Dear Friends & Family,
Greetings from Chicago and happy March to you all! After successfully skipping from continent-to-continent to avoid the winter cold for an entire calendar year, I find myself writing to you on my birthday bundled in fuzzy pants and a sweater with a pumpkin spice candle burning to my left and a warm oat milk latte to my right - a far cry from the tank top and swim trunks I donned nearly every day during my two weeks in Bali, the last stop of my yearlong adventure. This newsletter will stay true to its original format: Boarding, Takeoff, and Landing - with a few friendly additions. Each section will give you a peek into my personal and professional states of mind as well as highlights and “little moments” that brought me the most joy over the course of 2022. From here on out, you can expect a quarterly newsletter from me - with this one serving as a year in review.
Before I dive into reflection of this last year, I first want to wholeheartedly thank each of you. This year was one in which so much of my time was spent away from loved ones. Instead, I was deep in the digital universe of email, texts, phone calls, and Instagram to keep in touch with those who mean the most to me. Frankly, this was not always easy. I missed many birthdays, get-togethers, anniversaries, and holidays. Though there were moments I wished I was with you all, I knew deep down that what I was doing was right. I knew I was on the right path. Through every step of my journey, you all made me feel much closer to home than I actually was and that truly made all the difference. To say your support was unwavering doesn’t come close to doing it justice. Whether it was a text saying how proud of me you were, a voicemail wishing me a happy birthday, an email to discuss my latest newsletter, an introduction to a potential client, or a twerking chicken GIF - thank you. All of my individual engagements with y’all meant so much. Those who know me best know that I’m an extrovert, hugger, and jokester. Being alone for the majority of the past year made these traits all the more evident. So, for brevity’s sake, thank you for being there for me, loving me, and cheering me on. I value you all more than I can put into words. I’m so lucky to have the world’s best support system.
As I look back on 2022, it was a year filled with change, growth, and movement. Over the course of the last 12 months, I visited 105 cities across 22 countries and 4 continents. That’s a lot of packing and unpacking. That’s a lot of different beds. That’s a lot of time spent in transit. Yes, being on the move constantly was exhausting, but it also kept me hyper-focused on the present.
As the trip continued, I began to worry less and less about where I was sleeping next and more and more about what I was doing in the “now”. This focus on “today” reframed my perspective and allowed me to get comfortable in the discomfort. This mindset allowed me to flourish during my year abroad - both personally and professionally. While it was not all rainbows and butterflies, as you’ll read below, I can wholeheartedly say that 2022 was the most intentional and rewarding year of my life. Oftentimes I found myself thinking about the following quote: “Remember when you dreamed of where you are right now?”
Country #7 of 2022 (Santorini, Greece)
Packing: Pre-Trip Thoughts
Personal State of Mind: I boarded the plane for Ecuador experiencing many emotions, but the strongest one was excitement. Ever since I backpacked six months through Europe & Central America in 2015, I knew another long-term trip was on my horizon; I just didn’t know when. While it was always evident, I never thought it would be quite like this. First of all, it was set to be twice as long as any other I’d taken before. Secondly, the focus of this trip had a professional lens to it unlike any I’d taken before. Lastly, I’d never traveled internationally with this COVID thing floating in the ether. All of this said, I was excited because at the end of the day, this wasn’t my first rodeo. I was embarking on a journey I would never regret. Plus, my first few stops were in countries where I was looking forward to flexing my developing Spanish-speaking skills. It also helped that I knew people on the ground in each of the first three countries I was visiting. And to wrap this in a bow, I didn’t have grandiose expectations.
On my last long-term adventure in 2015, I had dreams of coming back a changed person. Not that there was anything wrong with the post-college version of me, but I didn’t want to return to Chicago as the same 23-year-old who dreaded his alarm clock every morning, dragged himself to a soul-sucking job, and got home with just enough time to hit the gym, eat, sleep, and repeat. I was expecting to come back and all of my problems would be gone. Frankly, that didn’t happen. Yes, I changed after those six months, but I still felt like I couldn’t truly live a fulfilling life if I had a job where someone else was giving me orders. How could I ever recreate the lifestyle I wanted for myself back home in the US? I knew the only answer was to work for myself. Flash forward to December 2021, my expectations and excitement for this adventure were sky-high, but in check. I was ready to set off for South America. Vamanos!
