In this short essay, I’m going to share with you, The TBP Reader, how I’m using ChatGPT (hereafter referred to as AI, for brevity’s sake) to make some real-world life changes. And yes, in the process, I guess I’m going to defend AI, and submit to you that it’s good at what it’s good at.

I understand it’s just a language model built on pattern recognition. It’s not a human therapist and it’s not sentient. But it’s turned out to be a useful tool for this guy.

Now, to get to the main river in my life, I have to tell you about two divergent streams that merged and became one idea:

Stream No. 1: Peer Influence: I have a friend I’ll call “Waylon.” His name isn’t Waylon, but he is, in fact, named after a country and western music star. I’ve known Waylon for 25 years or more. His career is briefly thus: I tried to get through college, but every time I saw sheetrock dust, I had to follow the footprints to see where they went. Whereas I was a middle manager in the construction world, he was a worker bee. I know, for a fact, he built restaurants for the Asian community in Houston, a cabin on the side of a mountain in Appalachia, and a hotel in Jamaica where they had to put a guy on the payroll to sit at the jobsite gate and drink beer all day so that he wouldn’t come torch the place at night. These are just a couple of the stories I can recount off the top of my head.

One day, Waylon has his tool belt strapped on, and he’s slogging through the mud, when a guy pulls up in a Corvette wearing khakis and penny loafers. The guy says, “Hey, you need a couple of scissor lifts next week?” Waylon did, in fact, need a couple of scissor lifts delivered, so he responds in the affirmative, and the guy gets back in his ‘Vette, never to soil his leather loafers. At the moment, Waylon realized he had selected the wrong career path, and began to work towards a sales career.

I don’t know the extent of everything he’s sold, but I know he’s won numerous prestigious sales awards, he’s done the Tony Robbins firewalk, he’s traveled here and he’s traveled there with his sales career.

In addition to that, Waylon and I found a way to arbitrage rural real estate and we made money hand over fist for many years. My point in telling you all this is not to brag or build up, but only to establish credibility. Waylon is the kind of guy, he’s always reading a book, he’s listening to a podcast, he’s taking a course online, he’s learning some kind of new skill or idea. In all the time I’ve know him, I’ve done exactly ONE social thing with Waylon: Many years ago, we saw Robert Earl Keen at John T Flores Country Store.

All of that leads to this point: Waylon and I were talking about life, career, money, and whatever it was we were talking about. I expressed some varying concerns about midlife, and the direction of my career, and all the things about my life trajectory that were bothering me. Waylon said: Give ChatGPT a try.
Me: What are you talking about?
Waylon: ChatGPT. The AI model. Sit down in front of it, and do a brain dump and see how it responds.

Now again, I told you about my history with Waylon to prove up the point: This wasn’t just an idea from a knucklehead I met off the street yesterday. I know him personally. I know his work ethic personally. And I know his willingness and ability to sit down and learn new technology. So I sat down, opened up ChatGPT for the first time, and started typing, which leads us to

Stream No 2. When is enough gonna be enough, TimBo?

About 5 or 6 years ago, I switched careers, also, based on Waylon’s advice. I left the construction industry to also pursue a sales career and continue pursuing land flipping as a sideline. As so often happens in life, rarely do things work out like we hope – I haven’t flourished in my sales career the same way Waylon has, but I’ve made some pretty good money, and I love the freedom of time. What I have done since I switched careers is partied with my wife. And when I say partied, I mean: We started at about age 50, and at age 53 & 54, we ramped up. We have partied like rock stars. You can use your imagination and you probably still won’t capture all the details. We’ve seen The Black Crowes and The Black Keys. We’ve been to Portland, Maine and Portland, Oregon. We’ve eaten steak and street tacos. And we’ve had 10,000 margaritas along the way.

For my 55th birthday in January, my wife, Stormy (also changed by default) took me to Key West, Florida via Miami for a bucket list trip. I hunted the invasive iguana. We ate and drank all the way from Fort Lauderdale and North Miami, with a couple of nights in Miami proper before driving down to Key West for a concert. And drinks.

On the way back, (Stormy usually drives; I’m a Passenger Princess) I had about 3 ½ or 4 hours to think. There were two things that hit me particularly hard on the way back.
#1) On one of the Keys north of Key West, on the east side of the highway, was a mobile home park, with a sign that clearly said “55 and older welcome” And it just hit me like a ton of bricks – Something formerly relegated to “Old Folks” was now something I was eligible for!! It’s like that sign says, “If you lived here, you’d be home now!” Instead, I was leaving the Keys, to get on a plane, to fly back to Dallas/Fort Worth – And for what?!? Time is real, and every day I spend on this earth is one step closer to my final breath. “Memento mori” Remember that you have to die.

