Navigating Your Future: 24 Questions to Guide Your Personal and Professional Journey

As a seasoned strategic thinker and planner, I specialize in guiding organizations toward envisioning and shaping their future. My role involves initiating critical conversations and asking pivotal questions about their current position and their desired future.

I use a similar process to create my own personal and professional future. I am happy to share with you the questions I’m asking myself as we go into this new year. Answering these questions forces a deeper level of thinking than simply setting New Year resolutions or defining goals.

Give yourself the luxury of answering these 24 questions, organized into 2 groups. After you briefly ponder these questions, I offer suggestions for crafting your most remarkable year yet.

Now is the time to reflect on the outgoing year look ahead and create a new one.

Looking Back Questions:

1. What was the best class, lecture, or workshop you experienced this year and what did you learn?
2. What was the best opportunity you took advantage of this year?
3. What new friends did you make?
4. In what ways have you become wiser?
5. What mistake did you make you forgive yourself for now?
6. What contributions to your work/company/business were most significant?
7. Whose life did you positively influence and how?
8. What personal qualities did you call upon to get through the tough times?
9. What obsolete goals are you willing to let go of now?
10. What did you do this year that most contributed to your life mission and vision?
11. What was the most fun you had this year?
12. What grudges and resentments are you willing to let go of?

Looking Ahead Questions:

1. Who are you most looking forward to supporting and encouraging next year?
2. What will you do to maintain a high level of health and vitality?
3. What is one change you can make in your home routine to increase your quality of life?
4. Who are you going to not let push your buttons anymore?
5. What “work smarter not harder” changes could you make to your work routine?
6. What skill sets should you develop or improve that would increase your performance and enjoyment?
7. How will you improve the quality of your personal and family life?
8. How will you have more fun?
9. If it were exactly one year from now, and you had lived this year as you dreamed, what would be different and how would that make you feel?
10. What would become possible for you if suddenly all your limitations disappeared?
11. What is the key to unleashing your greatness?
12. What are some specific goals and intentions for you this year?

How to Leverage These Questions

These questions are tough, and you might not be able to answer them right away. Take your time and think about them. Often, when you ponder a deep question, better answers emerge later.

You can think about these questions whenever you like. It's more effective to record your answers using a computer or on paper. Writing them down helps you think more deeply and makes things clearer. Plus, it's gratifying to look back at your answers next year.

Sharing these questions with people you trust, like family, friends, or coworkers, can be rewarding. Just make sure everyone is comfortable and trusting in the group. (If you're using these questions at work, you can change them a bit to be more appropriate.)

No matter how you tackle these, be proud of yourself for taking action. Asking questions is a way to find answers. Being honest in your answers is like going on an amazing journey that only the boldest people dare to take.

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Terry Schmidt is an expert in helping clients sharpen their strategic plans and turn them into actionable projects. He is the author of Strategic Project Management Made Simple (Wiley), which features a breakthrough systems thinking methodology to get better results faster. He helps leaders and teams to sharpen their strategies and deliver outstanding results. www.ManagementPro.com