Second Brain

Delegate What You Love, Not What You Hate

The Story

When Boris’s Instagram infrastructure project got too big to run from Japan, he needed to delegate. He brought in Jake Bolum to lead it on the ground in the US.

Boris’s rule for delegation, borrowed from Andy Grove’s “High Output Management”: never delegate the thing you don’t want to do. Always delegate the thing you do want to do and that you know well. Why? Because if you know the work deeply, you can monitor progress effectively and tell when something is going off track. If you delegate something you don’t understand, you won’t notice when it veers in the wrong direction.

With Jake, Boris had high trust. “The more trust you have, the less you have to check in. And with Jake, he’s so good technically and so proactive, there’s just very little I had to do.”

Boris gave up direct visibility for organizational impact. He “led from behind” by letting US-based engineers take the visible leadership roles while he guided from Japan. His reputation grew through enabling others rather than hoarding the spotlight.

Lesson for Creators

Conventional wisdom says outsource the tasks you hate. Boris says the opposite: delegate the thing you love and know well, because that’s the only way you can evaluate whether it’s going well. If you’re a creator who loves writing but hires a ghostwriter for your newsletter while you focus on admin work you hate, you’ve got it backwards. Delegate the admin. Keep the writing oversight, even if someone else drafts it.

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