And the other thing was this: Stormy (and the kids) often get onto me for watching short form video content. Doom-Scrolling, I think they call it. But some of the videos really hit home: The guy on this particular video says: I don’t have any special skills. I don’t have any special tools. But I make shit and sell it online. And then the tag line: Do whatever you want.

Do whatever you want. Now, this is not license to go out and harm others, and to behave in a way that’s malicious to society. But it does mean that there’s no more inherent value in selling roofs in suburbia Texas than there is living in a retirement community in Florida and drinking 3:00 PM margaritas with the locals. Do whatever you want. Why, at 55, was I not doing whatever I want? Why was I not living with the autonomy and freedom I wanted? Why was I attending the Tuesday sales meeting at 11AM when I hate it?

And with those two things rattling around in my head, I began to ask myself a bigger question: “How much is enough, Tim? You’ve partied with Stormy – And hard. What are you looking for?”

Stormy is a fun date – the best. I enjoyed every trip, every meal, (nearly) every drink and every laugh I’ve shared with her. But maybe it was time to look at something bigger. And with this mix of ideas rolling around in my head, an idea began to gel.

When I got home and had some time to decompress from the trip, I began to think about all the things in my life that were bothering me. I’m overweight and I’m tired all the time. My sleep is for shit, and I’m worried about money. My career is lackluster and I’m tired of grinding away at a lifestyle that I don’t want.

I didn’t need inspiration or vision. I didn’t need my “why.” What I needed was a tool to help me organize the many competing ideas in my head and put the chaos into some kind of order. I needed a way to systematically execute my ideas. I needed a way to track open loops and scattered thoughts.
 
PART II – The work begins – I did what Waylon instructed me to do. I sat down in front of ChatGPT and began a brain dump. Whatever was crossing through my head, I put it down. The basic format tends to be something like this:
Tim: Input of thoughts, ideas, or specific questions.
Chat: Responds with basic information, evaluation and usually concludes with another question.
Tim: Responds to that question, and so forth and so on.

It took us a few days of back and forth to establish procedures, how the software was programmed to respond, and basic communication styles, both mine and the software. After a few days, we were able to start digging in and detailing out some specifics.

When a tire is flat on a car, it isn’t just flat on one side. And even if only one tire is flat, the car is not going to run optimally, even though the other three tires may be fine. Through our dialogue, Chat responded that we needed to break all these competing ideas down into basic blocks. The first block we needed to address was “BODY.”

Sure, that’s intuitive – But I didn’t need to operate off intuition. I needed to create structure, an architectural framework around which I could build new habits. We talked specifically about sleep, exercise, diet, and yes, alcohol intake.

When I told Chat that my sleep behavior was shit, and I was awake most every night from about 3 AM – 6 AM, we made new habits. Leave the phone out of the bedroom. Try to go sleep every night at the same time, and wake up at the same time. If you wake up in the middle of the night to pee, don’t freak out. People pee at night. Just go back to bed and try to get back to sleep. Not magic advice. Not rocket surgery. Just a clear framework to arrange my sleep habits. Out of the last 14 nights, I’ve had 11 nights of pretty solid sleep – A vast improvement.

Next, exercise: I think lifting weights is dumb. I’ve tried it several times since high school football, and I always come to the same conclusion. This is the dumbest exercise in the history of dumb exercises. Well, what do you like to do, Tim? I like to swim. Using Chat is like having my own professional swimming coach available at any time, 24/7. I’ve been swimming for about the last month, solid, 7 days per week, and my aerobic capacity and my swim quality is improving steadily over time. I’ve been able to turn my morning swim into a 30 minute meditation. I swim on a 4-Count, and the strokes and flow come natural enough, I don’t have to strain over the count. My mind drifts, I think of things, I allow it to drift, and then I come back to the 4 count. And soon enough, my 30 minute swim is complete, and I can move on to shower and move on with my day.

Diet: A steady diet of beer, margaritas, late night cheeseburgers and chicken wings has led to (obviously) increased weight. Exceptionally heavy weight. Record-setting weight. I told Stormy recently that I understood why teenage girls had so much issue with the mirror and body image. There would be times, after a shower, where I’d look in the mirror and think, “Sure, I’m a chunky guy. I drink a lot of margaritas. So what?” But then, I’d see a picture of myself, and I’d think, “Oh my God! You fat bastard! You’re about to explode!”
Clearly, weight loss was going to be a dramatic part of how to put air back in the tires of my car. If I was willing to do a low-carb/no-carb diet, What’s Step 1? Chat helped me to line out a keto protocol that I could easily adapt to, and helped me through the transition points. It’s like having a dietary coach available if I need one. I had some early gastro-intestinal issues while my body was switching fuel sources. I would do a daily check-in with Chat, and we’d adjust accordingly. Now, at almost 30 days in, my body seems like I’m toning up, and I am beginning to feel muscle development under my soft layers. My pants and shirts are beginning to feel better, and I’m ultimately aiming to wear my smaller sized jeans in the closet.

