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.
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.
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 JessicaDore.com, on Twitter, Tumblr, and LinkedIn.