I sat down with Darren to talk straight about how small things in childhood turned into heavier trouble later on: milk‑bottle thefts, burglaries, arrests and his first time inside. He told me how the environment made some choices feel normal, and how that led to a prison term when he was still a teenager.
Growing up and how it began
Darren told me he grew up on an estate where, from a young age, he picked up ways to subsidise his income. Some of those things were minor and some were far worse, but he says they felt normal because of where he lived.
He also said he believed, even as a child, he knew right from wrong. That didn't always stop him: petty misdemeanours like nicking milk bottles led on to bigger offences as he got older.
Influence, decisions and the window examples
We talked about influence and choice. Darren was clear that at times he acted knowing something was wrong; sometimes he was the one who went along with friends' plans rather than being forced. He described being outside a house and deciding whether to reach for money on a windowsill or to join a mate who wanted to kick a door in.
He explained the difference between those choices — taking an easy chance and being a lookout while someone else forced entry — and how, more often than not, he chose the safer‑feeling option of staying outside and taking whatever came to him, rather than doing the breaking‑in himself.
First arrests and being sent to Feltham
Darren gives a messy timeline — he mentions a first arrest in the mid‑1980s connected to an incident after someone burgled his aunt's house, when he chased and assaulted a boy on a bike. He accepts responsibility for his part in that episode.
He said the first time he was incarcerated was in 1991 at about sixteen years old. He was sentenced at Crown Court and sent to Feltham Young Offenders Institution on what he recalls as a two years nine months term; he estimates he served around eighteen months of that sentence.
Inside Feltham and what it felt like
Darren described the shock of the cell door slamming — he’d visited mates in prison before, but he hadn’t really expected the feeling of being locked in. He said his thinking was ‘mad’ at the time and admitted he’d even wanted to go to prison because he’d run out of other limits to test.
He also talked about the day‑to‑day: association time, watching TV in a communal room, education and work opportunities, and the old incentive schemes that governed how much association someone got. Those routines were part of his learning and survival while inside.
How he looks back — and a message for kids
Darren estimates that, across a number of sentences and spells inside, the total time he’s served adds up to decades. He framed that as a bleak tally and a warning: the small choices add up, and the system moves fast for young people who keep making the wrong ones.
I wear a hat today with a message for kids, Darren told me — a practical nudge: get up, make your bed, get dressed. He urged young people to look for small, steady actions that change how you think and act, rather than chasing quick gains that can end in a cell.
Adapted from this guest conversation with AI assistance. Each person’s experiences remain their own. The video is the original conversation.
Read the video transcript +
Yeah, so what I'm saying to you now, yeah? You've been the little milk bottle thing, and now I'm getting from what you're getting. So this is between, when you was in primary school, secondary school, you had an estate across the road, couple of estates. Whatever we, from a young age, whatever I could do to subsidize any kind of income, that's little things I used to get involved with. Some of them are not so bad, some of them were pretty bad. But let's not, do you know what I'm trying to say? So the basic is, this is what I'm saying. Because sometimes, you might be doing something, yeah? And because it's normal to the environment where you're in, you might just think it's normal. And even it might be illegal, you might not kind of fathom really what the full implications or the consequences of what you're doing. Let me tell you one thing, let me tell you one thing so we're on the same page. As much as I've grown up and I'm younger than you, I'm asking you, I'm not going to, I'm going to be truthful with you now. I maybe come from a different teaching. I knew from seven, eight, nine, ten, what was wrong and what was right. That's me. I knew from earlier than that. Oh, so you know what's wrong and right. So you've been, so without sounding manipulative, because you're sounding a bit manipulative now, you know what's wrong and right. Yes? Yes. Because you're 15, 16 now, you know what's wrong and right. Yeah, you've done little misdemeanors. My grandmother's teaching, even my mom's teaching. Right, because they're teaching, we know that. You know what's wrong and what's right. Right, so before we go back. And then you can see other things from the outside looking in and think, do you know what I'm trying to say? Forget that. There might be a million ways in my head I could do stuff. No, no, no, no, no. I'll tell you what I want to make right now. I just want you to be clear now, because I