Most assumed Jason Carter lived a wonderful life. He had a remarkable wife, amazing kids, and an oversized house close to the country club but something reeked. While discussing thoughts of suicide with a renowned psychiatrist, the psychiatrist pinpointed the musky sock floating in the soup; his unchecked drinking. Days later, bristling from her rubber-stamped diagnosis, he set off driving from Texas to Telluride, searching for clarity.

Hypnotized by the open road, he finds himself wheeling through numerous sequences that accelerated his ruin. To Hell I Ride is determined, it’s darkly comedic, and it’s this journey into extreme self-awareness. As Jason explores his past, he confronts the inner personal demons haunting him today. Brutally honest, he bares it all; how alcohol crept into his life, the wolfish anguish lurking inside each drink and the sacred truth shielding him from salvation. Here’s my conversation with Jason Carter.

This is The Author Hour Podcast. I’m your host Benji Block and today, I’m thrilled to be joined by Jason Carter. Jason has just authored a new book, the book is titled, To Hell I Ride: When a Life Examined Became Worth Living. Jason, welcome to Author Hour today.

Jason Carter: It is really an honor to be here. I appreciate the time and I’m just looking forward to having a chat.

Benji Block: Absolutely. Jason, I know we’re going to talk a lot about your life over the next few minutes, but maybe just give people a little bit — tell us a little bit about your professional life and kind of what you’re up to these days before we dive into the book.

Jason Carter: Happy to. I have a communications firm that I run, boutique, working with two to three clients at most and supporting their communication efforts and it’s great. What I love about doing the podcast is one of the things that I had to do for my business was learn the art of podcasting, the technology behind it and whatnot, so I could produce those myself for clients. What I appreciate — and you may appreciate as I know you’re using Zencastr, I found that to be best of breed and the problem was, that so many people would forget to use Chrome. They would put it in Safari so you record the whole show and then you’d get to the editing process and their whole line of dialog was gone.

Benji Block: Yup, got to learn a lot.

Jason Carter: I want to double-check to make sure, yeah.

Benji Block: Absolutely man. Okay, let’s start here; why was this the right time to write a book? What made you go, “You know what? I want to be an author, I want to put my story into writing.”

Jason Carter: Well, I’ve been kind of cursed my entire life wanting to be a writer from the earliest age, even in grade school entering writing contests and whatnot and coming up a little short but not to be deterred. I always just identified myself as a writer and when I finally made it through college, gave copywriting and advertising a good run in New York and then moved out to Los Angeles to pursue screenwriting because — this was I guess in the, I will say, late 90s, ‘96, ‘97 when there was a spec script boom and you really thought that you could drive out there, crunch something out and get a million-dollar deal within two weeks.

I chased that dream and I think right around 29, got married, had to kind of give up the dream and I went into the corporate route and sales. I was there for about 15 years but I never really wavered on wanting to continue to do something. So, right around the time Amazon got into web hosting and whatnot, we were trying to figure out our messaging and our CEO and founder kind of approached me and said, “Hey, I heard you used to write screenplays” and all this stuff. So he pulled me into the communications department and then I was there for the next five years writing speeches and blog posts and it was really great and I decided to go off on my own and do that. 

The book itself was probably something I didn’t think I ever had in me until what happened in my life. I kind of felt it was time to tell the story, not to myself, [but] to share with my kids or even others that may need to hear it from a different perspective.

The 17-Hour Drive That Change My Life

Benji Block: Do you write a book like this, kind of as you’re doing that, obviously, wanting to share it but also was there this personal therapy that was happening as well putting these words actually on paper?

Jason Carter: Unbelievable amount of personal therapy that I really didn’t even expect. Just not to give the whole thing away, there was a — I guess they call it the moment of clarity, a spiritual intervention of sorts and you know what happened in Telluride, hence the name of the book, To Hell I Ride.

Benji Block: Yeah, I love it.

Jason Carter: After it happened, I was free from the grip of pretty long-term life of drinking, you know? I don’t really remember a time from eighth grade up until that point when I was, I believe, 43 where alcohol wasn’t just a part of the fabric of life, whether it’s a dinner party or going back to the fraternity days, high school, all that.

