We can ask ourselves the same question for weeks without ever really trying to answer it.
It comes up in the car. In the shower. In the few minutes between finishing one thing and starting another. We turn it over, feel the familiar frustration of not knowing what to do, and then get yanked toward whatever shiny squirrel crosses our path next.
Eventually, it can feel like we’ve spent an enormous amount of time working on the problem.
But...have we?
When we talked with our friend Mark England, co-founder of Enlifted, I realized something about the questions we keep carrying around in the backpack of our minds: It’s easy to give enough time and attention to ask them, but it’s much harder to make the effort to answer them.
In an episode we put out a while back, Mark introduced us to a principle called Kidlin’s Law: “Any question sufficiently worded and written down is half answered.”
I’m not sure we need to take the fraction literally — writing it down won’t magically resolve a career decision, repair a relationship, or put us on the path toward health. But I do think Kidlin’s Law points to something useful.
We can’t expect an actionable answer to a big question if we aren’t willing to do the work of asking it clearly.
Five Questions That Feel Like Five Hundred
A question in our heads rarely travels alone.
Should I take on that project? Do I even have time? Why do I keep saying yes to things? Would turning it down hurt the relationship? Maybe I need to rethink the whole business.
We start with a decision about one project and, a few seconds later, we’re questioning every professional choice we’ve ever made. No wonder it feels like a lot to sort out between answering an email and making lunch.
When we put it on paper, though, that enormous problem starts to look like several separate questions. Some are about capacity. Some are about money. Some are about a conversation we’d rather avoid. They’re related, sure — but they don’t all need to be answered at once.
In our conversation with him, Mark described this as a kaleidoscope: lots of fragments moving around, never quite settling into a clear picture. Five questions can feel like five hundred when they keep circling through everything else we’re trying to hold in our heads.
Writing doesn’t eliminate complexity, but it gives it somewhere to sit still.
Once the words are on the page, we can separate one decision from another. We can notice where we’ve bundled three problems together, or where we’ve quietly promoted an assumption into a fact.
And sometimes, we discover that the question we’ve been repeating isn’t actually the one we need to answer.
Give the Question Something to Work With
Consider this one:
Why am I always overwhelmed?
It’s an understandable question, but it doesn’t give us much to work with. “Always” turns a current experience into a permanent condition, and “why am I” can quickly become an invitation to catalog our character flaws.
We set out to examine the calendar and somehow end up putting ourselves on trial.
A more useful version might be:
Which commitments are taking more time than I have available? Or: Which yes have I given that I wouldn’t give today with the information I have?
Now we have something to examine: our responsibilities, the hours available, the gap between how long we thought something would take and how long it actually takes, and the difference between what we thought something might be and what it actually became.
That might lead to another question:
Which commitment can I renegotiate this week to make room for what matters most?
The workload hasn’t changed. Neither has the number of hours in the day. But we’ve moved from a vague feeling about ourselves to a question whose answer could help us do something.
Three qualities are useful here:
Specific, rather than vague. “How can I make time for two workouts this week?” gives us more to work with than “Why can’t I get my act together?” We can open a calendar and start answering the first one. The second mostly invites another round of frustration.
Neutral, rather than blame-focused. “What needs to be clarified between us?” leaves more room for a useful conversation than “Why does this person never understand me?” We don’t have to pretend we aren’t frustrated. We’re just trying to ask a question that helps us understand what to do with that frustration.
Outcome-focused, rather than only problem-focused. “What would help me prepare for this conversation?” directs our attention differently than “How do I stop dreading it?” One keeps us staring at the feeling we don’t want. The other gives us a way to begin.
The point isn’t to make every question cheerful or lightweight. It’s to make it answerable, which is necessary if we want to act on it.
❤️🔥
Nobody drifts on purpose, just like nobody chases excellence by accident.
That’s why we built ChaseTracker—a simple method for identifying, tracking, and chasing what matters.
One Thing Per Question
There’s another constraint worth borrowing from Mark: Ask about one thing at a time.
Should I change jobs, move closer to family, and finally start working for myself?
Those decisions may influence each other. But when we squeeze them into one question, we make it harder to see what each decision actually requires. It can start to feel like we need to figure out the next twenty years before we can do anything next Tuesday.
Separating them gives us a better chance:
What would I need from a new job to make leaving this one worthwhile?
What would moving closer to family change about daily life?
What could I do over the next three months to test working for myself?
We might discover that one answer depends on another. We might also discover that a decision can wait, or that a small experiment would tell us more than another month of thinking about it.
We don’t need to solve the whole life puzzle before we can move one piece.
Draft, Craft, Then Let It Breathe
Mark calls his process Draft, Craft, Supercharge. The names are memorable; the practice itself is straightforward.
Draft: Write down three questions we’ve been carrying around. They can be about work, training, family, or something we’ve been putting off. Use full sentences, but don’t worry about making them good yet. Getting the question out of our heads is the first bit of work.
Craft: Read the questions back and experiment with the wording. Are we asking about one thing at a time? Can we be more specific about the situation, less interested in assigning blame, or clearer about the outcome we want? A timeframe can help, too: what we can do this week is a different question from what we might do someday.
Supercharge: Read the revised questions aloud, pausing to take a comfortable breath between them. We’re giving ourselves a chance to hear what we’ve written instead of immediately racing ahead to an answer. Does the question make sense? Does it describe what we actually want to figure out? If not, we can change it.
We don’t need to produce a revelation. We might see a next step immediately. We might realize we’re missing information, or that the next step is a conversation with someone who has it.
Either way, we’ve given the question more than another passing thought between the shiny squirrels racing all around us.
Clear Enough to Begin
One thing I appreciate about Mark’s approach is that he treats the wording as something to experiment with, not something to get perfect.
He offers an alternative and asks which version the person prefers. Sometimes adding a timeframe helps. Sometimes it narrows the question too much. The aim is a question we can work with, not a sentence that passes somebody else’s test.
That distinction matters, because it’d be pretty easy to turn this into another reason to delay: I’ll act once I’ve found the perfect question.
Do that, and we’re still avoiding the decision, only we have a notebook open while we do it.
The writing is supposed to help us engage with what’s in front of us. Sometimes we’re missing information. Sometimes we’re facing a genuinely difficult trade-off. And sometimes we know what to do and would really rather not do it.
A clearer question won’t remove those difficulties. But it can help us tell the difference, which gives us a much better chance of choosing a useful next step.
We can keep asking ourselves the same question in the spare minutes of our days. Or we can sit down, put it on paper, and give it the attention we keep saying it deserves.
Not until we have the perfect answer. Just until we’ve asked it clearly enough to begin.
