Making the Leap from Teaching to Freelancing

Tim Thompson profileby Tim Thompson

Freelancing might sound like a dream come true. No boss to answer to, interesting projects to be a part of, the freedom to work as much or as little as you want, and the ability to charge what you think your services are worth are all attractive qualities of the freelancer lifestyle. But what are you giving up to take control of your career? In my case, it was steady income, five months of paid vacation every year, a light teaching load, a private office, name recognition (because I worked at one of the top universities in South Korea), paid health insurance, and a government pension. So, was it worth it? The short answer is yes.

Transitioning from being employed as a university professor to working as a freelance educational consultant was not easy. I started planning it three years before I left my job. A list of potential clients was the first thing I started to assemble. More importantly, I needed a network of people who trusted me and would pass my name around their professional networks. You can read more about some of these people in my blog post here.

If you chose to read this you may also be thinking about leaving your teaching job to pursue a freelancing career. But how will you know if you are ready to make the leap from a steady, salaried job to the white water rafting ride that freelancing can be? There are three important questions that you need to ask yourself before handing in your resignation letter.

 1. Why am I leaving teaching and why now? 

I wouldn’t say I was burned out but my career felt stagnant. I liked my students and my co-workers but there was no real opportunity for advancement. From time to time I would get opportunities to work on English level testing projects or run workshops outside of the university but my main duties were to teach the same classes that I had been teaching for the past eight years. I realized one day that I was enjoying the outside projects much more than my regular teaching duties and that was when I first seriously thought about leaving the university. I assuaged my feelings of dissatisfaction by making lists. I made a pros and cons list for my teaching job and new freelancing idea, a list of people I knew who might hire me, a list about all the things I would be giving up by leaving my job, and a list of my skills and experiences. I saw a lot of gaps and knew that the time wouldn’t be right until I had stronger lists, which took several years to accomplish.

 2. Should I specialize and have my own niche? 

The answer to this is maybe. I do a lot of different things and I wouldn’t have it any other way. The good part of having a diversified skillset and consulting menu is that you don’t get bored. I flip between editing, training, testing, and advising for a host of different clients. It’s great because I get to continue building my CV while getting paid to do it. Every project that I work on makes me better qualified to work on the next project. The downside of not specializing is that it is more difficult to efficiently explain to people what I do. “Consultant” is a vague term at best and if you can’t tell people you are something specific, such as an editor or a presentation skills trainer, then it can be challenging for potential clients to know what projects they should contact you about.

 3. How should I market myself? 

Most of my projects have come through mutual contacts. If you don’t have a strong network, you need to be prepared to spend a lot of money on advertising to create name recognition for your business. A freelancer needs to make sure that he/she follows these three rules to get more work: 1. Be qualified. 2. Be connected. 3. Be available. Cast a wide net and don’t be surprised when someone you reached out to three months ago suddenly contacts you about an urgent job. People who are always available are rarely good and people who are good are rarely available, so a person who is both good and available is a valuable commodity and should be treated accordingly.

Freelancing is both rewarding and terrifying, full of opportunities and full of loneliness. There have been days when I couldn’t believe I was getting paid to do something so exciting and unexpected and other days where I had to check my internet connection because I had waited so long to receive an email asking me to work. It is a career path filled with highs and lows and I have to remind myself daily that I have only been doing it for four months and next year will only be better.

My favorite thing about freelancing is the list of nine pending projects I have next to my computer monitor. Even if only half of them work out, I will be thrilled as each one will create a new set of opportunities. None of the ideas were on my radar four months ago and that is what excites me the most about the future. You never know what is around the corner and when you are your own boss no one can hold you back.

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Tim Thompson

Tim Thompson taught in Korean universities for 15 years before leaving to start Archer English Consulting in February 2016. In addition to helping his clients, Tim is currently working on a book project consisting of a collection of stories showing the importance of networking for boosting career opportunities. His professional website and infrequently updated blog can be found at

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