Hi, I’m Josh. I was inmate number 71690-509. I went to federal prison. I got a job after. Here’s what I observed.
This isn’t motivational. I’m not going to tell you to “stay positive” or that “everything happens for a reason.” If you’re reading this, you’ve probably already waded through that garbage. You want to know what actually works.
Fair warning: my crime was running a sports streaming website. That’s a “cool” crime in comparison to many. People hear it and go “oh, what?!” rather than recoiling. If you’re reading this with an assault conviction or something involving theft, your mileage will vary. I’ll get into that.
Also: this is my experience. One data point. Take what’s useful.
One more thing: this is for people who have marketable skills but don’t know how to navigate the job search with a record. If you can do something valuable—code, weld, design, manage projects, whatever—and your problem is figuring out how to get someone to give you a shot despite your background, this is for you. If you don’t have skills yet, the calculus is different. You might need to build those first.
Wait, no, one more: my email is open; it’s hi@josh.mn.
Disclose early, disclose to the decision maker
Here’s the thing I noticed: the longer you wait to tell someone, the worse it goes.
The conventional wisdom is to wait until they like you. Get your foot in the door, impress them in the interview, build rapport—then drop it. The theory is that by then they’re invested in you, so nothing bad can happen.
No, surprises are bad. Very bad. Waiting creates an awkward reveal. It feels like you were hiding something. Because you were.
My approach: I told them before we even got to the interview stage. For small companies, I’d skip the normal application process entirely. I’d find the decision maker—usually the founder or hiring manager—and send my resume directly.
Finding that person isn’t hard. LinkedIn shows you who works where and what their title is. Google “[company name] founder” or “[company name] engineering manager.” Once you have a name, figure out the email format—tools like Hunter or RocketReach will tell you whether a company uses firstname@company.com or firstname.lastname@company.com. Then you send the email.
The language I used: “Hey, I wanted to send over my resume. I just got out of federal prison—here’s some context.”
That’s it. No long explanation. No apologizing. Just the fact, stated plainly.
If I got to an interview through normal channels, I’d drop it at the end of the first conversation. Not at the beginning—you still want to have an actual conversation about the role. But before we wrapped up, I’d say something like: “Hey, just so you know, I can’t pass a background check.”
The logic: if the interviewer isn’t a decision maker, I’d rather they pass along “they were cool, also they have a record” instead of “they have a record.” Sequence matters.
Most people’s next question is “what happened?” Keep that answer to one sentence. Mine was: “I had a sports streaming website.” Enough to satisfy curiosity, not so much that you’re arguing your case. If they inquired further, I never felt the need to explain every detail.
What I noticed: nobody reacted badly. Not once. Part of that is probably the nature of my conviction. But I also think being direct about it signals something. It says you’re not going to be weird about this, that you’ve processed it, that it’s not a landmine they have to tiptoe around.
The people who would’ve had a problem with it? They filtered themselves out before we wasted each other’s time.
Target small companies
I aimed for companies under 50 employees.
It’s not that larger companies won’t hire felons. Some will. But the process is different. Large companies have HR departments with checklists. They have legal teams that get nervous. They have policies written by people who will never meet you.
Small companies have humans making decisions.
At a small company, the person reading your resume might be the same person who’ll be working next to you. They’re evaluating whether you can do the job and whether they want to be in a room with you. A conviction is a data point, not an automatic disqualification.
There’s also less bureaucracy to navigate. No applicant tracking systems filtering you out before a human sees your name. No mandatory background check policies that exist because someone in legal wrote them five years ago.
I don’t know the exact threshold, but somewhere around 50 employees is where things start getting more formal. Below that, you’re more likely to be talking to the person who actually makes the call.
Consider remote work
Remote work changes the dynamics.
You’re not in an office where people are going to see you every day and wonder about your background. The relationship is more transactional—can you do the work? Are you responsive? Do you deliver?
It also widens your options. You’re not limited to companies in your city. A startup in Austin or a company in New York might not care about your record—and you don’t have to relocate to find out.
Remote roles tend to be more output-focused. The thing that matters is whether you shipped the thing, not whether you have good office presence. For someone with a record, that’s an easier evaluation to win.
Contract and freelance work
Contract and freelance work is probably easier than full-time employment.
The commitment is lower on both sides. A company hiring a contractor isn’t thinking “is this person going to be here in five years?” They’re thinking “can this person finish this project?” That’s a simpler question to answer yes to.
Background checks are also less common for contract work. Not universal, but less common. Companies bring on contractors all the time without running them through the same process they’d use for a full-time hire.
It’s also a way to build a track record. Do good work for a few clients, get some references, demonstrate you’re reliable—then convert that into full-time if you want. Or don’t. Some people prefer staying independent.
