How I Started Freelancing and Built a Life of Travel

Table of Contents

I graduated from a private university in 2012 with a shiny degree and absolutely no idea how hard the job market would be. After months of rejection emails, I finally landed my first post-grad job… which was working the front desk of the W Hollywood hotel for $14 an hour. Spoiler alert: I wasn’t very good at it. I got let go.

It wasn’t the dream. But honestly, neither were my next few jobs.

I took an internship for $12/hr that didn’t lead anywhere, and finally ended up in a full-time, hourly, remote marketing role as a contractor (not employee).

It was “good enough on paper,” but I still wanted the corporate office vibe. You know, the one with breakroom coffee and potential new besties. So when I landed an office job in Encino (in the valley of Los Angeles), I thought I made it.

But what I actually made was a 45-minute commute to a windowless room that slowly sucked the soul out of me.

Does it sound familiar? This post is for anyone who’s stuck in that cycle.

If you’re tired of waiting for the weekend and wondering if there’s another way.

I’ll share the real story behind how I started freelancing, how I turned it into a full-time business, and how that led me to working from cafés in Lisbon, walking the Camino de Santiago across Spain with an iPad in my backpack, and eventually moving to Italy as an expat.

It wasn’t glamorous. It was pretty messy. But it was 100% worth it.

The 9-to-5 That Wasn’t Working for Me

After graduating from college in 2012, I spent about four months job hunting. I applied to SO. MANY. jobs. I submitted my resume into the black hole of application hell.

When I finally got hired at the W Hotel Hollywood, it felt like such a win. Even if it wasn’t the kind of job I had hoped for. I honestly just wanted to roll up my sleeves and make money.

But it didn’t last. They let me go not long after I started. I kinda messed up, big time. It really shook my confidence and made me question myself, when I was trying so hard to be good at my job.

I picked myself back up, took an internship for ~$13 an hour, and when that didn’t lead to a full-time offer, either, I kept applying.

Eventually, I landed my first full-time job as a marketing assistant for a woman who ran her agency working from home. Since there was no office, I worked from home, too, with occasional meetings at her home office.

But I still wanted that traditional in-person desk job. I wanted to work at an ad agency in Los Angeles. And at the time, I was already living in Playa Vista, right across the street from TBWA Chiat Day.

I could’ve walked to work! I could’ve had lunch at Whole Foods every day! If only I could land a job there.

I imagined myself working long hours, contributing big, creative ideas in meetings, and playing ping-pong with coworkers who would become friends.

I kept applying, and eventually I did get a desk job – not at Chiat Day, but in an office in Encino. I started commuting 40 minutes to work and an hour in traffic home.

This is what I’d been missing, I thought. Finally, a desk job!

A magazine, a corded office phone, a takeaway coffee cup, and a pair of sunglasses are arranged on a white desk—classic essentials for anyone who has started freelancing or is discovering how to freelance. — *Scene from my desk at my one and only full-time office job*

Except, I had no coworkers.

Except, the drive left me completely drained.

And, the frustrating part was, I knew my job could be done remotely. I had already worked from home before.

But now I was wasting hours in traffic, working in a small room with no windows, and counting down the hours to the weekend.

It felt like my time didn’t belong to me anymore. And it made me start thinking seriously about what I wanted my life to look like.

My First Freelance Client

How I quit my job, started freelancing, traveled the world (& you can too)

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After two years in that LA office job, I hit a wall. I barely had enough time in the evenings to make dinner, maybe work out, and crash before starting the whole thing over again.

I kept thinking, “I know this job can be done remotely.” Sitting in a stuffy, windowless room just to prove I was “at work” made no sense.

I wasn’t building friendships. I didn’t feel like my contributions made that much of an impact. I was just surviving the week to live for the weekend.

That’s when things started to shift. I landed my first freelance client while still working my full-time job. That one client covered my rent, and suddenly freelancing felt possible.

Looking back, I probably could’ve planned a bit better. I didn’t have a second client yet, and I could’ve saved more of an emergency fund before quitting.

But I was done waiting for permission.

So, I quit.

A woman with long hair sits smiling in an office chair in front of a desk with a computer, under a large framed photo of a bridge over a canal—reflecting on how she started freelancing. — *On my last day, office art of Venice’s Bridge of Sighs above me*

I decided to try out freelancing as a copywriter and social media manager. I had one monthly client on retainer, a bit of savings, and that was about it.

It was terrifying. But also, kind of exciting.

How I Built a Freelance Business from the Ground Up

Starting out, I had one client. That client paid my rent, which gave me just enough breathing room to focus on building momentum.

Also, at the time, I wasn’t living alone, I was living with my then-boyfriend, so fortunately, I had a safety net to fall back on if sh*t hit the fan and I needed help for a month or two (that never happened, but it was a ‘nice to know’ in the back of my head that made taking the risk easier).

