August Employee of the Month: James O’Brien

Congratulations to Mr. August: James O’Brien! We’ve come to absolutely depend on James as a leader, Indonesia specialist, and party starter. We’re so impressed by his ability to stay calm under pressure, the care he puts into every aspect of his trips, and how much fun he is to just hang out with on the beach! Way to go James, from all of us at Free & Easy Traveler!


When his fellow leaders were asked to give some insight into who James REALLY is and why he deserves this honour, there was one overwhelming response: his dad jokes. There were other points which we’ll lay out below, like how great of a friend he is, how much he knows about Indonesia, how talented he is at surfing… but every single person mentioned his dad jokes. I’ll let them tell you:

“So, if you’re looking for a leader that is always up to date on the latest dad jokes, has some of the best amateur magic tricks in the game, and routinely busts out impromptu Zumba lessons during flight delays… look no further than Free & Easy’s employee of the month – Mr. James O’Brien!”

“James is master of terrible dad jokes and bad one-liners. A collective eye-roll from people all trying not to give into him and laugh even though it actually was funny.”


He also teases all his female co-leaders like they are his sister, and he loves pranking people while they’re sleeping. Such as stacking things on top of his passed-out comrades or waking them up with a finger in the nose. James is a professional leader who we know we can count on, but that doesn’t mean he sacrifices his childlike way of seeing the world. 


 A real-life pirate, James knows a lot about boats, free-diving, and swigging rum. This guy is bad-ass. We’re talking the kind that hikes Mt. Rinjani in flip-flops levels of bad-ass! He’s also never one to shy away from a night of karaoke, usually treating the audience by singing a Kelly Clarkson song to damn-near perfection. So, maybe not 100% pirate, but he’s always down to crack another bottle after the party leaves and indulge in some good one on one time, and talk about “life”.

He is Free & Easy’s lightest packer, and he’s been rocking the same board shorts since he was 17. All he travels with is a frisbee, 2 boardies, 3 t-shirt’s, and a laptop. Done. Wanna get James a treat? He loves mei goreng more than any food in the world. And he’ll likely leave a bit in his mustache for later.


Beyond being a really great time, James is an absolute professional when it comes to our Indonesia trips. We are always extremely impressed by how well he speaks Bahasa with the locals! It’s such an awesome treat to travel with someone who knows the local language, and James will blow you away with his linguistic talents. The effort he has put forth to learn everything from the language, to the geography, to the constellations on top of Mt. Rinjani, has paid off in that he is so loved by all of our local friends.

On his time off he can be seen hanging out on Kuta Beach with all the local surf instructors sipping a Bintang Radler. Everywhere James goes, he’s got people who can’t wait to come and crack a few jokes. He really cares about the people we work with, and that type of connection can’t be forged. He truly is still so embedded in what he’s doing with Free & Easy, even after over 800 days of leading trips (wow!). He puts 110% effort into everything he does and his trip members always get the best of him!


How humble he is: “After a surf, he will always say ‘I’m not gonna lie. I am actually getting pretty good.’ He’s been surfing since he was 15, he’s an awesome surfer, it’s pretty funny. You’re not getting good, you already are.” 

How much he loves what he does: “He cares very deeply about people and just wants that Indo trip to be the best it can be, and make sure everyone leaves Indo loving it as much as he does.”

 This mind blowing moment: “On the top of Mt. Rinjani he always has such good star facts. He can point out so many constellations. He literally pointed out the small and large Magellan. Cause he just happened to know they would be visible that night. Those are other galaxies.”

His well-rounded leading skills: “Not only will you have a killer time partying with this guy, but chances are you’ll learn a thing or two from him in your travels. “

Had to mention it again: “His dad jokes and rhymes and magic tricks always keep everyone laughing. This doesn’t mean his jokes are always funny… but you laugh anyways ;)”


Congratulations again James! Keep up the amazing work, enjoy your time off at home, and see you on the beach!

If you want to travel with James, be sure to check out our trips to Indonesia HERE!

James is also helping to collect money for some of our friends in Indonesia affected by the recent earthquakes. To donate, click here.


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