I am in my early 50s and had a spotty work history. I didn't hear about Aspergers until a few years ago, and knew right away it sounded like me. All my life, I and my family knew I was different, but my family believed I could be "fixed" if only I tried hard enough to be "normal." Asperger's is a neurological condition present from birth. There is no cure or fix. There are therapies, treatments, and coping methods, but I will always be an Aspie, and never be normal. Unfortunately none of us knew what was wrong with me for most of my life, so my family was always on my case about any part of my life that didn't fit the normal pattern of living. I also happen to have other health issues, some from birth, and some that came later. As I got older my health issues got worse, so now I am no longer able to work, and am on SSI. My family still wants me to become normal, but they are glad at least that I have the benefits coming in to pay my bills. I get enough in benefits to also pay rent on an old, run down trailer I rent from my parents. They give me a price break on it. I just pay the amount of the lot fee and their mortgage and insurance on the place. (it's in a trailer park). I pay for these several rooms (2 bedrooms, 1 bath, eat in kitchen, living room, and laundry alcove) what most people around here would pay for just one room in someone's house, so it's a good deal, and I get to live alone. I am an introverted hermit type of person who really prefers to live alone. I lived with various relatives most of my life and it was horrible. We all drove one another crazy.
Since I never in my life incurred any large debts, I only have basic bills to pay, along with the rent--I don't have any loans to pay off, so I am able to get by okay on my SSI benefits. Every now and then there is a bigger expense that comes up, but I put aside a little bit of the SSI money until there is enough to cover the bigger occasional expenses.
I wish my health were better, so I could work, but even when I was able, I had trouble getting and keeping jobs, due to no real work skills, and to my Aspieness. I didn't fit in well at jobs. I hated most of the jobs I held, but did them as well as I could while I had them, as I needed the money. There were some jobs I didn't mind, though. Nowadays all the employers want you to have a resume, with lots of job skills and a great work history. I never had any fancy jobs, but eventually I had to have a resume anyway, even though I was only applying for basic low end jobs. Unfortunately, my resume, although neatly done, never helped much because of my lack of skills and frequent job changes.
My family used to give me a hard time about my job problems, too. I am intelligent in some ways, but not a capable type of person. Intelligence without ability is not enough. NTs have trouble comprehending the problems we face, and family members tend to get upset because what's a problem for us doesn't look like a problem to them, so we get labelled as lazy or rebellious, or one of any number of other unflattering terms. It is very stressful to be around family members when they don't understand our problems, or even worse don't see that a problem even exists. I am glad that I now live alone. It is much less stressful and more peaceful that way.
If you can manage a working life, great, but don't feel guilty for getting benefits if you need them.