Professional State of Mind: I left Chicago brimming with confidence. But why? How could I be so sure of a business that had only five clients to date? Some of it may have been wishful thinking, but I knew I’d put in the work. I’d done the reps. Uproute was still growing, but I was absolutely certain that the business had massive potential. I started building Uproute behind the scenes in 2016, but it wasn’t until 2020 that I began investing in myself via an entrepreneurial and lifestyle accelerator course (shout out to Cornelius & Everyday Entrepreneur).
Coming into 2021, I had a good foundation in place and knew that months of market research leading up to the trip would give me a chance to succeed. “So you’re tellin’ me there’s a chance?” I didn’t have it all figured out, but I had enough to see a path forward. I didn’t have the clientele and dollars to prove it yet, but I was confident those would come over time. My headspace was optimistically realistic. I didn’t have plans to make six figures in my year abroad, but I did want to cover my expenses which would be a tall task considering I hadn’t even made $1,000 upon leaving and was projecting to spend 25x that number over the next twelve months. Call it naivety, but I just had the feeling that everything would figure itself out. That’s always a good reason to do something… right?
About to shove off on the last day of November 2021 (Chicago, USA)
Boarding: South America (December 1 - April 18) (140 days)
Personal State of Mind: Everyone knows South America is beautiful, but wow! Ecuador was truly something special. Spending Christmas & New Years with my sister and brother-in-law’s family in their native city of Cuenca was next-level. Bolivia exceeded all expectations with its natural beauty especially because I experienced it all with a good friend whose family hails from Cochabamba. Brazil was nostalgic because I had met so many Brazilians on prior travels that I had a friend to catch up with in nearly every city I visited. Uruguay was a good place to get back to speaking Spanish before heading to Paraguay where I really got out of my comfort zone by visiting a small town of less than 5,000. My Spanish mejoró mucho (improved greatly!) over these months, but I was ready to get back home to see my peeps!
Professional State of Mind: Transparently, my clientele was still growing, which allowed me to focus on building processes that would streamline my workflow when the clients started to come in larger numbers. By this point, I had worked with 34 clients over the first 4.5 months of 2022 - nearly 7x what I started the trip with, but I knew I had the capacity for more. I continued to put in the work to make connections and improve Uproute for future clients. I knew it would be a busy summer since that’s when many of my clients would be traveling, so I made sure I got myself prepared.
Top 3 Highlights of Natural Beauty:
Galápagos Islands (Ecuador)
Uyuni Salt Flats (Bolivia)
Chapada Diamantina National Park (Brazil)
Top 3 “Little” Moments:
Dying my hair bleach blond in São Luís (Brazil)
Celebrating my 30th birthday during Carnival in Rio de Janeiro with dear friends (Brazil)
Receiving a text message from my cousin that nearly brought me to tears while sitting in a cafe in Montevideo (Uruguay)
One of the many shell-ebrities I came across while snorkeling (Galápagos Islands, Ecuador)
Pit-Stop: Home (April 19 - May 16) (27 days)
Personal State of Mind: After spending more than four months in South America, I was looking forward to spending a few weeks back home in Chicago catching up and relaxing with friends and family. Looking back, lots of catching up happened, but not much relaxation. I left after those four weeks exhausted, but very happy. I landed in Chicago on April 19, and was in Vegas three days later for my cousin’s wedding. The following week, I played in two playoff soccer games, saw John Mayer perform, flew to and from DC on the same day to renew my passport, and saw my brother graduate from college. The next week was more of the same leading up to Mother’s Day. I followed that up with a three-day trip to Denver to attend a travel conference hosted by a collective of travel advisors I’d recently come on board with. Needless to say, I was drained heading into Europe, but I had so much to look forward to! I had wanted to “summer” in Europe for years, so I was flying high - especially because I was about to hit some of the top countries on my bucket list (Greece, Albania, and Croatia). To make matters even better, I knew Europe would be teeming with fellow backpackers eager to enjoy a “COVID-free” summer. I boarded the plane for London without an ounce of uncertainty. Europe, here we come!
Professional State of Mind: Coming off the back of my wild four-week trip home, I took off for London buzzing with excitement. My last-minute trip to Denver was life-changing in many ways. I got to meet so many like-minded travel entrepreneurs and learned a ton about the industry. I stepped into the next chapter of my adventure with the enthusiasm of a young Justin Timberlake exclaiming “It’s Gonna Be May”!
