Many entrepreneurs credit strategy, timing, or gut instinct for their success. For one billionaire, a cult novel about surrendering control to a dice roll was an unlikely early influence.

When you face a challenge, how do you know how much effort to put into solving it? How do you determine whether you’re preparing or procrastinating?

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Hello and welcome to Modern CEO! I’m Stephanie Mehta, CEO and chief content officer of Mansueto Ventures. Each week this newsletter explores inclusive approaches to leadership drawn from conversations with executives and entrepreneurs, and from the pages of Inc. and Fast Company. If you received this newsletter from a friend, you can sign up to get it yourself every Monday morning.

Being penalized for using flexible working policies—remote work, hybrid work, parental leave, and more—can be subtle, or screamingly obvious.