Knowing Where to Start

I've been trying to work on learning the skills I've been told that I need to get a job in the games industry. And thankfully I've been given some great tips on where to look to start learning these skills. What I haven't ever really been taught though, is how to decide where to start a program. I feel like this is a really important skill, but I don't know where to go to get that information.

Starting a new program is a huge hurdle for me. Once I pick a place and start I can easily get in stride and keep going, but I don't know if I've picked the best place to start or just picked some random idea and started there. I've been wanting to create a cross stitch pattern design program, and I've planned out most of the features I currently want to implement. But where do I start to implement these features? I feel like most of the features are things that can't be tested without there being other features in place. Is there an easy way to make a decision? Or do I just pick a spot and jump in, hoping that things work until I get enough done to test?

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