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Reflections On Freelancing: It's All In The Approach

A perk of the job: I chilled with Afroman while working the Snowboard on the Block Festival last year.

If I had the time to share an opinion or hell, even just comment a few impulsive words, on half of the ‘tricks of the trade’ about freelancing I see spattered across the web or bitches and moans about how hard it is to get your foot in the door as a writer, I’d have surely made a name for myself as a hopelessly optimistic kiss-ass by now. But (because I’m a freelancer) I don’t have that much time, so I’ve written this blog post instead. Here, I’ll lay out the things I’ve found that work for me, the advice I’ve received along the way, and dispel a few pining notions that many of us writers seem to have as we enter the business. This list is primarily meant to serve as a daily reminder to myself and is far from complete, but hey, that’s the beauty of blog posts – I don’t have to impress an editor and the list can be addended later. For you, dear reader, perhaps this list can provide a bit of an attitude adjustment during the inevitable down cycles of freelance work. Sometimes, looking at your situation from a new vantage point can help turn a fearfully slow and unproductive week into one of hope, self-appraisal, and reconciliation. Here we go:

First and foremost, look at the real value of assignments.

Let me be loud and clear about my support for the ‘freelance isn’t free’ argument. We all need to make a living. But one of the catch 22s of this line of work is that many assignments and contracts offer value far beyond the financial reach of the work. I learned quickly that sometimes, especially as a newbie, a byline in a credible publication or a hefty dose of networking is equally as valuable as the crappy-to-mediocre article rates offered by most online pubs.

For me, one of the steepest learning curves of self-employment has been honing in on the long-term value in a piece of work before deciding whether or not it’s worth my time. A $20 stipend for an article based on a trip I took definitely isn’t reimbursing my cost, but if I play my cards right, having the editor on my contact list and the byline in my portfolio will pay off down the line. Whether that’s better pay for a long form feature down the line or a referral to an assignment for someone else, keeping the work train moving is an absolute necessity if you’re going to stay afloat working from your laptop. Freelancing is a case study in trickle up economics- work your ass off, strive to get better at what you do, and good things will follow.

Tip: Finding work can be tough when you’re starting out. But among the one-off press releases and 300-word listicle gigs I found myself – sometimes – landing, I managed to secure a contract with a small travel website that I found through the Matador Marketplace. While the pay is crap (only 1 cent per word), the publisher came through when I needed an assignment letter to land a press trip and couldn’t get one elsewhere. They’re also pretty lax about what I write about, and it has benefitted me more than once to be able to tell a PR rep ‘Yes, I can guarantee coverage.’

Maintain your contacts.

Let’s go further on the last point. The people you know, work with, and who respect and trust you professionally are going to make your career. Do what you say you’re going to do. Meet deadlines. Finish what you start. Stay in touch with people you meet on press trips, at conferences, and through email. It will pay off!

Tip: At the beginning of each quarter, I reach out to the clients I have worked with the most over the past three months and a few I haven’t heard from in a while just to let them know that I appreciate their business and am always looking to get more involved. The return percentage on this is actually quite impressive – I generate at least one extra assignment from more than half of the reach outs and have on one occasion landed a better (and more profitable) contract.

Get enough sleep.

If there is one thing I absolutely have to have in order to do my best work, it’s sleep (and avoiding mid-week hangovers). This isn’t a mindless clock in-clock out-collect paycheck type of job. If I can’t stay motivated I’ll end up taking a nap, won’t get anything done, and won’t make any money. Even with the freelance lifestyle, having a routine is key.

Tip: I segment my day into categories. Tougher or higher-paying work is done first thing, followed by a gym break or lunch meeting, and then tying up any loose ends or working on smaller projects. Any reach outs that need to happen get taken care of late in the afternoon, because it helps me end the day with some sort of hopeful intuition that I’ll find something good in my inbox the next morning.

Invest in your career. And, work your ass off to make things happen.

A year after I graduated college, I justified my restaurant job by telling myself that it takes a Master’s Degree to make it as a writer or journalist these days. I specifically remember saying that to a co-worker as I stood, sweating my balls off in the kitchen, placing two pieces of bacon on top of a burger (before placing the cheese on top, of course, so that it will melt over the bacon and secure it all nice and neat looking on top of the beef).

I was completely full of shit. The reason I worked in a kitchen was because I expected my English degree to easily land me a job with little to no effort on my part. When that didn’t happen, I resigned to excuses and a prolonged continuation of college-level partying. Two years later, I finally pulled my head out my ass after having an anxiety attack while pumping gas at 7-11. It was time to get my shit together and do something with my degree. So I went on Craigslist. After several failed attempts, I landed a $50 per week gig writing a music column for a local website. Alright, that’s something! That turned into me chasing down the publisher of a music magazine at an event I knew he’d be at, and drinking with him until I knew he’d remember me when I emailed him the following Monday. Six months and a couple dozen articles later and I had myself a job as an Associate Editor. Alright!

The point is, in the freelance world, nobody is going to give you anything. You have to scratch and claw for every dollar, every job, every byline. It’s never easy, but after a while, it becomes a routine. Stuff that may sound overplayed, like signing up for a writing course (and actually taking it seriously) and going to networking events often lead to opportunities you never knew existed.

Tip: I’ve built a strong Upwork profile by asking clients for reviews following completion of assignments. This leads to future clients seeing my 5-star profile rating and reaching out to me directly instead of my having to send in countless job proposals to find work. Yes, Upwork takes a cut of your earnings (20% for new clients up to the first $500 earned, 10% after that), but they are doing two things for freelancers that are absolutely critical – 1. Dramatically cutting the amount of time spent on ‘sales’ and cold calling because of their job boards, job recommendation emails, and the Top Rated Freelancer Program. 2. (this is HUGE) GUARANTEEING PAYMENT. Fucking guaranteeing that you get paid for your work! It’s like god came down and waved his wand over the contract and said, “Though shalt experience the fruits of labor within a reasonable timeframe!” Just doing a quick run through in my head, I’m owed over $1000 in unpaid work done outside of Upwork in the last three months. I’ll gladly shell out a few bucks for the peace of mind of knowing I’m going to get paid in a timely manner.

Be flexible, and look at the bright side.

People love to complain. Freelancers are no different, myself included. Every now and then, I have to take a step back and remind myself how stoked I am to be working for myself, traveling on my own terms, and making my own schedule. This line of work has its headaches and is always going to be a roller coaster with peaks and valleys. I’ve learned to be open minded about client feedback and have come to understand that different clients work differently. Posting a snarky comment on social media when a contract is cut short, or a payment doesn’t come in before the end of the month, isn’t doing anything other than making me look unprofessional. Instead, I try to remember that there’s no boss looking over my shoulder telling me not to crack an afternoon beer to take the edge off.

Tip: There are going to be slow weeks. I try to fill the time by doing reach outs, generating lists of story ideas to pitch, and going snowboarding or camping. In order to stay afloat during these times, I opened a business savings account that does two things for me: 1. Holds money for taxes. 2. Holds money for slow periods. If I could only get better about putting money in there, I’d be golden . . .

That’s it?

Yes, sadly, this is all of the antipathetic insight I have in me right now. But that’s why the masters of the web invented email, ensuring that conversations never have to end and your right to complain or call me a fraud lives on. I’d love to hear what works or doesn’t work for you because I’m always looking to make my workday a bit more efficient. Hit me up here. For now, I’m off to test out the new sake dispenser I bought yesterday.

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