He has problems finishing work, endlessly re-writing and editing. When a short story is finished he won't send it anywhere - he says doesn't want to send it to competitions because there might be issues over copyright should he want to publish a short story collection later on. He also worries that he hasn't yet found his voice. He tries different styles, different genres. He destroys a lot of what he writes. He researches agents and publishers, but somehow never finds one that is suitable for his work - he tells me that it's very important to start as you mean to go on and the wrong agent or publisher can kill your career before it starts. Well, yes, but...
What it amounts to is some beautiful writing which only gets read by a select few (I am now off his reading list after I ventured some criticism). I think it's great when writers write just for themselves - but this writer is ambitious. He wants to be launched in a blaze of glory. He doesn't want to follow the ordinary path, or so he says.
I suspect he doesn't send out because at heart he is frightened of failure. He has set his sights so high that he will be very lucky indeed to succeed. Ambition is a good thing, but it can also cripple you. Easier to say 'I'm not ready' than risk being turned down.
But failure is part of any creative endeavour. Without failure we can't judge our strengths and weaknesses. Without failure we won't grow. Without failure we stay in the same place and stagnate. Failure means development. If a writer gets 99 rejections but an acceptance on the 100th, is that writer a success or a failure? A success even though if they'd given up at 98 they would have been a failure.
I believe that we are all on the same road. Sometimes we move faster or slower than others. Sometimes we get a lucky break and jump a section, sometimes we go through bad times and slip backwards. Luck plays a big part, as does hard work. If you fail - that is, get a rejection - then you slip back a bit, but you only come off the road if you stop writing and stop trying to move forward.