I’m probably one of the craziest people when it comes to traveling overnight. I will usually take a trip for a single night just to get away from where I feel like I am encapsulated, whether it’s for business, pleasure, or to rectify a problem that existed.

One of my craziest trips has been to Muncie, Indiana. I won’t get into much detail about that one since it happened a couple of months ago but here’s the gist of it. Went to work in the morning, decided that evening to take a trip there, went to the airport, bought a plane ticket, got on a flight to Indianapolis. For those who do not know, Muncie is about an hour and a half drive from Indianapolis. Landed around 9ish, rented a car drove for an hour and a half, tried to rectify the issues at hand, went to bed at a Days Inn, got up 2 hours later, drove an hour and a half back to Indianapolis, got on a flight back to Miami around 7ish. Landed, went straight to work. Yes, a toothbrush is permanently packed in my backpack with my laptop everyday when I go to work.

Now that you understand the overnight syndrome I have, I can carry on with my Chicago trip. So I had this trip planned for a while now. One of my good friends, Natalie introduced one of her really good friends Jason to me. See, Jason is a young entrepreneur like me. I could really learn a lot from him even though he has fewer years than I. My main objective for this trip was to meet Jason, meet the people in his life that have made him better and could eventually make me better.

I stepped out of the airport and it felt as though someone punched me in the chest. I felt like I was running a hundred miles per hour the way that cold wind was hitting my face. I wasn’t moving. I had luckily invested in a very nice coat from Sisley (a clothing store in Aventura Mall, Florida) about a year ago but had never had the opportunity to wear it. “Thank you.” Finally managed to flag down a cab and proceeded downtown where Jason lived.

Walking into the flat I saw these two beautiful statues, which were supposed to be for his mom, but they were cracked. Actually they were broken. Nothing a little superglue couldn’t fix. My opinion on broken stuff that can be fixed is that it gives it character. I received a very nice gift once, a leather toiletries bag engraved with my initials. It’s beautiful. Unfortunately, on a recent trip some hairspray spilled and the leather now has spots and is pretty much ruined. Character.

One person doesn’t really need that much room to live, especially if they are traveling a lot. The flat was a studio he had moved into a couple months ago. Pictures all over the place, Hawaii, Thailand … Barbados soon maybe? Next to the television in a glass cabinet there were memoirs of previous jobs, EbaY, Natural Golf, a Golf program he used to sell and more pictures. When I mean he is a successful young entrepreneur … I meant it.

In the corner, something you really do not expect in a studio, a salt-water fish tank. I wish I could remember the names of the fish but unfortunately my memory is horrible. I’ll try and find out; maybe I’ll add it to my next Chicago trip entry along with a picture. The tank was custom made by the owners of the flat for that specific corner. And Jason was lucky enough to inherit it. I use the word inherit loosely since the price paid for the tank and fish was significantly lower than he can sell it for today. He’s a businessman recognizing an opportunity and taking advantage of it.

Coming close to 2 o’ clock in the morning and realizing that we had been speaking about business, personal lives and battles and how we have survived so far, family, our moms and how much they mean to us, selling RV’s on EbaY, everything you can think about really, I made my bed on the pullout mattress on the floor and went to bed.

Waking up at 6 o’ clock was tough. Even more tough was walking out into the cold that morning. I had an appointment that morning with someone Jason had recommended. It took about six good hours for me to get out of there. Eventually I did, with good news nonetheless. I was elated!

Took a cab downtown, met up with Jason and had lunch. Remember this is just before Christmas so I was lucky I was taking up his time when there isn’t much work going on in the office. At least that’s what he told me, I know I’m pretty busy this time of year in my office.

After lunch I took a cab to O’Hare, waited around for about four hours and hopped onto a flight back to Miami.

All in all Jason’s not a half bad person, no matter what Natalie might say :) . I had a really good time and the trip was definitely worth it. I got great news and can now proceed with my life and concentrate on bigger and better things. Maybe even do some business in the future with Jason. I’ll be back in Chicago soon … work related next time but I’m sure I’ll have more interesting stories.

Mahalo