want to make what is right. I'm asking you one simple question. You've done the milk bottles. Yes, that was wrong or right? Wrong. Cool. So after milk bottles, what did you do? Everything was right? No, majority of it was wrong. So majority of it was wrong. So that's fine. So the majority of it was wrong. Yeah, but this is what I'm trying to tell you. You can be in a kind of mind state or in a... Because if I was listening to this, if anyone was listening to us, let me tell you something. If anyone was listening to us, are you saying to me, this is what I need to know 100%. I want to know as well, because I've been on another... I've been whatever I've done through life. Are you... What are you saying to me? I just need to know, because you're bumbling, you're right with me. Do you know wrong and right? Yes, I do. That's it. So how you see wrong and right is different to someone else. That's what I'm getting. Is it different? Are you seeing wrong and right different to 95% of the world? At times, yes. That's correct. So straightforward. Because come on, man. We're having a public conversation. You're not sure what wrong and right is. And right is right. Simple. Yeah, from what we've been taught. There's no in between. Sweet. So now you're 16.
17, doing as you said, and correct me if I'm wrong, because I don't want to be wrong, 90% of the things out of 100 you're doing wrong. You're choosing wrong decisions, shall I say then. Making a very lot of wrong decisions. And some decisions, not like I'm being led, yeah, but some decisions were not necessarily mine, but I'm just going along with, I'm just going along with those decisions. So you are easily led? No, I'm not easily led, but what I'm just trying to, bro, it's like you're just trying to, you're trying to mark the book. I'm asking you, are you easily led? I'm not, look, no one ain't forcing me to do this, you know. Yeah. Like, I've got my own head in it. I know what's wrong and what's right in it. That's what we spoke about. But then, you've decided to do. No, not like you. I'm not saying you personally. You've decided to do something, and I know that it's wrong, but because of whatever the influence be or the motivation be, I'm going along with that. So you are easily led? No, I'm not easily led, but what I'm just trying to, bro, it's like you're just trying to, you're trying to mark the book. I'm asking you, are you easily led? I'm not, look, no one ain't forcing me to do this, you know. Yeah. Like, I've got my own head in it. I know what's wrong and what's right in it. That's what we spoke about. But then, you've decided to do. I'm going to make you try and live that life. Not like you. I'm not saying you personally. You've decided to do something, and I know that it's wrong, but because of whatever the influence be or the motivation be, I'm going along with that. So you are easily led? No. I'm not easily led, but what I'm just trying to, bro, it's like you're just trying to, you're trying to mark the book. I'm asking you, are you easily led? I'm not, look. So when I'm asking, no, no, no, no, because when I'm asking you a question, you keep bringing others in. So I'm asking you what you was doing. You're saying, I can see, I know wrong and right. No, but you're saying, no, but you're saying, you know wrong and right. You 100% know wrong and right, but then someone else comes in your life, and you know, and they're kind of leading you down a dead end. So I have a wrong and right, cuz. You've got influence or you're high. I know wrong from right. Yes, and you've got influence that think like you. And then, listen. But you've got influence that think like you, though, innit? Let's just give you a hypothetical scenario. No, no, don't give me. I'm not in a, we're not in an interview room. We're not in a police station. I'm asking you simple questions. I just want straight answers. So I'm saying to you. Bro, but I said that before I even answered the question. So you know wrong and right. We stayed there. No one ain't forcing me to do it, and a man ain't, and I'm not following no one. But scaring me from listening to you, you're constantly bringing someone else into your world anyway. Sometimes the decision wasn't mine. So someone else's then, so you've been influenced. Yes. Wow, we've got an hour. That's what I was getting from you. You've been influenced. But I said that. You didn't. But what was the influence? No matter what, I said to put you in the headlock, told you jump for a window, or go and jump off a building. It would have been money. That's the, sweet. But you like that anyway from what I'm hearing. That's exactly. So you got two pieces of the pod thing in a thing. Look, look, look, look. I'm on my own, and I saw, I saw the money over there. What money? Like, this is just a, look, I'm over, I'm on my own. I saw the money on the window. Yeah. On the window, on the window ledge, on a road where I'm just walking. On my own, I'd probably take that money. Yeah. But then watch this. On my own, I'm with my friend, and behind the window on the table is the money. What window, what window are we talking about in this house? I'm just trying to show you, look, look. No, no.
