10 Years of Freelance: The Lessons I’ve Learned

Written by Maari Casey on February 24, 2020

It’s been 10 years since I left a traditional job to boldly leap into the freelance/independent working world. Here are my top 3 lessons that I’ve learned along the way and how they frame my life and work.

It’s been 10 years since I left a traditional job to boldly leap into the freelance/independent working world.  When I look back at the last ten years a million things have changed— the births of my two kids, the loss of my mother, leaving a career, starting a new one, a new house and a new business—so many lessons. At their time they all seemed so immediate and intense but now seem like a thousand precious jelly beans scattered in a jar, too many to count, each unique in their own way. 

Here are my top 3 lessons that I’ve learned along the way and how they frame my life and work:

Be observant.  This is my # 1 top lesson. The concept of “being observant” was first introduced by my 4th grade Science teacher, Ms. Beeindillo. She had a sign that hung over the black board that said “Be Observant.” Every day when we would come into class, we would spend the first 10 minutes trying to notice what had changed in her room, with the weather, with ourselves. It taught me at a young age to notice things and to really pay attention to what was changing and happening around me. 

When I was working full-time I came to a place where life really caused me to stop and pay attention. When I finally stopped and noticed I wasn’t happy, and my priorities were out of whack I was able to redirect and adjust my effort. I’ve tried to maintain this careful observation technique throughout freelancing. I realized that paying attention to where the needs were is where there was really an opportunity for me to add value. 

I’m going to get on my soapbox for a second. I have a tendency to move at light speed through things without really noticing what I do. The power of paying attention, slowing down, asking questions and reframing, has dramatically helped me in how I run my freelance business. I am able to think more emphatically and intentionally about what I do and how I work with clients. When I am moving too quickly through things I miss key signs directing me where to turn. One way to drive is by flying down the highway of life at 80 mph with music blaring and things whizzing by. The other way is driving down a road at a good clip, taking a detour because you like the scenery, humming to the radio and noticing that you’re about on “E”. Lucky for you you saw a gas station is just up ahead. Metaphors are great. So is noticing things that are important. We should all learn to slow down a bit more often.

Believe there’s enough for you. The world, especially the working world can feel like it’s black Friday and there’s one HD TV left and an angry lady with a shopping cart barreling toward you. But don’t worry there are plenty of TVs for you and everyone you know! When I started working as a freelancer I knew what I needed to make to pay my bills and I figured anything over that was gravy or cushion. Once I let go of the “grab everything” mentality I was able to relax and the work flowed more freely. I didn’t take work I wasn’t interested in or not the best fit for but just passed it along. Funny enough whenever I did, another job I was interested in would come back my way. It was like a work teeter totter. Up and down, back and forth. Just enough. I’ve been doing this long enough now to know that there’s enough to go around and that if someone is successful it doesn’t mean that I am not. I’ve learned to focus on what is enough for me and not worry about what is enough for someone else. If you ever wondered about freelancing and thought “I can’t do that there are already a million great (fill in your job here)’s. There won’t be enough work or enough interest.” Well, my friend, take a look at the library. There’s been a thousand ba-zillion books and authors throughout the history of time with no sign of stopping. There will always be someone who wants to read the story you are writing so stop making excuses and seize the day, or your TV.

Do > Try. This is on our wall at the Uncompany office. It came from something a business advisor said to me. I was complaining about what I was struggling with in growing my business. I said something like “I’m really trying to do….” Wahh Wahh, poor me. He said to me, “Maybe you should stop trying and start doing.” Boom. Good point. I realized I was spending too much time trying to make my efforts perfect and so was suffering the “analysis paralysis”. The concept of the MVP was introduced as I was building Uncompany. The concept is creating a test (minimum viable product) and running with it to allow for feedback and changes. Don’t make your first attempt too perfect/precious. You need to give yourself room to change it or kill it if it isn’t working. When you spend too much time perfecting something it’s harder and harder to be impartial and honest. 

For example, When I was young I thought a perm would be a great idea. All the YM magazines I was studying ALL had girls with curly hair. I spent months studying how I wanted to style my curly hair. When it came to the day of my perm the pictures in my mind and the collage I had created for my hairstylist didn’t match what actually occurred on my head. Now in retrospect I could have just tried out my perm by curling my hair for a week before the full commitment of sink rollers and hair picks, but since I didn’t run a test I was in it for at least the late 80’s or until the curls washed out. The takeaway: don’t spend too much time perfecting before you know what you need, and should do. Just get going and adjust along the way.

Finally to wrap-up It’s hard to believe that it’s been ten years since I opted for this path. I am so grateful to all that I have learned and the people who have helped me. I realize that while good days are precious there have been really good things about the really hard days as well. Some of the biggest lessons I’ve learned have been on those shit-storm kind of days. Those are the days that force you to really pay attention to more than the immediate task. So congrats to everyone who takes notice of things beyond the screen. Congrats to those who aren’t afraid to “DO” even when it doesn’t make perfect sense…yet. And a big “thank you” to everyone who told me that there would be enough for me to make a way that made sense for my life.