Month: <span>July 2026</span>

The Eleventh Video

The eleventh video focused on a topic that I still feel strongly about today: content creation while actively driving. At the time, I was watching a growing number of rideshare and delivery creators producing content from behind the wheel. Some were livestreaming, some were recording commentary, and others were interacting with their audiences while operating…

Read More

OVERTHINKER COMMITTEEFIELD OBSERVER ENDORSEMENTReference: OI-PAGE-001

New Data Point Recorded. The establishment of the public-facing The OverThinker Files page has been observed and logged. The page serves as a centralized repository for committee reports, field observations, and related documentation. Field Observer Assessment This is a perfectly recursive development. The subject has now created a public archive about the committee that was…

Read More

The Tenth Video

The tenth video was not originally part of the plan. Like many content creators discover, sometimes an idea refuses to stay in your head. I had already put together a video, gone through the process, and called it a night. Then I woke up, watched what I had produced, and realized that there were still…

Read More

The Rolling Air Brake

I might be getting old, but there are certain things I see on the road that just make me shake my head. One of them is the person driving around in what is probably a six-figure Mercedes, or close enough to it after options, with all the windows down, the exhaust barking, and the whole…

Read More

The Real Hours Behind a $300 Gig

A $300 gig sounds simple until you start counting the actual hours. People see the event time. They see the music, the karaoke, the speakers, the lights, and everyone having a good time. What they do not always see is everything that happens before and after that. For this one, the event itself was from…

Read More

The Ninth Video

The ninth video focused on something that would become increasingly important to Massachusetts rideshare drivers: the newly established rideshare driver law and the changes it introduced for people working on the platforms. In the video, I walked through the information that was available at the time and discussed what the changes could mean for drivers.…

Read More

Breakfast Talk: Facts Verses Labels

Title: When Tolerance Turns Into a Label Gun Good morning. This is The GigMan’s Life, and this is one of those talks where language, public forums, Facebook moderation, George Carlin, and plain old bad behavior all run into each other. Because this started with a conversation. A conversation about birthright citizenship. Now, people can agree with me.…

Read More

Planning Around the Heat Is Still Part of the Gig

One of the things people tend to forget about gig work, event work, production work, DJ work, rideshare work, delivery work, and just about anything else that involves loading equipment is that the job does not start when the event starts. The job starts when you begin preparing for it. Sometimes that means checking the…

Read More

The Eighth Video

The eighth video was built around reviewing comments and responding to people who had taken the time to engage with the channel. At the time, the audience was still small, and I was not receiving a large volume of comments. Even so, I felt it was important to acknowledge the people who were participating in…

Read More