Help me think this through?

My boyfriend and I are in a long distance relationship. We used to work at the same place earlier (remotely) and we worked together.

We both work at different places now and I'm worried for him.

He is a very 'self-exploration' 'I will figure it out' sort of a person but in a bad way. He joined this place recently which is a startup, unlike the last company where we worked at - he pretty much has to decide his work, timelines and priorities himself.

He isn't doing a very good job at it. He has taken this freedom and does not much throughout the entire day. His boss told him the other day 'I wonder what keeps you busy'

I'm all for figuring things out in life but I dislike the idea of completely winging things all the time. I'm doing well at my job and I want him to do the same so that we can be like a power couple. We can focus on creating a good life once we have the source of income sorted.

I dont know how to push him. I have tried pep talks, he hears it, and is back at it again the next day. Now I don't want to be too pushy because:

1. He does not like being nagged.

2. Does not like to be answerable.

3. If it leads to a fight it will be an ugly one. (bad words, stonewalling)

Please let me know if I'm worrying too much. Also tell me what I should do.

Help me think this through?
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