You Don’t Need Better Answers, You Need Better Questions

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Questions matter way more than answers

Do you have any other advice for me?

Can you tell me what I should do?

If you were me, what would you do?

The more I write online, the more I get these types of questions. The reality is that I don’t have any answers. No one does, really.

A good self-help writer will experiment with routines/hacks/techniques and report back on their findings for others to try it out, but there’s never a point when that should be taken as the ultimate truth. It doesn’t exist.

I’ve written over 300 articles about self-improvement and I’ve reached the point where I’m questioning all the work that I’ve done. And when I see Medium’s home page plastered with self-help articles, I’m starting to cringe.

Who are they to tell me how to run my life?

That’s how I’m starting to feel about a lot of the articles I’ve written in the past 3 years. Who am I to give you advice? Frankly, I’ve got nothing figured out. I’m broke with a newborn son and 7 failed businesses under my belt.

But I’m not here to rant about that. I’m not here to rant about anything, really. Through all my failed experiments, there’s one important pattern I’ve identified:

The things that move me forward the most are not the great advice I’m getting, but rather the right questions that make me think.

Imagine yourself answering some of the questions above for someone else.

Would you be able to?

Unless you know a lot about the person’s life, you’re never going to be able to answer them properly. In fact, the only person who can truly answer those questions is the person asking them. The problem is, these questions are too broad!

The best advice you can get will come from the best questions you can ask. And the best questions are rarely that broad.

But here’s the reason why we suck at asking good questions: schools made it a habit for us to answer pre-made questions. We were taught that there is a right answer for everything.

This is entirely wrong.

In adulthood, there’s no such thing as right or wrong. Everything is circumstantial. In one instance, an answer might be good, but in another, it might be a disaster.

That’s why, when you read a self-help article or ask for help from a “stranger”, but wary. They don’t know your context. An article may tell you an optimal way to do something, but unless you’ve met certain unmentioned criteria, you might not be able to do it.

For example, I’ve written many articles about creating a perfect morning routine. In most of them, I was broad enough that it should apply to a lot of people. However, now that I have a newborn son, damn, there’s no way I can apply my own advice!

My context simply doesn’t allow it.

The best coaches in the world don’t have answers. I went to Tony Robbins’ Business Mastery last year and when he put someone on the spot to help them, he never gives them answers. He asks questions after questions, digging deeper and deeper. When the answer is closer to the solution the person is looking for, he hints that they’re getting there, but he never says: “this is what you should do!”

For the past 2 years, whenever people are asking me questions, I reply back with questions. I know this is helping them a lot more. And then they thank me for it, but in reality, they found the answers themselves.

You always have the answers within you. And you get to them by asking the right questions.

How do you ask the right questions?

I’m not going to give you an answer here! :)

Ask that question to yourself. What’s your answer?

Here’s an example to help you guide your reflection — a question I often get is: “How do I become a better writer?”

  1. What makes you think you’re not an adequate writer already?

  2. Who do you consider to be a good writer?

  3. What is their context? What makes them “special”?

  4. What are they doing that you consider good?

  5. What are some sub-skills of writing you possess?

  6. What are some sub-skills of writing you could learn?

  7. Why do you want to write better? Ask yourself that in 5 layers deep.

  8. Who do you want to write for?

  9. What do you want to write about?

  10. Who else writes about that?

  11. What would be the best way to connect with these writers?

  12. How often can you practice?

  13. Where can you practice?

  14. Who can help you (content, editing, proofreading, feedback, etc.)?

These are just examples. But for many things you want to learn and get advice on, you can borrow from the above questions.

The way I typically do that is by starting with question words (How, What, Who, Where, When) and brain dump everything I can come up with. And with every “how” comes a bunch of W-questions.

Every time you use an adjective, ask yourself what it means concretely. For example, what does “better” mean in the context of “better writer”. Every person you ask will have a different answer.

Here’s an exercise you can try:

Go to 10 different people and ask them the same question: “What does it mean to be good in/at <subject>?” For example:

What does it mean to be…

  • …a good writer?

  • …a good singer?

  • …good at sports?

  • …good in geography?

You’ll get different answers every time. Which answer is right? Probably none of them and all of them at the same time. There’s no black and white.

You should stop chasing pre-made answers and start asking better questions. Read articles to inspire you to find your own answers, and never take self-help too seriously. Life is all about experimentation, so experiment, my friend!

You can do this!