Your decision. I'm walking on my own. I see the money on the window. Don't look at me. I'm worrying if it's a true story or a movie story. I need a true story. Go on. Listen to what I'm saying. I can just reach my hand into the mic as well. Don't be scared of it. Go closer to the mic. I'm with my friend. We can see the money, but there's a door. My friend might think that I would have made this choice. If we were, we're going to stop the tape. I'm joking. There's a door. My friend might think we can kick off the door. Me, I know it's wrong and I should say no, but I might say go on then. Are you participating? I might say go on then. He can't tell me to kick off the door because I wouldn't kick off the door to get the money. Do you get what I'm saying? I would reach my hand there and take the money from the window. What's the difference? Well, you've got to kick off the door to get in there, innit? You don't know who's behind that door. You don't know who's behind that door. Right now, I'm outside and I can just reach the money and go. That's what I'm saying to you. I'm a good runner. I told you that already for a long time. No, listen. Remember, we're on the chair. It's your life. Yeah, we're not trying to glamorize. I'm just trying to show you about decisions. No, I didn't. If I could get the money and just go, I'd get the money and go. But I wouldn't kick off the door to do that. I wouldn't encourage or enable someone to do that. Can I get just some clarity on this situation? Yeah. Because what I'm saying, it's not about glamorizing. I'm just saying, what I'm getting from this, because I'm just trying to ask what you were doing as a young kid growing up had to obtain money. Yeah, we're doing a lot of stuff that we shouldn't have been doing. So you said to me, you've seen windows. In all honesty, we're doing a lot of things. We knew it was wrong. No, no, no. And we shouldn't have been doing them, but we've done them. Do I regret them? Not really. Cool. If I could go back and change it, would I? No, you're changing. I'll be real with you. I've been listening to you. All I heard you say, this is me being asking you something. Remember, I'm asking these questions because there's a reason behind me asking these questions. Would I change the way I was? No, you're asking me what I'm asking you. Let me tell you what I'm asking you. You can answer it. You said you walked down and there's a window. If I was talking to any kid or anyone was listening, no, for instance, and we're not sure what we're talking about, I need to understand because you've been doing a lot, 90% of breaking the law. That's what you're saying to me. 90% breaking the law. So if you're breaking the law, and I don't want you- Yeah, because that goes back to even-
Oh my gosh, I get it why you're gonna not answer the question. You're at a window, wait is it a shop window? House window? Any window. So what anywhere, so I can walk down the road and I see money in the window and the window ledge? Yeah, why not? How many times does that happen? Is that going to be a successful way to get money? My experience, that's happened so many times. That's happened to me more times than I've spent in dog shits. Okay, so I will give myself a slap, but I'm not going to give it to you. So basically, this is what I'm getting from here, your mate kicks off doors. So we're not talking about shop doors because they're open, you can walk in a shop. Any door, shop door, side door, back door, front door. All in shops? No, it could be houses. Oh, so you go to... Not me personally, but if he said to me, look, we can kick off the door and get the money, I say, go on then. Who's I say, go on then, get the money. Okay, and you're waiting outside? Definitely, and I'm definitely gonna be probably telling him, pass the money to me. So you're lookout? Whatever you want to say. But you're not gonna go in? Nine times out of ten, no. I can't say ten out of ten because sometimes... No, so you'll give myself a slap. But nine times out of ten, definitely, I'm not going in. That's the correct decision because at the same time, you know that you're doing a lot of stuff now, you're doing wrong stuff, yeah? And this can also end in getting arrested. Doing all these things, did you get yourself arrested any of these times? Yeah, quite a few times. Quite a few times? Quite a few times. What, before the glass bowls, after the glass bowls? After the glass bowls, innit? Glass bowls was really like... So if I say, when was the first time you got arrested, if you don't mind, when was the first time you got arrested? Oh, first time I got arrested was probably 96. 