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Use the ‘Surround and Conquer’ technique to make hard things easy

David Kadavy
2 min readMar 30, 2022

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There’s something you want to learn, or a project you want to take on. But it’s too big or too hard. The walls of that city are too high to scale, too thick to bust through.

Some challenges are too great to face head-on. Instead of doing the one big thing, do a bunch of small things that make the big thing easier.

You have to surround before you conquer.

If you want to appreciate Shakespeare, but you can’t understand what the f*ck Hamlet is talking about, surround, then conquer. Watch the movie, read the Wikipedia page, then read the play. For good measure, try to explain it to a friend when you’re done.

If you want to learn Spanish, but hate memorizing conjugation tables, surround, then conquer. Watch your favorite Seinfeld episode on Netflix, with Spanish overdubbing. There will be a bunch of things you’re curious to look up.

I tackled my first book head-on, which was excruciating, but now I write my books with the surround-and-conquer strategy: I write a bunch of tweets. I read a bunch of research. I take a bunch of notes. I write some newsletters, then articles. The next thing I know, this once-intimidating idea is nearly fully-formed in my mind’s eye.

If you surround before you conquer, you don’t have to scale the wall. The gates will be wide open.

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David Kadavy

Author, ‘Mind Management, Not Time Management’ https://amzn.to/3p5xpcV Former design & productivity advisor to Timeful (Google acq’d).