That division between passive optimizations and direct improvements feels like a great split.

For me, what you called passive optimizations are best at removing context switching. Keyboard shortcuts keep me from moving my hand to the mouse and finding a button I need. Tools like Alfred keep me from paging around to find the app I need. Text expanders, more than speeding up my typing per se, keep me from typing repetitive things that are annoying to keep entering, or help me remember things like HTML snippets that I'd otherwise forget. The danger is that you can go too far and essentially build a Rube Goldberg machine of little optimizations that take more time to figure out than they save.

Longterm, the biggest challenge to me is retraining myself what actual productivity is. At a certain level, replying to every email is being productive (say, when doing support for a new product). As the product matures and the volume increases, being productive is automating that (something that isn't worth the effort at smaller volumes). Then ideally as the company and team grows, your role changes and perhaps now being productive would mean answering no emails and instead focusing on broader team goals. That to me is the hardest thing to get right, to get myself to switch away from busywork that feels productive and then instead to focus on what's most impactful at the moment.

I feel the need to disambiguate here.

• There's Productivity in its true, perfect form. It's an elusive ideal to strive for, one that involves both quantity and quality – and aspects of quality that yield benefits we might not have thought of before or even ever be aware of.

• And then there's #productivity, the over-obsession that people and organizational structures often have with measurable output. This type of productivity is easily confused with machine-like efficiency. Often somewhat disconnected from the things that truly matter, these "proxy metrics" usually favor quantity as opposed to quality. They are definitely useful to a degree, especially when it comes to pleasing stakeholders whose sentiment matters to me, but I personally find myself resisting them.

So when you ask "how you personally assess productivity," it's a moving target, one that definitely keeps me up at night. What am I optimizing for?

So after spending ~5 years reading, watching, trying, talking, writing about productivity, I came to the conclusion that productivity isn't a goal, it's a byproduct. And the more you think about it the less you are actually living it.

Today, I think things like POMODORO, GTD, typing faster, {{insert another productivity keyword here}} are just shiny things to keep your mind away from the real stuff.