Initially I worked in food service and on phpfreelancer. I spun that into consistent consulting work until a client offered a full time position (less than 15 people, no background checks).
As the years rolled by, I kept moving around. Eventually I tried at a large company(around 8 years ago) and nothing showed on the background check.
I do NOT recommend being upfront, unless there are no formal procedures in place and being honest actually helps. We are talking about your ability to feed and shelter yourself, so give up on the “honesty” thing. I have -never- been able to provide for myself after having been “honest”. [edit: after reading felonintexas let me update this. If someone point blank asks, tell them. Don’t volunteer this information. There is nothing to be gained]
Also, you are now an edge case. That means most advice doesn’t apply. This is both exciting and horribly anxiety driving at the same time. You will have to become comfortable blazing your own path and doing things others say is not possible.
Seriously, good luck. It is possible. It is amazing what you can do that everyone else thinks can’t be done.
No better advice has ever been given on HN, from minor things to major stuff. Never volunteer any information about yourself to anyone in the office beyond what is required to complete your job. Never say too much about previous roles and keep it very general.