"I've been a Windows programmer for nearly 20 years, but I desperately want to be good on the Mac" This may be one of reasons. For many people the critical thin

"I've been a Windows programmer for nearly 20 years, but I desperately want to be good on the Mac" This may be one of reasons. For many people the critical thing about self-motivation is getting some kind of gratification quickly. That's why many big projects are constantly started but never finished. It's their size (and thus delay of gratification) that is discouraging. If I was you I'd start something what will bring you the gratification in a shortest time. Start with technology and problem you know. Get the results asap. Then add a little feature that will require a bit of learning. Just a bit so you'll be still seeing the results quickly. Than make another step and gradually increment the difficulty. You'll both learn and get something done. Also, some usual tips about productivity/time-management (like Pomodoro technique) might be helpful - they're often based on slicing this big-discouraging project into small bits where you get the results quickly.