96, so that makes you 96. Or 86. 86? Yeah, 86. 10, 11. No, yeah, 86. 10, 11. 86, 11, yeah. And that's for like little borrowing stuff? No, some bread of burglar in my aunt's house, and then my cousin goes... Wait, what's this? Someone burgled your aunt's house? Yeah, they burgled my aunt's house. That's a serious thing, innit? Because I'm hearing what you're saying five years later, where someone's kicking the door. Are they doing that in people's houses? Yeah. So it's a bit of a spiral, innit? It goes around, comes around. No, I like that warning, yeah. But anyway, some boy had burgled my aunt's house, and my cousin, like one day I was with my cousin, and he goes, look, there's my man. You get me? And he was riding a bike, so I ran him down and kicked him off the bike and beat him up, innit, yeah? And took his bike? And then by the time I got back to my aunt's house, did I take his bike? It doesn't matter, but you got arrested. You might have took his bike. I'm not going to tell you, but you got arrested. I probably did take his bike, in all honesty. So that's the first time you got arrested, yeah? Yeah, I went back to my aunt's house, and then they... You got arrested. I got arrested.
They just tried to tell me that I should say it was my cousin. We don't worry about that, you don't do all that. Did you say it was his cousin? No, definitely not, but it wasn't my cousin. It wasn't my cousin anyway, it was me. But that's the first arrest. First arrest 91, did you get arrested? Did you come in contact with any of these guys? Next arrest, we've done a, it's a little bit of an irony of it, that it was a burglary. So you've done a burglary, so you've been arrested for burglary. Listen, I'm not going to go too much into what, who and how, yeah, but you got arrested for a burglary. Yeah. Cool, and what happened then, you come out? Yeah, we got, yeah, we got. No further action? No further action. And then, so what's happening? So now that's twice in a row. Yeah, then I got arrested one time for like, motor vehicle. Alright, cool, let me just leave that there, because I'm not trying to give every of your crimes. So like, did any of these things, unfortunately when I say this, did that ever, have you ever been incarcerated? Yeah, that was in 1991, the very first time. He was incarcerated in prison in 1991? Yeah, 16. 16 years of age he was in prison? Yeah. And what prison did he go to? YY Feltham. Went to Young Offenders Institute, oh Feltham, what's Feltham? What is that? Feltham was like from the age of, I think, 15 to 21. So you went to Feltham prison, 16 years ago? Yeah, 15 to 21, yeah. So basically, alright, then what school were you in anyway? If you don't mind, what's the process? You get arrested, come on, give me a quick process. Yeah, well, I got arrested, Wolfen, Leighton, Leighton Police Station. Yeah, of course. Francis Road. Yeah, cool. Yeah, then I went to Wolfen Forest Magistrates Court. Yeah, of course. Which is near the town hall and the college. It's not there no more. Okay. And then went from there to Snaresbrook Crown Court. Snaresbrook, straight away? No, after Wolfen Forest. Oh, so straight away to Snaresbrook Crown Court? Yeah. At 16 to go to the Crown Court, it must be true. Yeah, then I got a term of two years, nine months. So stop, so you get two years, nine months, boom, you're on the road. In a young offenders institute. So you go to Feltham and you go into prison. Yeah. What was it like you going into prison anyway? Well, it's mad. And this is hard to show you how mad my thinking was back then. Like I said, in the area and kind of around neighboring areas, yeah, Hackney, Newham and beyond like that. This is before prison, yeah? I had a little bit of a reputation. Is this before prison? Before prison. Okay. And this is from about the age of 13. Yeah. 13 to the present day of 16 when I found myself in prison. Like I had a little bit of a reputation. I was a well-known face in and around, we had house parties then. Cool, so not to go back, I'm getting quite 100%, I'm not trying to, yeah?