I was excited for my personal travels, but I was also ecstatic at the idea of meeting hoteliers, contacts, and tour operators that would enhance the experiences of my future clients - many of which would be in Europe while I was there myself. It made perfect sense to be syncing these two pieces of the business. From Paris to London to Rome and from Athens to Santorini to Mykonos, I was set to visit the most popular tourist destinations in the world in unison with my clients during arguably the biggest travel boom in decades. Coincidence? I think not!
What happens in Vegas gets photographed for all to see (Las Vegas, USA)
Takeoff: Europe (May 16 - September 28) (136 days)
Personal State of Mind: What a summer in Europe indeed. It was everything I could have imagined and more. It started off with meeting my cousins in London before meeting my girlfriend and other relatives in Greece. I then spent three weeks with my brother traveling through the Balkans. After that, I took a trip through Italy with fellow travel advisors before running my first-ever marathon in Berlin as my sister and father cheered me on. I mean, does it really get any better than that? Morale was high heading into Asia and, while I knew the time difference would pose some challenges, I was confident I’d make do.
Professional State of Mind: The cohesion of being in Europe simultaneously with my clients was felt immensely - particularly via social media. Clients asked me to add items to their itineraries based on my IG stories and I was getting inbounds in unprecedented waves. I was truly living out the dream I had set out for myself. I stacked my calls on work days and created personal itineraries for my non-work days. I was logging 12-hour days on Wednesdays and hiking through national parks on Thursdays. My worst cases of the Mondays were in the form of spilling gelato on my favorite shirt. I often caught myself smiling and thinking to myself, “Wow, I could really get used to this!” Sure, there were days that were worse than others, but I was wholeheartedly living my best life and having the most success I’d ever had professionally. June saw my highest monthly paycheck of my life. July was even better. Total clients served reached triple digits by this point. Was this success sustainable?
Top 3 Highlights of Natural Beauty:
Theth National Park (Albania)
Durmitor National Park (Montenegro)
Lake Bled (Slovenia)
Top 3 “Little” Moments:
Sitting in bed eating the best Greek salad of my life while simultaneously closing on my most grandiose trip to date (Greece)
Spending the night in a rental car with my brother, Joe, as we laughed ourselves to sleep (Slovenia)
Watching the Eiffel Tower sparkle in The City of Love with my girlfriend, Laura (France)
Lake Bled in all its glory (Bled, Slovenia)
Landing: Asia (September 29 - December 15) (78 days)
Personal State of Mind: The stark contrast between Western Europe and Asia hit me like a wall of bricks and the homesickness started to creep in. I had spent the last eight weeks in European metropolises such as Paris, Florence, and Berlin amongst millions of maskless tourists having the time of my life. Fast forward to Asia and I was the only traveler at my hostel in Seoul where the streets were filled with masked locals who I had trouble communicating with. Upon landing in Seoul, I immediately felt a strong sense of loneliness. In many places, I was the only tourist - which I usually cherish and enjoy - except this time the added layer of COVID mandates made it far more challenging. I know I’m not painting the most beautiful picture here, but I was in a bit of a rut. It didn’t help that my first week in Seoul was extremely rainy and marred with the worst case of jet lag I’ve ever experienced. I’d be lying if I said the thought of cutting the trip short and coming home early didn’t cross my mind.
This all changed once I got into the Philippines though. Now, I don’t want you to take the moral of the story as “don’t visit South Korea'' because that couldn’t be further from the truth. It was really just a conglomeration of the factors I listed above - weather, lack of fellow travelers, and COVID restrictions. I honestly think my experience was just the luck of the draw - and it had to happen somewhere! I look forward to visiting South Korea again to give it the second chance it deserves. Of course hindsight is 20/20, but I think this bump in the road is what I needed to give me some perspective. Am I just rationalizing the experience? Of course I am, but I can’t help it!
Anyway, back to the Philippines & Indonesia - it’s very possible I saved the two most beautiful countries for last. This combined with many more backpackers and lessened restrictions made for an amazing final two months. I’m an extrovert, after all, and while technically I was traveling alone through all of Asia, I felt much less alone in these two countries. I met some incredible people, a few of which I can tell I’ll keep in touch with for years to come. After a bump in the road, I was back on track! The thoughts of returning home early quickly turned into thoughts of “Am I coming home too soon?” Southeast Asia proved to me again why it’s one of my favorite parts of the world!
If you haven’t been to SE Asia before, we need to talk. It’s so beautiful and affordable. Dollar-per-dollar you can’t get much better than here (or Central America)! I mean, come on, I was getting haircuts for 98 cents and enjoying 74-cent beers on the beach. To make a long story short, I had some wonderful experiences in Asia and felt like it was the perfect place to end my journey. What better place to come to grips with returning home than Bali?
