How I Launched My Freelance Career From the Caribbean

Hey, look: Cashville Skyline's very first guest post! It's from my sister, Jessica Dore. I think what she's doing is really inspiring, especially for those of us whose careers follow a non-linear path.

For as long as I can remember, I’ve dreamt of a life in which I could work from anywhere in the world. I’ve never been interested in whirlwind trips, packed with as many tourist attractions as possible in a week. Instead, I’ve favored long term visits—three weeks, a month, two months—to experience the rhythm of everyday life in another country.

During my fourth year as an editor for a psychology book publisher in the Bay Area, I visited Jamaica for three weeks to study yoga. I overdrew my vacation time by more than a week’s worth of work; it took me months to accrue enough time to go home for the holidays.

I knew then that if I wanted to experience living abroad, I’d have to either quit, or take a long-term unpaid leave of absence. But neither of those options were particularly attractive if I wanted to hold onto the property I rent in the Bay Area.

Taking the Leap

During the last two years of my job, I played with the idea of going freelance. The sensible thing to do would have been to take on a couple of clients in my free time to see how I liked it. But between two hours of yoga each morning, eight hours a day at my desk, and cooking an elaborate dinner each night, I was always way too exhausted to fathom doing a single marketing task after hours. The thought repulsed me so much I swore off the idea of freelancing entirely.

Fast forward to December 2015. During a period of particular frustration and burnout, I applied for and was offered a six-month yoga teaching apprenticeship in Kingston, Jamaica. I knew I’d go, but it took me a week to ask my boss for options, like working remotely, taking an unpaid leave of absence, or shifting my status temporarily to contractor while I was away. None were approved, so I resigned.

I’ve done almost none of the things people say you should do before striking out on your own. But it's been two months, and I’ve yet to dip into my savings. So I think I've done some things right.

I had a chunk of money saved.

The obligatory “what to do before quitting your job for any reason” tip.

My sister is a personal finance blogger and my father is a worry wort, so this rule is written in permanent marker on the fabric of my soul. I don’t think I need to explain why this is a smart idea, but here are some things I considered:

1) If no one wants to hire me, do I have enough to live off of for six months? It helps that Kingston costs half of what the Bay Area does.

2) In the case of the above scenario, the Bay Area will become unaffordable. Will I still have enough of a financial cushion to afford the cost of moving, and living, while I find a new job?

I did good work while I was at my job, even when I really didn’t feel like it.

During my six years with the company, there were times that having a bad attitude made me miss out on opportunities to build valuable relationships. Doing a half-assed job is not only demoralizing, it’s oddly enough completely exhausting, too.

I asked myself which parts of the job I liked most, and where I had opportunities to acquire new skills for the future. It was as simple as making a commitment to do better work, and to make the most of the opportunities I’d been given.

I may not have loved the traditional office job lifestyle, but I loved the content we published, and was personally interested in psychotherapy. So I focused on building out and populating our company blog, ghostwriting articles for authors, and making connections in the broader psychology community through our events and social media accounts.

I used my full-time job to acquire new skills and network.

Just by focusing on what I liked about my company, I was able to acquire skills, build my portfolio, network, and establish myself as a marketing professional with expertise in a super niche market. When the time came to reach out to my contacts about freelancing, several former authors were interested in hiring me based on our existing working relationship.

Today, the vast majority of the projects I’m working on came, in one way or another, from those contacts.

I gave myself permission to spend the first month relaxing and focusing on my passions.

I was burnt out from my lifestyle back in Oakland. I really just wanted to lay around for a while without thinking so much about money. I committed to letting myself relax as often as I wanted without judgment, and to do the things I enjoyed doing most.

I did yoga, took naps, wrote in my journal, went to the market, read only on topics I was interested in, went to the beach, met friends, cooked, made an inappropriate number of vegan peanut butter cups, and studied my tarot cards.

I set a really low financial goal for my first month.

If you’re the kind of person who believes in money over everything, this one may sound odd to you.

