When was the last time you met a goal that you’d set, stuck to an ongoing hobby or habit, or finished a project? What do you think led to your success? For example, maybe the last time you were able to paint consistently was in college — and it was probably because you had a structured environment keeping you accountable. Or maybe you started working out three times a week only when your brother said there was no way you could ever do more pushups than him — and you needed to prove him wrong.
What you *might* discover is that you react positively or negatively to different kinds of expectations, specifically outer expectations (like deadlines, assignments, pressure from friends) and inner expectations (things you do for yourself for personal reasons). According to Rubin, there tend to be four kinds of people: those who respond well to both kinds of expectations; those who meet outer expectations but have a hard time meeting expectations they impose on themselves; those who question outer expectations and need to do things for themselves; and those who resist all expectations, inner and outer. (Btw, Rubin calls these the Four Tendencies and you can find out more about them here.)
Once you have an idea of which of the four camps you fall into, you have a better chance at setting yourself up for success. For example, once you accept that you have a hard time self-motivating, that could be a sign that you need to come up with some sort of accountability to keep you motivated as you try to develop this habit.