My Freelance Career: How I Got Started


Most millennials view freelancing similar to how our parents saw “retirement” – the professional goal. It is so appealing – working for yourself. It can be empowering and at the same time as incredibly uncertain. Every freelancer has a different start. I’m not sure if there is any path that will make you more successful than others. Without any glamor, here’s my professional timeline!

How I Started My Freelance Design Career

College: Before I went to college, my ideas about my significant ranged from everything from fine art to architecture. Once I arrived at Smith, I was too insecure about my design abilities to take the fine art classes. I let my insecurity dictate an opportunity for me; perhaps I would be farther along in my career if I didn’t make this decision. Who knows? I’m not sure if I regret the decision, but I regret the reason for the decision. I ended up majoring  Cultural Anthropology and Art History, with a focus on documentary film.

2008 + Graduation: I graduated a semester early, December 2008. The economy had tanked, and Anthropology wasn’t a job of “necessity.” I decided to get my alternative certification in teaching. There were always jobs for teachers. I applied to NYCTF, Chicago Teaching Fellows, Teach for America, and New Orleans Teaching Fellows. Chicago was the first one I heard back from, and I was glad to come back home to the Midwest.

Teaching: For the next three and half years, I was a special education teacher at a Chicago Public High School. I earned my master’s degree in Special Education, and I coached the high school volleyball team. I enjoyed teaching, helping students empower themselves, and I became very aware of different learning styles, which is a very useful skill to have when trying to explain to people how to use their website better.

After my third year, I felt restless – emotionally exhausted and professionally unfulfilled –  I started learning how to design and code. I started dating Adam around this time, and a lot of our conversations involved the web and design. I could probably count the times on one hand that he has helped me do something in case you are wondering.

The Garden Apt: Around this time of restlessness, I started The Garden Apt. I had more fun building the blog than I did writing it. I decided to apply for entry level jobs in Advertising or Marketing so that I could get more skills related to this field. This job hunt was challenging and took about eight months. Companies aren’t keen on self-taught career switchers.

Account Executive: Finally got a job as an Account Executive, which was great. The firm was small, which allowed me to learn a little bit of everything from copy-editing to creative direction. The client management portion was the most valuable. However, I was working extremely long hours on direct mail. I decided that I had learned as much as I could from this experience and would try to work jobs to focus more on web design and development, or at least jobs that were more 9-5. During this period, in my free time (which was little), I took a few classes, but and building sites as small projects were my biggest sources of learning.

Consultant: For the next 6-8 months, I worked as a consultant writing RFPs and doing business development for a telecommunications company. This partnership was vital for me establishing White Oak. I was able to set my hours, and I learned a lot about small business development and woman-owned businesses. I spent these 6-8 months trying to establish White Oak Creative – wrote my business plan, set up my financial accounts, and started putting together my portfolio. Towards the last couple of months, I worked less and less as a consultant, because White Oak was growing. Eventually, I had to tell them that I could no longer work anymore since White Oak had become so busy. They were incredibly understanding during this transition.

White Oak Creative: I was fully White Oak Creative on July 1, 2014. I consider this my business birthday (my real birthday is the second, so it is easy to remember). I compare the first few years of freelancing to my teaching career – exhausting. I’ve learned more this year than I have in my entire professional career.

What makes a successful freelancer and what doesn’t? I’m not sure. I just know that I’ve been able to establish myself because I continued to figure things out. I’ve been able to develop and then continue to grow because I’ve continued to improve through learning. I never settled for how things were. I kept on trying to figure out or find something better. When I started this journey, I tried to learn how to do certain things, but the truth is I was learning how to learn.

How did you transition from side hustle to full-time? 

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Want more freelance tips? Check out these posts! If you have a question, leave a comment below!

How I Started My Freelance Design Career