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Wells Fargo by Dreamville

Impossible to not get pumped up when listening to this track!

Huge personal milestone yesterday: I bought my first vacation tickets in a looong time, definitely the first since college! Let me clarify a bit here. I’ve obviously gone on vacation before. My family would always go up to Maine for a week in the summers. We’d rent a cabin, enjoy the beach, eat lobster. All the nice Northeastern vacation things. Starting in high school, the combination of job and drum corps meant my summers weren’t really free anymore. Don’t get me wrong, drum corps was still awesome and I got to see a whole lot of the country, but it was not exactly a beachside vacation either. That last high school summer, I saved up to do my high school’s Europe trip. I’m pretty sure I’ve been riding that high for the last eight years or so.

In college, money wasn’t exactly free either. Most of the money I had saved up went right back to rent or flights back home. Chicago <> Boston should not be an expensive flight but man, all flights suck during the holidays. Everyone’s got their own situation, but man I could not stop being jealous of all my friends who would go to various islands or beaches during those weeks off. Even in the summer time, I was more focused on working as long as possible and as making as much as I could during those internships. I did sneak one festival1 in there junior year, which carried me through the next four years.

Look, I get that this all sounds like a bunch whining so far. My life is easy, I know that. But man, I have just always to go somewhere and see something like everyone else I’m friends with. Last summer, I was talking to a friend who finally convinced me to just pull the trigger on one of my dream trips: see China, specifically Beijing or Shenzen. I bought tickets in the fall from one of those cheap flight deal newsletters. I had to wait six months, but man, $400 round trip to China (from SF) was an amazing deal. I was so, so excited.

Five months later, I’m looking at the calendar and it’s not great. It (of course) ended up being the worst-possible period for work, at least according to my boss. I haven’t really planned anything out either: my visa paperwork was just getting started, I had only a cursory idea of what I was going to do when I got there. Work said “hey if you move your flight, we’ll happily pay for any cost changes”. It was hard for me to see the appeal of a vacation will all the work-related stress at the time. I know it sounds backwards, but I just kept thinking about how guilty I would feel if I was gone for that part. I could not get myself over that hump of pre-guilt, no matter how I spun it. I said sure, what, it’ll be a few weeks later? The flight will be super expensive now but what do I care? Not my dollar bills here.

That ended up being an awful decision. Those two weeks were exactly as critical as they had been predicted to be, which means they were rough weeks. If you’ve been here awhile, you’ll be able to tell when those blog posts started. The whole time my frustration was bubbling over how I had clearly made the wrong choice. It finally ended what, 3 weeks ago? Ever since came the next looming question: “When/where/how long are you vacationing?”. I just kept laughing and waving it off. I really had no idea what to do about it. I didn’t know what I wanted, I just needed something different.

Everyone would give me suggestions on what to do and I had no idea about any of them. Choice is overwhelming sometimes. If you can go anywhere, where would you go? It’s been what, six years since the last time I went on vacation and nine since the last time I left the country. What if I pick the wrong place? When will I get to do this again? Do I only have a certain number of these left in my life? How can I make this one count? If I can go anywhere, how do I maximize the value? Should I just go to the most expensive place and hope I enjoy it? Then the guilt thoughts would creep in. Can I take a week off? Can I take two weeks off? Other coworkers have done two, three, even four weeks off. I can do that right? Why can’t I? I can’t, can I?

I let the clock tick and tock away. Yesterday, I finally made a choice. I have a great friend who I haven’t seen in far too long. They’re in Japan, and have been their for nearly a whole year. They’re leaving in a couple months and coming back here, but I’m impatient. I miss them, and now I’m going to see them.

  1. BonnaaaaarrroooooooooooOOOOOooooooo ↩︎