Most Helpful Guy
I know that feeling all too well. I found that it heavily depends on who I am texting as to how good it goes. It is important to realize the conversation is not 100% dependent on you. The person you are texting with is also 'responsible' to keep the conversation going.
For example, if you ask "Hey, how are you doing?" and they reply with "oh yes, good." and nothing more, that is not on you. I would expect them to ask something, or give more information. In such a situation, you did all you could to start a normal conversation, and that is fine.
Most Helpful Girl
I feel like I'm the opposite, I talk way too much about myself when I text to the point that I'm usually the one holding the conversation up. Just talk about yourself and say whatever comes to mind