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How do I do this? The question I get asked the most. And one I ask as well to other travelers.

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How do I do this?

Where do I work?

I work remote for a tech startup in NYC with unlimited paid time off. Yes, I abuse it but I also work my ass off to be able to.

How do you pay for this?

I have the Chase Sapphire Reserve card which I use for everything to get points to pay for most of my flights.

Perks include:

  • TSA Precheck

  • Global Entry

  • $300 Travel Credit (airbnbs, cabs, metrocards, etc)

  • Priority Pass Lounge access (free food and booze while you wait)


I use Skyscanner as well as Google Flights to do my preliminary search. I also use Skiplagged (the app) to check for flight deals and set up alerts there. Kayak is great for exploring options with no firm destination in mind.

I love Skiplagged because I'm a light packer and the idea is to skip the last leg of your flight. For some reason, flights with a layover as your destination could be cheaper than a direct flight. Skipping the last leg of your flight means you'll be taking a direct flight so only pack a carry on!

How do I know where I'm going next?

This is a tough one and obviously a number of factors affect my next trip. What it all comes down to is weather at the time I'll be there. I'm a solar powered adventure seeker so I like to be away from the cities but off-peak season as well.

Currently I'm on a SE Asia binge so the last major country I need to visit is Vietnam. I plan on doing stints in South American countries as well and probably city hopping in Europe.

How do I plan the rest?

I don't! I'll book domestic flights within the country (buses take too long and I only have so much PTO) but as for what I plan on doing, I rely on the people I meet to plan my next day!


I'm always looking for new and exciting opportunities. Let's connect.


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