Someone asked me last week where I see myself in five years. Standard question. The kind of thing people ask in professional contexts, at family gatherings, in casual conversation. The kind of question you’re supposed to have an answer for.

I opened my mouth to give the answer I’m supposed to give — something ambitious, clear, confident. Something that demonstrates I have a plan, that I know where I’m headed.

And then I realized: I have no idea where I’ll be in five years.

What getting comfortable with not having all the answers actually means: Uncertainty is not a problem to solve — it is a valid state to inhabit. The pressure to always have clear answers about your career, direction, and beliefs leads most people to manufacture false certainty rather than engage honestly with genuine complexity. Real wisdom often lives in staying with the question long enough to understand it deeply, rather than rushing to a conclusion that stops the inquiry.

— Tomer Rozenberg, Strategic Life: How to Build a Life That Matters

We’ve been trained to always have answers — about our careers, relationships, beliefs, five-year plans. But real wisdom often means admitting “I don’t know” and being comfortable with uncertainty.

TOMER ROZENBERG

But instead, I said: “Honestly? I don’t know yet. I’m still figuring that out.”

And the person looked uncomfortable. Like I’d admitted to something I should be embarrassed about. Like not having a five-year plan meant I wasn’t serious or strategic or thoughtful about my life.

But here’s what I’m learning: the pressure to always have answers prevents us from being honest about the questions we’re still figuring out. And sometimes “I don’t know” is the most truthful, most wise thing you can say.

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The Pressure to Always Have Answers

We live in a culture that treats uncertainty like failure. You’re supposed to know what you want. Know where you’re going. Know what you believe. Have your career path mapped out, your relationship goals clear, your values articulated, your future planned.

And if you don’t know? If you’re still figuring things out? That’s treated as a problem to solve, a gap to fill, evidence that you’re not adulting properly.

But what if that’s wrong? What if real wisdom often lives in uncertainty? What if “I don’t know” is sometimes the most honest, most mature, most thoughtful answer you can give?

Manufacturing Certainty You Don’t Feel

I’ve gotten really good at manufacturing certainty. When someone asks about my plans or beliefs or direction, I can construct an answer that sounds confident and clear. I can present a narrative that makes it seem like I know exactly what I’m doing and why.

The answer isn’t exactly false. It’s built from pieces of things I’m considering, values I hold, possibilities I’m exploring. But it’s stitched together into a coherent story that implies more certainty than I actually feel.

I do this because saying “I don’t know” feels vulnerable. It positions me as less competent, less together, less reliable than people who have clear answers. And I’m not alone in this. Most people are doing some version of this — performing clarity they don’t genuinely feel because admitting uncertainty feels like failure.

The problem is that this performance has real costs. When you manufacture certainty you don’t feel, you lose the ability to explore your uncertainty, the opportunity for genuine connection, and the wisdom that lives in staying with open questions.

The Wisdom in Uncertainty

There’s a kind of wisdom that only lives in uncertainty. A quality of thinking that requires staying with questions rather than rushing to answers.

When you’re genuinely uncertain, you’re open — to new information, different perspectives, unexpected insights. You haven’t closed off the question by deciding what the answer is. When you’re certain, you stop exploring. And that decision — even if it’s right — closes off the possibility of discovering something you didn’t already know.

Some questions deserve to stay open for a while. “What do I want my life to look like?” deserves more than a quick answer. “What do I believe about this complex issue?” deserves genuine exploration. Sitting with these questions honestly is not failure — it’s wisdom. This connects to what I explore in Why We’re Afraid to Change Our Minds — the same pressure that makes us fake certainty also makes us hold outdated positions far too long.

Comfort With Questions You’re Still Figuring Out

What I’m trying to develop is comfort with being in process rather than conclusion. Comfort with genuine uncertainty about important things.

This doesn’t mean avoiding decisions or refusing to commit. Sometimes you need to choose even when uncertain. But there’s a difference between making decisions while acknowledging uncertainty and pretending you’re certain when you’re not.

I can say “I don’t know where I’ll be in five years, so I’m focusing on what feels right for the next six months.” That’s honest uncertainty paired with forward movement. I can say “I’m not sure what I believe about this yet, but I’m thinking about it.” That’s engaging with complexity while being honest about not having concluded.

The comfort comes from accepting that uncertainty is a valid state. That you don’t need to have everything figured out. That being in process is legitimate, not just a temporary problem to solve on your way to having answers.

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The Freedom of Not Having Everything Decided

Something unexpected has happened as I’ve gotten more comfortable with uncertainty: I feel more free.

When I was constantly manufacturing certainty, I felt trapped by the answers I’d given. If I told people I was planning X, I felt obligated to pursue X even when I started to question whether it was right. The manufactured certainty became a cage.

But when I’m honest about uncertainty, I’m free to evolve. I can say “I was thinking X, but now I’m not sure” without contradicting myself. I can change my mind because I never claimed to have fully made it up. There’s relief in admitting what I don’t know.

Permission to Be in Process

Here’s what I want you to know: You’re allowed to not have all the answers. You’re allowed to be figuring things out. You’re allowed to be uncertain about important things and honest about that uncertainty.

You’re allowed to not know where you’ll be in five years. You’re allowed to be unsure what you believe about complex questions. You don’t have to manufacture certainty to appear together. You don’t have to pretend to know things you’re still figuring out.

“I don’t know” is a legitimate answer. “I’m still thinking about that” is honest engagement. “I haven’t decided yet” is being in process, which is where real wisdom often lives.

Frequently Asked Questions

Why is it so hard to say “I don’t know” in professional or social contexts?

Because we’ve been trained to treat uncertainty as incompetence. In school, not knowing the answer meant you hadn’t prepared. In professional settings, admitting uncertainty can feel like admitting weakness. This conditioning runs so deep that most people perform certainty they don’t feel rather than risk being seen as someone who hasn’t figured it out yet.

Is it possible to make good decisions while being genuinely uncertain?

Not only possible — often necessary. Many of the most important decisions in life get made without full certainty. You can make a decision while acknowledging it’s your best current judgment, remain open to updating as you learn more, and still move forward confidently. That’s more honest — and often wiser — than pretending to have certainty you don’t have.

How do you tell the difference between healthy uncertainty and just being stuck?

Healthy uncertainty has a quality of active exploration — you’re genuinely taking in new information, sitting with questions, letting your thinking develop. Being stuck has a quality of avoidance — you’re going in circles, building sophisticated reasons why now isn’t the right time, hoping the situation resolves without requiring you to act. The honest question: am I still learning something from waiting, or am I just postponing the discomfort of deciding?

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