Ask HN: (How) Should I monetize this?
Years ago, I worked for a pittance as a Windows SysAdmin at a non-profit. In my off-hours, I hacked away creating many open-source tools in hopes of padding the resume and blossoming into a new gig.

I did eventually land a more fruitful role as a software dev at MegaCorp. Fast-forward to now, I'm a much more seasoned developer/engineer, though my passion for the Windows ecosystem has diminished (I still love you, Powershell). However, one of the Windows tools I developed years back has experienced impressive organic growth, despite getting few commits since its introduction. It's a tool for creating tools, specifically desktop apps for Windows, and it's dead-simple; the lowest learning curve one could hope for. In the past, I used this tool daily, but haven't needed it since switching to Linux some years ago.

I recently got some time off, and revisited this project. I intended to spend a few days on it. Those days naturally turned into weeks, but it was fun to reminisce. This old project is now refreshed and looking good, with new capabilities, and even decent documentation.

Now that I'm essentially ready to release, I'm just now asking myself "why?", and am feeling a bit foolish. Even with these updates, I'm not going to rely on this app; I'm out of the Windows space. But I like that the project has received sustained interest and is apparently providing value. While this tool can take many forms, the dominant use-case for this tool is IT folks creating desktop apps for their companies. But my tool is MIT-licensed, FOSS. With that understanding, I feel like a bit of a... cuck developer. With this tool, an individual can do in minutes what would usually take a team weeks. Despite the value-add my tool is introducing, I've never received (or asked for) a dollar.

I'm both deciding if I should monetize, and also how. I want this tool to continue to free for personal use, but if its being used at at a company, I want payment (even if its mostly symbolic). I do not want to assume an aggressive position, but I do want to be assertive and self-respecting. I'm considering the following:

1. accept donations, and strongly encourage tips/donations if this tool is used in an enterprise.
2. change the license, add telemetry to the app, check for license keys, nag users, yada-yada. i.e., follow the WinZip model. This is the Windows ecosystem afterall; maybe I could throw some ads in there x)

Seems like both approaches rely on good-faith, since any license-check measures wouldn't be difficult to block/bypass. I'm hesistant about #2 because (1) it would require additional work, and (2) user backlash. When I think about my goals here, I feel like there's a dilemma (possibly a false dilemma) between:

1. many users using my app for free.
2. very few (or none) using my app, but those users are paying users.

If money is the motivation, then one user paying $1 is better than millions paying nothing. But I also like the satisfaction I get seeing my work be consumed and appreciated by folks all over the world.

I never met my grandfather, but I'm told he was unanimously adored by his community, partly due to his endless generosity. Flat tire? He'd fix it; no charge. Help moving? Sure thing; no charge. That was his M.O. He also struggled to feed his family, Grandma divorced, and he died young and poor. I admire my grandfather's passion, but I took this as a lesson of what not to do. If my grandfather were alive today, I suspect he'd be slaving away on FOSS projects for GitHub stars, and I believe he would want better for me.

Money is not the motivation, but money is a motivation.

HN, what do you recommend?