What I wanted to do when I was going back to write the book is I was asking myself the question — when I drove up to Telluride with my family, I was not at rock bottom. Maybe so, but I mean I was borderline suicidal and for the 17-hour drive, I was just going over in my mind like, “How in the hell did it come to this? Really, when did it start?”


I really had the life flashing before my eyes for 17 hours just ruminating on that. Then, the event in Telluride kind of just stopped it all. When I got back, I quit drinking. I’ve lost all cravings, I couldn’t even imagine myself ever having a drink again and I didn’t go around telling everybody because I was pretty confused about it by myself and also as a drinker, you don’t want to open that door to having to say you’re done forever and then falling back.

For the longest time, I was just ruminating on this and like, “Wow, why did this happen?” And so, I go back, I write out all the things that I was thinking about on the drive, which was really just kind of a ghost of Christmas-past look at my life and up to the point — what it did for me is going back and reliving these moments all the way back to I think five years old and going over it and over it. The revision process was reliving it with such clarity and really able to humanize not only myself but really kind of figure out what was the pattern that started this love affair with alcohol that I really had no intention of ever stopping or believing was that big of a deal.

The things that you start really kind of picking up on there were remarkable and at the same time, on different tracks. When you stop drinking, you start having a lot of time on your hands.

Benji Block: Yeah.

Jason Carter: One, your friends stop calling. The other is that when life used to revolve around 5 PM and having a couple of cocktails after work before diving into the wine. Now you have time to read, exercise, do other things of self-improvement and it’s pretty wonderful. As I was writing this, I started reading a lot about manifestations, self-awareness, all of these things, vulnerability, and it was incredible to do that at the same time and see that it really does take, I think a lot of — I’m not a brave man for telling my story but I think it’s an important part of the growth process and there are mottos out there, don’t look back, just move forward. Of course, I think that was like Don Draper that was saying that, not the best role model. 

Benji Block: Yeah.

Jason Carter: I think that if you do have the time to really take a focused look at your past, you start noticing the things that are certainly causing issues, causing a problem and that’s the only way to really extract it by just complete ownership, acknowledging it because I mean, I started tap dancing about the drinking probably as early as college like, “Oh, this isn’t a problem. Everybody’s doing it.”

Benji Block: Right.

Jason Carter: To be clear-headed and going back and looking at some of the stuff and which I always had in a real shameful way, the remorse, “Oh my god, that wedding or that long weekend in Vegas.” These things would cause me sleepless nights but when I really got down to it and started really digging deeper into these things, I started just noticing a pretty remarkable connection to my estranged father that ultimately linked me to my own children, who I may have been a lot of things but I was a great dad. 

I mean, there was never anything more important or valuable to me than being a great dad, and the way I was drinking made it very difficult. It became too hard to contain and without even me realizing it, I was kind of repeating the cycle that happens in a lot of families whether it’s abuse or drinking or whatnot. It was just a really incredible discovery to go through all this stuff and the other challenge was making it readable because I’m not an avid reader, I’m a pretty aggressive reader.

The first thing that happened when I decided to stop was, I went and looked for books about other people that stopped and I had a real hard time connecting with a lot of them because they just didn’t seem real. I can’t associate with Ozzy Osborne snorting ants, it’s a great story but it doesn’t really resonate.

Benji Block: It’s not yours.

Jason Carter: Yeah, it’s not mine and I can’t even think about it. It doesn’t do anything for me or maybe there’s a real housewife from New Jersey whose book talks about her drinking a box of wine while picking up her kid. I mean, there didn’t seem to be the kind of everyday book that really — you know, I’m Generation X and that really takes anybody that is in Generation X through their adolescence, young adulthood, just through a different set of eyes.

I wanted to make it just for me especially entertaining — I don’t know if that’s the right word but — having trained in screenplay writing, if you can call it that. Story and structure is very important to me and I didn’t want this to just be a big sloppy rant.

The Wake-Up Call

Benji Block: Yeah, I would say that shines through, honestly. You’re like — I literally have “entertaining” written down as one of the ways I would describe it and I also thought the comedic relief you provide while covering incredibly tough topics to cover, you do a great job of kind of balancing that all at the same time. It’s not like a chapter that’s comedy and then a chapter, you know what I mean?

