How Are You Sleeping?
This article is part of Finding the Words, a newsletter that delivers practical insights on the day’s issues.
Only mid-month into this new year, and I’m hearing a familiar refrain from mission-driven leaders, including those in my own organization: overwhelmed, uneasy, holding a lot. The calendar may have reset to January, but the complexity didn’t reset with it.
And for all those well-intentioned efforts to reduce complexity….well, they only get us so far when life keeps throwing more at us. Which makes learning to manage complexity all the more important.
For years, when I noticed a client feeling this way, I’d ask, "What's keeping you up at night?" The idea is simple: name the challenge and then begin to chip away at it.
It’s an important question, but as I've watched people sort through their answer, I found that it rarely helps ease the feeling of tension.
So, in recent conversations, I’ve started asking a different question. Not "what's keeping you up?" but instead, "what would help you sleep better?" It’s a small twist, and it changes everything.
“What’s keeping you up?” invites the full inventory of risk, uncertainty, and responsibility. You know, those things that don’t resolve easily and aren’t fully within our control.
It's an important question, yes—but also a question that can leave us spinning.
“What would help you sleep better?” does something else. It creates space for relief.
And when I ask it, something fascinating always happens.
People don't ever respond in abstractions. They don’t say world peace, or moonshot cures or fully funded budgets.
They say things like:
Knowing I've figured out how to answer a nagging question.
Knowing I’ve made progress on my goals.
Having my team in sync.
Getting through that hard conversation.
What helps us sleep better is often surprisingly concrete. And almost always, it’s something within our control. That matters—especially in moments when it feels like too much is outside our control.
So, when you next have that feeling of unease, try flipping your focus and ask:
What is one thing that will help me rest more easily?
You don't need to recite the whole list, and you don't need to name every element of the five-year strategy. Just one thing that will help you move forward.
And that one thing, well, it's absolutely OK to ask for help.
You can't do it all alone. You're not expected to. And in times of complexity, when you're feeling overwhelmed, sometimes the very best thing is knowing that you have someone you can turn to, talk with, and work through the complexity together.
By focusing on what we can do or who can help, we regain momentum—even if it doesn't solve everything. Because progress, especially in uncertain times, is rarely dramatic. More often, it’s quiet and incremental. It's bit by bit.
So, if nothing else, remember this: You don’t need all the answers solved by bedtime. You just need to ask yourself, gently and honestly: What would help me sleep better tonight?
Start there, and see what happens next…
This post is part of the Finding The Words column, a series published every Wednesday that delivers a dose of communication insights direct to your inbox. If you like what you read, we hope you’ll subscribe to ensure you receive this each week.