Alcohol – The biggie. But not really. If I’m honest with myself – and I mean, really gut-level, strip away all the façade honest – In the dark hours of the night, I would often question my relationship with alcohol. Sure, on the surface level, Stormy and I had a lot of fun. But was I really enjoying the hangovers? Was I really in control and just letting loose once in a while? Or was I living a life of escapism? Chat and I discussed the role alcohol was playing in my life. I specifically posed the question: The disease model as presented by Bill W and developed in the late 1930’s doesn’t resonate with me. Can you tell me about the development of the psychology of alcohol abuse since that time? And I received a clear and coherent answer with lots of ideas about lots of schools of thought about what to do if alcohol is a problem in your life.
In the end, Chat proposed a solution that was so easy, so clear cut, it was impossible to say no. “Why don’t you give up alcohol for the next 30 days and treat it as an experiment?” I had to acknowledge that I could easily stand to take 30 days off and see what happened. I didn’t have to commit to one day at a time, and I didn’t have to commit to a lifetime without drinking again. I just had to agree to take a temporary sabbatical. And using Chat has been like having a sponsor and an alcohol counselor, all rolled into one.

We talked about what kind of identity I was forming with alcohol, and we talked about what kind of person I imagined myself to be without alcohol. Stormy and I went out one night to the Kava Bar, and she and I had some Kava, and I had one THC-Delta-9 drink. We talked about it, and the answer wasn’t a simplistic “You can never do that” – The discussion was more nuanced and it mostly revolved around my own identity and what I was trying to create.

Chat and I have also spent time discussing what Day #31 and moving forward look like in my life. I miss the effect that alcohol has in my life by quieting down the noisy ball bearings at night. But I was not just lubricating out the noise, I was also eliminating important signal, also. I miss going out and having a social cocktail or four or five with Stormy. We bullshit like old friends when we’re out, and we make friends with the bartender, or other folks at the bar. And we always walk or Uber, so there’s no harm, no foul. So what’s the conclusion on what happens next? The honest answer is, I don’t know, and I don’t have to know today.
Both my best friend and Stormy have asked me, independently of one another, a simple yes/no question: Do you feel better because of your actions? The answer, without hesitation, is “YES!” There’s really no talking around it, no way to explain it away. After nearly 30 days of sleep, proper diet, exercise, and sobriety, I feel better. Lots better.

Money was the real stranglehold. Money was the thing waking me up in the middle of the night. I had switched careers from something I knew very well but had grown to hate. That is to say, construction supervision. I switched to a career that allowed for freedom and ample money, but the results felt out of my control. That is to say, roofing sales. And, yes, there were times that I made really good money. But it all leaked out like water through a sieve. I was living out that old cowboy cartoon you would see hanging above the soda counter at the old five and dime: The old cowboy, beat-up and haggard, rolling a hand-rolled cigarette at the bar says, “Yep. I spent most of my money on tequila and concerts. The rest of it, I just kind of pissed away.”
That lifestyle came at a cost, both literally a monetary cost, and metaphorically, an emotional cost. Lots of stress and strain in my internal life and in my marriage.
I reviewed all the options I could think of with ChatGPT based on everything I had previously done, everything in my skillset, and everything I thought I might want to do. We came up with a two-pronged approach. #1) Keep roofing sales as primary income to keep the machine running and #2) Rebuild land investing for wealth building.

This may sound logical and simple to the reader here, but it can be a very noisy spot inside my own mind. ChatGPT doesn’t have thoughts or emotions, and it doesn’t “think” in the way that we do. Chat is able to organize everything I’m thinking about into some kind of logical order to work on things, each step in their logical place.

First step: Build some systems into roofing sales. For those of us who are new to an industry like this, for some reason, we think that knocking a door and talking to a stranger is a big, hairy deal. The very worst outcome is: They say “No.” AI helped me to build a repeatable process that accounted for getting “No’s” at the door and how to keep moving.

