Employment After Incarceration: Why a Background Check Will Likely Cost Me a Contract Job

There’s good news, and there’s bad news.

The good news is that Irish miraculously got a job, despite his active warrant. He was completely transparent with the business owner, telling him, “I will get this warrant taken care of, but it’s not going to be until my wife is set up with a good job. I need to know she’ll be able to pay for a safe apartment for her and our dog if I have to be away for a while.”

The person who hired him has a long history with Irish and told him, “I’ve got over a hundred felonies on my record. Who am I to judge what you’re going through?”

I’ve noticed that because legislation on employment and housing for previously incarcerated individuals has been painfully slow (or unwilling) to eliminate barriers, second chances tend to come from the community of business owners who have criminal records. They take care of their own.

The pay from Irish’s job is not enough to fully cover our monthly living expenses, but it is enough to stretch our savings into next year. That means we were able to renew our lease, and we will not be moving into our minivan.

More good news is that I picked up a client who needs me to write a monthly blog post for them, with the possibility of an occasional second blog post. One of my long-term clients also reached out with a couple of assignments – sadly, that work is sporadic.

Yesterday, I was selected for a 6-month contract role through a large talent agency. The role is remote, part-time, and pays very well. It’s the ideal opportunity I was looking for.

When Your Past Costs You Your Future

Now for the bad news: the agency runs background checks for all its contractors.

In light of this, I’m not celebrating being chosen for the contract. All I can think about are the words they will see on the background check. That kept me up for most of the night.

I’ve thought through every possible scenario, researched employment and EEOC laws, drafted responses to provide when asked, and even had AI analyze the situation numerous times. AI determined I’ll be classified as a moderate risk, but still have a high chance of getting the contract because my conviction is unrelated to the job, and the role is remote.

But I’m a realist, so I can’t let myself hope for a positive outcome. I’ve already emotionally disconnected and mentally prepared for the agency to rescind the contract offer. This is already a defeat for me.

Blaming Myself

I’m kicking myself because I should have known better – applying for a job through an agency is essentially the same as applying for a W2 job with a company. I messed up by venturing into a system that was never built for someone like me to succeed.

I won’t make this mistake a second time. If this goes badly (as I expect it will), I’ll never apply for jobs like this again. I’ll focus on building my own business brand, marketing myself, and truly being my own boss.

That means harder work on my end, but it also means I won’t have to go through this humiliation anymore. Being an actual solopreneur means never going through a background check for a job again.

The Myth of Second Chances

I proved that I’m qualified for the role. The interviewer and I clicked because we’re on the same page about content writing and AI’s part in it. The examples of my work showcase my skills and talent.

But when it’s discovered, the worst day of my life will be all that defines me. I experienced it with housing, and I’m certain I’m about to experience it with employment.

Second chances are the biggest lie incarcerated persons are told before they’re released because the system doesn’t deliver what’s promised about building a new life. As we saw with Irish, second chances depend more on who you know than who you are.