Anna Wintour Doesn’t think in Decades Anymore

Anna Wintour doesn’t think in decades anymore. She thinks in two-year visions. Shouldn’t we all?

On a recent New Yorker podcast, she described choosing her successor, Choe Malle: “We saw a lot of amazing, amazing candidates, and Chloe consistently came back with the clearest vision and the most original ideas and understanding of what a Vogue in—well, I don’t think we can talk about five, ten years anymore—in two years is going to look like.”

That line stopped me. We can’t talk about five or ten years anymore. Culture, technology, and politics are changing too fast.

And yet, paradoxically, vision matters more than ever.

David Remnick observed about Anna herself: “She had a clear sense of what she wanted her publication to be about.”

That’s the difference: prediction is a gamble. Vision is a choice.

Yes, insights, trend reports, and spreadsheets full of market data are important, but they all look backward. The real skill is transforming those signals into a point of view on what comes next.

The leaders who thrive aren’t the best at guessing the future—they’re the ones bold enough to define it.

Or as Anna herself put it: “David, I only look toward the future.”