Disclaimer: I originally intended to post this several weeks ago, having written it before leaving on my Europe trip. Unfortunately, I ran out of time to type it up and post it before leaving and the wordpress site would not cooperate while overseas. Thus, I ended up going a month without posting. I have plenty to say in the coming weeks though.

I often consider myself a seasoned traveler, capable of avoiding rookie mistakes, of blending in as a local rather than a tourist. In the past, this has also included reveling in my apparent ability to stretch my dollars farther than the average tourist while not sacrificing a bit of the experience. Lately, however, I keep making errors and wondering where my so-called magic touch went.

In the next few paragraphs, I will discuss a few recent mistakes before reflecting and sharing what I have learned. A couple weeks ago, I flew to Chicago for a couple days for the express purpose of a Global Entry interview. Since possible locations nearby had no appointments available for months, I decided to go to Chicago and perhaps stay with Laura. Since Dad happened to stay with Laura that same weekend, the Brownwood Inn had no vacancy. My first mistake of this trip came when I went to book the hotel. I chose a highly rated hotel – no mistake there – with a free shuttle to the airport. I neglected to check proximity to an EL stop. Since I planned to take advantage of the Lakefront Path for my long run, I should have forgone proximity to the airport and simply selected a hotel or AirBnB close to a Blue Line stop since I could use the EL to get to the airport as easily as an airport shuttle. Thus, I spent money I had not planned as well as quite a bit of time in transit. O’Hare may be Chicago’s primary airport but it resides far outside the city proper.

Also, if I had thought a little longer, I would have realized that the prince difference between the same day return and the two day later return was much less than paying for one night at the hotel. (Even though I had two free nights on hotels.com, I could redeem only one on a single booking.)

Now I turn to the Grand European Adventure, of which I am in the midst of at the time of posting. While I cannot pinpoint mistakes quite as obvious as the ones I detailed from my Chicago weekend, the price tag continues to rise with a few contributing factors that I could have controlled. The first and most financially impactful mistake which I do not know how to describe exactly concerned my airfare. With any international trip, airfare will end up forming the largest single item entry. This pair of tickets came in significantly over my original estimate which in hindsight may have been inaccurate. Regardless, I know I need to work on my flight research skills because high airfare could wreck a travel budget with the click of a mouse.

At another point in the planning I discovered that one of the AirBnBs I booked was too far from the central train station to be feasible for the trip. The seven day cancellation window had long since passed so I received only 50% of my money back.

I could continue to list different examples of mistakes I made or ways I could have optimized the trip to save a lot of money. That, however, is not the point of this post. Listing mistakes brings a level of humility, a level of understanding that I have nowhere near enough experience to come close to expert status; I have a lot to learn.

Although not as discouraged now as I finish the post, I started in a place of discouragement, feeling like I stood at a precipice of so much money slipping through my grasp. I wondered how I could make so many mistakes when I’ve done this before. That question prompted this post and this reminiscing helped me realized a few important things. One, I’m staying almost three times as long as I have ever stayed before. I should stop being so hard on myself when it comes to that because obviously, I will spend more. Two, even though I purposefully carved out more time for ground level planning after learning from the Spring Break trip, the final weeks of the school year and the first week of grad school limited the amount of time I could devote to detailed, nuanced planning. I simply did not have the time and should stop spending effort after the fact to try to change things outside of my control. Third, I place a premium on certain things, like a place to myself, which bumps up the price. I could search out good hostels with shared rooms and save money. As an introvert, however, I know that I need the time along to truly rest and recuperate each day. That costs a little bit more.

At the end of the day, it’s okay to be a novice, to not have everything figured out. That means there’s so much more to learn and I cannot wait to learn it.