Hi Marie-
I truly understand your worry. My BPDSD23 is currently employed but it was well over a year of doing pretty much NOTHING about getting a job before she finally motivated herself.
Mama-san- so spot on!
Lying around the house fed the self perception of being a failure.
When we think about the shame, guilt, fear, anger the pwBPD typically experiences it's no wonder they have difficulty stepping back into the work force.
For awhile SD sold her plasma to afford her cigarettes and gasoline. She turned to ?borrowing?, begging, and complaining/pouting until someone gave her money. It wasn't until she had really frustrated and burned out those who were willing to be borrowed from, begged at, complained against before she knew her time was UP. The way people were responding to her (negatively) and hearing this even from her biggest enablers/fans was actually a decent motivator for her.
The family member with whom she lives quit giving her money about nine months prior to her finding the job and we had cut her off from financial support a full year before this. So, as you can see, the hold that the anxiety had on her was significant.
One thing that has helped me in dealing with this aspect of her personality is to understand that she gets all caught up in the negative dialog going on in her head. I can't talk her out of it. For her the anxiety of going out and looking for a job super-ceded her need for money so long as she had any chance of someone giving her a little bit of money. I'm sure there were days when she had to bum every cig she smoked and days when she didn't have enough gas money to go anywhere.
You say you don't want to force the issue - what would be forcing the issue and why do you want to avoid this? What will you do once he runs out of bill-paying money. I guess I wouldn't worry too much until he is actually out of money- sometimes kids really procrastinate in a way that would make us lose sleep but for them, they are "like what is the big deal anyway?"

In our situation, SD has to fully understand the consequences of her behavior before she can motivate herself to make a change. Once she can motivate herself the kudos are hers and it boosts her self-esteem to succeed in this REAL way.
She can really get negative in her own head and will go out on all sorts of limbs to avoid throwing fuel on her low self-esteem. Everyone in her life (for the most part) had to get on the same page... .there was never a meeting or anything but one by one everyone got sick of watching her sleep all day and then worry about not having a job until the weekend. And everyone got sick of watching their hard earned money going to cigarettes to burn and gasoline to fuel her fun times (visiting with friends).
She did finally get off her bed and got a great job that she still has- great in terms of the paycheck. She got this job once she truly started looking for a job in earnest. From time to time she will talk about furthering her education or giving something else a try but from the comfort of her life as it is now, she probably won't go out on much of a limb and take a chance on failing (and thus feeling bad about herself). We give her lots of verbal support when she talks about change but we don't pressure her.
Best of luck to you and your son... .
thursday