In 2014 I wrote an LMS (Lesson Management System) that could be used by small schools to keep track of student progress through their materials. In 2015 a language school with three locations asked me to develop for them another LMS that would do all the things that the previous year's tool could do, but include a bunch of reports and a design better suited to cell phones. In 2016 I started to develop an even more complex LMS at the day job which would consume 70+ hours of my time every week for just over two years before the project was wound down. Here we are at the end of 2018, and I'm thinking about taking yet another crack at writing an LMS for small schools. However, instead of having the system be a self-hosted solution, this next system would be offered as a "cloud" service in an effort to simplify the technical side of the work for schools that have better things to do, and to build a small revenue stream via a reasonable subscription service.
Offering a hosted solution isn't going to be the only difference with this next project run. The previous efforts grew mostly through word of mouth or, in the case of the day job, executive deployment orders. As self-employment is a long-term goal, this next LMS will involve a team of people to test and market the project. I will likely remain the primary architect and developer in the near future while a team of three join to do the things that I clearly cannot; which is everything involving marketing and sales.
My goal will be to have six schools using the software by the end of 2019 and a minimum of 50 by the end of 2020. The initial market will be private tutors and small home-based schools with fewer than 5 teachers in the Asia-Pacific region, which means the system will need to support English, Japanese, Korean, Thai, and a few other languages right out of the box. If there's enough demand, then other languages will be added to the mix. Fortunately I have a great deal of experience working with multiple language websites, so this will be an area this new platform can excel.
There is no chance of success if other people are not involved. Far too many of the projects I begin rarely receive a large audience because I am simply bad at promotion. There's no denying this. By working with others who have a good deal of experience communicating with people and spreading information, this new attempt to create something useful might actually see a modicum of success.
Next year I'll be 40, marking 25 years since starting my first "real" job and 25 until I am expected to retire. Being self-employed is nothing new, though every attempt has been rather short-lived as a result of my failings. If I am serious about "being my own boss"1, then it will be crucially important to work with others who have a similar vision and desire to be part of something interesting.
Hopefully this venture will actually result in some dividends.
There is no such thing as being your own boss unless you're some sort of deity, but it's nice to imagine that one could run a company where every customer is happy and satisfied and have zero requests.