The single biggest mistake I made when I was an independent software developer was making my flagship product available for free. Of course when I first releas

The single biggest mistake I made when I was an independent software developer was making my flagship product available for free. Of course when I first released the application I had no idea it would become a significant part of many people's lives and would come to occupy all of mine. I also had a job at the time, and like you I felt conflicted about charging for my work. The application was Journler, an information management application for the Mac desktop circa 2006-2010, and I eked out a living on a "donationware" model for some time. Eventually the scope of the project became so large that I needed extra help, but I didn't have the income to hire help. I needed to start charging to be able to hire help, but in order to release a new version of the software with a paid model while continuing to manage customer support, I needed to hire help. I fell into a vicious circle, and the project collapsed. I open sourced it, apologized to the user community, and moved on to contract work. You cannot anticipate what will happen with the software projects you release into the wild. But as developers often underestimate how long it takes to complete a project, I'd speculate we also underestimate how much of ourselves we'll have to commit to a project that becomes even modestly successful. Charge from the beginning and put yourself into a position where you can hire help if it should come to that.