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.
I used to work in finance. Volunteering personal information about myself led to a close friendship with the CFO of the bank I worked for. I did good work, but so did many other people. The CFO and I got along so well only because we connected as people — mostly based on our personal lives and shared interests. My relationship with that person rocketed my career forward.
I don’t mean to take away from your experience. It sucks. But volunteering personal information can be beneficial.
Your risk tolerance should factor into the decision. The story above happened very early on in my career, shortly out of college. Taking those risks, to me, at the time, was totally worth it.
While I don't have IT experience, I can tell you as someone that both worked as an electrician and a FiOs technician that I also assumed that honesty reflects well on people and would be careful not to discourage it. I started at Verizon at like age 20 with that attitude and had no record and seldom anything to hide.
I learned fast that the policy of managers in both companies was, "Encourage narratives that honesty will always result in a better outcome to all employees... And for those stupid enough to believe it, punish them severely because only when they're honest do we know with certainty they're guilty."
First time I was questioned by management at Verizon, I made sure I was ambiguous in a way that made them think I was guilty. They said I was fired immediately and I said, "I'm fired? For what? I wasn't even in the truck. I told you what happened and I told you I was up a pole. The bucket truck was 2 blocks away when I saw it all."
Their faces turned white as they realized that I can tell everyone it's a lie and they can't just dismiss me as disgruntled for getting fired.