Hi, I’m Benjamin Chait. After backpacking around the world, I moved to Portland, Oregon which serves as home base for exploring and adventures. Say hello @benjaminchait (or email) and let’s grab coffee?


Building community is important to me. Whether we live together in a neighborhood, the same city, within a single state, in a country or merely on this same earth — our lives are connected. We (hopefully) spend our daytime hours working alongside like-minded individuals toward a common goal.

When moving to Portland, I sought out to build a new community and group of friends. I’m fortunate to have met and been invited to help support the folks who organize TEDxPortland. Last Saturday was my third event in the Rose City, and the team’s sixth year: TEDxPortland 2016. Our hope was to inspire, and celebrate, this amazing area which we call home.


Today, the city and region are changing fast. Growth is exciting, and brings with it new challenges. I’m here to participate, and to build a better place.

Delayed packing

This time last week, I sat in my childhood bedroom. Clothes and other goods ready to be packed, strewn across the floor and over the bed. But instead of packing in any reasonable manner, I spent the evening reflecting.

My love for Boulder is endless, a beautiful small town along the front range of the Rocky Mountains. Skiing is almost second-nature, having grown up spending weekends on the slopes only an hour or so away. Picturesque landscapes and exploration of the outdoors fill my memories. I cannot imagine growing up anyplace else. And yet, this place now feels small.

Returning allows me to see not just family, but those friends I’ve made over the years—whether from growing up here, to university, to my first few years after school. We’re all growing up, so quickly, so fast. We’ve found new adventures, new friends. But we have a common thread, those shared experiences which make us who we are today.

A lot has changed since I last called this place my home. Over the past few years, I’ve grown and learned and explored and made a new place for myself in PDX. But I always cherish those opportunities to visit Colorado. I finished packing past midnight, occasionally looking out into the moonlit landscape. Remembering, and celebrating, those moments which led me here.

Starting 2016 in Santa Barbara

With Sarah’s family in Santa Barbara for the holiday, a quick flight and ocean escape made for a fun and sunny way to bring in the new year. Days full of coffee and wine, great food, enjoying films and the beach, enjoying books, and spending time with delightful people.

Two years west

Portland has been home for two years, and in that time I’ve hardly written. So here’s a recap.

Moving to a new city is challenging. Part of it is overwhelming, the constant learning and discovery upon adventuring in a new place. Streets have silly names, I can turn at a stoplight with a red arrow (seriously, Oregon?). Another part is loneliness, not having those friends I’ve known for years. But over time, those feelings change, and the confusion is replaced with delight when encountering a new favorite coffee shop and building new friendships.

The Pacific coast is amazing for adventures. An hour west and you reach the Oregon coast, a perfect weekend getaway with friends. To the north, Seattle is a quick trip, with Vancouver only a bit farther. East of Portland lie the Gorge and Hood River, for hikes and quiet escapes. Some distance further, the town of Bend and its many breweries. And short flights south bring us to San Francisco and Los Angeles and Southern California, to visit family and find some sun in the rainy winter months.

This time last year, I had my Trek commuting bike stolen. It sucked. But it’s a good reminder that things are replaceable, and that good things take time. I have a new bike, perfect for these rainy winters. And I’m having even more fun riding around, exploring.

Excited for the next two.

One year west

A year passes faster than expected. Full of surprises and new adventures, Portland has been a chance for new beginnings. And no, I have not written nearly enough. Plenty of challenges and surprises filled the past twelve months; I’m looking forward to what comes next.

Moving west

Just like the “Oregon Trail” game, I followed the American Dream to move west and continue my adventures in Portland, Oregon.

Slowly, pieces are falling together. Plenty of coffee, good microbrews and exceptional food trucks (make time pass fast). And—without exception—lovely people. Already many days spent beside the window, rainy fog on the other side. A new place I’m only just beginning to explore.

Looking back at 2013 and everything which has come before, I am astonished and so incredibly excited for what comes next.

Portland, Oregon Branch Coffee


I’m sitting with my grandmother. It’s on me for not visiting during the past two years, but I’m here now. She asks about my future plans; listens as I describe stories from abroad; and shares her love and excitement for my next adventures.

Just a week ago, I was driving along an empty mountain road on Colorado’s front range. Snow began falling just after midnight, both picturesque and quieting.

Memories are beautiful and complex and tragic. While old memories are fast becoming fleeting, I aspire to leave a few new ones.

I sometimes find myself wishing that growing up were less challenging. This is a part of life; I’m struggling with acceptance. I never expected visiting my grandmother would be this challenging. Family frequently suggested I make this trip; it took far too long, but I’m glad I made it.

I have so very much for which to be thankful. More than anything, I am thankful to have such an amazingly supportive family. I am fortunate to have returned safely from travels. And to share this journey with an incredible partner, Sarah.

Ten years, online

Ten years ago, I registered my first domain name: benjaminchait.net.