You’ve mixed these themes together in a way that I think your voice really shines through very effectively. I love the style that this book is written and I think readers will definitely appreciate what you’re saying; the everyday feeling that this book generates but also the craft of the writing and the skill behind the way that you’re sharing these stories that are personal to you.

Stories really throughout your life are — I mean, that’s this whole book. You start and you alluded to this with a run and then a trip to a psychiatrist, right?

Jason Carter: Yup.

Benji Block: You talk briefly but you do talk at the beginning there about these suicidal thoughts. Talk to us a little bit about when that kind of started to happen for you and when you started to have those thoughts and was it – is it something you battled for a long time before you knew you needed help or what was that like?

Jason Carter: Yeah, well first, thank you for the compliment. I mean, that really means a lot because that’s really what I’m going for and I try to see the humor in a lot of things. I think a lot of people rubber stamp this guy, it’s a defense mechanism, he’s afraid of real emotion but I think humor is a real viable way to look at life, why not?

Certainly, without undercutting the kind of the dark things but anyway, I really, what you just said there just made my day. I appreciate it very much. The suicide stuff, I mean, that’s a word that — my god, everyone’s going to — they’ll have their thoughts on the word but I think it was just getting to the place where you wake up almost every single morning and you’re already behind with the hangover that you’re used to.

You’re just so weighed down, everything in life becomes just a great challenge and I certainly wasn’t taking a bath next to my hot toaster but there were thoughts of like, “Man, it would just be a real relief for me to not feel so guilty, so remorseful, so tired” — and this will be the second reference to Mad Men but there’s a great line when I think the first moon landing and somebody asks — I don’t think it was Draper but one of the ad guys. “Oh my gosh, what if it blows up?” and the guy just goes, “Yeah and then they wouldn’t have any problems.”

I think that’s where it was and in terms of just kind of unloading it for the first time with a psychiatrist, I think she saw the alarm bells. 

Benji Block: Right. 

Jason Carter: Not urgent but it was a wake-up call for me. It was actually a relief in a way that a professional, someone that’s very well-renowned said, “Hey, you know this isn’t good. There should be some changes coming.” And that was really the first time that somebody outside of the family or whatnot just seemed very genuinely concerned on a scientific level, I guess, instead of just like an emotional reaction when, “Well, you wrecked the buffet again at Sunday brunch,” you know? 

This was somebody that I was there wanting to go see and discuss this and they were kind of hard stop, “You need to think about these certain things.” That was the first time I really acknowledged it to myself. You know, I really wasn’t ever going [to] — you know, I say that and everyone is like, “Sure, that’s what they all say” but you know, I was never going to do it but it was something that it was almost like a fantasy. 

Instead of dreaming of going to Cancun or sitting on the beach, I was like, “I’ll take that a step further, wouldn’t that be great?” Yeah, no sunscreen needed. 

Benji Block: When did you — I guess until she said that you might have a drinking problem, would you have called it just straight denial, or was it just putting it off until tomorrow kind of vibe? 

Jason Carter: It was kicking the can down the road. I mean, I was very aware. My wife was very aware and I had two other times had stopped like gotten to a point — I think I was in my mid-30s and I was like, “I’m done.” Went along for about nine months, maybe longer. I don’t know, I ran a marathon, all the cliché things that you do and it just didn’t stick and there was another time. 

After that, it was kind of the same thing. It was more of a, “Maybe if I stop long enough people will quit paying attention” kind of thing. I mean, when I go back and read the book, it’s easier for me now to go, “Wow, that time when I was in 8th grade? Maybe I had a problem.” The other part of it is looking at life through my children’s eyes. My oldest is 18, my youngest is 13 and kind of shifting between what I was doing at their age, you know that really resonated with me because they’re living just such a good life. 

Despite some of the hiccups over bottles of wine, my wife and I have maintained a very tightly wound family unit. Part of the original kind of seed, at least part of the motivation why I write the book was like whenever they ask, “Hey dad, why don’t you drink?” I wanted to have something to give them like, “Here’s why.” 

