilled to hear that a couple of my friends back in Chicago were planning a trip to Ireland this coming spring, even if it means they are less likely to visit me here in Colorado later in the year.
I never seem to run out of travel ideas. In fact, I could probably make a list of 100 places I want to visit in only a few minutes. So, for me, the picture is quite different than it is for many others, who just have that one place they want to go to. Instead of just making a plan and executing it, to visit that one place, I just need to take advantage of opportunities as they come my way, and keep coming up with new ideas for places to go within the realm of the resources given to me. This means accepting that unless that weird long-haired guy whose picture I saw at the Museum of Science and Industry successfully develops immortality, I will most likely go to my grave with at least a few places I wanted to visit, and a few things I wanted to do, that I did not get around to. Knowing that I am taking advantage of opportunities, trying new things, and getting creative about a bunch of things makes this fact substantially easier to accept. I know taking this kind of trip and visiting people on a whim like this is more than most people do with their spare time. In fact, some may consider me odd for this, but most people I described this trip to, and saw on the trip gave me overwhelmingly positive responses.
This trip also gave me what I needed during what has turned out to be a frustrating year for me. It actually reminds me of the theme song to the show Cheers, which explains the reason the show’s characters go to the same bar over and over again. “Sometimes you wanna go, where everybody knows your name, and they’re always glad you came.” This is why I was quite fortunate to have had the timing on visiting all of the people I visited along the way work out (given everyone’s schedules, especially on weekdays) so that I could go to every single stop I planned to go to in this two week period.
Being new in a city whose culture and social scene ended up being more significantly different than anticipated can be a rough experience. While I advocate fully embracing new experiences, sometimes we take comfort in being around people where we know where we stand, and being in familiar places. I moved on, but I wanted to see many of the people that still mean something to me. I do see friendships wither away as people move to new cities and get too carried away with their day-to-day lives to keep in touch. So, it was quite fitting that the ONE time I had Chinese food, on this entire two week excursion, I got this fortune cookie.

This trip confirmed this fact for me. Reflecting on the experiences I had visiting everyone, I can safely say that all of the people I saw on this trip are still my friends, despite how long (in some cases over 10 years), it has been since we have lived in the same town. I know this because the experiences I had were not limited to simply reminiscing and catching up, as sometimes does occur with “old friends”. While I did reminisce, and catch up with all of the people I saw, new experiences were created as well. This includes getting a 5-year-old addicted to The Fox music video, a plethora of jokes at the expense of Kanye West and Justin Bieber (is there an ocean bigger than Kanye West’s ego?), more crazy party antics, but also some heart-to-heart talks about real stuff, the kind of stuff that people only talk about with people they trust.
I designed this trip to have a mixture of the new and the familiar. Chicago is very familiar to me, and so is Maryland, but I had never been to the Smoky Mountains, or Gettysburg, before, and have limited experience in places like Virginia and Kentucky. Now that I am back in town, I will inevitably have some conversations with people about my trip. When I give people the “highlights”, experiences like the Smoky Mountains and Gettysburg will most definitely come up, as well as the craziness that was last weekend in Chicago. However, the more I reflect on the trip, the more I realize that what meant the most to me were some of the more simple things, like the ridiculous jokes and games. One of the people I reconnected with in Maryland actually remembered last seeing me over three years ago, at a party in Chicago. She recalled me describing abstract art as looking like a “raccoon having a period” while intoxicated. Some of the best memories we have are of thing that weren’t planned. I planned out my road trip, the timing, routes, and everything, but many of the things I will remember from this trip were not planned, but just as memorable.
Perhaps the greatest display of friendship on my road trip is the fact that on the entire trip I actually only paid for one hotel room! I am truly grateful to everyone who let me stay over at their places. Some of these overnights were even on weeknights, which are always a lot tougher, and some even took some time off of work. That was a lot of money saved, but more importantly, it was also a better experience. Being alone in a hotel room can be refreshing occasionally, but is also quite boring, and not an experience I cannot have at home from time to time. Being around my friends was a lot more fun.
My greatest takeaway from this trip is actually something I had already known, but lost sight of over the past several months or so.
— Be Yourself —
Pure and simple, yet a major lesson we all have to relearn from time to time. There are many situations in the adult world where we are trying to impress people for one reason or another. We are often times either told by others to not be who we truly are out of fear of being rejected, or lose confidence in who we truly are due to rejection. We will often find ourselves considering how to “reinvent” ourselves to make better impression on others. However, reflecting on some personal experiences, both recent and in the distant past, I realized that my odds are almost always a lot better when I do behave in a manner that comes naturally to me, as opposed to when I hold back, or try to conform to what is expected of me.

No matter what reason you want to make a good impression on someone, your best bet will always be to be who you really are. Any relationship, of any kind, based on a false persona is a poor fit that will not last in the long run. I believe we are all generally better of without them. Time spent continuing to try to impress people who want a different version of you will often prevent you from finding the people, the jobs, or the situation that are truly the right fit for you.