Dear healthcare, 2008 called.

Dear Healthcare, circa 2008–2012,

Congratulations. You just discovered computers.

I know, I know — you'd had computers for years. But this was different. This was HITECH. This was the American Recovery and Reinvestment Act. This was $30 billion of federal money pointed directly at your clipboard problem, and by God, you were going to fix it.

The plan was elegant in theory: digitize everything, connect everything, save everyone time, reduce errors, and usher in a gleaming new era of data-driven medicine. Clinicians would spend less time on paperwork. Patients would get better care. Information would flow freely between systems like a beautiful, frictionless river of health data.

My readers, The river sure did not flow.

"We spent a decade digitizing the paper. We forgot to digitize the thinking behind it."

What actually happened — and I was there, I have the scars — was one of the most ambitious, expensive and magnificently botched digital transformations in the history of any industry. Not because the tech was bad. But because we confused digitization with improvement and nobody stopped to ask whether the workflow we were transforming was actually a good workflow in the first place.

We took a broken paper process and made it a broken digital process. A faster broken process, sure. With more dropdown menus. Sounds familiar? Keep reading.

While I say that 'The EHR era' wasn't all that bad. It didn't fix healthcare as it promised but it sure created THE foundation. Buried under the implementation disasters, vendor wars and the physician burnout was something real. It gave the gift of Data- imperfect, siloed, maddeningly inconsistent — but there was Healthcare Data. And any data that exists, however messily, is the raw material for everything that comes next.

Fast forward to 2026. We have AI now. Smarter technology, bigger promises, more zeroes in funding rounds. And if you listen carefully at the next health tech conference, you'll hear something that sounds remarkably, uncomfortably familiar — the grand transformation narrative and the skeptical clinicians cracking fingers in the back row.

History, it turns out, has excellent copy-paste skills.

The question isn't whether AI will change healthcare. It will. The question is whether we'll ask the right questions before we build the thing this time— or spend the next decade in implementation meetings fixing what AI delivered.

We've been here before. We have the receipts. Let's use them.

Retrospectively — and presently — yours,
Someone who sat through the implementation meetings. Both times.