2782 5:22 Q&A

Q&A: “How to prepare for a side hustle while incarcerated?”

In this episode, we discuss legal side hustles for prisoners, as well as how they can build the right kinds of skills to succeed upon release. Bravo to our listener for raising this question!

5:22

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Episode 2782

Today’s question comes from Kelsey in Birmingham, Alabama, who is looking for ways her incarcerated friend can build a side hustle. If you’ve ever wondered about starting a business under unique and challenging circumstances, this episode is for you!
"Hi Chris, I’m Kelsey from Birmingham. I have a question that’s a bit different. I have a friend who is currently incarcerated, and we’ve been discussing ways for him to build a side hustle from prison—potentially something he can do when he’s out. Are there any legal side hustles that prisoners can pursue? What should he be learning about, and how can he best prepare? Any advice or examples would be very helpful. Like I said, I know this is an unusual question, but I’d really be grateful for your ideas. Thanks so much."
Listen to today's episode to learn more...

Yours in the revolution,

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Read the full transcript

This transcript was generated from the episode audio and may contain minor errors.

Hey, I really appreciate our listeners who sent interesting thought-provoking questions about all kinds of different topics and business ideas, things that they might be trying to figure out, or in some cases, something they want to help a friend with. So I really appreciated the question we had today. Basically, it's about how to prepare for a side hustle while incarcerated. So we're going to talk about some legal side hustles for prisoners, as well as how they can build the right kinds of skills to succeed upon release. And I just think that's wonderful, right?

We all want to build our skills. But for somebody who's in the criminal justice system and is looking at a chance to get out at some point, relatively soon, let's say, or even if it's a few years from now, whatever it is, you want to build skills so that that person can be able to make a living, perhaps do something entrepreneurial because job opportunities are not always there for the taking. And that's true for anybody. But of course, somebody coming out of a situation of being incarcerated has an increased difficulty with it. So let's talk about it.

I want to take this seriously. Today's question comes from Kelsey in Birmingham, and she's looking for ways her incarcerated friend can build a side hustle or work towards that. So let's discuss detailed question and my answer coming up after this quick thank you to our sponsor Hi, Chris, I'm Kelsey from Birmingham, Georgia. I have a question that's a bit different. I have a friend who is currently incarcerated, and we've been discussing ways for him to build a side hustle from prison, potentially something he can do when he's out.

Are there any legal side hustles that prisoners can pursue? What should he be learning about and how can he best prepare? Any advice or examples would be very helpful. Like I said, I know this is an unusual question, but I'd be really grateful for your ideas. Thanks so much.

Kelsey Bravo for asking the question. As I said, it's very thoughtful one. As for what kind of legal side hustles prisoners can pursue while incarcerated. I'm not totally sure about that because I don't know, like I think there are lots of different rules and laws and different jurisdictions, right, state, county, federal, and beyond. We've got lots of international listeners as well.

I'm sure that some things are possible. I just don't know what they are. So let's focus the answer on how your friend can prepare for success. So that, you know, once he's out, he has built some skills that can then be deployed in a variety of ways. So some of this may depend on internet access, you know, to be fair, but I think one of the most valuable assets anyone can have is a strong foundation in digital skills.

So if he does have access to educational programs, focus on learning about computer literacy, coding, graphic design, even online marketing, I'll talk about that next. But these are kind of, these skills are highly transferable and can open a lot of different doors once he's released, both in terms of the job market and in terms of making something for himself. Now you might say, well, he's, you know, he's only able to learn on some older computers or technology is changing so often. And that is true, but these skills are transferable, as I said, and if you gain the skill of learning about computer literacy, coding, design, and so on, it's not that hard to learn new things. Again, we're looking at a foundation in digital skills.

I think that's so smart and important for anyone. He could also work on his writing because writing is something that maybe it's changing a little bit with AI in terms of all this AI generated content we see. But if you are a good writer, there's lots of ways you can do things online. But I've always thought if you are a good writer, then there's a lot of things you can do, right? That could be freelance writing.

It could be starting a blog, could be writing an ebook, it could be writing an online course. You could write a course for other prisoners, you know, for people who are going into the criminal justice system or people who are coming out and need help transitioning. There's probably lots of other needs as well. What could you do in terms of creating content for that? So that's something he could be thinking about regardless of his access to technology and so on.

But if you've got more access, I think I mentioned something about marketing. Learning about and starting an online business could also be great. If he is able to watch videos or if he can listen to audio such as this podcast, obviously it's completely free. I would recommend that he study e-commerce platforms like Shopify or Fulfilled by Amazon, Fulfillment by Amazon. We have talked about them many times.

Those are platforms that a lot of people, I think it might be millions, I don't want to exaggerate, but a lot of people are using to sometimes make a good living or at least make some income. So a couple options for you there, develop those digital skills wherever possible, learn about e-commerce and marketing online business wherever possible, improve writing because that can help with a lot of different things. And there might be some specific skills as well. Like there might be some certification programs he can undertake or something that's related to the system that he's in. I'm not sure about that, but hopefully a few things there to get him started.

Kelsey, again, thank you so much listeners. Thank you for being out there. Let's all support one another. Much more is coming up on the podcast, always completely free, new episode every day. My name is Chris Guillebeau, you're listening to Side Hustle School.

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