20 Questions to Plan Your Life

A guide for assessing the past and determining what's next

Posted Dec 30, 2015

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If you want to change your life you need to envision what is next. The reason many people don't follow their New Years resolutions or meet their isolated goals is because they don't have the bigger, purposeful, inspiring picture in mind. When you know the story you want to create, you are more likely to commit to taking the steps to get there.

Answering the following questions will help you assess your past and determine what you want to create for in the coming year. Although this guide is perfect for your New Year's reflection, you can refer back to it anytime to help you stay on a purposeful and satisfying path.

Look Back

Answer some or all of these questions to determine when you spent your time well or when you slid off track.

  1. When were you able to use your talents, skills, and gifts? What were you doing? How did you feel?
  2. Was there something you found you were good at that you didn’t know or claim before now?
  3. How did you grow? Did anything get in the way of your growth?
  4. When do you feel you sold out, where you did something to avoid confrontation or to feel comfortable even though you now know the convenience was not in your best interest?
  5. What did you put off that you wished you had spent more time on?

Review your answers. Note what you want to do more and less of next year.


Clearly See the Present

To objectively evaluate your current life, consider exploring these questions with a coach or trusted friend who will challenge you to expand your thinking.

  1. What impact are you making? Is this enough for you?
  2. What do you believe created your present circumstances? Are your assumptions limiting how you view your life?
  3. What did you enjoy doing in the past but now, the energy is disappearing?
  4. What are you clinging to that defines you but it is now time to let go of?
  5. What do you feel you should have done by this time in your life? What is stopping you now?
  6. If talent is the joyful expression of your unique abilities, how are you using your talents to benefit you, your community, or the world?

It is okay to be unhappy with some parts of your life. Feelings like regret, envy, and sadness can either help you articulate what you yearn to create. Clearly seeing the present will help you determine what you feel is best for you to focus on next.


Write the Story You Want to Live

You can either fine-tune your current story or decide to write a new narrative. If you want to write a new story, the following questions will help if you articulate your vision. If you have trouble answering the questions, you might want to work with someone to determine what types of activities give you a sense of purpose.

  1. If you had the opportunity to fully express your talents, what could you accomplish?
  2. What do you dare to dream of doing? What do you long to experience or create?
  3. Is there something you are called to do but you thought would be impossible? Could someone help you find your way?
  4. What inside of you wants to be heard or set free? If you listened to this longing, what would you know you have to do?

To move into a new story, you have to leave some things behind. You need to let go of what is uninspiring or draining to allow the chance for your higher contribution to take form.

  1. To step into your profound potential, what must you leave behind?
  2. What can you say no to now?
  3. What did you promise yourself you would do but you can now release? Crossing things off your list will give you more energy to spend on what is most important now.
  4. If you were willing to step into the unknown, what would you find on the other side?

Don't let doubt stop you. It’s difficult to envision acting on something new when you have bills to pay. Also, the more developed your expertise and career is, the harder it will be to let go and re-create yourself. Compose the story anyway. Don’t just craft a static vision; imagine your perfect day one, two, or five years from now where you are both doing and feeling what you most want.

The final question is – how can you ensure your commitment to living your chosen life? Plan your steps or at least create a way to remember your intentions so next year, answering the questions will be easier.