Udara Fernando is a partner at a quantitative trading firm, entrepreneur-in-residence at a compassionate leadership consultancy, and a part-time dating coach. He’s based in the US and has traveled throughout South-East Asia, Oceania, and Europe. When he’s on the road, you can usually find him in the kitchen making something toxically spicy and talking to an unsuspecting stranger about their last serious relationship.

Udara Fernando

Q. How did you get into traveling? When/how did you realize it was for you?
A. I spent my childhood in Sri Lanka, Papua New Guinea, and the Philippines before doing my undergrad in the US, so I've always been "at home" with travel. Right now, I have a home base in San Francisco where I spend about half the year, and I spend the rest working remotely.

Q. What was your first trip solo trip?
A. My first solo trip was to a surf camp in Tamarindo, Costa Rica called Witch's Rock in the summer of 2015. I'd always been intrigued by surfing, but the thought of being tossed around in the frigid waters of Northern California was never very appealing. Witch's Rock was a much less intimidating experience! Being out on the waves twice a day in the warm Pacific waters off the western coast of Costa Rica — and experiencing the relaxed dedication of surf culture — made me a surfing convert for life. Since then, surfing has been a through-line in my travels, and has taken me to Bali, Portugal, Maui, Gran Canaria, Morocco, Sri Lanka, and most recently to Santa Cruz, where I finally braved those cold NorCal waters (and found that it wasn't so bad — as long as you have a 4mm wetsuit!).

Fernando surfing at Tamarindo

Q. How did you feel during your first trip versus how do you feel now whenever you take a trip?
A. I would say that I was very brittle when I first started traveling. I had a lot of anxiety — did I pack everything I needed? Did I figure out how to get from the airport to the hotel? Did I have hard copies of all the right documents? I had backup plans for my backup plans. Since then, I've loosened up a lot. I've learned to trust myself to figure things out if something doesn't go as expected. I've learned to have a plan... but to hold it lightly. Things will sometimes go "wrong", and these can also be the times when you have the most memorable experiences.
I remember being on a hike with a friend in Gran Canaria, up in the mountains where neither of us had cellphone service. We'd been trekking for several hours, passing crumbling churches and Cappadocia-style cave dwellings, thinking we were heading towards a bus station in a nearby valley when it became increasingly clear that we'd gotten turned around somewhere. We stopped at a small bar to ask for directions — luckily my friend spoke Spanish — and the owner laughed at us when we asked about the nearest station... apparently it was over three hours away, walking. Just then, a local family happened to stop at the convenience store for coffee. The father overheard our conversation and kindly offered to give us a lift to the nearest bus stop. The family paid for our drinks, and we squeezed into the back of their station wagon with the kids and were treated to a beautiful sunset drive through the mountains to a small coastal town. One of the kids even volunteered to sit in the hatch so my friend and I could get a better view! Their kindness towards strangers was really moving and something I'll never forget. And it would never have happened if things had gone according to plan :)

A sign in front of the cafe
A sign in front of the cafe

Q. Out of all the places you’ve been to, what is your favorite destination?
A. There are two co-living destinations that I find myself drawn to — Mokrin House in Mokrin, Serbia, and Sun & Co. in Jávea, Spain.
I love Mokrin House for the pastoral tranquility (juxtaposed with the very modern and thoughtfully designed work/living space) and the wonderful hospitality. It's like being at a remote, happy tech campus, minus the brogrammers. Between the sunshine, fresh air, farm-to-table cuisine, gym, and bio pool, it's nearly effortless to stay healthy and feel your best. It's a great place for deep, focused work.
Sun & Co., on the other hand, is the place to inspire and be inspired. Community is at the heart of the S&C experience, and no one does it better. Between skillshares, masterminds, board game nights, blind wine tastings, PechaKuchas, sunset hikes, Mafia nights, it's a place to bond with people from around the world while enjoying the best of being in a gem of a Spanish Mediterranean town.

Q. If you could give just one travel tip to budding travelers, what would it be?
A. Keep it simple. At first, you may be tempted to squeeze the most out of every destination and find yourself worn out by all the organization and hectic running around. Instead, try resisting the urge to over-schedule. Give yourself time to feel into a place, to wander the outdoor markets and get lost in the little alleys. To duck into little coffee shops just because the croissant in the display case looks irresistible. Leave room for serendipity. Have a plan, but hold it lightly.

Some practical advice:

  • The actual travel part is my least favorite part about traveling, so the Chase Sapphire Reserve card has been a godsend. In particular, the Priority Pass feature which gives you access to numerous airline lounges worldwide has made many a long layover / unexpected delay far more bearable.
  • If I were starting again, I would get the Google Fi phone plan much sooner. Yes, you can get local cell data plans in most places for cheaper, but the peace of mind of having affordable data access as soon as you land almost anywhere in the world is completely worth it for me.
  • And finally, a plug for Icebreaker: their Techlite t-shirts are the only ones I buy anymore. Durable, comfortable, versatile, and eco-friendly... what more can you ask for.

We loved talking to Fernando and are glad he took the time out to answer our questions. He has his own website and is also active on Twitter. You should definitely follow him and his journey.