Stop Doing Things That Suck – Part 1
Yesterday (2/11/2026), I had two very insightful lessons taught to me, which I am going to share with you in a two-part series.
The first came from a YouTube video by Daniel Pink. (https://youtu.be/PjTaZvvOtxU?si=eEGNMPHyHmQenvBz) In this vlog post, he shares his conversation with ChatGPT about himself and his business. For him, it was interesting, raw, and sometimes maddening that not only a stranger but a computer stranger could be so honest and deliver the plan truth. The experiment was so successful that he shared all the questions he asked in a downloadable PDF, and Pink encouraged his audience to do the same exercise. I, of course, did.
I have never used ChatGPT, so I opted to use the AI feature in Grammarly, which I use all the time. After the first question, I was concerned that “she” wasn’t all that insightful. The answers seemed canned to me. Kinda like a doctor telling you to eat less and move more. I feared the experiment wouldn’t work.
Anywho, I then asked what I could share with “her” so she could get to know me better. Here was her response:
Here are a few prompts to get you started (pick any that resonate):
· What do you want most right now, and what’s in your way?
· What habits or patterns do you keep repeating, for better or worse?
· When have you felt most energized or fulfilled at work or in life?
· What’s a recent mistake you made—and what did you do about it?
· Who’s someone you admire, and why?
· What’s something you don’t say out loud, but wish you could?
Your real answers—not the ones that sound good—are what will help me be a brutally honest advisor for you.
After sharing what is most important to me right now and why I think I am stuck, she had enough information to draw some conclusions. Buckle up, Chris, the rollercoaster has left the platform!
Not surprisingly, some of my struggles are universal. I am stuck in a loop of self-doubt and overthinking. I am playing the “I need more information” game, which, as she states, is a sophisticated form of procrastination.
Ouch!
The fact that my struggles are probably your struggles doesn’t bring me comfort. It means we are all fucked up to a certain degree, and we are doing a shitty job trying to fix our situations. Her potent answer to, what lies am I telling myself? was: “You’re not protecting yourself from failure by telling these lies; you’re guaranteeing it.”
Well, that’s pretty sucky.
But, on the bright side, she gave me a response that was like a permission slip. The question was, “What am I pretending to care about that I actually don’t care about?” She came back with, I really don’t care about fitting into the normal and expected in my industry. I pretend to care about being ready, organized, and perfect, but deep down I value exploration, learning in public, and honest self-expression.
Wow!
I’ve never really fit in personally, but being a business owner has always been about appealing to others, not being true to myself. I have been consumed by the outside world and potential customers. I am not good at this, strike that, I suck the big one at it! And, as a result, my businesses have tanked.
If you build it, they will come.
I don’t have the faith that is true, and so, I play it small and try to ram myself into a mold that already exists. I am hobbling myself. I am both James Caan and Kathy Bates, grrrh.
Do you know how much weight I would lose if I stopped dragging around all the emotional and mental baggage? Do you know how much energy I have exerted? And how freeing it would be to just to let go? The notion not only excites me but scares the living shit out of me. Being myself, my true self in business means throwing up two middle fingers at the status quo.
So GenXer of me.
Moving forward, I am committed to showing my work in progress more, the shitty, messy, and raw parts of me, and the work in hopes that I encourage you to do the same with your work. My journey is one down a path less traveled, and I wish you are along for the ride.
To read part 2, click here.
How am I doing? Leave a comment below or email me directly at cjhanlonwrites@gmail.com.
