Lessons Learned From my First Year as a Freelancer

 Photo by  Chad Cassidy

Photo by Chad Cassidy

One year ago, I emptied my desk and said a surprisingly tearful goodbye to colleagues and three years of work at a digital marketing agency. In between announcing my departure and my last day, I had become accustomed to the constant question "what's next?" I concocted a default answer, one that I felt good voicing.  In short, I would travel. That was the immediate future. Two months in Europe to shake off a few nightmare projects, a monotonous Monday-Friday schedule and burn through some money that I really should have been saving. (Oops)

In reality, post-Europe me wasn't exactly sure how I would fill my time, but I knew it included exploring both geographically and creatively. After I got home, it would be time to test options; production work, modeling, photography, writing, social media..... I had a mental list of all the things I enjoyed doing in my spare time. Quitting gave me the open schedule to give them all a fair try.

I laugh now, a year later, knowing that I stepped away from my job and into the unknown with a fair amount of naivety. Then again, had I known too much, it's possible I wouldn't have even tried. Most of my learned lessons have come from the latter half of the year after I determined more of a direction, gained some momentum and stopped letting perfection get in my way. (*Still working on that.) 

So what are the biggest takeaways from one year of working for myself? 


1. Be Your Biggest Cheerleader AND keep supportive friends by your side.

Believe in yourself. You are braver than you think, more talented than you know, and capable of more than you imagine.
— Roy T. Bennett, The Light in the Heart

For me, freelancing is a lot about continually facing fears. My fears are the voices that tell me I'm not experienced enough, not good enough, not (insert any adjective here) enough. Those types of thoughts are dangerously debilitating and crushing to confidence. But at the end of the day, I know nobody is going to believe in me if I don't first believe in myself. Confidence is something I have to actively work on, and when it's failing me, I turn to my friends. They shine the best of myself back to me and remind me of my talent and purpose. In the midst of an emotional day, I know I can call or meet up with them for moral support and empowerment.  

Recommended Reads to Amplify Courage & Confidence

  • You Are a Badass by Jen Sincero
  • Daring Greatly by Brene Brown
  • The Places That Scare You by Pema Chodron
 Backpacking trip with my supportive gal pals - photo by  Miriam Subbiah  

Backpacking trip with my supportive gal pals - photo by Miriam Subbiah 

2. Voice Your Purpose and Goals Loud and Often. 

And, when you want something, all the universe conspires in helping you to achieve it.
— Paulo Coelho

Setting specific goals and getting them in writing is important to me. It helps keep me aligned and accountable. I think it's equally important to share these goals with your trusted people, both for additional accountability and support, but also because I've noticed people want to help. This has come in the form of someone recommending me for a job, providing a stellar testimonial, meeting me for coffee to answer questions, showing me their editing process, letting me borrow a lens, or telling me about a free online class on creativity and entrepreneurship.  Once I've shared my intentions, I look for little signs and opportunities from the Universe, and trust that it's engaged in supporting my work. 

Mantra to Practice: "I let go of all resistance to prosperity and it comes to me naturally."

3. Community is Everything. 

Freelancing can be a lonely endeavor. I split my time working from home and a wonderful co-working space. If my task for the day is writing, I know home is my better option because I can work in silence.  But too much time at home can make me feel isolated,  and distractions are easy to succumb to. A change of scenery and the ability to ask questions/ bounce ideas off of other creatives is invaluable. My community came about organically, because so many of my friends are already freelancers/business owners. I found other ways to connect with creatives, specifically female creatives through social media, my work with She Explores and finding meet ups in my city for lady bosses. The resources are out there, you just have to look for them and find the right fit. 

 Community > Post Outdoor Retailer trip in Bonneville Flats, Utah  - Photo by  William Woodward

Community > Post Outdoor Retailer trip in Bonneville Flats, Utah  - Photo by William Woodward

4. Learn When to Say Yes and When to Say No.

This is still one of my biggest challenges. I identify as a 'go-getter', a self-starter who is hungry for work and purpose. I said yes a lot whether I really wanted the job or not, and whether it paid me enough or not.

In my conversations with other freelancers, that seems to be most people's experience, especially in the beginning. I think there's an assumption that freelancers get to leisurely pick and choose their jobs, and that all the grind work got left behind at the office job. I call BS. While all freelancer's situations vary, sometimes you can't turn down a job because you need a paycheck. Sometimes you work for trade (or free) because there's experience to gain. Some freelancers hold a side job in the service industry so they can work on their business during the day and still have a steady income. 

The cool part about working for yourself is that you get to set your terms and figure out what you believe your time is worth. The challenging thing about working for yourself is, you get to set your terms, and figure out what you believe your time is worth! 

5. Practice Persistance, Persistance and more Persistance. 

If it's not a NO, the possibility still exists. Even if a company or client did say no, that doesn't mean it can't be a yes in the future. Running my own business has meant becoming intimate with rejection. For me the best way to handle rejection is to not take it personally. There are a number of reasons I may not have been right for the job.  It may not have anything to do with me at all.  But I can't spin my wheels and waste my energy on dwelling on it. The best remedy is to keep moving forward and trust that something more fitting will come my way. 

To all of my freelancing comrades, what have been the most important lessons you've learned while running your business?