What do I hope to achieve, here?

Whether I’m traveling or holding still for a while, asking myself why I’m where I am and what ambitions I have for my time in that place helps ground me and reminds me to establish some foundational tenets and rough routines for my time there: however much time that might be.

Thus, if I’m living in Prague for four months, I may make explicit my desire to see the local architecture, eat the local food, and finish writing the book I’ve been working on.

Such elucidations help me develop daily rhythms and routines, but also create guideposts and waypoints I can use as milestones and destinations.

I can then calibrate my compass appropriately from the beginning and, if warranted, recalibrate it along the way. I may discover some new, vital thing while in the area, and can incorporate it into my lifestyle by re-asking this same question periodically.

What’s the point of what I’m doing right now?

This question scales up to the size of a multi-year ambition and down to the scale of a momentary lark.

Sometimes I’ll become so embroiled in my plans and processes that I lose sight of the underlying purpose of that thing. As a result, I’ll deviate from the intended path, going with a flow that is not my own, and if I’m not careful, ending up someplace I didn’t intend to be.

This isn’t always a bad thing: sometimes allowing the current to take you where it will can land you someplace new and interesting that you wouldn’t have thought to go on your own, if you even knew it existed in the first place.

But this question can account for that, too, as it’s possible to answer, “I’m seeing where this leads and enjoying the journey,” which is a perfectly acceptable response.

Most often, though, I find this question helps me check in to make sure I’m spending my time, energy, and resources appropriately, gives me a periodic reason to assess the bigger picture beyond the trenches in which I’m toiling, and reminds me of the overarching purpose behind whatever it is that’s currently occupying my time and attention—shows me where my labor of the moment fits into the grander cultivation-schema.

Is this productive or unproductive?

The most common application of this question, for me, is in determining how I engage with other people; perhaps most especially how I respond to things other people say and do.

When someone says something hurtful, or ignorant, or wrong, there are times and places in which it makes sense to challenge them on those things.

There are other times, though, in which such a challenge would be personally satisfying, but otherwise unproductive: it might make me feel superior or like I’d achieved some kind of vengeance, but the person on the other end might then trust me less, desire vengeance in return, or feel diminished in a way that is punitive rather than productive.

Far better, in some cases, to do the productive thing, even if that productive thing isn’t as viscerally satisfying.

You have a better chance of maintaining a relationship and sharing information with someone if they don’t see you as a spiteful, hurtful person who only wants to tear them down, and you’ll be more likely to achieve productive ends—helping someone see things from another perspective, for instance—if you can sacrifice some reflexes in favor of achieving larger ambitions.

And that’s true whether we’re talking about interactions with other people, the way we do our work, or how we think our thoughts.

Productivity is defined by each of us, individually, and will mean very different things in every context we might assess. But pausing to remind ourselves of our intended outcomes can help us make better choices in the moment, making it more likely that such choices will bring us closer to our goals, rather than pushing those goals further out of reach.

I find myself asking these guiding questions a lot, as they consistently help me align my actions with my values, grow as a person, and shuffle ever-so-closer to a more ideal—based on my definition of the word “ideal”—state of affairs.

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