Sumit Gupta (@sumitgupta4all) header
Sumit Gupta (@sumitgupta4all) profile picture

Introverted engineer. Left 16 years in tech to go after things I wasn't sure I could do. Now I help founder-CEOs grow their companies and themselves. Amsterdam.

Amsterdam, The Netherlands
Joined November 2009
In 2011 I was an introverted software engineer full of self-doubt. I decided to organise an anti-corruption march. My mother said: "Yes, it is crazy. But you can do that. Just put one foot after the next." 400 people walked 11 km with us.
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Agree. Small companies often copy big-company process because it feels safer, then wonder why everything got slow. A ten-person team mostly needs people who talk to each other and decide things.
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In Jaipur, there's a trap for monkeys. A hole just big enough for an open hand, with a banana inside. The monkey grabs it and can't pull its fist out. It won't let go. Freedom is one open hand away.
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Pick one small thing you're gripping. Hand over one decision completely, including the right to get it wrong. Your hand will want to close again. That's how you know it was a banana. What are you gripping that's gripping you back?
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If you'd like to see how a startup founder, a farmer and a violinist each opened their hand, leave a comment. I'll share their stories.
In 2000, psychologists at Cornell sent a student into a room wearing a Barry Manilow T-shirt. He was mortified. He guessed about half the people noticed. Fewer than a quarter did. We negotiate with a crowd that mostly exists in our heads.
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Try this. Write down the decision you've been delaying. Under it, write the name of one person whose opinion you actually fear. One name. Not "people." Then do what almost nobody does. Ask them. Whose opinion has been running your calendar?
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Comment "CROWD" if you want the real stories of people who stopped performing for an empty room and went for their big thing.
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Every leader has a way of asking: am I doing well? For most of us the answer sits outside. The board. The numbers. The family. And outside things keep moving. The board changes its mind. A parent who wanted you safe now wants you successful. You never quite arrive.
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Try one question this week. Every morning: what would I need to do today to be proud of myself tonight? Every evening: did I do it? No attacking yourself either way. What would you need to do to be proud of yourself?
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Say "YES" in the comments and I'll share the behind-the-scenes stories of people going for the impossible. Athletes, artists, managers, all of them.
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A shipment is late. The customer says: "Fly everything to me." That would wipe out the margin. Two options. Lose the money, or lose the customer. The supplier found a third. Fly what's critical now, send the rest by road on Monday. It worked.
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Take your hardest either-or. Feel the fear for ninety seconds first. Write the two options. Underneath, write: "There is another way. I just don't see it yet." Then write five more options. Where are you a passenger, and what would the conductor do?
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Drop a comment and I'll send you stories of engineers, chefs and managers who found the third option when everyone saw two.
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