The Question Behind the Question

Someone says: I’m stuck.

I hear this often. What lies behind it is different every time. Sometimes it’s a job that hasn’t fit for years. Sometimes a layoff that just happened. Sometimes the feeling that everything works and something is still missing. What they all share: They know something has to change. They just don’t know what.

The usual answer is advice. Strengths analysis, personality test, coaching. Someone asks: What can you do? What do you want? What matters to you? Then comes recommendations. Or a plan.

It often doesn’t work. Not because the tools are bad. But because they skip a question that should come first.

When someone says “I need more freedom,” that’s not a statement. It’s a door. Behind it could be financial independence. Or control over one’s time. Or the absence of a particular boss. Or authority over one’s own work. All different things leading to different decisions. But most conversations about career change take such words at face value and move to the next step before clarifying what the person actually means.

What do you mean when you say “success”? Is that your success, or the one you learned to want? What do you mean when you say you want to do “something meaningful”?

This sounds like a philosophical exercise. It’s not. It’s the most practical question you can ask. Because the answer determines which direction someone goes.

I went through such a process myself. With a psychologist who has worked with biography for decades. The experience changed how I think about career decisions. Not because the process gave me an answer. But because it showed me I already had the answer. I’d just been using the wrong words for it.

The system I’ve since adapted is based on an assumption that sounds counterintuitive: The most reliable indicator of your future is your past.

Not your wishes. Not your ideas about who you could be. But what actually happened. What made you satisfied will make you satisfied again. What frustrated you will frustrate you again. Most people thinking about change look forward. They design a future based on hopes. Looking back would be more reliable. Biography doesn’t lie.

The process works with stories. Someone tells six key moments from their life, and through conversation, patterns become visible. What someone tells you matters. What someone doesn’t tell you often matters more. The patterns that emerge are more reliable than any self-assessment. Because they’re not based on what someone believes about themselves, but on what they’ve actually done.

Seven dimensions form the framework. What someone can do. How their story has unfolded. What kind of people they want to work with. What satisfies them. Under what conditions they function. What truly matters to them. And where all of this concretely leads. Each dimension is its own question, and each question has a question behind it. “I want to work with smart people” doesn’t mean the same as “I can’t work with people who just execute.” Even though both can come from the same mouth.

The result isn’t advice and isn’t a plan. It’s a profile. Abilities, patterns, values, conditions, a compass, concrete directions. Solid enough to test decisions against. Not because someone else said what’s right. But because the person themselves can see what fits.

Self-knowledge is the hardest form of knowledge. You’re simultaneously researcher and subject. You can’t observe yourself from the outside. You need someone who listens and reflects back what they see. Not as diagnosis, but as translation. Putting into words what you already know but have never clearly articulated.

Career clarity doesn’t start with the answer. It starts with the right question. And the right question is almost always: How do you figure out what you want?