Benji Block: That’s great. I appreciate the impact that writing, well, and even just the stories can have on the future generation. There’s things that my grandpa and great-grandpa wrote and they’re no longer here that I still have, right? That gives insight and wisdom a generation later and so that’s powerful, man. And I think obviously, this is something great for your kids and then others that read it are going to be impacted as well because there’s so many that struggle in this area and are addicted and need help. So, I think it’s good to write this.

One of the things I found really interesting that I wanted to chat with you about, you mentioned quite a few songs and just throughout the book and I saw you actually were like building out a playlist on your website as well.

Jason Carter: Yes. 

Benji Block: Can you give me a couple that maybe bring you back to specific memories in your life and what’s the power of music has been for you personally?

Jason Carter: Music is an incredibly important friend of mine. Just from the earliest days, there’s a chapter that is around my obsession with Van Halen starting in sixth grade. Specifically, I moved to New York after college — two days later after graduation and I graduated in December, I took a little longer — I took a duffel bag to New York and the two disks that I had, one was standard Dave Mathews and then the other was Tupac Shakur, Me Against the World. Every time I even think of or listen to that song, any of the songs, or see the skyline of New York, I mean that’s the first thing I think of because for the most part, I had my little Discman headphone set in my really small studio apartment. 

I would just put the headphones on and I would start writing and the thing with somebody like Tupac is, I think if you stripped away everything and it was just words written on a page, he would probably be one of the top 20 poets ever. I don’t know… So I just have a profound appreciation. Warren Zevon, another great troubadour. Sometimes it’s hard especially in today’s day and age to really listen, give a deep listen to lyrics because most of the time [when] you’re listening to music, you’re like working out or driving in a car filled with people but when you really stop and listen to the stories they’re telling in three to five minutes, that can really blow your mind. 

I just think that the appreciation of the storytelling ability of most singer-songwriters is what compelled me to probably make so many references to songs and also to timestamp the moments of my life in a linear fashion. 

Benji Block: Yeah, that’s a great way to say it, both that music is an incredible friend and it is a timestamp. Absolutely, both of those things are true. It’s crazy that when a song comes on, it could just take you back to a moment and a time and a space and even a headspace. 

Jason Carter: Yeah, almost better than anything. I mean, you know there’s maybe a smell or something but I have never eaten a bagel and I’m like, “Oh my gosh, I’m back on Broadway in 56th street.” 

Benji Block: Right. 

Jason Carter: It’s the song. 

Starting With The “Why”

Benji Block: Let’s do this, when you think of the end of that road trip you’re on with your family and you had these 17 hours of driving, how do you explain how different you are now compared to when the beginning of that drive started and just the clarity that you gained from that drive? 

Jason Carter: Well, it was also the drive itself and so a couple of days into the trip I literally was like, “You know what? Everything feels great. Maybe I’ll go get a glass of wine.” And as I was walking the streets of Telluride, that’s when the moment happened that really changed everything for me. Yeah, the sense of clarity, the first year or so you’re still kind of just, “Oh my gosh, I can’t believe it. I think I’ll run a marathon, maybe a triathlon.” 

You have this kind of manic energy, maybe making up for lost time but it’s not — I wouldn’t say it’s real. I think it’s more of a trying to play catchup or something but what I found in year four, let’s call it, it’s almost on six years, I didn’t really have the calendar out but there is a real sense of liking myself because I really — one of my thinking, my thoughts is it’s hard to really argue that drinking is a way to escape yourself or your reality because I mean, just on a scientific level, you’re shifting everything around with your third margarita or whatever, you become a different person and you are not the [same] person.

And what I found so hard to quit is that when you would wake up after a long weekend and you’re getting ready for work on Monday and you’re looking at yourself in the mirror and you’re just going, “Oh my god, I hate this guy.” But at 6:00 after work, I’m going to get rid of this guy and have my drinks and get back to my happy place and so you’re escaping something. 

When you take that away and you have to look at the person in the mirror every morning and learn to live with it and then you really start having a more appreciation for everything, life, yourself even. And I’m a work in progress on that but I can’t speak for anybody except myself but I think the reason that I had such a hard time stopping is because I was taking away my getaway car. Whether I was ever celebrating something or we were — if you had a bad day, a good day, an average day, it was like have a drink and it’s going to end up a certain way and I always felt very comfortable in the, I guess, the womb of alcohol. 

