I wouldn't classify myself as a pessimist. I try to not worry about anything. If something really bad happens to me, I'll just think to myself, I'll be okay tomorrow and that's what matters. However I wouldn't say I am cheery and happy. I have negative thoughts, but like with most things, I keep them to myself.
What I would say is that I am one of the least proactive people anyone could ever meet. I try and let things sort themselves out, but as with most important things in life, they require time, effort and dedication. Deep down I think I know that, but I still lie to myself, convince myself that it can be different. The day I stop doing that will be the day life opens up.
We all have a certain basic behaviour that makes us feel safe. Whether or not this behaviour is hurtful in the long run unfortunately makes little difference to the way you respond to situations. If your automated response is to sit back and watch, you actually have to do the complete opposite. But because this will feel unnatural it is very hard to do so. Maybe you can ask the counsellor to help set some minor goals that require some, but not an insane amount of effort. This way you would be slowly building up.
With regards to us facing similar problems, I was aiming for the vicious cirle that we both seem to be in.
what I mean with being pessimistic is that my automatic thoughts are usually negative. say I'm looking at a street full of people, I will tend to notice annoying things about them. This only happens when I am not aware of it. When I notice that I'm being negative, I will correct for it.
Fortunately for me I have a good sarcastic sense of humour, which works well with being pessimistic :P