Hi, Hello, & Welcome!
- Olivia Leonard
- Sep 30
- 6 min read
Updated: Oct 1

Hi! I'm Liv Leonard, and welcome to Olivia Outbound! This project is a culmination of everything I've ever wanted to do: write, travel, draw, and of course, chat. This project, this blog, and this platform, I never thought would actually become anything more than a pipe dream. This initial dream of creating a space that I owned, operated, and wrote myself was an absolute foreign concept of extreme magnitude. You being here right now helps this dream of mine stay alive. Thank you so, so much!
I know you have tons of options in how to spend your time online, and I'm incredibly grateful you chose to spend it with me.
I'd love to tell you the story of how this came to be, as I had quite the opposite lifestyle planned for myself, which didn't quite work out.
A dream's beginning...& abrupt end.
May 2024
I graduated from the University of Arizona in May of 2024, with a degree in Digital Journalism and Public Relations. I wrote all the time, as it was my job! I was fortunate enough to write for the Daily Wildcat, UA's campus paper, in addition to the Tucson Agenda and El Inde. It was quite an eye-opener working in Journalism, as seeing the behind-the-scenes of not only writing stories, but the timeline. It's extremely common, especially in breaking news, that stories are produced within hours or less. You learn to talk to strangers boldly and quickly. Sometimes borderline invasive! But we do what we have to do to get the story out and interesting.
Through my studies, I began to become fearless in what I thought was to be my forever career. I would walk the line, write the stories, do what was needed, and move up.
"Simple as that!", I thought.
Oh. How wrong I was. Internships, interviews, countless extracurriculars, classes, oh my! And come April, one month before graduation, I still hadn't landed what I thought would be the perfect solution, a full-time job. I wanted one, and BAD.
I would prep interviews to no end, one of them I had even prepped for a year. A FULL year - It was for a big-time sports league, with whom I had met a year prior. I walked into that interview with so much confidence. I did all the things! I prepped! I studied! I took specific classes and freelance jobs to spruce my resume even just a tad more. Only to be told (something along the lines of) 2 minutes after walking in:
"We don't have any open positions as of now. I hope we stay in contact!"
GAME OVER.
AAAAND QUEUE THE SPIRAL! I was quite unhappy to say the least. I felt so stuck. It felt as if everyone else around me was finding these incredible opportunities, and that they were just landing in their laps! And guess what, when you focus on something negative, it turns out, it starts to be your daily mindset. Like a virus, it will spread, and soon make everything, even the tiiiiniest bump in the road, the biggest thing in the world. Not only the biggest, but seemingly world-ending.
This is where I argue that having people in your life who, yes, love you, but also love you to the point of telling you to figuratively (and maybe literally), get your head out of your ass, may be the most priceless thing you can have.
My mom and my grandmother were those two people at the time. Before graduation at UA, they came down to Tucson from Chandler and Marana to have lunch with me and talk about graduation party plans. Now if you know me, you know I LOVE party planning, going to parties, putting up decorations, the whole shebang. But this was different. It felt really heavy. Like an elephant sitting on my chest, heavy (or Dumbo-sized since I'm quite small).
I just remember sitting at this pickleball restaurant in Downtown Tucson on 4th Ave, and sobbing at a ripe 11 am out of NOWHERE. There it was! There were the tears I had been fighting or suppressing way, way down in there. Now my two best friends - mom and G, took a look at me, looked at each other, and paused.
"Nothing's working, you guys," I sobbed.
"Nothing? Are you sure NOTHING is working?" said G.
"Yes! It seems like everything I do is wrong. Everything I'm doing here is going straight out the window. Oh look! There it goes now out the window next to us! I think I see it in the street next to Hippie Gypsy," I said as I continued to spiral.
"Then get out of here," emphasized G.
"Take this as time off. Go travel. Explore. Go SEE things that you've studied, talked about, dreamt of. Go," said G.
"That's exactly what you need to do, Liv," said Mom.
...Why had that never occurred to me as a possibility before?
The conversation quickly turned into how long I would go for, where I might go, and what I could see. I felt an immediate weight off my shoulders and chest, yes, the elephant decided to move along. No pressure. It was the most liberated and free I'd felt in months, and this was just an IDEA.
What was an idea turned into a rough plan. Work a seasonal summer job. Save. Buy a one-way plane ticket to Europe (first country TBD). See amazing monuments, museums, go to concerts, eat great food. Volunteer via Worldpackers to save on accommodation and food costs. And say arrivederci! to dryers.
This rough draft of a plan somehow made the intimidating factor of graduating from college just disappear. I was excited to move on. I was thrilled to tell my friends, the rest of my family, and colleagues what I was planning on doing. Everyone was excited.
Even Nate, my boyfriend of 3 years, who still had another year of school at UA, left.
Telling your partner that you're going to solo travel for a couple of months is not an easy conversation to have, some may say. But that "some" hasn't met Nate. He was on board from the first few sentences and knew I needed to do it. With happy tears in his eyes, he told me he was proud of me, was excited for me, and couldn't wait to see all the pictures and selfies.
So, I did it.
Olivia headed outbound.
late August 2024
Months of planning. Research on countries, cities, museums, music festivals, and of course, food, was done across numerous Google Docs. Birthday gifts in the form of universal adapters, travel bottles, hostel towels, and, of course, my 40L backpack were prepped and ready to go.
But none, none of that prepared me for the feeling of stepping onto that enormous Dreamliner plane for the first time, and having a ticket on it. After very tearful goodbyes and an initial flight from PHX to ORD (Chicago), I boarded my flight to Amsterdam.
That's right! 5 days in the vibrant, cyclist, canal, Van Gogh-filled city, with a musical festival smack dab in the middle of it all. I was so excited. After a 9-hour flight full of firsts - first plane pillow, plane blanket, plane food, plane white wine, and plane breakfast, we were off the flight.
It was just me and my 40L backpack, so I got used to looking like a Koopa Troopa REAL quick. Once you have that big thing on your back, you don't care who sees you; you just want to get to your destination to un-Koopa yourself. Now, going through International customs for the first time looking like that, I was so terrified for some reason, they wouldn't let me in. Especially after zero sleep on the plane, I also had authentic Gucci bags attached to my under eyes. I was definitely a sight for (super) sore eyes.
I had my first run-in with European public transportation and fell in love. The eldest daughter gene in me loved configuring the app, kiosks, and perfectly timing a streetcar or metro ride. I took the train from Schiphol Airport straight to the city center of Amsterdam.
I will never, ever, forget the feeling I had when I walked outside of Amsterdam Centraal. When you walk out, you're faced with a grand riveria full of ships of all kinds. Cargos, Tugboats, Fisherboats, and Police boats, all waving hi to each other. This was accompanied by a symphony of cyclists, the first time I had ever seen that many bikes, but more people on bikes than walking. I was awestruck.
That very moment solidified an idea that became a really cool experience. I believe I felt more emotions that day than I ever had before, and absolutely loved it. The best part was, I started writing again. Immediately logging my initial emotions and thoughts - even just for a minute. I thought I had lost that side of myself.
I'm happy to report, I was wrong. Just needed some fresh air, new scenery, and a new place to write.
"Nothing" was my lack of seeing any new things. Both inside and out.
I could truly write thousands of words on my experience last summer, and I definitely plan to, in smaller segments so they get their own true spotlight as deserved. I hope you enjoyed this first little glimpse into what's ahead. I can't wait to chat with you soon!



