The Mistakes I Made When Going Freelance (and How I Fixed Them)

 

It is early July and in one month from today I will have quit my full-time job in advertising and will be on assignment in Morocco; officially turning the page on a new chapter of my life aptly titled: Going Freelance. I’d like to say I have no idea what to expect after I swap the comforts (and constraints) of a 9-5 office job for one spent writing at local coffee shops, but the truth is this is attempt #2 at embracing a freelance lifestyle.

 

In early December 2014, I had reached my wit’s end with working at an advertising firm and staring blankly at Excel spreadsheets and Outlook inboxes for 10 hours a day. I wanted to indulge in my passion of travel writing, focus my efforts on crafting stories and pitching publications and building my blog; but each time I sat down to write it seemed my attention was pulled away into meeting X with client Y to discuss project Z. It felt like a half -existence to be spending hours doing something I tolerate only to come home and bask in a few late night hours doing what I love. I didn’t dream of being the world’s best travel journalist or most popular travel blogger, but rather longed only for the freedom to wake up each day and simply do what makes me happy. I decided to go freelance and place all bets on my love of writing and budding travel blog; not fully grasping the weight of the decision I had made.

 

January 2015 and after spending time at home for the holidays; the first “working” Monday back was when my new freelance status hit me. There was no alarm, no grumbling as I trudged to the subway, no blank-faced commuters, no greying office furniture and lackluster lunches; instead I woke up leisurely with my boyfriend, had breakfast while watching the previous night’s Daily Show and then flipped open my laptop to begin writing. I could get used to this. As the month progressed, I noticed some strikes against my freelance decision that I had not thoroughly thought through:

 

 

1) I had not saved nearly enough money and seemed to be hemmoraging what funds I had put aside.

 

2) I didn’t have much of a game plan. Being a rather romantic and impulsive person, I usually am like this but being freelance required I have a little more going on then simply writing a blog post. I hadn’t done much “groundwork” in preparing to go freelance beyond securing one or two infrequent copy-editing gigs; and so was scrambling to create opportunities for myself.

 

3) I was not prepared for the sporadic payments. Some freelance articles I published were paid after months, while others paid me instantly. Some stories earned me a couple hundred dollars while others barely gave me enough to buy a dinner in Manhattan. On top of that, my blog was not generating much money in advertising or sponsorships yet.

 

4) Had health insurance even crossed my mind? I mean what was my game plan there? To simply live my life and avoid all health ailments and sickness (God, willing)? Clearly, I did not think that one through.

 

5) Lack of money meant lack of travel and the lack of preparation for freelance meant I had not planned anything beyond a January press trip to New Orleans. Not surprisingly, travel is essential to being a travel blogger and journalist, so not having any trips on the books (or any promise of money to afford them or opportunities to earn free travel) threatened the very reason I had chosen to go freelance in the first place.

 

 

Suffice it to say, I was ill-prepared when I first went freelance and as January drew to a close I found myself applying for temporary jobs in advertising like a dog coming home with its tail between its legs. I didn’t want to go back to an office; already could feel my spirits dropping at the thought of client requests, office politics and pointless meetings; but had blown through my money and was backed against a wall with only one way out: to work.

 

I took a job in advertising in February 2015 (yes, I lasted just a little over a month as a freelancer) and began to learn from my mistakes as I braced myself for going freelance in August (hopefully, for good). Being back at an office fired up my determination to be freelance more than ever; so I used my time (and comfort of a consistent paycheck) to lay down the ground work for leaving advertising..again. Learning from my attempt at freelancing round 1; here is how I’ve prepared myself for round 2.

 

 

1. Spending time to create opportunities.

 

The first thing I’ve been doing is hitting the ground running with The Pin the Map Project and my travel writing. Networking, e-mailing, pitching, writing, promoting-whatever it takes to build up my personal brand and secure opportunities in the coming months. I connected with companies, pitched brands on working together, collaborated with bloggers, published my work and eventually secured myself a trip to Morocco via Topdeck Travel, a trip to Vietnam with Contiki and a trip to Ecuador with Explora Travel for August, September and November. Just like that, I had three paid for trips on the horizon to ensure that no matter what happened, my travel writing and blog would remain fueled…at least in the short term.

 

Beyond trips, I’ve been reaching out to every company, brand, PR person, editor and opportunity I can think of. At the moment I have almost 20 pending opportunities for both my freelance writing and The Pin the Map Project. Some have blossomed into game-changing developments like joining the Mode Media blogger network, others allowed me to publish work in top publications.

 

 

2. Line up all the paying jobs you can find.

 

Contributing writer for Mode.com, advertising campaigns with various brands, contributing writer for Topdeck Travel, freelance writing for Roads & Kingdoms, copy-editing for PepsiCo-whatever gig I could find within my passion points, I have tried to line it up so that come August I have various ways to generate money for myself.

 

I’ve also connected with creative staffing agency, Creative Circle, which matches my experience with short-term (1 week to 3 months) opportunities for me to choose from. Creative Circle sends me job matches that I need only apply for should I be interested; giving me yet another way to earn extra money once freelance. As much as I hate working in an office, if it is a short-term gig of a week here or month there in advertising, writing or social media than that is a good way to generate cash (not to mention, Creative Circle offers health insurance and 401K options for freelancers, which is HUGE!).

 

 

3. Get social-and keep it up!

 

About half a month into going freelance the first time around, I noticed that I could go days without seeing anyone but my boyfriend. I needed to connect with other writers, bloggers and freelancers to swap ideas, inspiration, tips and contacts; but instead would stay at my local coffee shop or my living room and stick to myself. This time around, I have connected with local writers and bloggers, am making an effort to attend local journalism, blogging and travel events to surround myself with people who mirror my passion for travel writing and who can serve as a positive force once I am fully freelance again. Recently, I was chatting with a friend and fellow writer about meeting at a local coffee shop each week to brainstorm pitches and swap editor contacts, which is an amazing idea and just goes to show the importance of staying social when freelance.

 

 

4. Be my own boss (and mom).

 

As much as I’d like to tell you that I spent every day of that first month being freelance being productive, active and responsible; the fact is that there were days I didn’t leave my living room and was in PJs all day. Yes, I was pretty good about hitting the gym often and would go to my local coffee shop, but I should have been more of a boss when it came to my work and more of a mom when it came to pushing myself out of bed and starting my day.

 

In a brilliant stroke of luck and a ballsy move on my part-I managed to negotiate the remaining month of my full-time job as working from home (did I mention I really hate working in an office?). The beauty of this is that working from home for my last month as a full-time employee forces me to bring the habits of the workplace into my home. Sleeping in late? Not when I’m supposed to begin answering emails at 9am. Taking midday naps and being lazy? Not an option when I am tackling projects and to-do lists. Working from home means keeping myself organized and being productive; all things that I will need to keep doing when I go freelance next month.

 

 

I am still navigating all the nuances of freelancing as I prepare to (once again) jump off that corporate treadmill come August; yet I feel I am much more prepared than I was last year. When August 5th comes, I’ll be armed with three upcoming trips, a game plan, paying jobs, some savings and temporary job opportunities. As much as I dropped the ball when going freelance the first time around and as embarrassing as it might be to admit it, I have learned from my mistakes and am ready to give the freelance lifestyle a second chance!

 

Are you a freelancer? Share your best tips for living a freelance life below!