How I Made AI My Personal Coach
From DIY Chatbot to ChatGPT
I’ve spent the last few months deep in the final stretch before publishing Life on Offense: Do HARD Things. I’ve been formatting the print and Kindle editions and reviewing the audiobook files with Jay. It’s almost done, and that feels incredible.
While I was heads-down finishing the book, one of my side projects had to be put on hold. Back in 2023, I tried building my own AI-powered coach based on the frameworks we use. The goal was to turn our book into a chatbot that could help guide your habits, mindset, and personal growth. The reality was a mess. Between short memory, laggy responses, and an impossible tech stack, it became more trouble than it was worth.
So I pivoted. I stopped trying to build something from scratch and just started using ChatGPT directly. Once I gave it some structure, it turned into a surprisingly effective coaching tool.
In this article, I’ll share what I learned from the failed build and how I now use ChatGPT as my personal coach. I’ll walk through exactly how I use it every day, week, and quarter to enhance my life. I hope you can take what works, improve on it, and make it your own.
From DIY Disaster to Everyday AI Coach
In early 2023, I got ambitious and decided to build my own AI coach. I wanted to create a webpage that would walk someone through the Life on Offense frameworks in real time. An engineer I hired built a rough prototype using five different tools. My goal was to build a chatbot that could help people reflect on habits, mindset, and personal growth, all based on the book Jay and I were writing.
It looked great on paper. In practice, it was a mess.
The biggest problem was memory. The earlier versions of OpenAI’s large language models (LLMs) couldn’t hold context for long, which made any kind of meaningful coaching nearly impossible. I kept repeating myself just to keep the conversation coherent. On top of that, the tech stack we built was a fragile mix of Application Programming Interfaces (APIs). When one updated, the others broke. Lag times were awful. I’d ask a question, then sit there wondering if the bot had frozen or just quit on me. The whole thing was glitchy, frustrating, and more trouble than it was worth.
After a few months of trying to debug my “dream coach,” I finally admitted it. The tech wasn’t ready, and I wasn’t impressed with LLM integration for chatbots in general. We shelved the project. But I came away with two valuable lessons. First, AI coaching only works when the system is fast, smooth, and remembers what you said. Second, chasing the perfect custom tool can make you overlook the simple solution that already exists.
Months later I opened up regular ChatGPT and just started using it as-is: with no plugins, integrations or setup. And to my surprise, it worked. The model had improved, context handling was better, and it ran reliably on all my devices. I could start a conversation on my laptop, continue on a walk, and pick it back up on my phone later. Once I brought some structure and purpose to how I used it, ChatGPT became the coach I had been trying to build from the beginning.
How I Actually Use ChatGPT as a Coach
Here’s how I use ChatGPT as a daily performance partner. It’s basically my coach, teacher, financial advisor, therapist, and accountability buddy in my pocket.
Daily: Reflection, Mindset, and Habits
Morning check-in: I start each day by telling it my top one to three priorities. Just saying them out loud or typing them helps me lock in and focus.
Journaling partner: I summarize what I wrote in my journal. “I felt off yesterday, skipped my workout, and am anxious about that project.” Then I ask for feedback. It usually follows up with something smart like, “What do you think triggered the anxiety?” That back-and-forth helps me be more honest and less reactive.
Affirmation tool: When I’m unsure about something or stuck in a slump, I ask it to reframe the situation. It gives me a short, positive reminder that lands like a pep talk from someone who knows my goals and wants me to keep moving forward.
Habit tracker: I report wins and slip-ups. “I exercised every day this week.” “I skipped practicing on the guitar again.” It responds with encouragement or helps troubleshoot without judgment. It doesn’t nag but it nudges and calls me out when I need it.
Weekly: Reviews and Recalibration
Weekly review: Every Friday, I send over a quick summary of what worked, what didn’t, and what I’m thinking about. I ask, “What do I need to change?” It picks up patterns I miss and helps me reset for the week ahead.
Fitness planner: I share my workouts and ask if I should keep pushing or back off. It usually tells me to recover more, but I usually ignore it until my lower back starts yelling.
Accountability check: If I have avoided the same task for two or three weeks in a row, it points that out. I either commit to doing it or admit it is not a priority. No more hiding from my own to-do list.
Quarterly: Audits and Big Picture Planning
Priority audit: I list my HARD goals (Health, Affluence, Relationships, Development) and compare them to how I’ve actually spent my time. ChatGPT calls out the gaps.
Future pacing: I say something like, “It’s December 31st. Here’s what I want to have accomplished.” Then I ask it to describe that future version of my life and help reverse-engineer the steps to get there.
Decision support: For the big stuff like career moves or major life changes, I lay out the context, the pros and cons, and my core values. ChatGPT helps organize the mess. It does not make the decision, but it sharpens my thinking and clears the emotional fog.
That’s it. I treat ChatGPT like a coach who always has time, never gets tired, and doesn’t care about impressing anyone. It’s not magic, but if you use it with consistency and honesty, your clarity sharpens. It helps you stay focused and moving forward at full-speed.
Frame It as a Coach, Not a Guru
The biggest lesson I’ve learned is to treat ChatGPT like a coach, not a guru.
It still gets things wrong. Sometimes the advice misses the point or feels generic. But that’s true for human coaches too. The key is staying in charge. I use it to test my thinking, not replace it.
If something feels off, I ask a sharper question or come at it from a different angle. Lazy inputs get lazy outputs. You still have to do the work.
What it’s great at is helping me see my thoughts more clearly. It helps me sort ideas, frame challenges, and pressure test decisions. But it only works well when I give it direction. I treat it like a smart assistant. If I ask for help planning my week or preparing for a tough choice, it usually comes up with something useful.
This only started working once I stopped thinking of it as just a tool and started using it like a teammate. That shift made it a regular part of my process.
If you’re already using AI for things like journaling, parenting, or learning, I’d love to hear what’s working. Send me a note or leave a comment. I’m always interested in how people are putting this stuff to work in real life.