One of the tools Challenge Day is best known for is an activity called "If you really knew me." Though most people don't start by disclosing their deepest secrets, completing this simple phrase has the power to literally transform shallow "chit-chat" into intimate conversations with life-changing opportunities for depth and connection.

Oprah called our work simple. And she's right. This tool and the others in the book can be used everywhere by everyone. We particularly like to use the "If you really knew me" tool at the dinner table with family and friends. We use it to open every meeting in our Challenge Day office. We use it to bring people close at parties and other social events. In our experience, the more open and honest we are willing to be, the more intimate and connected we become. The simplicity of this lead-in sentence naturally opens a doorway to a vulnerability and truth that generates a level of understanding we all crave.

Many of us live our lives as if we are icebergs floating aimlessly in the sea of life, and largely submerged. We hide most of ourselves, and especially our most tender, secret places, far below the surface, or what we like to call "the waterline." Like a typical iceberg we show only about 10 percent of ourselves, the part above the water. For the purposes of this discussion, let's call this 10 percent our image.

"Dropping the waterline" and getting real means facing most peoples' biggest fear—rejection. We're so afraid of being rejected we often even hide who we really are from the people closest to us. For some, this looks like acting hard or tough, keeping secrets, being cool, being a jokester, or maybe even pretending we don't care about anything at all.

Many of us get stuck trying to live up to an image we believe will be acceptable to others. We fall into groups or cliques and learn to label ourselves and other people in ways that seem to define how we should act and what we should let people see—jock, stoner, cheerleader, socialite, geek, loser, gangster, executive, coach, parent, etc.

We often feel so ashamed or embarrassed that we are afraid if anyone really knew us, they could never love or accept us.

If you never take the risk of dropping the waterline and letting people see who you really are, you can never feel all the love, celebration and acceptance you deserve. The only way you can experience authentic intimacy and connection with others is to risk exposing your true self.

What's your image? What secrets do you have? What parts of yourself do you keep hidden? How does your image keep you separate from other people? Do people know what you go through and what really matters in your life?

As you begin to drop the waterline and explore, your depths, consider this thought. If we investigate the word "intimacy" we find: "into"—"me"—"you"—"see."

In addition to the questions above, consider these:


  • Who in your life knows who you really are?
  • Are there people whom you wish really knew you? What keeps them from knowing you?
  • When was the last time you dropped the waterline and risked revealing yourself to someone who mattered? What happened? How did it make you feel?
  • In general, how often do you drop your waterline—with strangers, with family, with a partner, with friends? Are you comfortable with how often you become vulnerable?
  • What (if anything) keeps you from showing yourself and being vulnerable?
  • Are there things you intentionally hide? Why? How might your life be different if you didn't hide these things?
  • How much do you know about the people closest to you? Do you know who they really are?

  • Among the people in your life who really know you, is there more of yourself you would like to share with them? Under what circumstances might it be possible?
  • Are there people to whom you'd like to be closer? If you dream about the perfect relationships in your life, who does it involve and what does it look like?
  • How might you become more vulnerable with the people in your life? What circumstances might have to be present in order for you to drop the waterline?
  • Is there any support you need in becoming who you really are? Do you need a different set of friends? Do you need a therapist? Do you need more understanding from a parent?
  • How can you create more opportunities for connection among the people you love?

  • Find someone you'd like to be closer to and share this chapter of the book with them. Tell them you'd like them to really know you, and ask them if you can tell them one thing about yourself that you keep hidden.
  • Once you've gotten vulnerable yourself, ask them "What would I know if I really knew you?" Be patient with any resistance. Getting real can be uncomfortable, especially at first. A word of caution. Sometimes the question can feel like an ambush to people. Make sure you've dropped the waterline first before you ask someone else to do it.
  • Use "If you really knew me" as a conversation starter to bring depth and connection to families, friends, school and work. We challenge you to try using this tool at your next family dinner or group gathering.
  • Approach someone with whom you'd like to be closer. Try the model of Notice, Choose, Act by telling them one thing you notice about them that you'd like to know more about; tell them how you envision your relationship deepening; and ask them if they would create a deeper connection with you.
  • Start an on-going "if you really knew me" support group. Create time for people to get together and share the truth of who they really are and how they really feel. All that's needed is a timer to equally divide the time and a group of people willing to participate.
If you are dealing with secrets or any dangerous patterns, habits or addictions, reach out and get the help and support you deserve from experts or people you trust. Take the risk of sharing what you're really going through. You don't have to do it alone!


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