My Freelance Career: How I Got Started

How I Became a Full-Time Freelancer

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:

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? 

Other Helpful Posts: Organizing Your Freelance Finances + Schedule of a Freelancer

  • Meet Lindsay Humes

    Hi! I’m the designer and owner behind White Oak Creative. I partner with creative entrepreneurs, lifestyle publishers and content creators to design the best brand identity to grow their audience and brand. My blog is full of resources on Branding, WordPress, SEO, and more!

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    18 thoughts on “My Freelance Career: How I Got Started

      1. Lindsay Humes

        Thanks, Katherine! It was definitely a very uncertain time, but I’m so glad I made it through it!

    1. Jess Zimlich

      I had no idea about some of the steps that got you to the place you are at now. This gets me excited for this new series 🙂 I hope your Monday is off to a great start!

    2. Pingback: 10 Inspiring Blog Posts on Self Employment - The Blog Market

    3. Aukele | 91DASH

      So I appreciated this post – as I’m trying to get my feet off the ground with my own business – but I was really excited to see you’re a July 2 baby, because I am too!! 🙂

      1. Lindsay Humes

        How exciting! The process is definitely scary and overwhelming when I was in it, but it didn’t last forever! And July 2nd bdays – yay!! Thanks for commenting!!

    4. rachel

      you are awesome! so encouraging to hear your journey and to see how you made it work for you. i studied accounting in college and i am always wondering/wishing that i had studied design, so i totally feel you on that one! very very encouraged that you have been able to end up right where you wanted! way to stick through it all!

      1. Lindsay Humes

        Thanks, Rachel! I think that there are a lot of people who are career shifters. It just takes a lot of hard work and persistence.

    5. Pingback: 4 Tips To Go From Freelance to Full-Time | White Oak Creative

    6. Mariana

      Thank you for sharing your experience with us, it is very inspiring. I still work in an office, but I have yomi together with my sisters, and I still do not decide to go out and go with everything to yomi.
      I think the most difficult is to get you to change, but if it is really what you want then you only have to go for it.

    7. Angela Kim

      This is great Lyndsey! I find myself learning so much from you both as a blogger and freelancer. I would’ve never guessed you have a MA in special education! I have a daughter with special needs so I’m very familiar with its challenges. I started college as an art history major then graduated with a degree in English. Then I got my MA in English, taught a bit and ended up staying home to raise my special needs daughter. My journey too, was full of changes and I would’ve never guessed I’d be a blogger. Thanks for sharing your personal story. I enjoyed this post a lot!


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