When To Let Go of a Dream

“There may come a time when you’ll be tired, as tired as a dream that wants to die…further to fly.” Lyrics from one of my favorite songwriters, Paul Simon, may bring to mind a familiar and disconcerting feeling for many of us. The lyrics so vividly describes the plight of all dreamers; when is it time to let go of a dream?

I am grateful
photo credit: I am grateful via photopin (license)

Some A-listers with type A frame of minds, say never. Others with a bit more life wisdom and experience with change and uncontrollable shifts may say to move on if your intuition tells you that is what you need to do. Dreams are often like pages, once you get the message, just maybe it is time for the next chapter.

You may find it dissapointing that this post has no answers. However, it may shed some light on the question and enable you to see your dreams, their beginnings and endings, in a more illumnated way. So I will share a story from one of my favorite authors, Gary Zukav.

Those of you who are familiar with Gary Zukav will know him as the quiet and humble spiritual teacher who appeared on Oprah years ago. He told a story about how he used to be a real estate developer. And during this chapter in his life he sought to develop a piece of land in Florida into a business center or another strip mall. He put his dream into action and vigorously searched for financial backing and support, only to be disappointed each time the deal fell through.

Gary tried to develop this piece of property, he saw as promising, over a span of seven years, witnessing what he then called, failure after failure. Finally, he walked away from the dream, disheartened. Not so long after he let go of that dream, he had a miraculous and life changing awakening that led him to years of soul searching and study that would eventually reveal a dream that would flow without resistance. He later became a spiritual teacher, speaker, and author of The Seat of the Soul, The Dancing Wu Li Masters, and many other enlightening books.

So maybe if we asked Gary Zukav the question, When should you let go of a dream?, he might say, when your deepest gut feelings tells you that it is over, and when you feel that something else is calling for your time, energy, and passion. And maybe he would say that you’re not really “letting go”, but instead, “allowing flow”.


Everything we do has a place in our lives. We may take off on one certain path, only to find that it leads us into another, and all that we have learned about ourselves, life, and people, we take with us on this new leg of the journey. So nothing is truly done in vain. And we can always change the question we ask ourselves. Instead of asking, “should I let go?”, a better question may be, “what is there for me to learn from this current experience, so that I can also carry that wisdom with me into the next journey?”

Maybe none of it is about letting go or holding on, but instead, about being where you are and simply doing what you do, while squeezing every ounce of joy and wisdom out of it while it lasts. And so I ask myself, what is my current dream attempting to teach me, how will I grow inside of this dream, and what can I take from this experience that will make the next one even more joyful and eye-opening. How can I start to enjoy my life without seeing everything as a beginning and an end, a success or a failure, complete or incomplete, but instead ride the waves of my passions and desires into each next chapter with a knowing in my heart, that one dream flows and bends into another in the same way you cannot tell a wave from its ocean.

And by the way, shortly after Gary Zukav decided to let go of that promising piece of real estate, another developer came along and turned it into a huge success. Just thought I’d let you know that.