Even still, the pressure was real.

Networking IRL and Online

Two women smile in front of a red "Jersey Boys" step-and-repeat at the Ahmanson Theatre, chatting about how to freelance, with event dates and sponsor logos visible. — *Work event with my colleague and mentor*

I found my second client at an event put on by my current client. One in-person conversation turned into paid work, and more importantly, it turned into confidence. It created momentum.

I also reached out to a colleague who worked in public relations. I’d met her through my prior work-from-home job as a marketing assistant.

She needed help with social media for her clients. We made a great team. She graciously brought me on as a contractor, which helped me build a portfolio and get my feet wet.

From there, I created a profile on Upwork. Not every opportunity was great, and I scrolled past a lot of questionable jobs, but after digging, I found real opportunities.

I used those first jobs to polish my process, raise my rates, and pitch more clients.

Lessons from Early Freelance Life

A small white dog sits on a person's lap next to a laptop, as the person, who recently started freelancing, types on the keyboard near a window with vertical blinds. — *WFH freelance life*

That first year was a whirlwind. I had left the 9-to-5 life behind, but I brought some of its habits with me.

I treated my freelance work like someone was still hovering over my shoulder, monitoring my hours.

I barely took breaks. I worked really late. I felt like I had to constantly “prove” that I was working hard, that my work was ‘legit,’ and worth taking seriously, even when no one was watching.

The freedom was real, but it was also part of the problem. I had to hold myself accountable and create a structure and focus for myself.

I learned everything as I went. Contracts, boundaries, invoicing, finding clients, keeping clients, managing a fluctuating income.

But little by little, it started to feel normal. This was my life now.

The Pros and Cons of Traveling and Working as a Digital Nomad

An airplane window seat with a tray table holding a red water bottle and an open laptop showing an American Airlines Wi-Fi login page—perfect for those who just started freelancing or searching how to freelance while traveling.

About six months into freelancing, I had a wild thought: What if I just… work and travel at the same time?

So I booked trips to Australia, New Zealand, and Italy. I packed up my laptop and gave the whole “working while traveling” thing a try.

And for the most part, it worked. I managed my deadlines in different time zones, took client calls in cafés and coworking spaces, and actually enjoyed my workdays.

More and more women were traveling solo. It was a rising trend gaining a lot more visibility because of social media. I joined Facebook groups like Women Who Travel.

I saw examples of more women like me going places alone and having adventures of their own, and I thought, why don’t I do this, too?

A woman with a backpack and a duffel bag walks on a cobblestone street next to a graffiti-covered wall in an urban area, embodying the spirit of someone who just started freelancing and seeks inspiration for how to freelance on her own terms. — *The street I lived on in Lisbon*

A woman who just started freelancing poses playfully on a sidewalk at night, holding a drink near a large sign that reads "BUDA FCKN PEST" outside a building. — My *Budapest era was such a VIBE!!*

And then, in 2019, almost two years into freelancing and working for myself, I tried something new: I stayed in Lisbon, Portugal, for a month. And later that year, I did the same thing in Budapest, Hungary.

Lisbon and Budapest became my home bases while I worked remotely. That slower pace of travel (staying in one spot longer vs. moving somewhere new every ~3-4 days) helped me get to know the culture, join a coworking space, and meet local people and make friends.

It wasn’t really vacation. It was a glimpse of a different way of life. A non-American, non-hustle culture way of life.

Modern office with empty desks and chairs, indoor plants throughout the workspace, and large windows flooding the area with natural light—ideal for those who have just started freelancing or are exploring how to freelance in a bright, inspiring setting. — *My coworking space in Lisbon*

A woman in a red swimsuit holds a drink while standing in a rooftop pool with several other people, sharing laughs about how to freelance; city buildings and a bridge are visible in the background. — *At one of the Budapest thermal baths*

Coming back to the U.S. after Lisbon, I realized I wanted more. I didn’t want to be isolated at my desk. I loved the European way of life – getting wine with friends after work, walking everywhere, taking public transit, and generally living simpler.

Working to live vs. living to work.

And eventually, that realization would lead me to something even bigger: moving abroad, permanently.

Scaling My Freelance Business

A minimalist workspace with a wooden desk, white chair, potted plant, wall art, and decorative bowls—perfect for those who just started freelancing—set against a light gray accent wall and wooden floor.

A woman who recently started freelancing sits on an office chair next to a desk with various items in a bright room with a large window and white walls.

After those first few years of freelancing, I decided it was time to grow. How could I make this a sustainable career path?

In 2020, when the world shut down, I couldn’t travel and had a lot of time at home sitting in front of my desk, so I invested in business coaching.

I started refining my offers and learned how to pitch prospective clients. That’s when my agency, Velvet Leaf Creative, was born. I focused on offering social media and copywriting services, and for the first time, I wasn’t just freelancing. I was running a business, hiring contractors, and scaling.

