Some Questions That Could Change Everything…

For a Regret-Free, Intentional Life

The Past, The Present, The Future

“Judge a man by his questions rather than by his answers.”


We have a natural instinct to seek answers, but most great leaps forward come from finding the right questions to ask yourselves.

The least known and valued, but most valuable, skill for intentional, regrets-free living is asking the right questions. Without this skill, we may waste our time solving the wrong problems, or going blindly in the wrong direction.

Asking the right questions is never easy, because they often lead to more questions, time, energy, and resources than seem to be available.

However, they can also inspire us to take action and gain a better perspective on what we want in our personal and professional life. In the same way our daily habits shape our reality and our life, the questions we ask determine how intentionally we live.

Here are 18 of the most inspiring and provocative questions I have unearthed in recent years.

They have helped me and my private clients gain insight, and have also sparked quite a bit of positive actions.

I hope this motivates you to reassess what you TRULY want, to aim higher, lead and live your life intentionally, based on your most authentic self, and on your own terms.

gold-we live one life

Asking Life-changing Questions For A Regrets-free, Intentional Life – The Past, The Present, The Future

Go through the below list of 18 questions about your past, present and future. You can go through all of them at once, or take 5-10 minutes every day picking any question that captures your attention. Either way, spend time answering them.

Pause after reading each question, and see what thoughts and emotions come to you. Rather than focusing on answering the questions, focus on questioning your answers when they arise. There is one golden and simple rule of thumb that will lead you in the right direction: Ask why, three times in a row. It often leads to a deeper understanding of whatever you are considering.

You do not need to know all the answers straight away. And if you do not get an answer immediately, it doesn’t mean there are no answers. The more you ask, the clearer your mind will be, and the more ready you will be to receive the answers.

Remember: There is no one final answer. It’s a continuous circle of discovery processes. If you resonate with any question, you can turn them into an affirmation, empowering statement, or meditation mantra by playing with the words.

gold-we live one life

18 Questions For Intentional Living, In & Out Of Work

The Past
  1. What are your top 3 business or career successes – that you are most proud of? (e.g. the impact you had, the difference you made, the income you created, the acknowledgements you got). It is often hard for people to share what they are proud of.

  2. What are your top 3 personal or life successes – that you are most proud of? (e.g. family, relationships, growth, health and fitness, contribution).

  3. What is the hardest thing in business / life that you have overcome? What did you learn from the experience?

  4. How much time off have you taken, each year, for the past 3 years? Why was it not higher? Why was it not lower?

  5. How did you choose your current job?

  6. What is one truth / unique strength / gift / talent – that you have held back – that you know the world needs to hear?
The Present
  1. How much of a life do you have, regardless of how much money you have?

  2. How much are you really making when you factor in what success as defined by net worth only is costing you?

  3. When you are old, how much will you want to pay to travel back in time and relive what you are experiencing now?

  4. What (secret) dreams do you have that are still unfulfilled?

  5. What would you regret not doing, being, having or saying in your life?

  6. What are the 3 biggest reasons your life, business or impact might not yet fully where YOU want it to be?
The Future
  1. What would you do differently if you knew nobody would judge you?

  2. What would you like to accomplish – that may look impossible, right now – but if it were achieved would change everything?

  3. If you were to look back 3 years from now, and say, “these have been the best 3 years of my life” – what has to have happened, personally and professionally for you to feel thrilled with your progress?

  4. What were the 3 tiniest shifts that made the biggest difference in those 3 years?

  5. What could hold you back the most in those 3 years? ( external reasons – e.g. economy; internal reasons – e.g. mindset).

  6. What have you done about your “best 3 years in your life” so far?
gold-we live one life

I hope that these questions have provoked you to think harder and more intentionally about the type of personal and professional life you wish to lead. Most of the time, we don’t know what we don’t know, and it always helps to seek out new questions.

Let me know how it goes! And if you think I have missed some powerful questions, or if you want to provide feedback of any sort, contact me here!

To your most vibrant life & career,

gold-we live one life