My Life as a U.S. Based Freelancer

When I was in my early 60’s, I decided that I could no longer tolerate the daily grind. I was working as a Human Resources Manager at a university. The commute was about 70 minutes each way, and even though I could continue, I felt that life is short, and I should find alternatives. Before I left, I worked on obtaining a TESOL certificate from a local college. I found the in-person courses rewarding, and I was soon teaching for a local community service twice a week at night while I worked full time. I then worked on resurrecting an old teaching certificate and took additional courses to certify in ESOL.

I surprisingly found a teaching job at a public middle school on a part time basis. It was not for me. I struggled controlling a classroom of 18 middle schoolers from many countries. There were gangs in the school, and I was always calling security. After three months, I resigned. Once again, I was left with a small pension and Social Security and a need to find additional income.

My sister was a retired piano teacher. She suggested that I try to teach piano. After all, I had taken over 20 years of lessons and was still taking lessons. I went on the websites Wyzant and Thumbtack and slowly started to build a business tutoring ESOL and piano. The hard part was that everyone wanted me to come to their homes, and I hated to drive. I did it, because there really was no better choice. I started with one piano student. Then, I had one ESOL student. After building up to 10 students, I was in a car accident driving home from a lesson at night. I decided that I was going to have to think of a new strategy. The problem, which I believe is the biggest problem with freelancing, is that it is very hard to make a meaningful income. Everyone wants to pay less than you need, and your time is never properly compensated. The one car accident with its deductible wiped out several months of earnings.

I started teaching group piano as an employee for a music school and a private school. I taught classes at a Senior Center and taught piano to students who were as old (or young) as 93. I also taught the little children at the private after-school. I was building up a practice in my home at the same time. One day, I just felt worn out. It was time for a new plan.

I started to edit work for one of my adult piano students. Then, I started to teach reading comprehension and writing on Wyzant and Thumbtack. I realized with my HR background I could help adults and college students with career counseling. For a time, I also tutored pre-algebra, but I dropped it because it just seemed too hard. I gave up driving to homes, and I started Skyping with my ESOL students and writing students. Skyping made up about 50% of my work. Without the driving time, things were becoming more manageable.

Although I found most of my customers on the same two sites, I started advertising on my neighborhood electronic bulletin board. I found another 5 piano students, and they all came to my home. I left cards at the local supermarket, but I never found a student that way. There were just too many cards, and too many others with the same idea.

Building a website would be great. I am not sure how I would advertise myself since I have too many different skills. I find freelancing very challenging. There is this constant need to replenish your business as students leave and as jobs are completed. It is very hard to draw lines between your private and professional life. There is always the temptation to go on the internet and search for more clients. It is extremely difficult to make more than $1000/month unless you are highly specialized and in demand. Even with multiple areas, I am competing against so many others who charge even lower rates. On Upwork, many of the jobs already have over 50 proposals before I bid on them. The competition is too steep, and I have lost several jobs because my rate of $35 an area (for which I receive $28 an hour) is still too high.

I am currently teaching piano in-person, ESOL in-person and via Skype, Zoom or Google Meet, career counseling in-person and via Skype, writing in-person and via-Skype and doing editing as well. About a third of my current business is via Skype.

While it would be wonderful to have a universal basic income, I am sure it would not apply to me as I am on Social Security. I think it is a great idea for many people. I do have health insurance through Medicare, and I do pay a set premium, but I am far better off than some younger freelancers when it comes to health insurance.

Although this essay may have a negative tone, there are many things I have enjoyed while freelancing. The flexibility in my schedule is something I cherish; I have met through Skype as well as in-person many wonderful people and even some friends. I am mentally challenged which is always important but even more important as I get older. I have over 20 semi-permanent students which provides me a base level of security. It did take me over six years to get to this point, so I recommend extreme patience and some type of safety net for anyone who wants to become a freelancer.