How to Find the Promised Land (In Less Than 40 Years)

Popped red balloon

Photo Credit: Kat…B (Creative Commons)

Few of us consider ourselves to be leaders. But I think each of us is called to lead someone. That can be an intimidating notion. But it doesn’t have to be. You have all the tools you need for leadership. In your heart…

Summer is dwindling in Chicago, and the shadows are long in the early-gathering dusk. My five-year-old son is in the back yard, bouncing a large balloon above his head. I look on as the red orb drifts toward a rosebush and I can see it coming—the loud pop of balloon on thorns and the even louder little boy, mourning his shredded prize.

As the tears flow I walk casually to his side. I pat him on the back. I reassure him there are other balloons—it’s not the end of the world, and we should be grateful for what we do have. But all my soothing only enrages him and now I’m angry he won’t accept my wisdom and guidance.

But why should he?

Why should he listen to this calloused adult? This big-indifferent creature who is apparently clueless about the grief in this moment? Why should he listen to anyone who can’t relate to the pain he is in?

And he’s right. Because if Daddy cannot touch this place of grief in his own heart, how can Daddy know the means of deliverance?

Leadership is Always Deliverance

People don’t follow leaders because they are hip or fun or friendly. People follow leaders because they want to be delivered out of bondage into the freedom of the Promised Land. From loneliness into companionship, from poverty into affluence, from sorrow into joy, from obscurity into influence, from dependency and submission into empowerment.

Henri Nouwen wrote, “The great illusion of leadership is to think that man can be led out of the desert by someone who has never been there.” As leaders, our only real authority is our intimate knowledge of the bondage itself and the ways we were delivered into freedom. When we lead, our authority is our experience of the freedom-journey.

Maybe this is why the Israelites wandered in the desert for 40 years? Perhaps it wasn’t all about their opposition and rebellion. Maybe it was a failure of leadership. Maybe Moses couldn’t lead because he had experienced a life of privilege and then of exile but never of slavery. How could a man who has never experienced the slavery of his own heart efficiently lead a bunch of slaves to the Promised Land?

A Daddy Leads His Little Boy

As my son weeps anguished tears, mourning over the sudden loss of his prized possession, I try to find his place of bondage in my own heart. I try to find the place of loss. I know this beautiful boy is my prized possession and an image flashes through my mind—a sudden darting of boy into street, cars racing past, and my prized possession broken and shredded. Lost.

His grief wells up in me, and suddenly my eyes are wet like his. And I know that leadership in this moment is not a lesson in letting go or gratitude. Leadership is an embrace—a steadfast reassurance of I-am-with-you.

Deliverance Always Begins in the Leader’s Heart

As a leader, you must first walk the lonely journey into the substance of your own soul. You must find the place of bondage in your own heart—the loneliness, restlessness, frustration, emptiness, loss, helpless dependency, or whatever.

And you must trust that your most personal experience is also most universal.

Because the people you love and lead do have the same conflict in their hearts, and they are starving for a leader who knows the experience and is prepared to lead them out of it.

The preparation is simple, but it may be painful:

You must feel the place of bondage in your own heart, rather than running away from it. This is your preparation for leadership: you must become intimately familiar with the place you want to leave. It is the only way to truly understand those you are called to lead. And they won’t respect your authority if you don’t understand them.

Having experienced the slavery, you will then learn how to walk out of it and into the freedom of the Promised Land. Having walked the walk, those who look to you for leadership will trust the authenticity of your calling. And they will feel real hope.

Finally, your calling as a leader is to clearly communicate the nature of the freedom-journey. You are called to spread the message of hope and point the way toward the Promised Land. In vulnerability with your spouse, a late-night cuddle-talk with your child, a cup of coffee with a friend, as referee in the neighborhood soccer game, or in an encounter with the aching eyes of a stranger.

It’s that simple. And it’s that hard. But I think if you’re willing, you and the people you love and lead won’t have to wait 40 years to glimpse the Promised Land.

Questions: What do you think about this view of leadership? What do you think are the keys to leadership? Leave your thoughts in the comments section.

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Kelly is a licensed clinical psychologist and co-founder of Artisan Clinical Associates in Naperville, IL. He is also a writer and blogs regularly about the redemption of our personal, relational, and communal lives. Kelly is married, has three children, and enjoys learning from them how to be a kid again. You can find him on Facebook, Twitter, and Google+.

Please note: I reserve the right to delete comments that are offensive or off-topic.

  • Val

    The idea in this article is exactly why I became a physics teacher. Because a lot of math and science didn’t come easy for me. I had to work for it, and I understand the confusion, I understand it not making any sense in any way the first five times you see a topic in a class for it suddenly to feel like, “Well! Why didn’t someone just SAY that?!?” when it clicks into place.

