To build something successfully, there needs to be a certain motivation. This motivation comes from your goal. The question to ask is why do I want to build something?

1. Are you building something for fun? Look at what you do for fun. Narrow down on these topics and then decide to build something. For e.g. spend a lot of time on HN? Build an HN Chrome/Firefox add-on that does things you want in HN.

2. Are you building something for learning a new technology? Narrow down on the technology that you want to learn about. Now think of apps to build using that technology.

3. Are you building something for additional revenue? Find pain points in your industry and create apps to solve them.

Without the right amount of motivation, even if you had started with any of the projects mentioned above, it is very likely that you would not be able to follow it through.

Hmm, that is very wise. I've never thought about things that way.

My motivation for projects has always been kinda screwy. On the one hand, I want to make an income on my side projects in order to someday move away from my rather boring job. On the other hand, I want to make fun and personal things like games, that aren't necessarily things that people would pay for. Most of the project ideas in my list reflect this split of motivation.

Wow, thanks for the insight. :)

I think coming up with good ideas is like exercising its own muscle in your brain. I think with practice and constant reflection / analysis on whether or not ideas are likely to work, you will likely improve over time. I've enjoyed brainstorming new ideas for the web since around 2000. Many of my ideas early on I thought were good, but it turned out (on further reflection) I was probably wrong.

In the past few years, however, I've accumulated a pretty substantial stockpile of what I think are truly legit ideas that I am not in a position (without funding) to do justice to. To make things worse I'm not really seeking funding so I may never find out. Eventually I'll probably revisit the list and start putting them out there if the time that has passed hasn't made them irrelevant, or someone else hasn't already done it.

I think choosing the ideas you will pursue really needs to be tied closely to your goals / objectives.

[EDIT: After reading through some other comments it appears one in this thread is quite similar to the content that follows, but in my estimation different enough that it may be worth posting anyway]

Just interested in learning? Do a project that will allow you to learn about what interests you.

Just interested in making money? For starters my suggestion would be take an existing product / service (not patented) and make it better, or maybe tweak it slightly. The tougher / far riskier objective would be to take an untested idea to market and try to make money with it. Extrapolating that a solution to a pain point I experience is likely a viable business, or that just because a few people I know have an interest in an idea it must mean that many other people in the industry would likely pay for a packaged solution IMO is risky.

Want to do something to help make the world a better place? This, IMO, is probably the hardest type of idea to really turn into something worthwhile. Perhaps one of the easiest ways to chip away at this type of objective is take something you know well and share it with the world. Make an open source project out of it and license it with a nonrestrictive license such as MIT, BSD, etc.

I'm assuming you are a developer of said enterprise software. Talk to your support engineers and operations folks who run this software on a day to day basis. Ask them what their pain points are. You may find they have plenty of ideas that may inspire you. You may also find they have built their own projects that they use for managing and supporting the software.

Source: support engineer / operations folk who spent many years running enterprise software on a day to day basis

Someone at work writes a lot of Python for doing this already - this is a great idea.

Don't work on an idea just for the money.

Work on something that you will use. Something that you really want to exist and there are only sub-par or no alternatives out there. Whether this is something that will entertain you or fix a problem of yours.

It is most likely that if you find this product of use then someone out there in the world will think the same as well. However, this could be five people or thousands of people, it is hard to predict.

If it is really good then the money will follow, but instead of money, take satisfaction that you have created something from an idea and that there's at least one person other than you that is using it.

No. Coming up with ideas is easy. Coming up with ideas I'll care about in a month & be willing to make sacrifices to have time for often enough to make meaningful progress is what's hard.

Most entrepreneurs underestimate the difficulty and challenges that they'll face when they start something and if they knew how difficult it would be at the outset they wouldn't have started. Similarly, you seem to be assuming that you start with a great idea and you move in a straight line to its realization, however ideas evolve and where you end up may not be where you start. Maybe you just need to get started on something, and only by working thought the problem will you then discover the great idea.

Maybe your intentions are wrong.

Some people build things simply for the joy of building it.

In each idea you've discussed, you could easily carve out a special niche version you need for yourself.

If your goal is to make money from said project, well that is a different thing altogether.

I personally suggest you abandon punching keys into a keyboard and get into something like hardware-hacking.