The first time someone ever offered to pay me for my writing skills I was stunned. Elated to finally be recognized as a “real writer,” but also completely terrified that I just stumbled into work I had no business pretending to know how to do. At the time, I didn’t realize what that work was, I didn’t have a name for it – I was merely helping a friend out and getting paid at the same time.
I’m still pretty new to the freelance world, and perhaps you are too. I’ve been writing as long as I can remember, secret blogs here, too wordy social media posts there, verbose letters of undying love to the unrequited, and I’ve often wondered as perhaps you have, can I hack it in the world of freelancing? The desire to create a life of our own choosing is often a strong motivator for creatives getting into freelancing but the comfortability of a stable work environment has long kept some (ahem, me) from plunging head first into freelancing as a real source of work.
That first paid writing gig I was offered entailed scheduling interviews with talented New York based artists and interviewing them in real time via Zoom and then somehow turning that cluster of spliced together questions and answers into an intelligible bit highlighting these very talented persons on a blog devoted to very talented people.
I was in way over my head.
I started to shrink at the thought that I would have to conjure up a whole slew of questions to ask these very talented folks and also talk to them and have them believe I was a very talented interviewer and somehow understood the basics of art and method.
Needless to say, that first interview was somewhat of a disaster. Nervously rambling on through unscripted tangents that had nothing to do with art or method, somewhere around the 18 minute mark of what should have been a 45 minute long interview, I was already bidding adieu to my very sweet and somewhat unlucky first interviewee. It was over as quickly as it had begun and I breathed a sigh of relief. The discomfort of not knowing what I was doing was still palpable but it was like ripping the Band-Aid off quickly, the hardest part was behind me - let the healing begin.
If you’re new to freelance work like I am, perhaps the discomfort is what’s keeping you from progressing further in your freelancing career. Let’s discuss ways in which that discomfort can be embraced, specifically in the freelancing and entrepreneurial realm.
“How long will you put off what you are capable of doing just to continue what you are comfortable doing?” —James Clear, author
As a normally high achiever, it sucks to suck, especially when attempting something new. Society says produce more, be more, you’re not doing enough, and your worth is attributed to the value you provide the world. We tend to run ourselves ragged trying to be and do too many things at once. Giving yourself ample time to rest and reflect is key. Give yourself permission to screw it up and learn from sucking a little bit. Rough drafts are rough for a reason.
Look at discomfort through the eyes of childlike wonder – have fun, play, and let discomfort wash over you.
“Embracing the tough stuff is my favorite part of growing and running my business. It’s those unexpected challenges that motivate me to do my very best every time I turn the closed sign to open.” - Perri Salka, owner + curator, The WonderMart.
When I was a preteen and started training in classical ballet, I did not know my grande jeté en tournant from my pas de bourrée, or just how terrible my turnout was but I LOVED every minute of learning something new. It was hard and sometimes the challenge felt tremendous yet children are malleable, adaptable creatures. Don’t forget you as a human are too. Those foundation steps created the building blocks of the movement and when they linked together, a dancer emerged. The same is true of learning the ropes of freelance and entrepreneurial work, you’ll adapt as you keep learning.
When you bury the feeling of discomfort it often comes out in other ways, like snapping at a friend or unmitigated anxiety – cue the panic attacks. But acknowledging that this too shall pass helps create some resilience. Feeling overwhelmed is natural when faced with new obstacles outside of one’s comfort zone and by giving it time to percolate and be acknowledged, the feeling can pass.
As Nicole Rivera, founder of the Home Ec Studio says, "Be prepared for struggles. Also be prepared to get through them."
<tweet-link>Growth does not happen in a vacuum.<tweet-link> Get out there and brush up on your research skills. I love a good old fashion book on a subject I’m learning but as we know the Internet is chock full of freelance and entrepreneurial forums, blogs, and experts in your chosen field. Hectic is a wonderful source for all things freelance and has immensely helped educate newbies like myself. Discomfort yields to knowledge and education.
Admire someone who sucks a little less at writing or freelancing than you do? Ask to pick their brain. I aim for dinner and coffee meet ups over Zoom hangs but whatever helps you gain insight and gives you quality time with your mentor. You can have more than one, I highly recommend hearing different takes on similar skills. My inner child is nourished and feels less lost when I feel like I can reach out to someone with a bit more wisdom than I for guidance.
