The Rule I Never Tell My Clients
by Diane · 12 July 2026 · Psychology & Living
Diane is a career coach in Chicago who has spent twelve years helping people who want to quit their jobs but don't know what for. Her key tool is a simple question: when did you last work two hours without checking the clock? Her unspoken rule is that most people already know what they want — they just need someone to listen while they say it out loud to themselves for the first time.
Diane works as a career coach in Chicago and has, over twelve years, guided more than four hundred people wanting to quit their jobs without quite knowing what for. Most arrive with the same question: how do I find out what I really want? Diane has learned that the question is almost never answerable as asked. So she's stopped answering it and asks a different one instead.
She asks: when did you last work two hours without checking the clock? The answer, she says, reveals almost more than any personality test. One client, an accountant, couldn't recall a single such hour in five years — until he mentioned spending weekend afternoons sorting his daughter's sports club accounts, never once feeling, for a moment, like work. He now works in finance for a non-profit, for less money, but, as he puts it, for the first time without that pull in his stomach on Sunday evenings.
The rule Diane never says out loud, because it sounds too uncomfortable, is this: most people already know what they want. They've just learned to ignore it, because it looks impractical, unprofitable, or embarrassingly small. Her job as a coach is rarely to find something new. Mostly it's to let someone believe what they've known for a long time.
"People pay me to tell them what they want," she says. "But really they're paying for someone to listen while they say it out loud to themselves for the first time."
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