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Jason has a degree in Philosophy, was a Captain in Air Force Space Command, Plant Manager, then rock star Headhunter. Also a published author, a black belt martial artist, and a former chess champ who likes to cook and tinker – his curiosity about all things lets him see the big picture. Using all that to help others, he has built a reputation as one of the most truly gifted coaches and trainers in the country. His specialty is getting into the minds of people and unlocking the big picture, clearing the next obstacle. Sherlock Holmes has his face on a dart board, and James Bond was heard to remark, “I ordered shaken, not nerd.” You can see the timeline of his life and learn more about him here. Want to book coaching? https://mooreessentials.com/course-catalog/
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Wrapped Up With a Bow
By Jason Thibeault | Friday November 28, 2025
I’m not pulling punches here. Gift wrapping is a pain in the ass. You’re trying to smoothly cut a line and it wants to bunch up and rip a little. Then you’ve got to cut the right amount for the size container you’re wrapping, assuming it even is a regular shape. Then you’ve got to tape it (I am great at that part.)
Today we are considering automating that process because I don’t like it. I know of big paper cutters, which can easily slice to exact measurements. It’s a big tool, and now I still don’t have the right sized paper or decent technique.
So I can invest more. There’s a machine called the Giftwrap 3000 (really) It’s huge, six-figure expensive, but I never need to wrap a box again. So long as it is a rectangular box. Which means, 50% of my wrapping still needs to be done.
The tools exist to help me gift wrap, but I haven’t mastered the techniques which would make automation necessary, or even helpful.
Another problem. I don’t love paying my bills, and I never schedule a time to do things I don’t want to do. I understand how to pay them online, and there was always money in the account. So, I automate it. If you know how to pay a bill online, you can easily set up auto bill pay. Unlike gift wrapping, this is repeatable automation.
Entrepreneurs need to stop trying to automate what they don’t know how to do. A recent MIT study showed 95% of AI projects failing. This is partially because they’re trying to use an automation tool to outsource expertise. If you don’t know how to do it, you don’t know when the process is going wrong or how to fix it. And without discernment, you won’t even know if the finished product is wrong.
Automation is great. In manufacturing, we often automate our way out of pinch points in the process. Automating your way out of something you don’t know how to do is better served by buying the finished product or the services of an expert
For entrepreneurs, that means giving instructions to a virtual assistant, or employee, or gift wrapper, or attorney, or whomever is needed. It doesn’t mean automating something you don’t do well. Or hoping Agentic AI will for you.