The Intersection of Passion and Risk
At some point, you have to decide to go after what you want
What exactly qualifies as risky behavior?
Sky diving? Motorcycle racing? Running without warming up?
Like most things in life, I’m sure the true answer to that question is a matter of perspective.
My thought, usually, is to err on the side of caution (6 broken bones over the course of one’s life does tend to inspire a healthy respect for safety). I love back-up plans, exit strategies, and an online preview of a food menu.
Yet, when presented with the opportunity to fly 4,400 miles across the world, by myself, to meet up with 13 strangers, share a hotel room with one of those strangers, and spend a full week traveling around with those strangers, I said:
Sign me up and take my money 🤷🏻♀️ obviously.
I was desperate to travel internationally, this was my chance.
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I had never seen a stack of Euros that tall. €770 roughly, a mix of whatever denomination everyone had on hand. It felt like playing Monopoly, everyone passing their money to the banker like it was all part of a game. In a way, I guess it was.
We handed the stack of cash to the waiter, settling our bill for the night. In addition to our meal, we had just witnessed the most spectacular Fado show I had ever seen (okay, it was the only Fado show I had ever seen, but I imagine it would have been the most spectacular amongst other options).
Nestled within the hilly Alfama neighborhood of Lisbon, this restaurante pequeno has hosted Fado shows since 1939. If you’ve never heard of Fado, it’s a style of Portuguese music filled with passion and nostalgia. The best way I can describe it is if an Appalachian folk singer with a banjo and a campfire fell in love with an Opera singer and they had a baby who grew up to play music and sings only in Portuguese, that is the sound of Fado.
It’s intense. It’s storytelling. You have no idea what they’re saying but you’re crying anyway.
In between dinner courses, the musicians fill the space between tables, their sound reverberating around the room. No windows, no place for outside thoughts, just emotion.
I still think about how I never would have been in that room had I not found my little group travel trip and taken a chance with a 13 strangers.



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When I was little, I always assumed that when I was grown the only thing that would stand between me and travel was money. No one ever prepared me for how difficult it would be to actually plan trips with your friends. Everyone has different schedules, preferences, and priorities (shocking!!). Eventually, you have to make a choice between going it alone or waiting for all of the stars to align.
I hated both of those options, if I’m being honest. My life feels incomplete without travel, but some of my best memories involve other people.
In my search for a way around this dilemma, I found a group travel company that plans trips for people in my age group. Was it a perfect solution? Probably not. Did it give me hope? Absolutely.
I’ve since been on three trips with this company and loved every single one.
I also have these trips to thank (partially) for this Substack. My main theme with this newsletter is creating an interesting life. I don’t think I fully realized how much of my life I was putting in the hands of other people. (This isn’t to say we don’t need help, I actually have a whole other story about that). Once I realized I can get creative with how I build my happiness, it unlocked an entirely new way to look at my choices and how I spend my time. It’s definitely NOT easy and I’m still learning (struggling) to make the right choices, but I at least have a new perspective.
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Is traveling with strangers really a risk?
Maybe, maybe not. I think that’s the wrong question though.
I think the real question regarding any risk is,
Is it worth it to chase your dreams?
Or better yet,
What do you risk losing by staying still?



