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From http://www.paulgraham.com/kids.html,

I hate to say this, because being ambitious has always been a part of my identity, but having kids may make one less ambitious. It hurts to see that sentence written down. I squirm to avoid it. But if there weren't something real there, why would I squirm? The fact is, once you have kids, you're probably going to care more about them than you do about yourself. And attention is a zero-sum game. Only one idea at a time can be the top idea in your mind. Once you have kids, it will often be your kids, and that means it will less often be some project you're working on.

I have some hacks for sailing close to this wind. For example, when I write essays, I think about what I'd want my kids to know. That drives me to get things right. And when I was writing Bel, I told my kids that once I finished it I'd take them to Africa. When you say that sort of thing to a little kid, they treat it as a promise. Which meant I had to finish or I'd be taking away their trip to Africa. Maybe if I'm really lucky such tricks could put me net ahead. But the wind is there, no question.

Is wind children, ambition, or something else?

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  • The first emboldened sentence is an idiom. – Decapitated Soul Mar 31 '20 at 6:00
  • @DecapitatedSoul Thanks. It makes sense now. sailing close to this wind = sailing into the wind – tejasvi88 Mar 31 '20 at 6:09
  • Sail close to the wind: to do something that is dangerous or only just legal or acceptable. – Decapitated Soul Mar 31 '20 at 6:15
  • I'm not sure about the last sentence. – Decapitated Soul Mar 31 '20 at 6:19
  • Another literal meaning is to sail against the wind. The last sentence says that the wind (downsides of having children) still exists irrespective of the author's tricks. – tejasvi88 Mar 31 '20 at 6:34
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In the second occurrence: "Maybe if I'm really lucky such tricks could put me net ahead. But the wind is there, no question*", wind = risk or danger.

This use is uncommon but appropriate here because the writer is extending the metaphor of sailing close to the wind. He is explaining that his "hack" (= method of solving a problem) does have some risks/dangers/possibilities of going wrong, etc.

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Sailing close to the wind.

To understand this metaphor, you really have to understand the basics of sailing.

No boat can sail directly into the wind. So if your direction is in the way from which the wind is coming, you need to "tack" - i.e. sail from side to side in order to make progress.

The narrower the tacks you take, the faster you complete the course. That means "sailing close to the wind", not directly up-wind but close to it. You need to keep the sheets (sails) close-hauled, and (in a small dinghy) move your own weight to the other side to prevent capsizing.

But if you do not quite get it right, and a gust of wind arrives from the other direction, the boom can crash over and potentially knock you overboard. Certainly your weight will be wrongly positioned.

I have never sailed a large boat but I assume the same principle applies.

That is why, unless you are very experienced, it is inadvisable to "sail close to the wind".

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