2017 Travels – Chicago Edition – Lessons Learned

One thought that occurred to me frequently throughout that Spring Break was “this is why I am frugal. I have prioritized my spending on what brings me joy.” That’s a post for another time.

(This post was originally supposed to go up on May 2 but unfortunately something went wrong, most likely user error, and the post stayed in the draft folder.)

Each trip, no matter how many I take, teaches new lessons and reinforces old. Chicago served as fertile proving ground for the big one, the UK trip with Mom coming up in barely a month. I had to figure out what worked and what I needed to work on. Teaching has thrown my old trip planning techniques almost completely out the window. As an obsessive planner, it was difficult at times to let go of mapping out every detail. At other times, everything moved so quickly that all I could do was hang on for the ride and just wing it.

The biggest thing I learned is that planning should be strategic. It is necessary to put some work into making a plan come together. Simultaneously, the stress of jamming all the things into each day subtracted from the enjoyment of the vacation.

In the post from a few weeks ago, I talked about the specifics of my plan, the few that I had, so I will instead talk about the nebulous plans and the nonexistent plans that I went into the trip with.

The OCD planner in me shudders at the knowledge that I had not planned the following: public transportation to get around the city and to the various events, snacks to keep the runger monster at bay, food for breakfast and other meals so that we wouldn’t have to eat every meal out and how much I was prepared to spend each day.

While I did manage, barely, to stay under budget – only $10 to spare – that does not include the Uber we took to and from the symphony, to the race start and to the airport for departure. The Uber app resided on Dad’s phone, connected to his debit card. He told me not to worry about paying him back since it was connected to his card. I will likely payhim back even though that means going over budget.

The lack of a plan for food was the budget’s near downfall. I failed to plan and thus ended up eating all but two meals in a restaurant. All the food was delicious for sure. However, I could have planned better. Thankfully, Mom is not prone to eating quite as much as Dad; that will help. Specific lesson: plan and budget for meals including restaurants, snacks and meals at the airbnb.

On the flipside, sometimes the plan can get thrown out and yet result in a completely awesome experience. I had written an idea in my day planner for each day of the trip. While we got to one of the items I wrote down, it was five days later than I wrote and we happened upon it completely unintentionally. This M.O. was the best part of the trip. We found restaurnats with delicious food, the Federal Reserve, museums and numerou other amazing places along the way. If we saw something that caught our eye we went to go see it. The stress free aspect of the M.O. was the perfect respit for the break from school. Lesson learned: let go of rigidity.

Lastly, staying within budget requires daily upkeep. I didn’t do this during the trip but one time. Only on Sunday after I had already returned did I see how close to the limit I had come.

I had such an amazing time in Chicago and can see why Laura fell in love with this city. I’m a bit infatuated myself.