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There are always more things to do than there is day to hold them. Accepting this reality has been one of the stranger lessons of this season of my life. Building Transcendent Software, taking care of our property, keeping up with the Jibo Revival Group and everything happening there, writing, thinking through CoffeeBreak and the products I want to launch inside of it, helping clients, staying…

I missed my normal Sunday writing window this week. That is not a complaint. It is just what happened. We hosted a party on Saturday for the 250th birthday of the United States, and by the time Sunday came around, the weekend had already become the lesson. The party was spectacular. The fireworks were great. Friends came over, kids ran around, food was cooked, decorations went up, people helped…

I meant to write this before the weekend. That was the plan, anyway. Sunday is supposed to be blog day. I had the idea. I had the theme. I had the intention. Then life happened. Good life, but life. On Saturday we hosted a party for the 250th birthday of the United States. It was spectacular. Friends came over. People pitched in. There was food, setup, decorating, cooking, cleaning, kids…

Most conversations about artificial intelligence begin with capability. Can it write content? Can it summarize documents? Can it analyze data? Can it automate a process that currently requires human effort? Those questions are important, but they are also relatively easy to answer. Modern AI systems are increasingly capable, and each new generation of tools seems to push the boundaries a little…

I used to think the reward was the result. The launch.The finished project.The clean before-and-after.The moment where all the work finally turns into something visible enough that other people can understand it. And those moments are real. They matter. But lately I have been noticing something else. A lot of the reward is not waiting at the end. It is hidden inside the routine…

Most businesses do not start with an AI problem. They start with a business problem. Something takes too long. Something breaks too often. Something depends on one person remembering every hidden step. Something lives across spreadsheets, inboxes, old software, shared drives, tribal knowledge, and a few “just ask Jake” moments that somehow became part of the operating model. Then AI enters the…

When I first started thinking seriously about CoffeeBreak, I was thinking about software. That makes sense. Software is the world I know best. I have spent a long time around teams trying to plan, build, review, test, ship, support, fix, and improve systems. I have seen the good version of that work, and I have seen the version where everything depends on memory, heroics, scattered notes,…

AI has gotten very good at creating impressive moments. A prompt turns into a plan. A model summarizes a document. A chatbot answers a question. A prototype looks magical in a five minute demo. That is useful, but it is not the same thing as a working business system. Real businesses need more than a clever response. They need software that fits into existing workflows, respects approvals,…

I have been thinking a lot about the word expert lately. It is a strange word, because most people do not become experts while looking like experts. They become experts while trying things that are half-working, while fixing something that broke for the third time, while realizing the elegant idea from yesterday does not survive contact with the real world. That has been true for most of my…

Being a builder is a skill. I have spent the last few days helping a client prepare for a website launch. He designed the vision. Another company handled the original build. I came in afterward to help tie everything together, refine the rough edges, and make the entire experience actually work the way it should. That part matters more than people realize. I would never speak negatively about…

I have always been someone who appreciates the changing of the seasons. There is something grounding about them. Spring becomes summer. Summer becomes fall. Life moves forward whether we are ready for it or not. Memorial Day, while not technically the start of summer, has long felt like the unofficial beginning of it to me. The pools open. The grills fire up. Baseball settles in. The evenings…

Right now, most AI conversations are obsessed with one thing: the model. Which model should we use? Which one is faster? Smarter? Cheaper? More open? More capable? Those are fair questions. They are just not the most important ones. A model matters, but a model by itself is not the system. If the model is the instrument, the system is the orchestra. And in business, the magic rarely comes…