    I am finding I struggle with leadership in my very, very, very new marriage (six weeks and going strong!), because one thing leadership implies to me is a power inequality. I’m good at the empathy part, or at least I try my hardest to be so, but when do you lead and when do you walk together? And when do you throw up your hands and just do whatever it is yourself?

    • drkellyflanagan

      Val, I’m not sure if this will be helpful, but as I read your questions about leading in marriage, I had this thought: sometimes it makes perfect sense to lead unilaterally, but if it is to be successful, it must always be with the permission of the other. If you have sincere permission, then your leadership is likely to be more fruitful. For what it’s worth!

  • Elizabeth Newhouse

    I think this is a very interesting spin on leadership. I’ve never thought of those moments when you let yourself be vulnerable or broken as the moments when you were being a strong leader, but I think it makes sense.

    I just had a moment that reminds me of your words a few days ago. I was talking with the mother of a little boy just diagnosed with a brain tumor. She was telling me that a friend had visited her and was encouraging her to pray and talk to God, and she said “I got so angry. I didn’t want to talk to God. I didn’t want to pray. I just wanted to be angry”. In that moment I knew I could either encourage her to do those “helpful” things, too, and move right past the real hurt, or tell her “it’s okay to be angry” and be with her in her pain. Because while I don’t know what it’s like to have a little boy with a brain tumor, I do know what it’s like to have my father die. I know what it’s like to be so angry at God, to not want to pray. I loved when you wrote: “And you must trust that your most personal experience is also most universal.” This is so true. And so scary. Sharing the personal, intimate things is not what comes naturally to me, or to many of us. I appreciate your writing that encourages me to have those hard conversations with people who come my way. To not just make “small talk” for the rest of my life, but to dive right in!”
    Thank you!

    • drkellyflanagan

      I think you nailed it here. You found a coinciding place in your own heart and gave both of you permission to feel it. Well done. Reminds me of something I just read in a book called “The Gifts of Imperfection.” The author would have called your wise action both vulnerable and courageous.

  • Arka

    I find some people do not want to leave the desert, or they do not know how. Perhaps, they are used to feel in the same way for years and years. It’s hard to let them know that there are other ways of feeling, but I find it is possible to communicate how to get out of the maze. Only if they ask for help? I ask myself. Only if they decide to leave the desert? Otherwise, it is perhaps better to be seen as a reference without being too invasive. Maybe it’s just a matter of feeling empathy for those who are in the desert and it is enough to be present. Otherwise, Would it be a loss of energy?

    • drkellyflanagan

      Good observations, Arka. Perhaps in these situations the place of empathy or connection is some time in your life when you felt hopeless, too overwhelmed to change, not motivated to get unstuck? When I feel hopeless as a therapist, I know I’m discovering what it must feel like for my client.

  • Greg Taylor

    You know, I think maybe this is a huge idea.

  • Jennifer Newell

    I think about the people in my life who have shown the best forms of leadership and they all have the same key elements. First, I would say they are able to show true
    empathy. They are able to meet you where you are at and in those moments feel your heart ache. It is after that occurs that you would be able to help lead someone out of that darkness. Second, Leadership is shown by people who treat others with respect for the common man regardless of where they are from or what their type or level of job. In your workplace there are people that are sometimes treated like they are invisible as they go around emptying the garbage or cleaning the bathrooms. A real leader is one who respects everyone and sees them. A simple hello to the person who empties the trash at your desk shows they are valuable and worth acknowledging. Respect is earned by giving respect to others. Third, your ability to effectively lead is based on your ability to listen and hear the people you are trying to lead. If you cannot listen to others and hear what is on their hearts you will not be able to show empathy, nor will you be respected. Listening and considering other people’s views and thoughts is how you build effective teams and families. Fourth, real leaders are humble individuals. It is not about getting all the recognition. It is not important for you to be in the spot light. It is more important that you give someone else the courage to take the spotlight. The team/family members are taught to be respectful of each other, encouraging for each team/family member, and learning to value each other. Based on these key elements I agree with you that we all can have these skills to be effective leaders.

    • drkellyflanagan

      Jennifer, I really like these four traits of a good leader! Especially the respect of everyone and the humility–often overlooked traits!

  • TiAndrine

    Simply BRILLIANT! Thank You.
    Shine On Dr. K, we support You.
    Love, Peace and Light to You and Yours fra Norge.

    • drkellyflanagan

      Thank you!

  • Andrea

    What a great read. I do feel that calling that you write about, but sometimes I lose that amidst the soul searching. It can be very painful at times. I wish someone could be here experiencing it with me and leading me along the way bc it can be very lonely and even scary at times but it is becoming more and more clear that I have been equipped with everything I need to get through this. In the end, I will be the change I wish to see and only hope I can lead others on this spiritual journey of one’s Self. The promised land seems like a beautiful place but my oh my…the journey there is quite the ride 🙂 Thanks for your great work!

    • drkellyflanagan

      Thanks for sharing your thoughts, Andrea. And you’re welcome!