I’ve been traveling and meeting strangers for decades now, on airplanes, at conferences and church functions, in waiting rooms. Somewhere along the way, I noticed something about the questions most people reach for when they sit down next to someone they don’t know.
What do you do for a living? Where are you going to school? Are you married?
These seem harmless. They’re the standard conversation starters everyone defaults to, and most of the time they work fine, but I’ve sat next to enough people in enough hard seasons to know that those questions are not always safe.
The person across from you may have just been fired, and asking what they do for a living forces them to either disclose something painful or lie about it. The young man you’re talking to may not be in school for reasons he doesn’t want to explain to a stranger. The woman in the next seat may have just come through a divorce so fresh she can hardly stand to talk about it.
I didn’t realize this overnight. I realized it by paying attention to the way people flinched when I asked the wrong thing, and by remembering what it felt like to be on the other side of questions I wasn’t ready to answer.
The Question That Changed How I Talk to People
I found one question to ask instead.
Where are you in life?
Five words that give the other person permission to tell me whatever they want me to know, in whatever order they want to tell it. I’m not pushing them into a category or forcing them to perform. I’m just opening the conversation wide enough that they get to decide where it starts.
That question came from my own experience. I grew up in an orphanage. I know what it feels like to be defined by a single fact about your life that you didn’t choose, and to have people react to that fact instead of seeing you past it. When I was trying to date as a young man, every girl I told about my childhood dropped me. I wasn’t the good boy from a good family, and that was the end of the conversation, before I got a chance to speak. What I wanted, more than anything, was for someone to ask me a question that let me be more than the worst thing that had happened to me.
That’s what “where are you in life” does. It lets people be more than the thing they’re most worried you’re going to ask about.
The Red-Haired Boy Who Loved Fishing
I met a young man at an event not long ago who was red-haired, he might have been high school or college. I asked him where he was in life, and he started talking about fishing: where he goes, what kind of fish he catches, and what he likes about being out on the water. I kept asking him questions about it, because you could tell that’s what he wanted to talk about, and because I was genuinely interested in hearing about it.
His father came up to me afterward. He told me his son is on the autism spectrum, that he would be college age but isn’t able to attend, and that he hates it when people ask him where he’s going to school. Then, he said something that has stuck with me. He said his son shared with me things in that conversation that he had never told his own parents. This is not because I’m particularly gifted at talking to people, but because I didn’t put people on the spot. I let him start from the place where he felt most himself rather than from the place where he felt most deficient.
That is what emotional safety looks like in a conversation. It’s not a technique; it’s the decision to let someone else set the terms.
The Man in First Class
I fly first class, and I’ve sat next to a lot of men in their forties who are between jobs. There’s a particular tension in a man who used to have a title and doesn’t anymore, who might be flying around the country trying to find another position with a family at home waiting to hear how it went.
If I ask that man what he does for a living, I’ve just put my fingertip on the bruise. He doesn’t want to say he got downsized or explain the layoff. He doesn’t want to feel like he’s failing in front of a stranger.
So I ask him where he is in life, and he tells me about his wife, his two kids, how he loves golf, and what his kids are into: what he wants me to know. If at some point he circles around to telling me about the job, then we go there together. But I never bring him there myself, and because I didn’t, something shifts between us. He doesn’t have to perform, and I become someone it’s safe to sit next to for three hours. When you are in a hard season and everyone you meet keeps accidentally reminding you of it, safe space is important.
The Woman Who Wasn’t Ready to Talk About Her Marriage
The same thing works in the other direction. I’ve sat next to women in their thirties and forties who have recently come through divorces, and the standard questions, are you married, what does your husband do, are land mines. They don’t want to say the word “divorce” to a stranger. They’re not ready, and they shouldn’t have to be.
I ask, “Where are you in life?” and she tells me she’s got two kids and is working harder than she wants to because of situations she’s not comfortable talking about.
I didn’t ask about the marriage. I didn’t need to. She told me what she wanted me to know, and she didn’t have to lie or deflect to do it. That is the difference between a meaningful conversation and one that just makes someone perform their biography at you.
Why This Is Different With Kids
For at-risk kids, the problem is more concentrated, because these kids don’t trust adults to begin with, and for good reason. In many cases the adults in their lives gave them half-truths or outright lies about thiers situation, about what happened to their parents, and what was going to happen next. When a child has already concluded that adults are not honest, the last thing they need is an opening question that could be interpreted as an interrogation.
One of the challenges I’ve witnessed working with kids in group homes, juvenile detention, and on the streets is that many of them don’t have the words for what they’re feeling. Part of that is trust; they don’t trust you enough to try. And part of it is that nobody has ever asked them a question open enough for them to choose their own starting point. They get asked about grades, about behavior, about placements, about what they did wrong, but they don’t get asked where they are.
Asking “Where are you in life?” works with kids for the same reason it works with adults: it doesn’t put them in a box. It lets them start wherever they feel safe starting, and if that means talking about fishing for twenty minutes, then you talk about fishing for twenty minutes and you count that as a good conversation. Because it was.
What This Requires From You
I want to be honest about what this costs the person asking the question.
When you ask someone where they are in life and they actually tell you, you have to be prepared for whatever comes. You can’t redirect them toward the topic you were curious about. You can’t cut them off when they go somewhere you didn’t expect them to. You have to follow, and you have to be genuinely interested enough that they can feel it, because people who are struggling can tell the difference between a sincere question and a technique being applied to them. If you’re asking “where are you in life” as a strategy, they’ll know. They’ll give you a surface answer and move on.
Supporting someone who is struggling often starts before any advice, resource, or referral. It starts with an emotional connection built on nothing more complicated than asking a question that lets them be who they are, and then having the patience to listen to the answer. Support doesn’t always announce itself. Sometimes it looks like a question asked well, followed by the willingness to stay in the room for whatever comes next.
Where are you in life? I’ve been asking that question for years, and I am still surprised by what people will tell you when you give them the room to answer it honestly.
In Hope.