I went direct to full-time, but if I’d had more trouble, this is probably the route I would’ve tried. But, the conditions of my supervised release were to maintain employment; I’m not sure if contract or freelance would have been an issue, or just a point to run by my probation officer.
Own it on paper
I put my incarceration on my resume. I listed myself as an inmate. I included my inmate number.
This sounds insane. I know.
Here’s the logic: I wanted to get there first. I didn’t want someone to Google me, find out, and wonder why I didn’t mention it. I wanted to control the narrative.
Under my work history, there’s a gap. In that gap, it says I was an inmate in federal prison. The description says something like “this explains my employment gap, right?”
Same thing on LinkedIn. It’s there, in my profile, for anyone to see. It’s been described as cracked.
You might think this would cost me opportunities. Maybe it has. But here’s what I noticed: the opportunities I got were with people who already knew and didn’t care. No awkward reveal. No “oh, I didn’t realize…” conversation three weeks into the job. They hired me knowing exactly what they were getting.
In hindsight, I probably should have included a link to my actual site. That would’ve been even more useful context.
The gap question
If someone asks what you did during your incarceration, the answer is: prison.
That’s it. You were in prison.
No system in the US is designed to teach you a marketable skill while you’re inside. The programs are mostly a joke. If you happened to learn something useful, great—mention it. But don’t feel like you need to justify that time or prove you were “productive.” You were incarcerated. That’s the explanation.
What matters more is what you did before and what you can do now. The gap is just context for why you weren’t working.
What employers actually care about
They care whether you can do the work, and if you’re good to work with.
I’m a software engineer. I have skills. When I talked to potential employers, they wanted to know if I could build things. The conviction was a thing they had to think about, but it wasn’t the thing.
What I noticed: the employers who hesitated weren’t people I wanted to work with anyway.
This sounds like cope, but hear me out. Trust is foundational to any relationship. If someone’s default is suspicion—if their first instinct is to see you as a risk to be managed rather than a person to be evaluated—that’s going to color everything. Every mistake you make will be viewed through a different lens. Every time something goes wrong, there’s going to be a voice in the back of their head.
The people who default to trust? They’re better to work with anyway. For anyone. The conviction just surfaces this faster.
If you’ve been locked up for a while, you’re also dealing with a lot at once. New routine. Recalibrating to normal life. Society is generally willing to acknowledge this. But you have to advocate for yourself. You have to be honest about where you are. People will usually give grace, and (hopefully) additional resources—time, attention, understanding.
Being incarcerated can actually be useful context for an employer. It explains things. It gives them a framework for understanding why you might need a little flexibility, why certain things might take you a minute to adjust to. Most decent people will give you that space—if you’re upfront about needing it.
Background check basics
Here’s the mechanical stuff, since you might be wondering.
Background checks typically show convictions, not arrests. How far back depends on the state—some have a seven-year limit, others don’t. Federal convictions generally don’t have a time limit on reporting.
Under the Fair Credit Reporting Act (FCRA), if an employer uses a third-party background check and decides not to hire you based on what they find, they have to give you a copy of the report and let you dispute any inaccuracies. This matters if there’s something wrong on there. It happens.
Ban the box laws exist in a lot of places now. The idea is that employers can’t ask about criminal history on the initial application—they have to wait until later in the process. Whether this actually helps is debatable. It delays the question; it doesn’t eliminate it. And plenty of employers still ask, law or not.
For me, ban the box was mostly irrelevant because I was disclosing upfront anyway. I wasn’t waiting for them to ask.
If an application has that checkbox—”have you ever been convicted of a felony?”—I’d check yes. But I’d also try to get to the decision maker directly with context, so they weren’t just seeing a checked box with no explanation.
Ignore most re-entry advice
The re-entry staff told me I needed to get a job at McDonald’s.
Their reasoning: they didn’t think I’d be able to get a job with a computer crime on my record.
This is degrading. It’s also wildly out of touch.
Even the officers at the prison were like “oh, that’s marketable.” They understood the market better than the re-entry people.
The re-entry system is built for people without resources, without skills without networks. If that’s you, I hope it was useful to you. But if you’re reading this—if you’re the kind of person who Googles for real information instead of accepting what you’re handed—you’re probably not the person that advice was designed for.
Most of the re-entry material assumes you’re useless. It assumes you have no options. If you have marketable skills, if you’re resourceful, if you’re capable of reaching out directly to people and making a case for yourself—ignore their “playbook.” It wasn’t written for you.
If you keep getting rejected
I didn’t have problems finding work. But I had skills, a “cool” crime, and some luck. Not everyone has that combination.
