The situation“Every option on the table feels the same and none of them excite me.”
Leaders who made the same call — what each did, and how it went.
WorkedHalf-workedShouldn’t have been tried
Before founding Leading Niche in 2010, Tamara Nall was on the partnership track at Booz Allen Hamilton — the credentials, the projects, the set of senior colleagues who were about to say yes.
When Zhang became CEO of Alibaba in 2015, the company was already one of the largest e-commerce businesses in the world, and the available strategic options all looked similar — more categories, more markets, more merchants, more logistics.
When Whitney Wolfe Herd returned to Bumble as CEO in March 2025, the dating-app market was running on a set of growth metrics the industry had accepted for years as the measures of health: paying user counts, monthly active users, revenue growth.
Gowalla launched as a location-based app with a distinctive vision: see the world through the places your friends had been.
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