When I set out to write The Pin the Map Project, it was with the promise of being transparent with my readers about what it takes to become a travel writer and the hope of tracing a path from a 9 to 5 job to a full time traveler. With the start of the new year, I took a massive leap of faith and jumped head first into the renegade world of freelancing. Having worked at a large advertising agency since graduating college, I was more than eager to swap cubicles for coffee shops and Excel for WordPress to focus on my writing and travel blogging ambitions.
Admittedly, when my last paycheck was deposited into my bank account I felt nervous but when I woke up that first Monday with only my writing to focus on, I felt inspired. It had grown increasingly difficult to balance my passion for travel and writing with a full-time career and as a result I found my love of writing conflicting with my work responsibilities as both competed for the mere 24 hours I have in a day. For those dreaming of putting in that two weeks notice and sitting with a cappuccino and laptop at your local coffee shop, consider these things before making the decision to go freelance.
1. Put Money Aside
I am quite the dreamer and when I imagined going freelance I naively pictured a wave of assignments and press trips quickly filling up my calendar. The truth is that freelance writing is a competitive world and sometimes it is difficult to snag that paid story, which is when having money put aside becomes imperative (especially when first starting out). When first going freelance, it helps to have at least a few months of expenses saved up so that you’re not living dollar to dollar and desperately searching for paid work.
In the same vein of having some money saved up is also remembering the important details such as health insurance, 401k and other benefits that often come easily and aren’t given a second thought with a full-time job. In terms of health insurance, when leaving your company you often have the choice to continue your health insurance coverage with Cobra or to seek alternative health insurance plans with Obama Care.
2. Adapting to a New Payment Schedule
Say goodbye to getting paid on the 15th and 30th because when you go freelance your payments are random, sporadic and often unexpected. A story for that epicurean website may only pay 30 days after publishing while that copy editing gig pays bi-weekly and that travel publication pays immediately; your freelance payments will be on different schedules and as a result incoming funds are inconsistent and scattered. In my first month of going freelance the inconsistency in which I am paid has been one of the trickier things to adapt to-some payments arrive immediately via PayPal while others arrive via check weeks after a story was ran. To keep track of the various payments, I recommend creating an Excel spreadsheet to track all your freelance projects, the date you completed them, the pending earnings and whether you have received payment or not. Keep track of how much you are earning per month as well so you can get an idea if your freelancing is making ends meet.
3. Finding Freelance Work
I consider myself both a freelance travel journalist and travel blogger, as as result my time is split between updating The Pin the Map Project and networking on behalf of my website, and pitching editors and looking for paid assignments. The reality of travel writing is this: although I can snag a free hotel, gratis food tour and complimentary dinner, I can’t pay my bills with a gourmet meal or boutique hotel stay. Likewise, airfare is rarely paid for (in my case it has been arranged twice) so while I love going on travel assignments, it rarely equates to a payday and usually requires me to cough up the flight (this is where tricks to save on airfare comes in handy).
As a freelance writer most of the money I earn does not yet come from travel writing but rather from freelance copy editing gigs and paid freelance stories. I often rely on sources such as ed2010 for temporary editorial job listings, Indeed for freelance listings and Craig’s List for writing/editing gigs. Other freelance sources such as ELance and Odesk are useful for picking up projects, while the website Freelance Writing is a great place for job listings.
4. Keeping Yourself Organized
Without a set schedule dictated by an office job, it is up to me to keep myself organized and mark the difference between a productive day or one spent watching VICE News episodes on HBOGo. Every day I update my to-do list of tasks that need to get done for the week and then will push myself to stay on top of my list-which usually includes completing articles, pitching editors, reaching out for press opportunities and copy editing projects.
Admittedly, there are days where my productivity refuses to kick in and on these occasions I find relocating to a coffee shop and changing the environment from my living room to a social setting to be conducive to productivity. Also, as temping as it may be to wake up and pad around in PJs all day, it is better to try and wake up early and get ready for the day (even if you will be working from home) as it puts you in an active mindset.
5. Staying Social
When I worked in advertising a social schedule was built into my daily life by default-whether it was after work drinks, in-office happy hours or lunch meetings. Going freelance takes you out of an office setting and more than likely finds you working on your laptop in the comfort of your own home. While the idea of waking up on your own time and wearing fuzzy socks to work sounds appealing, it is important to stay social and make an effort to meet with people as you no longer have a job that will help do it for you.
6. Knowing When to Go Back to Work
As my first month of freelancing comes to an end, I find myself looking around at opportunities for temporary work or office positions to put aside some extra money in my savings and fuel my freelance career and travel. When I first began looking at jobs again, I had felt as though I were throwing in the towel-that perhaps I was letting down this colorful world of artists, writers and filmmakers who live by their art and struggle dollar to dollar. Then I realized that almost every artist I meet has a job-completely unrelated to their passion-that sustains their work. Some may have a 9-5 office job, others are juggling odd jobs but almost all realize that unfortunately dreams don’t always pay the bills.
There is no shame in seeking an office job-whether permanent or temporary-or looking for odd gigs to help make ends meet. It takes a brush of bravery to walk away from the corporate world and jump into the freelance one but once that decision is made your passion will never again be a side hobby but rather will stay your priority.

Pavla Walsh says
This is very eye-opening post. Thank you!
Glad you found it helpful!
Entrepreneurs Odyssey says
It’s a bold move to leave a paying JOB and go freelance. I’d be trying to build the freelance side of things up a little and hope for some regular gigs before pulling the pin. But, no pain, no gain right. The thing is, it’s not easy and it does take a lot of searching.
Agreed, there are a lot of things to consider before going freelance and it’s smart to not only have money put aside but to have some continuous gigs lined up to help make ends meet.
departmentofwandering says
Such a great breakdown Nikki! I’m transitioning into full-time freelance work in July and leaving my steady 9-5 job behind. It’s exciting yet terrifying at the same time! Thanks for a great list of tips 🙂
Glad you found this post helpful! Best of luck going freelance! It is scary at first but also incredibly freeing!