As i’m sure you’re aware, travel prep can be pretty  stressful, especially when you have no clue how long you’ll be on the road for. Weeks? Months? The rest of your twenties? This is when, thinking about my trip, I began to realize it is not vacation: it is life. So after careful research and consideration my master plan is Not to have a master plan. Genius, i know. This way, if something goes wrong I won’t need to freak out because I had no solid plans to begin with.

Here’s a layout of what I had to do in order to leave for six months; hopefully it will give you some inspiration if you’re embarking on a lengthy trip.

First To-Do: graduate! (this may not apply to you, but it did to me, dang!)


The day before I moved away from Chicago, my home of 5 years, I was throwing all of the junk I didn’t want and never needed into large boxes and sending it off to Goodwill, giving it to my roommates, and tossing it out in the garbage-bin ridden alley behind my apartment. When trying to minimize your life in order to be more flexible, travel wise, it is best to make 3 boxes: give away, throw away, keep. Before you decide you really need a pair of shoes that were worn once (in 2001),  ask yourself, “Can I live without this?” and if the answer is “yes” then I strongly suggest throwing the item(s) in boxes 1 or 2. Even if you’re not moving it is best to pack systematically and get rid of the extras; when dragging your luggage around an unfamiliar town you will certainly regret having brought 2 pairs of black heels instead of one.

2nd TO-DO: meet up with friends to say farewell.

My last Chicago breakfast with friends:

The Last Breakfast

The Last Breakfast

Saying goodbye is nice. It gives your friends the opportunity to realise what a good gal you are and how much they’ll miss you when you’re gone. It also helps you remembering what you will eventually be coming home to (if you ever do).

So the 3rd TO-DO: Frown for a bit.



When I say, “For a bit,” I’m talking about a couple of days before you leave. Don’t let the your travel induced Serotonin rush to be ruined by a sappy, eye watering final 3 hours. Save yourself the stress of thinking, “but I didn’t get to…” and remember: you’re traveling somewhere you’ve never been, so sack the homesick shit, enjoy your goodbye, and get going.

Okay, Okay. Fine. Let your friends hang their heads, as well. (then take a photo and put it on the travel blog you just set up).

The Sad One

So we got through the hard part. Right before departure we shoved the possessions, that I hadn’t thrown out or given away, into the car and 3 humans hit the road to head from Chicago to Alabama. It was necessary that I drive to Alabama in order to drop off my car, say goodbye to my mother, and eat some southern food. For some completely unfortunate reason, my friend Alex and I toted a guy I had been dating (BRIEFLY) in the car with us for the 20 hour trip. Let me say this: the car was small, and I’m glad we broke up. I truly should include that as a TO-DO: don’t let your relationship drama ruin your travels; you’re already stressed out enough, so if he’s heavier than your carry-on, let him travel alone.


On the road in the summer heat with the Beatles, massive amounts of cigarettes and fruit, and a large, unruly map. Nashville here we come….