Get Rid of the Boring

“If you were financially independent – say you had $100 million – would you still work here?”

Patrick O’Shaughnessy of O’Shaughnessy Asset Management told me yesterday that they ask every employee this question.

Ideally the answer is “yes,” of course. But Patrick said most people add a twist. “I would still work here, but I wouldn’t want to do X, Y, or Z anymore,” they say.

X, Y, and Z tend to be repetitive and monotonous tasks that no one likes doing. And those, he said, tend to be the tasks you should try to automate out of your daily work.

The question is almost a trick. The point isn’t to gauge your loyalty. It’s to uncover your job’s inefficiencies.

Data entry. Formatting. Documenting. Calculating. Reporting. Modeling. Invoicing. Testing.

Few people enjoy these tasks because they’re rules-based and don’t require much creativity, which are exactly the kind of mind-melting things software can increasingly take off your plate.

What’s often left over is creative work that constantly forces you to do new things in new ways.

And that, you might find, is the kind of work that keeps you so engaged you’d be happy to do it without a paycheck.

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