Professional State of Mind: While I was feeling out of place personally in Seoul, I didn’t let it affect my business. In fact, it gave me a much-needed connection to some normalcy. Even if my personal days weren’t riveting, I made sure to hold myself accountable on the business front. That meant many early morning wake-ups to ensure I was waiting outside the local Starbucks in time for them to open because I needed a reliable Wi-Fi connection for client calls. The 15-hour time difference meant that when people were getting off work in the US on Tuesday, I was just waking up on Wednesday - so I had to make sure I started my days early enough to catch people before they went to bed. After a few weeks of this, it became easier and I found a great groove. Not to mention, I was making US Dollars and living in Philippine Pesos & Indonesian Rupiah. Translation: My money stretched further than it did in most of Europe & South Korea.
By the time I returned home, I had worked with 161 clients and met my goal of covering my expenses during the year abroad. This was a massive accomplishment for me and allowed me to head home with my head held high. I did it, but knew this was just the beginning of something special. If this year taught me nothing else, it’s that Uproute is for real. If this is what I could do during a year on the road, what can I accomplish during a year spent in one place to give myself more dedicated time to reach new heights?
Top 3 Highlights of Natural Beauty:
Jeju Island (South Korea)
El Nido (Philippines)
Sumatra (Indonesia)
Top 3 “Little” Moments:
Hearing a stranger cover one of my favorite songs ("Falling" by Harry Styles) on guitar while reading in Olympic Park (South Korea)
Witnessing the most beautiful sunset of my life in El Nido (Philippines)
Seeing a wild orangutan swing from tree-to-tree as I sang "I Wanna Be Like You" from The Jungle Book (Indonesia)
I mean, come on - this sunset looks fake (El Nido, Philippines)
Un-Packing: Post-Trip Thoughts
Personal State of Mind: Coming to the realization that this trip was coming to a close was a lot more challenging than I’d thought. It took many conversations with my best friend, Adam, and girlfriend, Laura, to help me wrap my head around the experiences the last year held (thank you both)! It got easier and easier as my departure day came closer. By the time I was on the way to the airport, I found an overwhelming sense of relief and peace because as they say: nothing is permanent.
On the 20-hour commute back to Chicago, I reminisced on each and every place I visited and made a few notes about what I remembered most. Sometimes this was seeing a wonder of the world, others it was a warm smile from a stranger. Seeing the last year from a bird’s eye view thousands of feet in the air was the perfect way to end the trip of a lifetime.
Professional State of Mind: When I look back on the past year, my heart is filled to the brim. Knowing that Uproute brought smiles to so many faces is the greatest accomplishment of all. Whether it was a honeymoon, a group trip, an experience to shake the routine and get a new perspective, or the “trip that COVID ruined”, it’s a great honor knowing I played a monumental part in people making lifelong memories together. By the numbers, Uproute sent clients to twenty-five countries and saw a quarter million in gross sales - something I can safely say I didn’t think was possible two years ago. It’s wild to look back and remember I had worked with only five clients before boarding my flight for Ecuador - a number that has grown 30x in just one Earthly orbit of the sun. What a year 2022 was!
Toward the end of it though, I started to realize that deep down traveling non-stop wouldn’t be so sustainable now that I was picking up steam and getting busier. I knew the majority of the next year would have to be spent on the ground back home in order to take Uproute to the next level. It was cool to see what I could accomplish out of a backpack all over the world, but I was excited to see what I could accomplish back home with some solid ground under my feet (of course with a few trips sprinkled in here and there). I closed the book on 2022 grateful, elated, and hungry. I can’t wait to see what’s next!
Home Sweet Home (Chicago, USA)
To end on a heart-warming note, I’ll leave you with the text my cousin sent me in April 2022 that kept me going when times got rough in Asia. It’s my North Star for 2023.
“It’s easy to say ‘find something to do and you’ll never work a day in your life’. It’s another thing to have the audacity to believe it, pursue it, build it, breathe it, and bring a smile to the faces of those you meet along the way. From where I’m sitting, you’re the epitome of success whether or not you make a penny. Keep following that big ol’ heart of yours!!”
May your 2023 be filled with unconditional love, faraway destinations, the pursuit of something more, and people who make you feel extra special. Until next time!
~ Sam