How to Become a Freelance Writer (I hope…)

become a freelance writer


The following article is about a giant crazy experiment I am trying where I am going to learn how to become a freelance writer. In the lifetime of my career as an IT member, I have had six bosses over four jobs. I have not gotten along with 2/3  of them, because I felt their vision was different from my own or lacking. This has led to years of working with bosses I don’t really care for. I just got laid off from a position where I’ve disliked my bosses for the last three years. So instead of jumping right back into IT, I am trying out building my own business and become a freelance writer.

Here is the big picture:

  • Freelance writing requires a platform / base / reputation built up. Most people build this slowly as a part time for  a year+. I am going full blast for 6 months.


  • I have started up  and am running this freelancing as a business (licenses, accounting software, business accounts). The end goal is not a short term gain, but to learn the entirety of freelancing. The hope is that by the end of the 6 months I’ve made up enough ground where I can do this full time.


  • I am going to convert my 401k to a solo 401k with loan options. Freelance writing is a feast and famine occupation, so I want to have a loan option ready should I need to smooth out cash flow.


  • I am going to be applying for health insurance in the health exchange.


  • I am building up reputation among content demand websites (Writer Access, The Content Authority, Text Broker) . The idea is to use these sites to even out cash flow from private clients. I will also be using this website to help supplement the savings during the next 6+ months.


  • Generate a lot of “long tail” content that pays very little (if ever) over a long period of time. The idea, again, being to even out cash flow. Some of this content includes article marketplaces, short stories, and this blog.


Here is the fiscal picture next 6+ months:

  1. I’ve reduced my expenses drastically! So much so I can get by with a 31% pay cut. In another perspective, this represents all the pay increases I’ve had over the last 3+ years. Poof, gone!
  2. I am applying for unemployment, then getting into an unemployment program designed for entrepreneurs.  Unemployment will pay about 60% of my needed living expenses, and joining this entrepreneur program will allow me to be 100% honest with the unemployment office regarding my intentions.
  3. I am paying healthcare premiums with a HSA savings account (which you can only do if receiving unemployment)
  4. The rest of the living expenses are being paid for with savings and severance.


Hopefully all these steps will allow me to become my own boss! If I am able to become a freelance writer, this would be like never having a job again. Hopefully this dream will come true! If it doesn’t, I at least have a fall-back career.