Freelance tip #1: Make sure you notice your accomplishments
On some days, a successful day of freelancing just feels like a series of small victories.
About half a year ago, I made my longtime dream happen and became a freelance artist and designer, and I'm forever grateful for the career trajectory that lead me here. My first job out of college was an in-house design position for a large skate e-commerce company called CCS. When I started, we were known as Daddies Board Shop, but when the well-known and iconic skate brand CCS was about to be shuttered by its parent company Foot Locker, our company bought the brand. Suddenly, our small team was running a business that became five times larger overnight. We were scrappy and we all wore many hats— for me, this resulted in a lot of learning, growing, and having a strong say in the creative direction and relaunch of the brand, with a hand in each step of the creative process. After several years there and searching for the next step, I was offered a position from what I considered the dreamiest branding studio in my good old town of Portland, Oregon: OMFGCO. And I was right; it was dreamy! In contrast to CCS, OMFGCO fostered a more organized and therefore more supportive work environment. I got used to really leaning on my team— especially my producers and project managers— to manage the ebb and flow of each project.
As a freelancer, I am the team.
For me, staring down a fresh work week often feels like gazing at a long to-do list. The list tumbles into the following week, with more tasks stretching constantly into the horizon. Since I'm now responsible for so much more than just designing, the way I look at a day has become very different. Managing my relationships with clients and facilitating projects seem to become my main focus points on most days, and coming from a work history that allowed undivided focus on design, it was strange at first to think of design as an almost secondary task. For me, this adjustment period resulted in a sense of feeling stuck at the beginning. Despite checking off a bunch of administrative tasks each day, it was hard for me to recognize my days as productive when it sometimes felt I had barely chipped away at the actual project. My mind was always focused on what was to come next; what needed to be done and how soon so that I could possibly begin to catch up to the end of that list.
And then I learned the importance of noticing my progress.
I try to be thoughtful about my freelance trajectory as it unfolds. I've consumed a lot of information and advice about working for yourself within the last half-decade. As someone who has always dreamed of someday achieving a greater sense of autonomy and agency over my time and work-life balance, I'm constantly holding my experiences thus far against the many pieces of wisdom I've learned from podcasts, articles, books, and friends I've hungrily delved into for advice over the years. In my opinion, it's really important to be self-aware when you're working independently, with the ability take a step back and see your path objectively. What can you tweak to make things run smoother and make sure this thing stays afloat?
For me, the answer for this particular struggle was to honor those steps it had taken to build this thing, and then keep it afloat. For this, I used an agenda book. I bought the Slingshot Organizer just because I was excited one day when I saw the newest one had been released. Its pages list important events in radical history for each day, and it's peppered with inspiring sentiments and resources to help empower us all to make strides toward a better world. Despite this impulse purchase, I don't really use agenda books. Even when I have one handy, I find that I gravitate toward simple Word documents that feel more malleable and create more of a living, changing resource for myself.
One day when I was feeling particularly buried in tasks, I had the impulse to write down what I had accomplished. I knew that I'd checked a good chunk of tasks off my list that day, and despite feeling overwhelmed, I realized that I needed to acknowledge those tasks. I knew I needed to do this for myself. I searched for a piece of paper, and found the untouched Slingshot Organizer. From that day on, I dedicated a few minutes each day to record what I had actually gotten done.
Thinking back on how this impulse came about, it seems natural. 2016 and 2017 were years of enormous growth and challenge for me. And with hardships come adaptation. I sure picked up a lot of thoughts about coping mechanisms during that time; I learned so much in that time about gratitude and striving to notice the good when everything seems bad. I truly believe that gratitude is the key to coping, living, and thriving. This concept translated very naturally and instinctively to my thought process regarding my progress as a business owner.
After the first few days of journaling each day's successes, I felt feelings of pride and confidence trickle into my impressions of what I was able to accomplish in a day. I took my new routine a step further and dug up some colored art pens, and created a color-coded system for myself that helped me recognize the small victories of each day in the following categories:
I use a green pen for health-related accomplishments, like starting the day with a long walk or going on a vigorous bike ride to exercise and clear my head, and allow my thinking and ideas to flow more subconsciously (much in the way they do when you have an epiphany in the shower).
For social experiences, like meeting up with friends for drinks, talking to my mom on the phone, or going on an adventure with my partner, I use an orange marker to remind myself how productive the experience was for the soul. When you work from home, these experiences need to be very consciously built in to your life, and are just as relevant to a healthy freelance career as drafting proposals. (It's only an added bonus that the people you grow close to often end up being the ones who offer support and connections that can lead to unexpected opportunities and collaborations).
Housework and errands are recorded in purple, and give me a good sense of how much time I end up spending on house tasks (these ones are especially gratifying to check off, too, because it's easy to put these off, and when they get done it feels like a bonus).
I use a pink pen to highlight progress on my personal art endeavors. As someone who makes a living off of my creativity, fostering a creative outlet that is only for myself is very important to me. My professional design work is subject to countless limitations, expectations, and opinions. That's why it's so important to have an outlet for creativity that is completely for and of me. I'm constantly striving to carve a larger place in my life for my passion projects. Plus, the visual exploration, experimentation, and thinking that I put into my everyday work life has a powerful positive effect on my growth as an artist after-hours, and vice versa. (Check out what I've been up to on my instagram).
And lastly— perhaps the most gratifying to jot down— are my professional accomplishments, marked in black. I record things as mundane as finally typing up an email response that I've been putting off, to project completions, to brief words of pride about a successful phone call. I feel especially good when, at a glance, my journal is filled with lots of black writing.
This practice has shifted my entire perspective. Suddenly, I have hard evidence of the strides I'm making day to day. Each day I'm accomplishing far more than I felt I was while staring down my daunting list. And I might add that this rigorous list-making is coming from a person who, in many fundamental ways, does not have a type A personality.
The list has also made it clear to me how things like exercise and socialization are just as important to the health of a freelance endeavor as successfully pitching an idea, and I see all of my color-coded categories as integral to the health of my workflow.
The nature of the freelance lifestyle is much more fluid than a structured office job. Although this may be obvious and is to be expected, it was certainly a transition for me to train my mind that it's okay if I'm not hyper-productive during the 9-5 window of each work day. Escaping the pressure of that binary is a big part of why I chose freelance in the first place, and that flexibility is the beautiful fruit of the hard work of self-employment— it just takes some getting used to!