Generative AI, Memory and the Value of Struggling
- Bill Holmes
- Sep 26
- 3 min read

My first job was as a cashier at Piggly Wiggly, a southern grocery store. The registers were manual, which meant I had to calculate sales tax on every order — fast — with a line of impatient customers watching. That pressure sharpened my math skills in a way no classroom exercise ever could.
Later, in my first graduate-level statistics course, the professor insisted we do calculations by hand. At the time, it struck me as absurd. Why grind through formulas when a calculator could do it instantly? But the act of struggling with the math by hand gave me something no device could: the ability to spot statistical errors with my own eyes. That pain turned into pattern recognition.
Fast forward to today, when most people carry more computing power in their pocket than NASA used to land on the moon. Why memorize anything? Why practice skills you can outsource? Why not just let AI do the heavy lifting while you scroll LinkedIn?
PMI draws a line between explicit knowledge (the stuff you can document, Google, or have an AI spit back at you) and tacit knowledge (the judgment, instincts, and “feel” you only develop by doing).
Explicit knowledge is everywhere. It’s in your PMBOK, your Kanban board, your AI chatbot’s cut-and-paste status report. Useful, yes. But tacit knowledge — the ability to sense when the numbers don’t add up, when the plan is brittle, when the team is quietly unraveling — you don’t get that from a prompt. You get it by sweating through the math, building the WBS yourself, or calculating sales tax with six angry customers tapping their feet.
Tacit knowledge is what lets you recognize when the explicit knowledge is lying to you.
Generative AI is the calculator of our era. And like the calculator, it’s indispensable — but dangerous if you don’t already know the basics.
AI can generate a risk register, but if you’ve never built one manually, how will you know what’s missing? AI can draft a schedule, but if you’ve never fought through a critical path yourself, how will you know if the dates are fantasy? AI can summarize lessons learned, but if you’ve never run a retrospective, how will you know if anything meaningful was actually learned?
The tool is only as good as the human checking it. Without tacit knowledge, you’re just a passenger in the back seat of your own project.
Memorization, manual math, handwriting — these aren’t quaint rituals from a pre-digital world. They’re the scaffolding for real expertise. Without them, you’re just another professional who “knows where to click.”
AI isn’t here to replace project managers; it’s here to augment their experience!. And the only way to get it is the old-fashioned way: you earn it.
So no, the question isn’t “should we still memorize?” The question is: when the machine hands you garbage wrapped in confidence, will you even know?
Coda
If organizations now feel the need for a Value Delivery Office to track benefits realization, isn’t that really an indictment of how poorly benefits management has been practiced all along? Shouldn’t benefits realization be the responsibility of every project from the start, not something outsourced to yet another layer of bureaucracy with a new acronym? We’ll talk about that next.








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As a young senior NCO in the Army Guard, an old goat told me "knowledge without experience, is like having water without a bucket to hold it in". It took years of experience to understand this. Organizations will always look to decrease costs, and a smart organization increases project management skills as they decrease other costs. We retain the organizational knowledge that can't be replaced by AI or offshoring.