June 3, 2026

I was talking with a friend recently, and the topic came up that a mutual CIO colleague had recently tendered his resignation. It’s for all the reasons you’d suspect, and many I’ve talked about before. Probably too often.

The old joke about the title CIO meaning “Career Is Over” ain’t far removed, and how the average tenure of a CIO is approximately 3 years.

Which brings me to a CIO joke…

A newly hired CIO is handed three sealed envelopes, left to him by his predecessor, with instructions to open one only when a crisis occurs.

• During his first crisis, he remembers the envelopes, and opens the first one. The note reads “Blame your predecessor.” The CIO does, and survives the crisis.
• Some time later, a second disaster strikes. The CIO opens the second envelope, which says “Reorganize.” The CIO restructures the department and lives to fight another day.
• When the third crisis hits, the CIO immediately opens the final envelope. It reads: “Prepare three envelopes.”

What strikes me, after all these years, is that the envelopes joke isn’t really about incompetence or inevitability. It’s about the cost of a role that’s still maturing faster than organizations know how to support it.

CIOs aren’t failing because they’re bad at the job. They’re burning out because the job is still misunderstood — still treated as a tactical function dressed up in a strategic title. Tip: if your CIO reports to another C-titled official (other than the CEO that is), then they’re not really a CIO. They do not have ownership of their domain.

The organizations that thrive are the ones that finally recognize IT leadership for what it truly is: strategic architecture and stewardship of the digital nervous system of the enterprise. Not order-taking. Not heroics. Not envelope-opening.

And maybe that’s the real punchline: the CIO role isn’t “Career Is Over.” It’s “Culture Is Overdue.” Overdue for clarity, for respect, and for the kind of partnership that lets leaders lead instead of constantly preparing the next set of envelopes.