What a Former Prisoner Taught Me About Freedom

What is freedom and what is it like to lose it?

Photo by Dev Asangbam on Unsplash

Day 1

Harley: It’s weird. When you’re incarcerated, you think about this “day” all the time.

More than you ever thought about Christmas or more than you ever thought about your birthday, this is like the day you think about every day when you’re incarcerated.

And people constantly talk very regularly about what are you going to do the day you get out. Who are you going to see? What are you going to eat? Where are you going to go? People talk about it in excitement, like they’re almost reminiscing on all the things they’re missing out on.

Day 2

Harley: I was lucky. Now, I know I was lucky. At the time, I thought I was unlucky. When I got out, my Aunt said, “Look, if you’re going to stay with us we have a list of things you’re going to have to do.” She was like, “You have to get a job. You can’t stay out past 8 o’clock. You’re not allowed to have a cell phone while you live here. You can only use the internet if we’re supervising.”

Getting back into society

Me: What percent of your life was dedicated to making sure you didn’t go back?

Probably 10–20% of the time was me doing community service or going to my parole officer. 100% of the time was me intentionally talking to myself during the day, “This is what you need to do, this is why you need to do it. This is why you shouldn’t be focused on fun.”

I’ll tell you, incarceration in America, for the most part, is punitive and it’s not-rehabilitative. So most people, including me, in prison, we’re not given much opportunity. In fact, where I was at, there was nothing but church and GED. I got my GED in like two months of being there. So the other 8 months there was no development opportunity at all, which sucks because when you get out, tax dollars had paid for you to be there every day, but there was no value-added while you’re there. In fact, it’s just diminishing your value significantly.

You can’t care about your professional career, or love, or many things until you have food and shelter. But when you get out of prison, you can’t have any of them because don’t have money and you have no place to live.

I was lucky, but many people come out and they are staying in a halfway house or a homeless shelter while they try to get a job. And they can’t get a house without a job, and they can’t get a job without an address. It’s just a bad cycle.


I was struck by so many parts of this story: The fight to become normal again. The struggle to save money. Being deathly afraid of going back to prison. Initially, I thought that once you served your time, that was it. You’re good to go, but that is so far from the case. Harley had a choice. He could work his ass off and make himself into a completely different person, or make a couple of mistakes and go right back to prison.


In America, we love our freedom, but when we start to get into the weeds of the meaning of that freedom, that’s where we start to disagree. How much do you have to be forced to be considered unfree? How many trade-offs do you have to make? How much of your mental life has to be consumed by thoughts of survival in order for us to say that you’re not free?

Learn more: Harley Blakeman now is the Founder and CEO of HonestJobs.co, where he helps formerly incarcerated people find fair chance employment opportunities.

No financial incentive has been provided for this article.

Writing on personal growth in business, culture, and relationships. BA in Philosophy

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