Sure, I had a few Skype meetings with potential clients, wrote some proposals, and reached out to editors I thought might be looking for contributors. With pretty minimal effort I secured one ghostwriting job, and a weekly column for a popular psychology website. And voila! I’d reached my goal. The success gave me confidence and made me feel good about aiming higher in the next month.

Jamaican Fruits on Colorful Tablecloth

Because I focused solely on covering the month’s living expenses, when I did meet with potential clients I presented myself as someone who was not desperate for work. I was not afraid of being passed over (this just meant more time for naps and snacks.) So I was comfortable asking for the rates I wanted.

I would never have imagined that so early I’d be in a position to be picky. But I was comfortable saying no to a couple of jobs that didn’t feel like a match.

I wanted to be mindful about acquiring projects that were aligned with my longer term career goals (see below), would provide relevant networking opportunities, and would grow my knowledge in the things I’m passionate about.

Now, I’m in week six. I spend time in the local coffee shops, and work for a few hours a day most days. I’ve set higher goals for myself. My new and improved objectives include gradually increasing my rates, building my savings, and stashing away cash for graduate school. Which brings me to my next point…

I make downtime a priority so I can suss out sustainable long-term career goals.

Don’t tell my clients this, but I don’t think marketing other people’s work is my calling.

Before I left my job, I’d applied to graduate school for the upcoming fall; years of working with clinical psychology books had inspired me to pursue psychotherapy training. Because I was so burnt out, it was hard to tell whether it was what I truly wanted, or just a ticket out of the 9-5 office life I’d come to loathe.

What I’ve Learned So Far

So what have I learned so far as a freelancer?

One of the most important things I’m learning is how much my time is worth. Now that I set my own rates, I’m more likely to consider the cost of something—a piece of food, a plane ticket, a bottle of wine—in terms of the hours it would take me to pay for it.

When I decide to slack off and go to the beach for three days, or turn down a project that doesn’t align with my future professional goals, I also know I’m passing up dollars in the bank.

Moving abroad for six months to build a freelance business appears to be a solid game plan. Depending on where you’re based and where you choose to go, the potential to cut your cost of living does a lot to ease financial pressure. And that pressure might otherwise lead to taking clients you don’t want, or charging too little for fear of being passed over.

If you’ve been doing good work and you’ve built a good network, getting projects will probably be easier than you think. Your biggest issue will be saving enough time for yourself to enjoy the added benefits of cultural immersion, solo travel, and completely resetting your life.

Headshot of girl with long curly brown hair

Jessica Dore writes, edits, and does a range of digital marketing projects as a freelancer within the clinical psychology and mental health communities. She also practices yoga, cooks, DJs, and reads tarot cards. To follow her adventures in Kingston, Oakland, and wherever she winds up next, follow her at, on Twitter, Tumblr, and LinkedIn.

Related Post


Discussions — 34 Responses

  • Tonya@Budget and the Beach February 22, 2016 on 8:03 am

    Good for you for taking a chance in life and following your heart!

    • Jessica Dore Tonya@Budget and the Beach February 23, 2016 on 7:36 am

      Thanks, Tonya!

  • Michelle February 22, 2016 on 9:53 am

    LOVE this! So awesome.

    • Jessica Dore Michelle February 23, 2016 on 7:37 am

      Thank you Michelle! It’s been a great experience so far, but encouragement is always appreciated.

  • Abigail @ipickuppennies February 22, 2016 on 12:00 pm

    Huge, scary risk, but it seems like it’s working out. Also, lots of time for naps and snacks sounds like an excellent way to spend your time. Meanwhile, as long as you’re not dipping into savings too much (or at all) I think it’s great that you’re not obsessed with earning a huge amount. My mom is finally at the point where she’s more concerned with covering living expenses and making enough for trips to see relatives (via buddy passes, so extra affordable). It’s made her life a lot easier.