I never imagined the value it might have. Some years earlier, I had published my first web content via Pico (in Unix) and was jumping between static HTML pages and into dynamic frameworks, learning more advanced techniques and dabbling with ASP.NET and MySQL. At some point, it made sense to centralize my identity online, before Facebook and Twitter and everything else we have today. The world wide web has grown and changed immensely in the time since I first “settled” online. It impacts every aspect of our modern lives, acting as both a tool for work and providing entertainment. Without the internet, backpacking would have been a far different experience, from booking flights to communicating to sharing stories. My current endeavors as a freelance consultant rely upon the web. And yet, I’m fortunate to have my name as my identity.

A lot has changed in the that time. But I’m even more excited about what the next ten years might bring.


I had the great opportunity to work with some incredible folks in the Boulder community these past few weeks to produce TEDxBoulder 2013.


Waking up Saturday morning, I was already exhausted; putting together any live event is daunting. The preceding week was packed with meetings, responding to messages and getting everything ready. But walking on-stage during sound checks, meeting speakers and volunteers—the excitement and energy grew quickly. Time blurs among all the preparation. Then, at 5 pm sharp, I hit play on the TEDx intro video—no turning back.

Some four hours, three musical acts and fourteen talks later, we finished. And even with technical challenges, I think the evening was great. I am constantly impressed by people in our community and what they do every single day.

Culture shock, reversed

The hardest part of travel is returning home.

My friends warned me of this. Almost everyone shared that for all the culture shock one finds while abroad, the first few weeks back home are the worst. However ready I thought I was, nothing prepared me for this.

Landing in America was a blur. Oddly enough, US Customs and Border Protection screened the entire flight in Dublin allowing us to land in a domestic terminal in Philadelphia. One moment, I was in Ireland; some anxious few hours spent hopping across the Atlantic; and suddenly, I was walking about on American soil. My iPhone worked again with full service, messages began to light up the screen. People once again spoke the same language as me; signs were readable once more. Prices were in US dollars—my credit card worked and I was no longer playing a game with exchange rates. A short time later and Sarah and I met with Brooke, one of my closest friends from university; we relaxed and caught up for a bit before departing for an evening in Newark with Sarah’s family. Still dark when we departed, an early-morning flight had us in Denver almost an hour early; the Rocky Mountains just waking for the day.

The first weekend home was almost a dream. I was more emotional—happier—about being home than I would have imagined. Seeing the front range, I realized how much I missed this place. And for all the experiences abroad, part of me was so incredibly happy to not be traveling—at least that instant.

Somehow, others had a perception that my travels were a simple vacation, a “holiday” of sorts; nothing feels further from the truth. It’s hard to describe but for me, backpacking on its best day was more challenging than my job on its worst day. Yes, certainly each and every day was rewarding and rich and what I made of it. But that itself is what makes travel challenging: I have to make something of each day. Extensive planning, research and exploration kept the past year in budget and safe. I accomplished goals while abroad, saw places I had set out to visit. So yes, I had a blast, but it was far from “easy.” Being home is thus bittersweet.

Some few weeks later, it still feels surreal to be in America. In some ways, it’s almost as if the past year was just a dream. A blur. My world has changed, yet everything remains the same.

Looking around me, I wonder how much has changed—or how much I have changed myself.

America feels loud.

Everywhere I turn, noise follows. Part of me wonders how much is based upon language. When traveling, I often ignored those conversations around me when I could not speak nor understand the language; now I find myself constantly bombarded. Small moments like sitting in a café or even music on the radio seem overwhelming. My days are a cacophony; only at night can I truly find quiet. By no means is this bad—I just find myself more aware of my surroundings than before travel.

Maybe being hyperaware of my environment is a side-effect of extended time abroad? For the first time in nearly a year, my days are not full of learning new places, people, things. Boulder is a place I can navigate, I have family and friends and my favorite local spots. We drive on the right side of the road. I feel comfortable with the culture—tipping, how to be polite and so forth. Yet parts of it nag at me. Why do we tip? Who decided upon sales tax rather than VAT? Small questions lead to bigger ones. I’m confounded at our insecurity as a nation, our paranoia. How have we become so ill-at-ease with our neighbors?

I realize I’m exhausted.

Unexpectedly, the most aversion and challenging reaction I have to any culture is none other than my own. Without question, I am happy to be home. I’m thrilled to sleep in the same bed more than three nights in a row. Learning new languages and exploring new cities was absolutely a thrill but so is being here, in one place, where I can find some stability. Build some true connections and relationships. Not constantly say goodbye.

In many ways, I’m thankful for the chance to slow down and breathe.

Maybe one day I’ll have more of a plan. But not yet.

Right now I’m devoting time to focus on myself. I’m trying to make more time to take better care of myself and to grow as a person. I hope I’ve done that these past few months; for now, I’d like to dedicate just a little more time to me. Working on simple projects. Learning new skills. Starting to run once again. Small things in the hope to make each and every day count.

Whatever happens next, I look back upon my experiences and have no regrets.