Relationship Advice

Hello everyone!! I am a new member and this is my first post. I'm really hoping to get everyone's thoughts and opinions on a problem I don't know how to handle.
I have been with my boyfriend for almost four years. I absolutely love his personality , my son adores him, and he is a great person that I enjoy spreading my time with.
The only problem I'm having is that he cant keep a job for more than usually 4/5 months at a time. The longest one was when we first got together which was a year.
He knows I'm a very giving person and I always end up picking us up out of the hole he digs himself into when he loses a job. I'm just so sick of being the responsible one. He is not good at money management at all. A few months ago, we decided to not live together anymore. Theres been talk of us living together again but I'm very hesitant.
Due to his laborer jobs in the past he is physically not as in shape as he was when he was younger. Hes decided to get his CDL so he doesnt have to do physical labor.
Sometimes I think I cant live without him (I can, I'm a very independent person) and then theres days where I'm really just not feeling good about our relationship anymore. It's hard to stay in a relationship with no real consistency as far as employment goes. Should I just be done with him or should I believe that this time I need to move on?
It seems very shallow to me to dump him for not being consistent with his jobs. But then again I cant plan a future with someone who doesnt work as hard as I do..... thoughts?

I think you may have answered your own question with the last sentence of your post. You just don't want to be with someone who is not able to work as hard as you do. And, for whatever set of reasons, this fella just cannot do that. Maybe with a CDL there will be more stability. I guess that's possible. But are you willing to wait for that and see, or, are you just sort of done?

Having been in two long-term relationships/marriages spanning about 30 years, I can tell you that it is never a good sign when two people living together decide to not live together any further. That choice is saying something major. Maybe you need to sit with yourself and decide if you're done here. It's okay to be done. People split up all the frigging time. Of my four other best pals from childhood, all great people, each of whom married terrific women, only one of the five is still married today. Everyone else got divorced.

So, don't feel bad if that's the road you are on. Divorces and splitting up after long committed relationships is so common that I, personally, at this stage of my life, would never enter into another relationship with a woman. I just, myself, feel they generally tend not to work out and just create a lot of heartache and anguish. And I do get asked out. I just always say 'no.' Oh well.

You need to figure out you. What do you want? Once you have that sorted out, go get it. Life is short. Don't waste time on something you don't really want to do. There are plenty of men out there looking for someone to be with who is solid, like you. Maybe you should go find one of them...