    • Jessica Dore Abigail @ipickuppennies February 23, 2016 on 7:47 am

      Thanks, Abigail. I think it differs for everyone but for me, going into the situation with minimal pressure has made sense and worked out well. I’d like to see my income increase, of course, but the beauty of living in a less expensive city is that it affords me the luxury of taking my time to get there.

  • Shannon @ Financially Blonde February 22, 2016 on 2:06 pm

    First of all, your sister looks just like you Kate. And secondly, I love that she followed in your footsteps of taking a big leap and following a career path that’s more enjoyable for her. Good luck Jessica!!

    • Jessica Dore Shannon @ Financially Blonde February 23, 2016 on 7:48 am

      Thank you, Shannon!

  • JC @ Passive-Income-Pursuit February 22, 2016 on 7:32 pm

    Congratulations on making the big jump to freelance and in another country no less. Life should be about being deliberate in your actions. You were in a situation that didn’t jive with yourself or your long term goals anymore and found a way to try something else that aligns with your preferred pace of life.

    • Jessica Dore JC @ Passive-Income-Pursuit February 23, 2016 on 8:20 am

      Thanks, JC. Exactly. It’s very easy to get stuck. It seems to me that identifying what matters most and having longer term goals in mind can be tremendously helpful when making bold moves like quitting a job, moving, etc… I’ve been really lucky to have some solid options.

  • Melanie @ Dear Debt February 23, 2016 on 12:12 am

    Such an inspiring story!

    • Jessica Dore Melanie @ Dear Debt February 23, 2016 on 8:20 am

      Thanks for your comment, Melanie. 🙂

  • Jaime @ Jaime Donovan February 23, 2016 on 1:48 am

    I think you went about this really wisely. Good for you for working hard for your dream. I like that you just didn’t up and quit your job. I’ve known so many people that have done this and they usually went back to their company bitter about their dream not working out. This is the right way to follow your dreams!!!

    • Jessica Dore Jaime @ Jaime Donovan February 23, 2016 on 8:23 am

      Thanks, Jaime! In a way it felt like I was just “up and quitting” but I think one of the morals of the story is that if you make it a point to do the best you can exactly where you’re at, and you make the most of the options available to you at any given time, when the time comes to make a bold move you’ll be better off.

  • Mel @ brokeGIRLrich February 23, 2016 on 9:38 am

    I love your tip to move abroad! Life is so much cheaper in lots of areas and just such a cool change from the hustle and bustle of America. As long as you have a decent internet connection, you can make money from pretty much anywhere!

    Good luck sorting out all your goals and growing your business!

    • Jessica Dore Mel @ brokeGIRLrich February 25, 2016 on 7:49 am

      Thanks so much for reading and for the well wishes, Mel!

  • Broke Millennial February 23, 2016 on 9:53 am

    I hope you come back and write a follow up in six months or so! It would be great to see where this journey takes you. So few people take such risks in life and no matter how it turns out, there is no way you’ll regret doing this. Best of luck!

    • Jessica Dore Broke Millennial February 25, 2016 on 7:50 am

      Thank you! Hopefully in six months I won’t be broke. Just kidding. 😉
      I would love to write a follow-up in six months. I’m personally so excited to see where this journey takes me. And that alone is a fantastic feeling. Thanks for reading.

  • Barely Vegan February 23, 2016 on 8:03 pm

    Very inspiring. I definitely plan to follow your journey since you’re living my dream life at the moment!!! I like that you spoke about setting small goals first. I think that’s smart. Thanks for sharing. 🙂

  • Jessica Dore February 25, 2016 on 7:55 am

    Thanks for reading. From your username I think you’d like some of the food I’ve been making here as well. 🙂 Feel free to follow me on IG @dancehallyogi. Lots of good vegan treats!

  • Kurt March 1, 2016 on 10:40 am

    Congrats on your boldness and your transition! Please ignore if this is too personal, but would be interesting to have a sense of your income and lifestyle. I’m curious to know your monthly living expenses in Kingston, and what sort of lifestyle that translates to.

