It was not an easy decision to turn my comfortable life upside down and try something new.

So not easy to leave a great job of 6 years, to move out of a cool apartment in Brooklyn, to put belongings in storage, and to say “See you in 6 months” to my parents, brothers, niece, and best friends from high school and college.

It was an emotional roller coaster just to come to the decision in my mind.

Breaking the news to my family and employer was scary, tears were shed, and I braced myself for the backlash. But, all I got were positive responses. I was surprised how many people treated me as brave, as if I was fulfilling a regret that they'd never done something similar.

Leading up to my departure, through my first month in Colombia... here are my self-deprecating, perhaps relatable notes and feelings on the whole process:

The crazy thing about backpacking is besides never being alone, I also would spend entire days with complete strangers. Some I got their name and contact info, others I shook hands with and said "See you somewhere!"


  • Second Guessing: I spent this time second guessing my choice constantly. I was neither proud nor excited about my trip, instead I felt timid and crazy for giving up a secure job, retirement fund, consistent income, and good health care.
  • Vague Stockholm Syndrome: Suddenly I loved everything that I’d grown to resent before: my routines, commutes, favorite places, I began to get anxious over the last yoga and cappuccino Saturday in my hood.
  • Too Much Google: It was also challenging to research my first destination, Colombia. There was so much information to sift through while conceptualizing the distances between places.


  • Healthcare Headache: What to do about healthcare…apply for COBRA or take shitty healthcare with the worlds highest deductible? (I went with the latter)
  • Flight Prices: To book more expensive flights with bags included or budget flights with bag fees? That is the question.
  • Plan Ahead A Little: I booked my first few hostel nights to have a destination upon arriving.


  • Set Yo Budget: I recalculated my budget with actually approximate prices of things instead of completely guessing, as urged to do by my older brother. Thanks Justin.
  • Do Your To-Do List Last Minute: I had go to CVS on my to-do list for the entire month, but of course didn’t go til 2 days before my flight for toiletries.
  • Goodbye Tour: The month of 1,000 goodbyes. Goodbye before the holidays just in case I don’t see you after the holidays.


  • Get Acquainted with Luggage: The ‘ol pack and repack your bags 50 times.
  • Bring Crappy Things: I thought about buying some new clothing items and then realized I was going to South America so best to bring things I wouldn’t care if they got lost (except would be devastated if I lost my Salvation Army flannel from 2010).
  • Transitioning: Weird limbo of things to do/people to see/and being ready to leave!


  • Feels: Nervous and excited.
  • Best: Total bliss of getting through security, sitting in the airport, completely ready. Falling asleep at take off and waking up mid flight, which became a weird time lapse where I used to be someone who lived in NYC and now I have no home and know no one.

While my time in Minca wasn't what I needed, no doubt it was still a gorgeous place to see.


  • Airport Psycho: If you’re anything like me, then you’re clumsy and awkward in the airport too, and get nervous at customs as if you have broken multiple international laws.
  • New Environment Woo: Medellin was so dreamy with mountains in every direction. I found the nearest rooftop bar and drank a beer in total happiness of my surroundings.
  • Lol You’re V Alone: I did it! Made it to my accommodation, proud that I’d spoken Spanish on the bus. Then it hits me that I know no one.


  • Get Bearings: I like to walk around the neighborhood a few times and take note of the infrastructure, what food is around, where to buy water, where’s an ATM, and what’s happening with the weather? Logistical mental note taking.
  • Make 12 New Friends GIRL! I was sitting on my hostel bed eating almonds, thinking about whether to be social or not. The girl in my room didn’t seem to be interested in friendship. Coulda called it quits but I went down to the hostel common area and immediately succeeded at making two friends. What I came to realize is everyone met 20 minutes ago. Not only were 8/10 people traveling alone, but also a lot of people were 28, had just quit a job, and taking the time to travel. I spent my first night dancing with 12 people from all around the world who had just met. It was incredibly validating.


  • It’s OK to Say No: After all the excitement, I got pretty tired, fast. I was saying yes to every invitation that came my way, and it was exhausting. I allowed myself to chill at the hostel, lay in bed, whatever. Listen. To. Your. Body.
  • Hablas Inglés? Though everyone speaks English at hostels, I wanted to learn Spanish. So I did! Even if I practiced the most via text with a friend in Boston... it still counts.

I met Simona on day 2 in Medellin. We ended up traveling together for 12/30 days. Never would I have anticipated such a wonderful and natural friendship like that!

DAY 17

  • Alone For the Very First Time: It no joke took 17 days to have a day alone. And it was just that, a day. I’d made friends in Medellin, we met up again in Cartagena, traveled to Santa Marta and Taganga together, and they went to Parque Tayrona without me. That was the first day in the entire month that I was solo. How NUTS?
  • Get Help from Strangers or Get Sunburnt: I don’t know how this never gets talked about. It was either get roasted or ask a stranger to put sunscreen on my back.

DAY 21

  • Sleeps In Hammock Once: Not for me. But! Good that it sucked because it was the same night that I woke up at 3:40am specifically to go on a sunrise hike. It was so damn beautiful.

    We hiked 3 hours in the dark to the top of a mountain in the Sierra Nevadas with a view of the Caribbean Sea, Palomino, Tayrona, Costeño, Minca, and the tallest snow capped peaks in the range, Cristóbal and Bolívar. We saw big spiders, bats, moths, butterflies, poisonous snakes, frogs and stick bugs en route. We hiked with two friendly dogs and a Colombian guide, and it was a lovely feeling to see the sunrise with three new friends.

DAY 24

  • Not My Vibe: 'Twas a day to feel tired, restless and unsociable. While Minca was highly recommended, it just wasn't where I wanted to be. I went and left first thing in the morning.
  • When Home Catches Up To You: When I allowed the time to let my thoughts wander, or FaceTime with friends and family, I realized that whatever I left at home both good and bad is still there, and I’m not untouchable just because I'm in a different country.

DAY 27

  • Pool Day: Chill the F out and talk to no one. Read a book. Watch the sunset and the moonrise. Go to bed at 9pm. WHO CARES!?

DAY 28

  • Ready For the Next Destination: My trip is different than yours. I had a time limit and a next destination to fly to. I imagine with a different schedule, I’d feel this tangent of ways at various points in the trip. By the end of my month in Colombia, I was excited for the next stop.

The environment in Colombia was so gorgeous. This was taken from one of my favorite days, a sunrise hike from El Rio Hostel in Buritaca, with 360 views of mountains, ocean, and banana plantations.

If you've got your ticket booked, then no regrets!

Long term travel will have so many ups and downs, but it is worth every minute of it.

For more inspiration and sentiments, check out Prepare for Your First Solo Adventure, As Told By Some Badass Women, a longer form piece of writing and interviewing about what it's like to travel alone.