Performing a google search for “how to turn 20 vacation days into more” (or similar queries) results in links that are mostly Australian media. After being in this country for the last week of 2017 and first week of 2018, I can see why: these folks work to live and not the other way around by a long shot.

That’s always been my attitude too. Which is why, although I’ve worked at some tech companies that had unlimited vacation policy, even when I didn’t, I was able to travel to the point where coworkers and friends always ask me where I have the time (or time off, really).

My solution is to spend just as much time travel planning as financial planning. I’m always on the lookout for travel deals, using Google Flights to monitor trips I’m considering. No matter what time of year it is I’ve got trips queued, up to a year out (or as far out as airline booking sites allow). Here’s all the flights I can remember doing in 2016, 2017 and planned for 2018 so far. Some of these were for work, but 90%+ were for pleasure.

Each of those years I’ve had 20 days paid time off. How do I do it? The answer is simple. I make sure to put company holidays on my personal calendar, and I try to book trips around those times. From my time working in the airline industry, I’m used to going places quickly and maximizing my time there, going almost nonstop from activity to activity. If you live in a place with bountiful international flights, you can be a weekend warrior internationally even.

For example, I’m going to Mexico City at the beginning of February. I take a 4 hour redeye flight Friday night, arriving early Saturday morning, staying one night, and return Sunday evening, arriving back in SFO around 10pm. I’m taking no time off.

For president’s day weekend mid-February, I’m hitting up Rome thanks to Norwegian’s affordable, well-timed new flights from Oakland. We leave on a Friday night right after work, arriving into Rome Saturday afternoon, spend 3 nights there, and return Tuesday late morning, arriving late afternoon the same day. I’m taking one paid day off.

I’m a maximizer in many things in life and love finding deals for food, gadgets, travel and more. People are always asking for advice, so I figure this is a good way to share out!

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