My discomfort often snags me when I am first getting started, I wrestle too long over what to even start writing about. I often think I have no more “good ideas.”
I stumbled recently over a favorite author and something he said just struck the right chord, “I’m writing my new book and I sit down wondering if I have anything to say. I think every artist hits this sometimes. I feel dull. Silly.
But then I thought, and I swear this thought visited me like a whispering angel,
Write because the Universe has never had the chance to be seen by you. As only you see it. And it never will again. Existence as it passes through you comes out a new color. Get that down. Grab it as best you can.” - Jedidiah Jenkins, author.
Sometimes just biting the bullet and letting the critical self pause long enough to get it on proverbial paper is all it takes. People who haven’t had the opportunity to ever meet you may discover your work and decide that’s exactly what they needed at that moment.
I prepare my space for ultimate focus. I tend to work out of my tiny Harlem apartment but when my roommates are all home, it can be quite distracting. While writing this piece, I found myself in the Rose Reading Room in the very grand New York Public Library because that felt like something a “real writer” would do. I also always have focus music on, typically LoFi Beats on Spotify or something classical are my jams.
If I’m beyond saving and am starting to panic, I take a long walk to sort out my racing thoughts and let the creative juices flow. Being in nature often opens up the wellspring of creativity. Find a place to let yourself be creative and have a plan if discomfort or distraction decides to creep in.
W-2 job sucking your soul? Seek balance by adding boundaries for creative time and allow yourself to daydream. Let the mind wonder and rest and guide it into focused action.
"Every morning, waking with all the reminders, alarms, pings, and my own sense of responsibility, I allow myself to lay there and push everything out of mind. I don't let any stressors, overflowing awareness of minutiae, or random worries enter. It took a lot of practice but it allowed me to approach my morning more grounded and with a clear focus. I was waking up heavy for so long I knew I had to create a change in my routine and being. I realized the discomfort was because I wasn't redirecting that feeling into clear, grounded action. The uncertainty feeling will always be there but I work to be proactive in redirecting it into action which in turn eases my mind."
Carve out the time needed to work on freelance projects. I have a pretty set schedule of when I allow myself to work at my W-2 job and when I reserve hours in the week to only focus on entrepreneurial and freelance pursuits. I don’t check my work email or Slack notifications during this chunk of time and allow myself to be fully immersed in the project. Is it perfect? No, but I gently remind myself to keep focus and clear the mind of distractions.
“We are what we repeatedly do. Excellence, then, is not an act, but a habit.” philosopher Will Durant interpreting works of Aristotle
As Perri of The Wondermart recalls, “I started my business without any real “knowledge” of how to run a retail business but what I did know was that I wasn’t going to give up on myself and that there was no option to fail, but every option to pivot and learn (read: Google) in order to keep things growing in the right direction. I’ve always been someone that feels pride in the act of getting everything done myself - the ultimate one-woman-show. But eventually that mindset will bite you in the ass and burn you out.
To convince myself to give up a morsel of control and trust someone else to help me get a particular part of the job done, I was in constant battle with myself - writing and rewriting social media posts so every-single-word was on point (nobody cares!) and constantly editing my website copy and layout to be-just-right (nobody pays that close attention!).
Eventually I talked myself into hiring a social media coordinator and email marketing expert this year and boy did I have to push hard to get myself out of my own way. And you know what? The house didn’t burn down. The business is humming along. I’ve learned that I have to trust myself, my voice, and my gut. Having a perfectionist attitude was holding me back and stifling the natural ebb and flow of creatively running my business.
Sometimes the best parts of business ownership are found in the in-between moments, the unexpected ones - where you have to think quickly on your feet and you wind up surprising yourself because you handled the damn thing LIKE A BOSS. Because you are a boss - a literal one! You run a whole business and you show up for it everyday. It’s yours and there’s no better feeling than that.”
Finally, take comfort in knowing that clients WANT to hire people like you, with your skill set because at the end of the day you make their lives easier. It may be challenging to get started but your clients are likely dealing with discomfort also and trying to make all the pieces of their business sing in harmony. <tweet-link>You’re the key to unlocking even more success for a business and ultimately, yourself.<tweet-link>