Benji Block: Well, I want to do this as we start to wrap up here, I’d love to have you talk to someone who might find themself in a similar space to where you were of addiction or other, maybe battling those internal mind games. What would you say to that person? What encouragement would you offer? 

Jason Carter: I want to preface it by [saying that] I want to be really careful. I’m not a doctor, I’m not, I guess, a therapist or anybody but what I would tell my friend is ask yourself why and start there because you would need — you just have to have an honest conversation with yourself. You can’t allow the external — because I doubt there is anybody out there if you have a problem drinking that’s really supporting you, you know? 

Like, “Oh, don’t worry about it. Really it’s fine, everybody is doing it” and I think that the fear, there is a fear in that but what I would say is grasp onto the power that you do have total control to at least entertain the questions. The way I did that was going back and looking at my entire life. Maybe it wouldn’t take somebody else to do that thorough of a look back but just ask yourself the question, “Why am I doing this?” 

See, if you can be honest and sit on it and go on a jog or whatever, watch a movie and just let that question keep floating around. That’s really all I can — I guess I’m ready to say to somebody because I never wanted to come across as like, “Look what I did and here’s how it’s done” because we’re all made of like what? A trillion different kinds of cells and everybody is different; chemical reactions to certain things and spiritual things are all different for everybody but in my humble opinion, I think starting with why is a great place. 

Also, a start [is to] absolutely know that you do have control over it. As impossible as that is to say because there were times where I know I didn’t and there are certainly — I don’t know if you watch the show recently, Dope Sick, about the OxyContin stuff, that’s a whole different beast because that actually changes your whole brain to where people don’t have a choice. I do like to talk from a drinking standpoint if you are struggling, just ask yourself why. 

Let that linger for a while and just kick it around and do some brainstorming over the next couple of days or weeks until an answer comes because I assure you, it will. 

Benji Block: Yeah. I heard someone say one time to ask yourself, “Why am I doing this?” and then ask, “Why am I doing this really?” and it’s kind of in that follow-up where sometimes, some of that real stuff starts to come up when you think about it long enough where it’s like – 

Jason Carter: Boy, that’s a good point. 

Benji Block: My first answer is probably my defense mechanism but I love that because if we don’t start with why and drinking doesn’t have to be your issue. We all got stuff, right? We all got baggage, when we get at the heart of it and why we’re doing what we’re doing. 

Jason Carter: Right and now I’m dealing with sugar and trying to apply the same principles. It’s like, “Why am I eating this second pint of ice cream? Well, it tastes good.” Really? So yeah, I think I might have to, I learned something from you today. It’s very valuable to drill down. 

Benji Block: That’s awesome. Well, Jason, as we start to wrap up here, where can people find you and reach out online? 

Jason Carter: Well, I have a website,, and it’s a work in progress but it is a place where I’m going to start putting up more materials. One of the main reasons I think that getting the book out and behind me is I feel like it gives me an offer to join the conversation that’s worldwide. The WHO organization claims there’s over 400 million people that have problems with alcohol — what problem drinker really admits it, so that number could be a billion. 

I think that there is a lot of great people just having discussions and talking about it. I think it’s something that we can rally around and talk about. In the way that people climb Mount Everest and go to talk about it, I feel it’s kind of the same thing. It’s not a hobby, it’s more of a subject that I really love and I don’t know everything about and I want to keep learning. The other parts are — would be Facebook. 

Someone’s trying to get me to do some TikTok stuff, I’m not there yet but if I get there, it will be somehow linked to my webpage. Also, there is a To Hell I Ride Facebook page that’s very easy to find and that would probably be the best place to get any active content or if you want to reach me directly, I would love to chat. 

Benji Block: Amazing. Well, it’s been such an honor to discuss the book. Again, the book is called, To Hell I Ride, it’s on Amazon, you can go buy it. It’s going to be a great resource for so many. Jason, thanks for being on Author Hour with us today. 

Jason Carter: It was great and I appreciate your time.