If you’re getting rejected repeatedly, a few things to consider:
The pool might be wrong. If you’re applying to big companies with formal HR processes, you’re fighting the system. Switch to smaller companies where you can talk to humans.
The timing might be off. If you’re disclosing too late, it feels like deception. If you’re disclosing too early—like in the first sentence of a cold email with no context about who you are—it might be the only thing they register. Find the balance.
The framing might need work. How you talk about it matters. If you’re apologetic, defensive, or clearly anxious, that energy transfers. Practice saying it plainly until it feels routine.
The skills might not be there yet. This is harder to hear, but if you don’t have something to offer that outweighs the risk someone perceives, you’re going to struggle. That doesn’t mean give up—it means figure out what skill you can build that makes you valuable enough that the conviction becomes a footnote.
And sometimes it’s just numbers. You might have to talk to more people than someone with a clean record. That’s not fair, but it’s real. Keep going.
I’m happy to talk to you—or anyone—about any of this.
Telling coworkers
Be open about it.
In my industry, people Google their colleagues. Yours probably do too. If your record is findable—and it probably is—someone’s going to find it. Better they hear it from you than discover it and wonder why you never mentioned it.
I told my whole company at the first all-hands I was in. That’s not the only way to do it, but the principle is the same: own your story, be your own narrator. If you let other people tell it, you don’t control how it sounds.
This doesn’t mean you need to announce it on your first day. But don’t hide it either. If it comes up, say it plainly. If someone asks where you worked before, and the answer is nowhere because you were incarcerated, say that. Most people will move on faster than you expect.
The people who can’t handle it were going to be weird about it regardless. Better to find out early.
Owning your story
Here’s something that happened after I got hired at my current job.
The entire company was in a compliance meeting with the company lawyer. I was there too—flown in, I was the only remote employee. New face. Hadn’t met most people yet.
Turns out the lawyer does both corporate law and federal criminal defense. She didn’t know I was in the meeting. At some point she jokingly said something like “and nobody here would do anything to go to prison, so…”
I said, “Hey Kelly.”
She looked at me, confused.
I said my name. She smirked.
Then I announced to the room, “Oh yeah, I just got out of federal prison. Tell you guys later.”
And I did—at the all-hands. It was well-received.
I think owning your story matters. If you treat it like a shameful secret, people pick up on that energy. If you treat it like a thing that happened to you, that you’ve dealt with, that’s part of your history but doesn’t define you—people pick up on that too.
My employer has since mentioned to the team that my background was a factor they considered when hiring—and that it’s been a success. That’s only possible because I was upfront. No surprises. No awkward discoveries. Just a fact on the table from day one.
What this doesn’t cover
Different crimes land differently.
I have a “cool” crime. Sports streaming. People hear that and they’re intrigued, not alarmed.
Drug dealing convictions can be reframed. You were in sales. Technically true, and it lands better than “I sold drugs.” You managed inventory, handled customer relationships, dealt with cash flow. The framing matters.
Assault makes people uncomfortable. They’re going to look at you differently. That’s reality.
Theft will preclude you from certain positions. You’re not going to be handling money. Possibly not handling inventory. That’s just how it is.
There are crimes I’m not going to address here. You know which ones. If your conviction involves certain categories of harm, this advice doesn’t apply and I’m not going to pretend it does.
Time matters too. My older boring white-collar state crimes are more than 15 years back—that makes it essentially irrelevant. If you’re recently convicted of something serious, the calculus is different.
The psychological part
The hardest part isn’t logistical.
It’s understanding that society can accept you. That you’re not the worst person in the world because you went to prison. That the narrative in your head—where everyone is judging you, where every door is closed, where you’re permanently marked—isn’t accurate.
I’m humbled by the experience. I’d be lying if I said otherwise. But I don’t let it define me.
There’s a difference between being desperate and being humbled. Desperate makes you accept things you shouldn’t accept. It makes you undersell yourself. It makes you grateful for scraps.
Humbled means you understand what happened, you’ve integrated it, and you’re moving forward. You don’t carry it like a weight you’re dragging. You carry it like something you’ve processed.
It gets easier over time—emotionally, mentally. The first conversation where you disclose is the hardest. The twentieth is routine.
The summary
Disclose early. Disclose to the person who actually makes the decision. Use plain language—”I can’t pass a background check”—and give a one-sentence explanation if they ask.
Target small companies. Under 50 employees. Talk to humans, not systems.
Own it on paper. Put it on your resume, put it on LinkedIn. Get there first.
Care about whether they’re the kind of people who default to trust. The ones who don’t aren’t worth your time anyway.
Ignore advice designed for people with no options. If you have skills, use them.
You’re just as good as everyone else. Act like it.