The six month plan to travel has been extended… indefinitely. And despite this new adventurous chapter, I’ve noticed feelings of loneliness creep in as I reflect on the prior six months and the first 48 hours abroad.
Let’s start with my decision to extend.
The first six months of travel were incredible. Incredible is too reductionist but if you’ve been following along, you can understand how hard it is to summarize in one word.
Unsurprisingly, the time flew by. And when I got back to the states for EDC Las Vegas, I gave myself no time to digest.
In the days and weeks following EDC, I was met with a lot of uncertainty, as encapsulated in my latest post. The only semblance of direction (psychedelics) was not materializing and I felt lost.
MINUTES after drafting the post on uncertainty, one of my closest friends from backpacking texted me checking in. After catching him up on my life, I was surprised to learn he had been feeling a similar way.
He had been traveling for nine months and was feeling a bit rundown. He also shared he was feeling lonely. It’s tough to make friends only to have them depart as quickly as they came.
Seeing that he had already been out for nine months (several months past his original plan), I asked when he was thinking about going back home. His answer blew me away:
“If it continues to be like this and I don’t turn it around, I’ll probably go until April.”
“APRIL!?” I asked. “That’s like 10 months from now!”
“Yes,” he responded with a chuckle.
That’s when it hit me. I had spent weeks thinking about my next move and hours articulating it to all of you… and here was my friend, without a worry in the world, saying he was going to travel for another 10 months minimum.
In that moment — literally in that exact moment — I said fuck it and decided to go to Costa Rica.
No more analysis and irrational worry.
THE NEXT DAY, the host from a work exchange program I was interested in messaged me. After initialing not having space for me, someone backed out and a bed was mine… if I wanted it.
Yup. The universe was up to something.
In the following days, the inner knowing feeling deepened as I returned to NYC. As soon as I stepped onto the bustling streets, I was met with a wave of anxiety. The buzz of the city that fueled me just years ago was wayyyy too much for me now.
And it was weird. I walked around both in awe that I lived there for so long and in sadness because I knew it would never be the same again. A fish out of water, if you will.
So that brings us to today.
I arrived in San Jose, Costa Rica two days ago and am currently on a four hour bus ride to a city called Dominical for this work exchange program.
Cool, but what does that even mean?
Basically, I’ll be working at some guy’s house in exchange for accommodation and food. I’ll be working for 4-5 hours per day doing a variety of tasks that might include farming and building stuff.
Surprisingly, these exchanges are very common in the backpacker world so I figured I’d save some money and give it a go. Plus, read this excerpt from the description and tell me this does not sound like me:
This space is based in the ethos of self sustainably, health/wellness, food as medicine, farming, yoga, meditation, play, community, and the practice of both ancient & new traditions of self development for ourselves & the human collective as a whole.
Kinda cool, right?
This is great and all, but I’d be remiss if I didn’t acknowledge some of the other stuff on my mind. I don’t just post highlights… 😅.
I’ve been aware of feelings of loneliness.
These feelings arose in Cape Town, continued in the states, and hit hard in the last 48 hours when I was the only person in my eight person dorm.
While I was part of an incredible yoga community in Cape Town, my copious amounts of alone time gave rise to feelings of loneliness. I went from being surrounded by 50+ people my age every day to living alone in a studio apartment. I loved my friends in the training but it couldn’t compare to the hostel scene in Asia.
Back in the States, I thoroughly enjoyed catching up with friends and family, but I felt a bit odd. Everyone was going about their normal lives (aka working) and here I was sleeping on couches and playing Fortnite with my eight year old cousin on a random Tuesday. I missed the felt sense of ~living~ shared by travelers. I flashback to a core memory often: by the pool in Ubud, in awe at the scene of travelers just ~being~ with huge smiles on their faces and not a worry in the world.
Now, despite going back out again, the loneliness arose in my dorm last night. I couldn’t help but question if the work exchange was the best next move. There were only three other people there — would that be the community/vibe I was looking for?
In reflection, I can’t help but question why I am seeking community so much. Part of me sees it as a natural human tendency, but the other part of me wonders if it’s compensatory for making me feel “enough” in my current state. I’ve written about this ad nauseam, so I won’t go into it again.
Interestingly, I do believe I felt the happiest in the first two months of travel, but that could be due to a million factors aside from community, including novelty.
Also, in radical candor, part of me is yearning to meaningfully connect with a girl and travel together. It’s been a while since I’ve had a very strong connection in the romance department. I’ve done the Eat and Pray parts… and now I’m open to the Love (speaking it into existence).
So, what’s next?
As I’ve told many of you in the last few weeks “I have no plans haha.” The only thing on the calendar is my brother’s graduation in Orlando at the end of July. Maybe I stay at this work exchange until then, or maybe I hate it and leave for a hostel two days in. I’m open to anything, including going back to Southeast Asia and joining my friend.
And this is what is making it feel so different. There is no tentative end date in six months and zero desire to return back to a city I called home for five years.
One thing is for sure, though, I’ll be practicing Spanish. It’s comical how bad my Spanish has gotten since achieving fluency in Spain seven years ago AND interesting to observe the part of me that desperately wants to regain it.
Con amor,
Jacob

I’m terrible at taking pictures and have no pictures with any of you that I visited in the States. Sorry 😢 I’ll be better!
You express yourself beautifully – honest open and vulnerable. It seems like everything fell into place for you to be there. And just like everything else you’ve sought out I’m sure a girl will appear. ! Enjoy the beauty of Costa Rica 🙏🌄
I once did a work exchange on an island for two months, met a lot of new friends, blew the sea breeze, ate delicious food, watched fireworks... It will be something I will remember for the rest of my life. Exploring the unknown every day makes work exchange meaningful...