She Left Everything Behind to Travel for a Year—Should You Do The Same?

On maximizing travel time, turning a passion into paid work, and alternatives for when your job ties you to one place—Interview with Caitlyn Lubas from You Are Where You Go

“I’ve ‘had it all’ in the past with a traditional six-figure remote tech job, a beautiful apartment near the beach, and a boyfriend waiting for me every time I returned home from my frequent travels. This year, I have none of that [...]. But, I’ve truly never been happier than I am right now.”–

Caitlyn Lubas

Dear readers,

This week, I have the pleasure of interviewing

Caitlyn Lubas

, the writer behind You Are Where You Go, a Substack newsletter where she reflects on “sabbaticals, living intuitively, and intentional personal growth through travel.”

When I discovered Caitlyn’s newsletter, I was immediately captivated by the energy radiating through her words and her unstoppable drive! At just 26, Caitlyn has already visited nearly 100 countries, published a book, and leads travel groups around the world.

How does she do it all???

That’s exactly what I set out to find out—so let’s dive in!

Hi Caitlyn,

I’m so happy you’re here! As soon as I came across your Substack publication, You Are Where You Go, I knew I had to have you as an interview guest! Going through your newsletters, I’ve learned a bit about your life recently: you’ve traveled from the arctic to the desert, written a book, been laid off from your tech job, decided to end your relationship, started a sabbatical to travel… Woah, that’s A LOT!

I guess, my first question for you is: what are the top-three values that have motivated your choices at this stage of life?

I would say three main philosophies have guided my decision-making processes in the past year:

1. Time is our most finite resource (not money) – you can always earn more money in the future, but you cannot buy back time, especially during your peak years of independence and health in your twenties!

2. Learning to say “no” to things that aren’t a great fit is so important to enable you to say “yes” to the places, opportunities, and people who are truly meant to be part of your life.

3. I care more about impacting a million people than making a million dollars.

My core values—maximizing my time, following my intuition to make sure the people and places in my life are the right fit, and focusing on impact—have all motivated me leaving behind a predictable corporate job, saying goodbye to a kind but ultimately incompatible partner, and starting to experiment with ways I can create a career that allows me to share my expertise at the intersection of travel and personal development with the world.

I totally agree with you, especially about following your intuition—it has played a major role in my own decisions as well.

Moving on—I was really impressed to see that you’ve traveled to almost 100 countries! I’m sure many of us wonder: how did you make that happen at such a young age of 26? And for a reader with similar travel aspirations, but who’s stuck in an office-based 9-to-5, daydreaming of building a nomadic lifestyle, what’s your top piece of advice? Where should they even begin?

I did the majority of my traveling during college, actually, and would encourage anyone still in their college years to do the same! When you’re on a college student budget and a non-full time work schedule, you have so much more freedom of time and are willing to sacrifice comfort for the sake of just making a trip happen.

As I’ve gotten older, I prefer certain levels of privacy and convenience that I didn’t require when I first started traveling 8 years ago (my college self wouldn’t bat an eye at sleeping on an airport floor or in a crowded hostel dorm!).

Back in college, I worked every semester and every summer, sometimes doing multiple jobs at once, to save up as much as possible and then travel to a new country every weekend during the year I studied abroad based in Italy and Singapore.

In the past 5 years since graduating, I have worked remotely and frequently traveled while working anywhere there was reliable internet connection across Europe, Africa, and Latin America. But as much as I loved the flexibility of remote work, since my job revolved around meetings based in the Pacific time zone, I found myself having to stay up and work late into the night depending on the location, which felt unsustainable.

Ultimately, specific goals of traveling to remote places on the other side of the world was the trigger for me deciding to take a full year off of work to travel full time without the restriction of timezones or wi-fi reliability.

Regarding your second question, for anyone who yearns to travel more and doesn't have the flexibility of a remote job, I would encourage looking up more local adventure destinations! For example, the US National Parks system is incredible and I heavily took advantage of the proximity while I was working largely based in California.

If your skills and expertise simply don’t line up with a remote-friendly industry and you’re not looking to pivot jobs entirely – saving up for years to then take a full career break to travel before returning to work is another great option to squeeze years worth of travel experiences into just a few months if time and location freedom are not part of your current career path.

These are all very valid options—thank you for sharing them with us!

Now, you recently shared the news, 10 months into your sabbatical, that your career break had turned into a career pivot. Pretty early into my own 6-month career break in 2023, I also realized I didn’t want to be done with work (duh, as if it was possible!), and I was eager to return. I felt I had skills I wanted to further develop, especially to continue building my freedom-based lifestyle—I just wasn’t okay with the exhaustion that had become standard at my previous job.

Back to you—what helped you come to your realization? Was it a particular experience, a mindset you adopted, or a set of habits?

I wouldn’t say there’s any single moment I decided to never go back to a normal job… that’s a Plan B that will always be there!

I more so had a realization that I’m already in the thick of a career break, and currently have no fixed expenses or obligations tying me down, so this is the perfect time in life to try out some entrepreneurial projects that enable me to maintain the degree of time, location, and energy freedom I’ve thoroughly enjoyed during this sabbatical so far.

Reflecting on my unique skills and interests led me to understand that there’s potential to turn my passions into a profession by planning trips for clients and pitching myself for paid public speaking gigs to motivate students and corporate audiences to see travel as a powerful tool for personal development.

I’ve already been leading group trips around the world, which started out simply just for fun and never as a business venture until recently when my travelers keep reminding me of the value I’m providing them. So, I’m giving myself the rest of this year to continue to experiment with doing things I find enjoyable, but also happen to be able to get paid for – and will reflect, iterate, and evaluate as I go!

Thanks so much for taking the time to be with us today, Caitlyn! I guess my last question is–where can our readers keep up with your stories?

I post on my Substack, You Are Where You Go, whenever I have time to sit down and write a full in-depth reflection.

However, if you want to keep up with my travels on a day-to-day basis, I post in real time on my Instagram! I’ve just arrived in India for a three-month trip around South Asia, so lots of exciting sights and experiences are coming soon.

Also, if you’re interested in joining me on my upcoming travels, you can check out my website to see the group trips I’m leading that are an open invite for anyone to join (Next up are Pakistan for Himalayas trekking in April, Mexico for scuba diving in May, and South Africa for ocean safari in July!).

And for a full deep-dive on my first 70 countries and all 7 continents that I visited during college, you can pick up a copy of my memoir You Are Where You Go on Amazon.

Thank you for reading Freedom Focus! I hope you enjoyed this interview with Caitlyn from You Are Where You Go and found valuable insights.

Now, over to you—I'm curious to know:

• If traveling is your calling, would you rather find remote work or save up to take time off for full-time travel?

• What are your hesitations with either option? E.g., financial concerns, fear of loneliness, lacking courage, …?

• Lastly, do you have any questions for Caitlyn that you’d like to ask?

Feel free to share everything in the comments!

And don’t forget to subscribe to stay updated on future interviews and articles!