Hey, Everyone! My good friend Jack DiSanto approached me about doing a guest blog on my website over the next few weeks and I instantly said yes. He’ll be writing a few pieces to highlight his experiences abroad and reflect on life as a whole throughout his time across the world. Jack, being from the Chicago area, has a raw, evocative style and has found respite in travel to help deal with his personal demons, a commonality in which we all share. So, without further adieu, and introduction by Jack DiSanto on his travels to the beautiful country of Portugal.

When is When?

A question my Uncle Patrick once posed to me in regards to getting sober. In what exact conditions was it right to finally make a step forward. It’s been three and a half years since I got clean but I still often pose that question to myself, especially in my current situation.

The stark reality of my current state; my life is stagnant. I’m in a dead-end job that I can’t stand and I’m living in my parents’ basement. So when is when? I don’t know exactly if these conditions will ever be “ripe” but with that said, the Windsor Knot is starting to feel like a noose. Which brings me to the reason I’m writing this.

2 years ago to the day, June 24th, I hit rock bottom. I had just left an inpatient treatment facility and finally diagnosed with Obsessive Compulsive Disorder (OCD). A lot of the 2015 summer consisted of sitting in my basement crying, absolutely terrified of my own thoughts. When I was in the midst of trauma, my world was small, because it had to be as a means of survival. Ideas of returning to school or even leaving my hometown were a luxury I couldn’t afford. Now, trauma removed, I’m still stuck in the basement but these once unaffordable luxuries are within reach. The fact is, a bland existence is not a consolation prize for overcoming trauma. My boring life isn’t going anywhere that I can’t get back to.

So, when is when?

On June 29th, I’ll be backpacking in Portugal for 10 days. This will serve as a means of reparative therapy while also allowing me to nerd out in a truly historic country. I’m really looking into delving into Portugal for its history and there’s no better place to start than its capital, Lisbon. The city is the ultimate redemption story as it was rebuilt entirely after a catastrophic earthquake in 1755. I’m not going to compare my story to Lisbon, that’s so cliche it makes me nauseous. So, I hope you enjoy historic sights, food, and rigorous people watching. Beyond history, Portugal has some of the most picturesque beaches and cliffs in the world, which means I’ll take pictures of them for the sole purpose of adding #wanderslut to my Instagram. This trip is a trial run for a much bigger project so if my cynicism is your cup of tea, you might be in for more.


On September 4th, I have a one-way flight to London. I have no idea what my next permanent life move will be, but insight comes from discomfort and LaGrange, IL is the antithesis of that. This will be nothing like  “Eat, Pray, Love”, I am way prettier than Julia Roberts.

Here’s “Out of the Basement, Into the World”. I hope you like it.    

– Jack DiSanto –

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