As you are very well known, you're very respected.
Yeah, well, well.
You're very well known and you're very respected.
Well, I don't know about that. I don't know about that. In some circles, in some circles, you're well respected in some circles.
But so you end up in farms, you go to prison, first time in prison.
Yeah, yeah.
What's the question?
Because what I was trying to say about the mad thinking, because if I really think back to that time, yeah, I actually wanted to go to prison.
Cool.
Yeah, how mad.
Nah, nah, I know people that can relate to that.
Like that, no, no, you know people, but then you're not just an average nine to five guy. Do you get what I'm trying to say? So to the average nine to five person, it must really sound, when I actually say it to myself.
No, I'm saying to the majority of people, even me, it sounds crazy.
Like I needed, I needed and wanted to go to prison to have my last, that's my last.
Last, but you went at 16.
No, what I'm saying is that's the last, like I've done it.
Oh yeah, you've got.
I've done it, I've done a lot of stuff.
So you get to prison, all right, you get to prison.
I've done a lot of stuff.
Let me rush you through this.
But I even been in prison, like that's my last thing in the book.
So you go to prison.
If you can understand.
In 1991, I definitely understand.
You go to prison in 1991.
What is, what, like, so what, you turn up to prison, you go in a room, they shut the door.
Yeah, well, I'd had friends, close friends and friends that I'd grown up with who'd been to prison and I'd been to visit them. Yeah.
Before you went to prison?
Before I myself went.
So you kind of know what you're doing from the other side?
No, I'd never really, I'd never really accounted for what it actually feels like when the door shuts.
Right, cool. So what I want you to say now, quickly, just because I don't, what I want to get from the prison, because remember, you know, we're watching in there, prison, there's got people in there. Someone could tell you about prison, you know.
I could never really prepare you for you personally, what you would feel when you go.
Just for one thing, not going, no, I'm still sticking on your first time in prison. Because remember, we're living in an influential world and there are a lot of things on the media. This is important, isn't it? And where you're in prison, this is your topic, because I want you to address them kids that are trying to be 16, yeah? And because of the system's fast, isn't it? It's faster, isn't it? So we know the system, yeah, how it's looking today. Yes, well, delve into what they've got right now. I want you to, because I don't know your journey yet in prison, but I'm assuming in 1991, there was no, no, what am I looking for? There wasn't no technology in prison, was there?
No television. Yeah, you had TV.
Technology, when I say, oh, you had TV.
You have TV in your cell. You had one TV. That was what you'd get to watch on association. So you'd sit.