I like helping people who are in a troublesome spot with their insurance claim. Sharon Z. had a high-end, luxury rubber-tiled roof, made in Canada, but discontinued. USAA denied the claim multiple times. Sharon stuck me with, and I stuck with Sharon, and in the end, we got her full roof replacement paid for. I’m her hero. I got it done. She got to the point where she started calling me “Kid” and I liked that. For a woman to call a 55 year old man, “Kid” that was pretty cool. A term of endearment, and a sign of familiarity. During the course of working with her over about an 18-month time span, I had been inside her home numerous times. I had seen her well stocked liquor cabinet, and I found out her preferred drink is Bourbon. When we finally closed out her project, I bought her two different bottles of whiskey and took the two bottles over to her home, and we sampled each of them, until I finally said, “Ms. Sharon, I still have to drive home. I’ve got to put the plug in the jug. OK, then. Just one more.” lol

ChatGPT has helped me to analyze my strengths and weaknesses and we’ve put together a plan to help accentuate the former and build on the latter. AI has helped me to set weekly goals for knocking doors, and has helped me to analyze my conversion rates. AI has helped me to draft letters to send, and has helped me to coordinate a systematic way for me to operate efficiently, even if the owner of the company has a scattershot approach and navigate internal chaos.
Before the use of AI, I knocked doors when I could work it into my schedule. I had one of the partners take me out to lunch for my birthday and we talked about how he’s been able to be so successful. He discussed the idea of “time blocking” on his calendar. I’m pretty decent at managing my calendar. I rarely miss appointments and I keep the day to day activities pretty clear. But I had never heard about time blocking. I went home after that lunch, and I told AI, “Explain time blocking to me, and explain it to me like I’ve never opened a calendar before.” And once I understood the concept of time blocking, we got to work laying out my work week, and now I knock doors 4 or 5 days per week. The other thing that it helped me with was my anxiety about knocking the doors. I have a buddy that I enjoy knocking with, and we’re very productive – We have a natural rapport that meshes well with most homeowners. The trouble is, how to split a job 50/50 when working together? It gets messy fast. So as I talked to AI about this, it broke it down into very simple components that makes it easy to knock doors, whether with my buddy, or without.

Now, we’re beginning to think about long-term positioning as to how I can build a brand around what my natural gifts are, rather than just tell me to become a closing machine. Becoming an “ABC. Always Be Closing” closer is not my natural bent, and it feels unnatural to me. With all the resources of the internet at our disposal, and a clear thinking, logical structure has me thinking about larger plans for later.

Land investment: Waylon and I made a bunch of money in a few years time, many years ago with arbitrage of rural real estate. When we jumped in, we were fortunate enough that not many people knew of the methodologies we were utilizing. It wasn’t hard to find someone who needed some cash money compared to a piece of land that had no sentimental value to them. Pretty soon, though, the secret got out, and word got around. More and more people got involved and our edge disappeared. Now, it requires precision to find motivated sellers.
AI has been helping me and Waylon to identify markets in Texas and Oklahoma, how to use software to effectively target motivated sellers and how to find fast buyers. AI is good at large picture stuff (How much time do you want to spend on LAND this week? Here’s how we can block that time in.) Down to very detailed items: Here’s what land is selling for in Johnston County, Oklahoma. If you want to make X, you need to buy it at Y.

I’m still at the very beginning stages in turning the MONEY block around, using the AI as a resource. I’m not telling you that the use of AI has reversed my financial circumstances overnight. It’s not like buying a lottery ticket. What AI has done, is help me build systems so I can focus my attention where it really matters.

In addition to the above, I’ve asked AI to remember and placemark some other things for my life development. I have creative pursuits I want to follow. I asked Chat to remember I want to take charcoal sketching lessons when the time is right. As my swimming improves, I want to hire a diving coach. I will never be an Olympic level swimmer, but maybe I can learn to do a gainer at 60. Wouldn’t that be cool? Longboard surfing. Not many opportunities to learn that in Fort Worth. But ultimately, I get to design the course of my life, and if the future includes longboard surfing, let’s remember it so we can design around it.

AI is an extremely pragmatic tool, as well – I need this from Amazon. Please put it on my list. I want to buy ribeye steaks in bulk. Where do I buy it and what’s the best chef knife I can buy?

As mentioned at the beginning, I am aware of what AI is; and what AI isn’t. The evidence is simple: I’m sleeping better. More consistently. I swim daily. I’m sober. I knock doors consistently now, rather than haphazard. I’m rebuilding my land business. I’m thinking long-term. I feel better, overall.

I have lots of peers willing to point out the downside of AI. And I get it. I don’t know where this path will lead. I’m not “10 X-ing” my business because of AI. I’m not suddenly rich, or shredded, or enlightened. The engine is running quieter. All the tires have air. I’m living my days with intention and planning outcomes. For the first time in a very long time, being able to see the road out in front of me is good enough for now.