    Looks like you’re eating a healthy diet!

    I’m also curious how you learned to read tarot cards.

  • Joseph @ Medschool Financial March 6, 2016 on 6:45 am

    The ability to be able to successfully negotiate a fair value for your time and work is key here. That is awesome, and getting to work it a place where most people go to vacation is an added bonus as well.

  • Vanna Lindholm March 11, 2016 on 8:05 am

    Great place for great spirit, Congrats on big step!
    Hope you are going to make it.
    Last summer I found Caribbean as very inspiring place on earth. Hope sometime I will visit again.

  • Rob @ Money Nomad March 13, 2016 on 9:33 pm

    Fantastic read! And congrats on making that transition. Giving yourself a break is a good idea and deciding to having an adventure while you work means you’ve definitely discovered that life is about more than just money.

    Congrats and best of luck as you continue in this direction!

  • Pamela Car March 16, 2016 on 8:46 am

    Great decision, I was thinking same thing two years ago before I accepted full time job as Staff development specialist in here in Portland. Now I am bit sorry, but who knows life is unpredictable. Thanks for sharing.

  • Liz March 28, 2016 on 1:59 pm

    Envy, you’ve worked hard and are now enjoying the reward. I did it the other way around, travelled the world, found jobs that turned into a career and then returned home. 6 years later, I’m yearning for the more relaxed approach I had with work when I was abroad, but at home.

    Step 1 – pay off the debt that’s holding me back 🙂

  • Jaymee March 31, 2016 on 6:25 pm

    Wow awesome and inspiring story Jessica.

    This just made me rethink my career choices – I have some work to do 🙂 Glad I read this!

  • Derek @ MoneyAhoy April 4, 2016 on 6:47 pm

    Nice that you risked a more steady job for something really cool and it seems to be working out for you. Very inspiring!!!

  • Taylor April 6, 2016 on 9:20 am

    This is really awesome! So cool that you figured out what you want and you can enjoy yourself at the same time. I’m also interested in writing more about psychology and mental health so I’d love to connect with you Jessica.

    Leaving the U.S. I’ve always been concerned about internet connection. My husband and family is from Jamaica he told me the internet is touch and go. I thought it would be impossible for me to even vacation there long term bc of that. Good to know there’s working internet! 🙂

  • Spiced Carob Candy Bars + Salted Peanuts - JESSICA DORE May 22, 2016 on 3:19 pm

    […] I quit my job and moved to Kingston, Jamaica for a few months to launch my freelance career. I like to have a bite or two of rich dark chocolate every day, but good quality bars are […]

  • Julie @ Millennial Boss June 7, 2016 on 11:41 pm

    Just moved to the Bay Area! WHOA is it expensive! So inspirational though that you just took a leap of faith and moved! I hope to achieve digital nomad status some day. Awesome to know that I don’t have to wait for a blessing to do it – I could be OK if I wanted to step out at any time. 🙂

  • Josh June 17, 2016 on 2:12 pm

    Congrats on being able to go freelance abroad. I used my full-time job to get experience as well. Since what I’m doing isn’t related to my previous career, my connections don’t mean much right now. And that is the one thing that can help making the transition easier I would imagination.

  • Brian Meiggs June 29, 2016 on 3:35 pm

    Congrats on the taking the big leap to go freelance abroad. I have toyed with this idea for the past few months but after reading your post it has changed my mind. I’m too much of a city person and set in my ways. I think for me, I much more enjoy being home after I’ve been away for a while. I think I’ll have my cash stashing years in my 20’s and then later once I have a large nest egg do a little exploring. Nice read.

  • Lisa April 1, 2017 on 12:04 pm

    I’m glad you decided to make the leap, Jessica! It’s one of those things you just don’t look back from. I know I haven’t looked back. I’ve had my struggles on this journey but I refuse to regret it. I wish you the best of luck, Jessica!


This site uses Akismet to reduce spam. Learn how your comment data is processed.