The Biggest Obstacle to Dreaming Big & How To Overcome It

Terri Wingham is the founder and CEO of A Fresh Chapter, a cancer survivor, and someone who believes that we are not defined by the most difficult aspects of our story.

Written by Terri Wingham | October 22, 2013

Nothing limits achievement like small thinking; nothing expands possibilities like unleashed imagination. ~ William Arthur Ward

photo-57When is the last time someone questioned your ability to do something? I know you know what I’m talking about. You’d carried the spark of a dream like a newborn baby – nursing it and letting it grow before you felt ready to swaddle it and share it with the world. When you finally wrestled your own fears of failure into submission and had the courage to take a deep breath and tell someone about your dream to _______________ (start your own company, go back to school, have a baby), you looked up – anxious for approval, expecting to see support and instead you saw that look.

You know the one. Raised eyebrows, pursed lips, pale face. You want to do what? Even if he/she didn’t say it out loud, those words hung heavy in the air between you. Your _____________ (friend, mother, wife, sister, husband) needed to sit down, drink a glass of water, or take a few deep breaths on your behalf.

That look made your heart race and your limbs tingle with adrenaline. Sweat beaded on every surface of your skin as you gulped in oxygen, stared at the floor, and wondered if the person in front of you was right. Maybe it was too risky. Maybe you would fail.

You debated cracking a smile and saying “Just Kidding!” Every part of you wanted to make that look go away as quickly as possible. Maybe if you boxed up the dream and stuck it on a shelf, you would forget about it. With a nostalgic sigh, you justified all of the reasons why that dream hadn’t been possible and why you’d been crazy to even hope for it.

photo-53Too often, that look robs us of amazing adventures and new friendships. That look makes us shrink behind the high walls of our comfort zone where we numb ourselves with distractions so we forget how much it hurt to have our dreams shot down.

But, can I tell you the single most important thing I’ve learned about dreaming big?

The bigger you dream, the more often you come face to face with that look. When you challenge the status quo, make sacrifices to keep a dream alive, or do things other people only dream of doing, you will constantly face other people’s concern for you. Well meaning people will tell you constantly what is NOT possible. Your own fears will rise up in you. You will wonder if you’re strong enough to persevere. You will be tempted to quit at every turn. But, if you ask yourself two questions, I promise you, you will find strength:

  • Will I forever regret NOT doing this?
  • Am I limiting my belief in what is possible based on other people’s fears?

Let me be clear – I’m not advocating irrational behaviour – like leaving your wife and kids to backpack around the world while running yourself into such bad credit card debt that you have to declare bankruptcy. We all have responsibilities. We all need to balance pragmatism and big dreaming. But, if you have a dream and you know in your heart and soul that achieving it is possible, don’t let that look rob the world of the positive impact you can make.

Terri Wingham.Rwandan OrphanageAfter I finished treatment for breast cancer and I first had the dream to volunteer in Africa, plenty of people asked me if I was really sure that this was the right decision. Some even told me all of the ways I might fail. Their doubt almost made me back out, but amazingly, when I committed to going and began fundraising to make it a reality, some of those same skeptics became my biggest supporters. They truly loved me and wanted me to be happy. I bet you would find the same thing in your life.

What obstacles have you overcome to move closer to a dream in your life? We’d love to hear from you. Please share your comments or thoughts below and you will inspire the rest of us to expand the possibilities in our lives.

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Comments (3)
  • Cierra steel • October 22, 2013

    I couldn’t have said this any better! Thank you for writing this. These are my exact feelings at this time. I almost didn’t apply because of some of those looks I got. But I knew this was something I’m so excited about possibly participating in, so I had to take that leap of faith! Amazing feeling!

  • Terri Wingham • October 22, 2013

    So happy to read this comment and glad the post helped. Congratulations on taking the leap of faith and choosing to dream audaciously. I’m looking forward to speaking with you next week!

  • Catherine • October 23, 2013

    Hmm, yes. I’ve gotten “That Look” more than once. It can be hard to push past, but the times I have, (chasing after my husband, going forward with my book, living in England, prioritising travel, etc.) have been highlights in my life. Knowing that gives me strength to keep pushing expectations. The decision to leap lies within us; those outside opinions only test our determination.

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