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How Do You Deal With Ambiguity While Doing Deep Work?


Chapters

0:0 Cal's intro
0:15 Cal reads the question about ambiguity and Deep Work
0:27 Cal suggests to work at the way your career is going
1:19 Cal talks about Derek Sivers
2:40 Cal's summary

Transcript

All right, let's see what we have here. Next is a question from Lily. Lily asks, "Given the nature of deep work, it is often hard to determine the quality of the work produced because it's rather nuanced. How do you deal with such ambiguity?" Well, Lily, I would say maybe look at how your career is going.

So what is the non-nuanced factor here? Am I getting promoted? Is my salary going up? Am I in more demand? Am I being given more interesting projects? That's a pretty good proxy for am I producing high-quality output. So even if you can't look at the thing you just produced in the small scale, the report you just wrote, the strategy memo you just put together, and say, "Hey, this is an A+ or a B+ or whatever," if over the course of six months or a year you're getting more interesting work, you're being eyed for advancement, other people are trying to poach you away, that's a pretty good sign that things are going well.

I mean, this reminds me of the maxim that I included in my book, "So Good They Can't Ignore You," a maxim that came from the entrepreneur Derek Sivers, where he said, "When you're working on new things, deep things, money is a good neutral indicator of value." And what he meant by that, and we've mentioned this before on the show, but what he meant by that was people are reluctant to give other people their money.

It's not a big deal to ask me to give you praise. I'm happy to do that. That doesn't cost me much to be, "Hey, this looks great." You know, like, "Hey, Jesse, I really like what you're doing over there. Keep up the good work." It doesn't cost me much to give praise.

Ask me for money, though, I'm probably not going to give you money unless the stuff is actually good, unless the work is actually good, unless there's actually value in the product you're selling, there's value in the position you're filling in the company. So it's actually a really great way of getting honest feedback.

So if you're getting promotions and raises, if people are trying to hire you away, then you're probably doing better work. And I always make the distinction, Derek was not saying money is what is valuable. So he wasn't saying your goal, therefore, should be to acquire as much money as possible.

Obviously, he did the opposite. When he sold his company, CD Baby, for something like $20 million, he gave all the money away. It wasn't about having money. It was about, if I'm making money on this, if people are willing to pay for this, if people are willing to hire me for this, and that means this has value.

And if they're not, I need to go back to the drawing board. And so keep that in mind. Look at the unambiguous indicators of your career going well. If those are trending in the right direction, you're probably doing the right amount of deep work and applying it to the right types of things.

If those indicators aren't going well, then maybe it's time to rethink things.