8 Great Questions You Should Occasionally Ask Yourself

Including one that completely changed my life.


Brian Pennie

3 years ago | 4 min read

A friend of James Clear’s once suggested that he occasionally asked himself the following question:

“What am I really trying to achieve here?”

Whenever he remembers to do it, he finds the question generates useful answers. In a recent Twitter post, he asked others what is their one question — the one they find useful to ask themselves.

Great question after great question began to fill his thread, which made me think about questions that have made an impact on my life.

The 8 questions below have been the most impactful for me — some of which were in the Twitter thread — and another that completely changed the course of my life.

1. What Part of This Situation is Under My Control?

This is a powerful question because very little is actually under our control. This includes external forces such as the economy, the weather, political issues, and the behaviour of others.

Many people see this as a problem, but if you focus on what you can control, you’ll realise that this is not a weakness — it’s a strength. Why? Because it’s only by focusing on what can control, such as your reaction to challenging situations, that you can actively move the needle.

2. What Are You Constantly Avoiding?

This is a strange paradox: we avoid what we must do. Maybe you need to join a gym, eat more healthily, or begin that meditation practice you’ve been talking about for years. Or the worst culprit: having difficult conversations with others.

It’s easier to put these things on the long finger, but they always come back to bite you in the ass. More times than not, you know what to do, but you constantly avoid it, despite the evidence.

3. What Would My Mentors Think About This?

We’re easily caught up in today’s busy world, and when this happens, it’s difficult to see the forest from the trees.

That’s why this question is so useful. It allows you to take the perspective of others. And better still, the perspective of someone you greatly admire.

Next time you feel stuck, instead of looking at the forest floor through the eyes of a worm, take the perspective of a mentor, and you’ll be able to see the entire forest through the eyes of a bird.

Sidenote: You don't have to personally know your mentor. Many of mine are dead hundreds of years, and most of them come from books.

4. What Would Tomorrow Me Think?

Everything happens in a context, and our decisions are often reflected by that context. You might be in a bad mood, a gloomy environment, or maybe you’re surrounded by low-energy people.

The fact is, all of these things will have a bearing on your current mindset, and ultimately, the decisions you make. That’s what makes this question so valuable. Just like taking the perspective of a mentor, you can take the perspective of your future self, or your former self, whatever serves you best.

5. If I Am Saying Yes to This, What Am I Saying No To?

Steve Jobs once said that it’s only by saying no that you can concentrate on what’s important in life. I love this line because it helped me to realise the potency of this question.

It’s quite simple really. Be it our relationships with loved ones, our career, or our health, we need to reflect on what we hold most dear. Then, when we say yes to one thing, we know we’re not saying no to something that’s more important.

6. Does This Align With My Mission?

Not everyone has a mission, so you can reframe this question in many ways.

  • “Does this align with my values?”
  • “Does this align with my purpose in life?”
  • “Does this align with my long term goals?”

People often make decisions that do not align with their values, purpose, and goals. There are many reasons for this, but most often it’s because they don’t ask themselves these simple questions.

Next time you’re doing something and it doesn’t feel quite right, ask yourself how it’s serving what you value most in life.

7. What’s the Worst That’ll Happen if I Attempt This?

Sometimes the worst thing that can happen isn’t as bad as you think. And if it is that bad, you can put contingencies in place by reflecting on this question.

There are several other advantages to this question. Most people follow societal rules without ever questioning why. By asking yourself this question, however, you can challenge societal norms. Follow your passion when people think you should play it safe. When the crowd goes one way, you go the other.

When all is said and done, the only limits in your life are the ones you put on yourself, so dream big, and be bold.

8. What Would This Look Like if it Were Easy?

In 2017, Tim Ferriss was struggling with various aspects of his life, and he asked himself the question above. After several hours of journaling, throwing hundreds of ideas onto the page, one idea jumped out: “What if I had a tribe of mentors to help me with the challenges in my life?”

What followed was his most recent book Tribe of Mentors, where Tim reached out to his dream list of interviewees and asked them the very questions he was struggling with himself.

I was struggling with my own issues at the time, but I was asking myself the wrong questions. When I found Tim’s book, however, it suddenly hit me. I needed a tribe of my own.

With that, I set out to build my tribe, and over the course of the last two years, it has completely changed my life.

This article was originally published by Brian penne on medium.


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Brian Pennie







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