In many ways, September is a new beginning. Or at least it can be. It’s the start of the Jewish New Year, usually the start of the school year, and, for me, the start of another year of life (as I’m a tried-and-true September Virgo).

The chance for a new beginning is almost always welcome, and always a chance to reflect and refresh. It’s an opportunity to find a new path, set new goals, chart a new direction – or an opportunity to recommit to the current path you’re on. Either way, it’s worth a pause, and a moment of contemplation, to make sure that you’re moving ahead Thoughtfully and intentionally.

Moving ahead Thoughtfully means that you’ve thought through where you want to end up, what your objectives are, how you need to show up and be in each moment – and each day – to lead yourself, your life, and your team or organization forward. Over the years I’ve guided myself and many clients through a process that clarifies their final destination as well as their journey along the way, and it nearly always includes the following five key questions:

  • What do I really, really, really want? This can be for yourself, for someone else, for the world. It can be short-term or long-term. You’re looking for the thing that turns you on and lights you up. You need to know what it is in order to go for it.
  • Why do I want this? I don’t really believe in digging into a lot of “whys,” but knowing why you want what you want can help you define if it’s really what you want, or simply a step to something else. Or something you think you “should” want. Or something someone else wants for you. You need to know a bit of why you want what you really, really, really want in order to make sure it is really what you want.
  • What do I need to do to get there? Once you have a destination, you can begin to trace the steps you need to take in order to get there. If you want to publish a book, you may need to actually write the book, or find an agent or a publisher, or contract with a ghost-writer, or set aside time for the project. By calling out the steps to your desired end goal, you can begin to take the steps and to move forward.
  • What might get in my way? It might be you, it might be others, it might be circumstances – either way it’s important to have a sense of obstacles you may face so that you can prepare your path around, through, and beyond the obstacles.
  • What will keep me going? What will motivate you when the going gets tough? Who will support you and challenge you when and if you want to give up? Will you set up a reward system, or an accountability group? Will you partner with a coach who can help hold you to your plan and your dreams? It’s best to plan how you’ll keep going before you even feel tempted to give up (or before you forget to keep going).

September can be a great time to start anew – and to set your goals for the rest of the calendar year (or the rest of your life)! These five key questions can help you define your dreams and develop your plan to reach them.

How do you start anew?
Please leave a comment.

If you enjoyed this post, you can read more like it in our book, The Power of Thoughtful Leadership: 101 Minutes To Being the Leader You Want To Be, available on Amazon.

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