The man behind Catching Planes

Hi. I'm Miguel. I'm an experienced traveler, an expert at traveling light and finding the cheapest flights and hotels.

 

This is the story about how a trip to Puerto Rico changed my mindset forever. Even if I didn't know it at the time. 

I was fresh out of the best summer of my life. I had just wrapped up an amazing internship at an ad agency.  I had beat out many ivy league applicants and now had an offer letter to come on full-time. I had worked so hard for this and I finally had my foot in the door in my dream industry. 

I was living in San Francisco and working on global brands. The work was demanding, the commute in the Bay Area was too, but I was loving it! 

I was non-stop and on autopilot when a sudden and last minute invitation to go to Puerto Rico made me pause. I agreed to go.

Prior to this, I hadn't really travelled for leisure. Growing up, we used to drive places, but we never flew anywhere, and if we did, it usually meant a family emergency.

 

My parents and family immigrated from Mexico. Growing up, my parents were always working and working hard! The extent of a family vacation would be a road trip somewhere. 

Even if it wasn't true, getting on a plane and going somewhere for leisure was something that only others did and just wasn't attainable for me. 

So, the simple experience of booking a flight, selecting a seat, and intentionally only packing a backpack made me feel so free!

 

Here was a Mexican kid with US citizenship that now had freedom! 

I flew from SFO to a layover to Puerto Rico. It was an overnight flight. I arrived very early in the morning to Puerto Rico. Like, way too early.

 

I hadn't done sufficient research. For example, I didn't know how far the drive from the airport to Old San Juan was, or where I wanted to go. I just knew the name of the hotel. I grabbed a taxi and headed there, but of course it was too early to check in, so I took a long walk to the beach.

 

I was sleep deprived and didn't even change into shorts. Being the newbie traveler, I didn't even think to ask for an early check in at the hotel or have them store my bags while I explored.

There I was looking stupid on a beach lounge chair with full-length pants and my chucks on. Laying down with the sun in my eyes, I realized this was the first break I had really taken in a while. I started questioning why I hadn't catched a plane before. Travel feeling so attainable was a new feeling, but I loved it. Something sparked in my brain. I wanted more of this! 

Once I my trip was over, I went back to my day to day but I couldn't get Puerto Rico out of my head.

 

And Puerto Rico was great, but let's be real, it's a low impact trip. I mean I didn't even need to use my passport. I was hungry to see more of the world! I was spending hours a week looking at flights and different countries I could visit. 

The only thing holding me back was the amount of vacation time I had available. I also realized that my prior dream to climb the corporate ladder just seemed outdated. I still wanted to be successful, but just not in that way anymore. I was also witnessing some of my colleagues going through mental burnout. 

 

That's when what I wanted became very clear. I wanted to see the world, and still earn money. (This was when remote work wasn't as common) I had to give myself permission to even think this was possible. I had to fight the feelings of guilt for wanting this. Especially when compared to the struggle my parents went through growing up. 

This is a concept that they would have laughed loudly at. They would've said something like, "que no quieres?" meaning "what DON'T you want?" as if something like this is more than can be attained. And, I wouldn't be able to blame them for thinking that. 

 

Still, I shifted my focus, I had a new goal and I was going to achieve it. Today, I'm happy to say I am not only living my dream of having the freedom to travel, but I am able to make money while doing so from a few different revenue streams. 

 

What's even better, I am now able to help others fulfill this same dream, because I'm definitely not the only one who wants this. The world is changing and so is the way we work and travel.

 

I started a company and I named it Catching Planes because what seemed so impossible, was just a mindset. Now I am a travel expert who loves Catching Planes to the next destination. 

Follow me for travel stories, cheap flight and hotels, or to learn how to make money while traveling. 

Took a Telefèrico (aerial cable tram) up
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