Should I write to him a second time?
A second message is neither a loss of dignity nor a way to earn an answer. Its usefulness depends on what the first message left open. A practical question with a deadline may warrant a follow-up; another greeting may add little.
If he has asked for no contact, that ends the decision. Otherwise a follow-up can clarify the outstanding point without a stream of new topics designed to draw a response. Your next plans can proceed even if the answer never arrives.
The line you can send
Following up on my earlier question: is that plan something you want to do?
Yours will sound different
Bring the message you keep rereading. The first reads are free, and nothing is sent to him.
Ask about mine