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How's work?
Not just at happy hour—it's a question worth asking yourself
A catch-up question, a check-in question, a kick off the conversation question.
"How’s work?" has become a go-to question of mine—the answer revealing important information on the state of my conversation partner's work life.
Originally conceived as a happy hour question—a trio of events on a recent day had me expanding its use as one that doesn't have to wait for an after work cocktail at all, or coffee, or the phone call catch-up for that matter—it's also a question to ask yourself.
A friend, deep in healthcare startup life, was venting about the emotional whiplash of the whole thing—the dreaming, the planning, the burning through cash—and then the waiting. The particular agony of a signed contract that hasn't arrived yet. And then, same day, the relief of it finally coming through. The full arc in an afternoon.
Later, a conversation with an acquaintance about a team member who wasn't pulling their weight—at least not in the ways the acquaintance needed. "More proactive resourcefulness," was how they put it. The team's responsibilities were growing. The headcount wasn't. And somewhere in the conversation it became clear that the acquaintance had played a real role in creating the conditions they were now frustrated by.
And then, the one nobody wants: layoffs. People I knew. That first wave of concern for them—what comes next, are they okay—and then the quieter, more uncomfortable question: what does this mean for me?
Three events. Three different situations. And in all of them:
How's work?
This day got me thinking differently about the question. Because none of those three situations called for immediate action. What they called for was a moment, maybe several moments, to take stock—not to ask someone else the question, but to turn it inward.
A lot of what we absorb at work—the anxiety, the frustration, the low-grade dread—comes from systems and structures doing what systems and structures do. Identifying it doesn't make it disappear. But it can change what you do with those feelings.
It's here where I believe "How's work?" becomes essential, and the more often you ask, the more useful the answer gets.
Asking it regularly of yourself—as a check-in with your emotional state, at the start of the day, after a hard meeting, on the drive home—the answers get more specific. "I'm anxious about this conversation." "I felt dismissed in that meeting and I'm still carrying it." "I've got an opportunity to do something different here." "That actually went better than I expected."
How's work right now? Not in the broad "how are things going?" sense. But right now, today, in the wake of this conversation or that piece of news. What's happening? What are you feeling? And importantly—is this your stuff to carry, or is this our system of work doing what it does and handing you something that you didn't ask for?
Stepping slightly outside the experience to get a look at it. Not to fix every problem. Not every problem can be fixed. Just to know where you are, how you're feeling.
It's a skill.
Work is hard. And we do a lot of it. So it's okay to reflect. Perhaps a lot more than you might think. In the moment. Before the moment. After work when you're in your chill zone.
Take a minute: How's work?
Around The Water Cooler ⛲
Nothing but AI highlights from my reading this week. And you know what makes for a boring conversation? More AI thoughts. So instead, how about just a little quiet:
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Thanks for reading. Hit reply and let me know your thoughts.
How To Work is healthcare-focused work design inspiration (from the experts!) to nudge your perspectives and practices into better alignment with the world of work as it is, and away from what it was. Here’s my take on what we’re working through.
