I wish somebody had told me to keep a straight job going, even if it was just a Saturday job in a small boutique or similar. Not being able to convincingly talk about 'work' is very isolating in social situations, unless you're out and proud.
The bigger the gap in your CV, the less likely you are to find your way back to a 'straight' life, unless you have the personality for self-employment or small entrepreneurism. Maybe start building an ebay channel. A girlfriend of mine picks up stuff in charity shops to re-sell for a small profit on ebay, and now has reached superseller status. It's not massively profitable, but nobody questions why she hasn't got a fixed work schedule or how she makes a living. Also, she really enjoys it.