In my first year, I hit my revenue goal and made over $100,000 (before taxes). I was proud — but also exhausted.

Woman in a green dress stands outside a white building, smiling at the camera with one hand behind her back and a brown bag on her shoulder—she looks ready to share how to freelance and the confidence she gained since she started freelancing.

Woman in a green dress sits on a purple ledge outside a building, smiling and touching her hair, reflecting on how she started freelancing, with plants visible in the background.

I had pushed hard to grow, but I also put my travel blog and content creation on pause. Everything went into client work.

By 2022, I hit a wall. I had poured a lot of time and energy into a major client proposal that ultimately fell through.

It kinda broke me. I realized I was burning out — again — just in a different way this time. So I took a step I hadn’t expected: I applied for a remote full-time senior copywriting job on LinkedIn.

I got the offer. I negotiated a slightly higher salary. And I said yes.

I told myself it was temporary. It was a bridge to something else. A chance to catch my breath and reset.

And for a while, it was. I needed it. It helped me financially, a lot.

But deep down, even though the job was WFH, I knew that kind of structure wasn’t for me anymore.

Reclaiming My Freedom, A Second Time

That full-time remote job started off fine, until it didn’t. About a year in, things shifted.

The leadership was pretty toxic. Morale was low, and I found myself back in a version of the grind I had worked so hard to escape.

What bothered me most wasn’t just how I was treated — it was watching how undervalued my coworkers were, too. I really couldn’t ignore it.

I didn’t want to keep building someone else’s business at the expense of my own well-being.

So I quit. Again.

But this time, I didn’t dive straight back into work. Instead, I gave myself a reset.

I walked the Camino de Santiago. I spent over 30 days walking 15-20 km a day across northern Spain, just me, fellow pilgrims, and my iPad. No Slack notifications. No Zoom calls. Just space to spend time with my thoughts.

Person hiking with a backpack and trekking poles on a dirt path through a flat, open field under a clear blue sky, reflecting on how they started freelancing and enjoying the freedom that comes with learning how to freelance.

I remembered why I started freelancing in the first place — freedom, flexibility, and the chance to build something on my own terms.

And I realized I didn’t need to “go back” to anything. I could keep building forward.

What I’d Do Differently (and My Advice to You)

If you’re thinking about quitting your 9-to-5 to freelance full-time, here’s what I wish I had known:

Save more than you think you need

Aim for 6 to 9 months of living expenses. I had some savings and I was living with a partner at the time, which helped, but looking back, I would’ve felt a lot less anxious with a bigger savings buffer.

Land at least one consistent client

Ideally two. That first client gave me confidence, but having multiple clients before quitting would’ve made the transition smoother.

Build your brand before you need it

Set up a simple website. Create a portfolio. Make business cards (or at least a clean email signature). Write a short, professional bio, or have a friend write one for you. It’s hard to promote yourself when you’re still figuring it out, but trust me, it’s worth doing early.

Don’t wait for permission

I spent a long time hoping someone would validate me. Give me the raise, the role, the opportunity. Freelancing taught me I could create my own opportunities through outreach.

It’s not going to be linear

I’ve quit jobs, taken jobs, started an agency, scaled back, taken low-paying clients, turned down opportunities, and gone all-in again. That’s part of it. You’re allowed to evolve.

At the core of all this, it’s really about reclaiming your time. How you spend your days, who you work with, and where you work from.

That kind of freedom is the real win.

Final Thoughts: It’s Not Glamorous, But It’s Worth It

A woman with long brown hair sits on a stone bench beneath a wall covered with yellow flowering branches, reflecting on how to freelance as she gazes thoughtfully to her left. — *Boboli Gardens, Florence, Italy*

Freelancing isn’t always pretty. There’ve been plenty of late nights, slow months, and moments where I broke down crying because a client had a meltdown or because I felt so alone trying to figure it out on my own.

But freelancing for the past 9 years has also given me the freedom to travel the world, walk across Spain, start my own agency, and eventually move to Italy.

My life now in Florence is something I never could’ve imagined back when I was stuck commuting in LA traffic, watching the hours waste away.

A woman sits at a desk with a laptop, taking a selfie in a modern office filled with large green plants and glass partitions—showcasing the excitement of having just started freelancing.

A wooden table with a laptop, empty glass, coffee cup, and AirPods case in a cafe hints at someone who just started freelancing; in the background, a person sits reading a newspaper.

If you’re standing on the edge of that decision and debating whether to leap, I hope this helped you see what’s possible. It’s not perfect. It’s not always easy. But it’s definitely possible.

And most importantly? You don’t have to follow the traditional path to build a meaningful, fulfilling life.

If you’ve got questions or want me to dive deeper into any part of my story, send me an email at jen @ jenontherun.com.

I’d love to hear where you are in your journey — and how I can help.