In a room, a TV room, and you'd be there and you'd be able to watch family. How many hours would you be in your soul? It depends. It depends. So could you go to work? Yeah, you could go work. You could work at education. Then you'd have like evening association where everyone would come out. But depending on how you behave. Depends on how long you'd be out of your soul, innit? So it's the same kind of like the IEP incentive and privilege scheme what they've got now. In 1991 you had IEP incentives? Yeah, you had the same thing. Like we used to have some book. Wasn't it a red book? No, we just had some paper. And it depends on what colour the face is on the league. Yeah, yeah, yeah. You might have a blue face. Yeah, yeah, yeah. You might have a brown face. He's mad. Then you'd have a yellow face with a smile. Do you understand? Yeah, it was that kind of thing. So that's okay. So what I'm trying to ask is, so when early you went from there, so what, there was lots to what other schools where you could do all sorts of, well, I don't know, what are you going to, painting, decorating, plumbing? Yeah, you had various. Where from? You had all them schools? Like you might have had builders. I'm sure we had builders. And a building course? I'm sure there was mechanics. Mechanics. So what I'm trying to say, watch this now, yeah. Gardening. So gardening. So you experienced from prison, yeah, watch this, yeah. Kitchens. And then you could come out for evening meditation time, you said, between six and eight. Yeah, and if you was on the wing and you was normal, like when I say normal, like you're not getting into trouble, you might get an association in the afternoon. And in the evening? No, in the morning, in the afternoon, and in the evening. So what I'm saying, yeah, so see when I'm looking at that set up there, yeah, because I'm going to say, yeah, so you went to front and you've done like, you was getting all them courses, yeah. Nah, the reason I'm going to say this, because remember we can talk in it, because unfortunately, we're going to say unfortunately, I've done a few little, yeah, in front of us wearing it. So I just wanted to just try and hit your brain for experience. Because if I remember, I must have done what? How many years you spent in front? I'm just curious. All in all, totally. Well, I'm sorry, sorry, sorry, sorry, totally. You got two years. You must have come out from two years. I done, I done, I done, I think I done like something like 18 months. That two years. So you've done 18 months all in front of them? Yeah. That's a long time. It's around about 18, because I wasn't meant to do 18 months, but I got in a little bit of for fighting. I done, I done, I think I done like something like 18 months. That two years. So you've done 18 months all in front of them? Yeah. That's a long time. It's around about 18, because I wasn't meant to do 18 months, but I got in a little bit of for fighting.
Anyway, see that now, because I don't want to kill your prison experience. I want to say, so you've done, let me just, in a nutshell, if I can ask you, how many years have you done in prison altogether? Just curiosity, if I, because you went in at 16. What, up to 17? Up to today. I don't know. If I had to say, I'd say I've done nigh on 30 odd years. 30 years totality, 30 years sentence, or 30 years spent in prison. 30 years spent in prison. So you've done your 51, and you're saying 21 years you've had on the road, and 30 years you've been incarcerated. Yeah, not 30 years from, not one hit, obviously. Not from 21 to 51, yeah. But even then, looking at that, that is... Yeah, and like, that is like kind of like a conservative estimate, because I could only estimate. But I know, I know that I've... That means you've been sentenced to 50 years then? Yeah. Are you calculating it by what the sentence you've been served, that they've given you? Are you getting it when you break the sentence? No, because look... A lot of sentences get harsher as it goes. If I added up all my previous sentences, yeah, right, and what I've served out of those previous sentences, it would be more than 30 years. So you've done, what's your, what's your... 30 years in prison threw me off completely, yeah? So for me to know you've done 30 years in prison, and I'm dying for the kids to listen to this, because this is very much, see, for that 30 years, I need to see you. We're going to continue, yeah? So, Darren, stepson. Yeah, love. 100%. Respect for coming on, you know? Anyone listening, welcome to Wheatley. This is Wordland, and maximum respect. Can I just say that we was actually meant to do this long, long time ago? No, don't worry about that. 100% is meant to be a long time ago, but because of, well, you do a lot of time in this, and I'm not exceptional. No, no, no. No, no, no, I'm just saying, so I'm not immune to that. But one more thing, because I said to my brethren today, I'm wearing this hat, yeah? And that's his brethren as well, so there's a message on this hat. Yeah, my brethren, I lived in Serbia then. So we're going to, the message behind this hat, I said to my brethren, this is for the kids that are sleeping in bed after six, don't know how to get out of their bed, and the best thing is wake up in the morning, make your bed, get dressed, right? Right, that's from your son, by your bomba. And listen, wear the T-shirt, Stuart. If you haven't got motivation, and that's why I'm wearing it, you know, wear the T-shirt, because it can kind of give you a different motivation just by wearing it, and you might start changing the way you think, but happy for listening. Thank you very much.
