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11 Uncommon Questions that will Transform your Career & Life

I used to think I needed to have all the answers to be successful.

Turns out the opposite is true. If you want to build a successful career and design a life that you love, you need to learn how to ask the right questions.

Life is a journey full of choices and opportunities, and sometimes it's the questions we ask ourselves that can lead us to extraordinary transformations. I want to share some of the most powerful questions I have used over the years to manage my career and life, achieve my goals, challenge limitations, and drive change.

Dive in to find out how these questions can shape your career and bring about a profound impact on your life.

11 Questions To Transform Your Career and Life: 1. Why not me?

Ask this question to push back on limiting beliefs. Every time you start thinking “I’m not good enough” or “it will never happen” ask yourself: Why not me? And then make your case.

2. NO BS what would it take?

We tend to blow things out of proportion when they are stuck in our heads. “It’s too complicated”, “No way we can do it in time”... Instead, get super tactical and ask: No bullshit, what would it take? Breaking big goals into the specifics will help you think more realistically.

3. What am I optimizing for?

This is one of the most important questions you can ask in your career and life. What you are optimizing for can drastically change over time, and as a result so will your decisions. You’ll make different choices about your career when you are optimizing for the highest salary, vs. opportunities for progression.

Always start with your end goal in mind to make decisions that will get you there.

4. Will it move me towards my goals?

Once you know what you are optimizing for you have to make sure the decision you are making will actually support your end goal. Ask yourself: Will it get me closer to my goals? That’s how you avoid wasting time on niceties and “things you should do” but won’t actually serve you.

5. What would my role model do?

Becoming the next version of yourself can be a painful journey. Whenever you are in doubt ask yourself: What would my role model do? It will inspire you to act as the person you want to become and give you the motivation to keep going.

6. How can this be a good thing?

No matter what you do or how good you are, bad things will still happen. You’ll make mistakes, things won’t go your way, the circumstances will change. You can’t control everything, but you can manage your attitude. Instead of letting challenges bring you down, ask: How can this be a good thing? You will figure out a way to make lemonade with your lemons more often than you think.

7. Will I regret not doing it 10 years from now?

Regret minimization is a powerful decision making tool. It helps put things in perspective and draws out your real desires. Every time you need to make a tough decision just ask: Will I regret doing (or not doing) this 10 years from now? You’ll have your answer.

8. Do I have proof my thoughts and fears are real?

Our brains are powerful machines. They can help us achieve anything, or be our biggest obstacles. When your fears creep in and you start feeling like an imposter, remember that your thoughts are not facts. So ask yourself: Do I have proof that my thoughts are real, or is this a case of fake news?

9. Who do I need to become to make this a reality?

Growth requires more than hard skills. It requires you to change your identity so you can become a bigger, better bolder version of yourself. It’s not enough to acquire knowledge or degrees to grow as a person, you also need to ask yourself: Who do I need to become to make this a reality? What values, qualities and beliefs do I need to hold?

10. What is the worst case scenario? What is the best case scenario? What is likely to happen?

Fears can make things seem bigger. It’s called the magnifying effect. This is why we tend to catastrophize and blow things out of proportion. Every time you imagine the worst case scenario ask yourself: What is the best case scenario? And what is a probable scenario? It will help you put things in perspective.

11. What would I do if I had all the money in the world? What would I do if my budget was $0?

This is a great problem solving tool for your personal life and work life. By using two different lenses you encourage yourself to think outside the box. Asking “What would I do if I had all the money in the world” forces you to think big and remove limitations. Asking “what would I do if I had no budget” makes ditch the conventional way of thinking and get extremely creative.

The quality of your life is determined by the quality of the questions you ask.

Tony Robbins said that and I agree.

The right questions have the potential to reshape your career and life. Each question holds the power to unlock new possibilities, shift perspectives, and propel you forward. Use them as guideposts, reflecting on them regularly to gain clarity, make informed decisions, and pursue your dreams with determination.

Asking the right questions will help you develop self-awareness, push you to challenge your assumptions, and give you the courage to take bold action. And that’s how you’ll build a career and life you love.

I believe in you and I’m rooting for you.



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