About Don’t Know Jack
Every week, Selena deploys something. Bart objects. JJ asks what it costs. Raja explains it in one line. Loo Loo Paper Parts keeps going.
One narrative article every Tuesday, built around a cloud decision that went sideways in a meeting you have probably attended. The characters and the company are fictional. The decisions are not.
The problem
Cloud literacy used to be optional for business professionals. It is not anymore.
The knowledge demanded of project managers, finance leads, product owners, and executives working alongside engineering teams has changed materially in the last three years. Cloud spend is a board conversation now. Security decisions carry regulatory exposure. Architecture choices made in sprint planning show up on the quarterly bill and in the audit report sixty days later. The professionals in those conversations are expected to engage, not just to approve. Most of them want to. They just need the technical concepts explained in a language that was designed for them, not for the engineers in the room.
Certification was the traditional answer. It is the wrong answer for most people in this audience. Cloud certification exams test whether you can identify the correct answer in a controlled scenario. They do not test whether you can ask the right question in a meeting, push back on an estimate that does not add up, or understand why the decision made on Tuesday is going to cost you in the next billing cycle. The exams were designed for engineers. The problem they solve is not the knowledge problem you have.
AI has reduced many technical information problems and made the judgment problems harder. You can ask any AI assistant what a mount target is and get a technically accurate answer in four seconds. What you cannot get is the accumulated understanding of why it matters, when it matters, and what question to ask next. That is what Don’t Know Jack is for.
What you get on Substack
One article every Tuesday in plain language. Business consequences first. Zero jargon left unexplained.
What you get at dontknowjack.club
The full daily product. One cloud concept and one question in your inbox every day at noon. The moment you click your answer, the full rationale loads: why the correct answer is correct, why every wrong answer is wrong, and what one word change does to the whole answer. Selena’s Crossword arrives every Sunday at 5pm, built from the week’s article. Free. No credit card.
Who wrote this
In 2010, a product manager at Global Knowledge named Ashley Neace needed someone to build a training course on cloud and virtualization. The conversation went roughly like this: “Mark, do you know all the cloud?” “Oh yes Ashley, I was just outside checking the weather patterns.” I did not know all the cloud. I knew virtualization and networking. I had looked at the public cloud and dismissed it as interesting but possibly a fad.
I built the course anyway. And somewhere in the process of building it I realized I had been wrong — not about a detail, but about the direction the entire industry was heading. The public cloud was not a fad. It was infrastructure, and it was going to run everything. What struck me immediately, and has not stopped striking me since, was how badly the people who built it explained it. The documentation assumed you already understood what it was trying to teach. The vendor training recycled the same terminology without ever grounding it in anything a non-engineer could hold onto. The words were technically accurate and practically useless to anyone who needed to make decisions rather than write code. Since then I have spent fifteen years trying to fix that specific problem for very smart people who needed cloud skills and kept getting handed cloud jargon instead.
Fifteen years of watching intelligent, capable professionals get caught off guard by concepts they were never given a fair chance to understand. That is the lived experience behind every article, every question, and every rationale in Don’t Know Jack.
I have also realized that most technical cloud training is built on a fundamental flaw. The words it uses mean something specific and counterintuitive in a cloud context, and the training never stops to explain the gap. It assumes you already speak the language it is supposed to be teaching you. Serverless, for example. We checked. There’s servers. Lots of them.
The resume behind that fifteen years, if you need it:
Mark Wilkins. Five years as Cloud Evangelist at IBM’s SoftLayer division. AWS Solutions Architect and SysOps certified. Cloud training content for O’Reilly Media, LinkedIn Learning, and Pearson Education.
The technical content is accurate because it has to be. The plain language is deliberate because the people who need this are not engineers. Handing them documentation written for engineers is not education. It is obstruction dressed up as helpfulness.
The checkbox course your organization will eventually voluntold you into is not going to help you. This will.
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