We like to read lists. We like to make lists. When we cross things off a list we feel productive. We are getting stuff done! Check the box. Complete a task. Keep moving forward.

The list never ends and we are busy.

Check, check, check

I see a lot of checkbox diversity.

• “Need to get a Latina on the board”
• “We have to fill this position with an African American.”
• “Let’s have an anti-bias training.”

I have witnessed an avalanche of checkbox philanthropy.

• “Only give to organizations that have low overheads.”
• “Will not support non-profits who receive government support.”
• “Won’t be involved with any advocacy efforts or anything “political”.

We like checkboxes to give us the illusion of control over the world and yet we miss the big picture.

We all crave a straightforward recipe for life. We want simplicity and reliability. We want more certainty in determining our futures, in the outcomes and decisions we make.

But do we?

Can you imagine a world that is fully predictable and follows the rules? Yes, but whose rules?

I remember Coach John Wooden told me a little story. Another coach asked him, “In a nutshell, what is your coaching philosophy?” And Coach Wooden responded, “Any philosophy that can be put in a nutshell belongs in a nutshell!”

When we reduce to life to checkboxes we can miss what is happening around us. We miss the serendipity, the possibility and any awe and wonder that the world offers—that’s all  

My college roommate used to make a list of the steps he would follow on his date. He wanted to do things “right” and he did not want to forget what to do. Never mind what his date was saying or doing. Intellectually we can defend his process, but his dates were disasters!

Yet we make these lists of future elements of our intended happiness/success—On paper they are really interesting……….. As Korzybski said, “The map is not the territory.” I would say is never the territory.

Years ago, I went to my cousin’s wedding. She looked radiant in her white dress. She asked me to dance. I was filled with pride and love looking at her and seeing her joy and beauty. She looked at me and said, “Uncle John I am so happy, because my life is going exactly as I planned it.” Her words were like machetes slashing through the tranquil oasis of my thoughts. “Yep, getting married today by 25—check!” “In 2 years we will have a child—check!” “Then we will buy a house with a yard—check!” and she kept going. Her eyes looking over my shoulder into the distance as if she could truly see her future. “And by age 60 we will retire and travel the world—check!” In the matter of 90 seconds between my poor dance steps, we had ridden a time machine to 35 years hence. I listened intently in horror, trying to suppress all my instincts—reminding myself this is HER wedding day. But intention is never enough. I erupted. I grabbed her gorgeous face that was fit for a painting. “I am so happy you have a plan, but don’t get ahead of yourself. Enjoy today. This is the moment that will determine the future. Be happy with what you have, what you have achieved and your marriage. Forget the plan. What happens next you can’t predict– stuff happens.” (yeah I said “stuff”) At this point, my awkward dance moves had stopped and we were just frozen in the middle looking at each other. My wife Sarah immediately took notice and leapt to her feet to rescue my cousin. But before the cavalry arrived, my cousin said, “Uncle John why don’t you like my plan?!” I feared I had ruined her special day.

18 months later she was filing her divorce papers after a bitter marriage and thankfully no children. Stuff happens. It always does, making a mockery of our linear checkbox plans and opens new vistas. We all want the escalator to the top. The frictionless, seamless, smooth journey to happiness. But outside of Hollywood, our stories are filled with mountains, valleys, highs and lows. Great expectations. Great victories. Great setbacks. That are interconnected. No way to have one without the other. Trying to envision and wish the world ahead into some order is paving a ten lane freeway to disappointment. Yes, you should set goals but they must emanate from your heart, from your soul—not from some script that you think will bring you fulfillment and meaning. Why? Because life is to be lived. Living requires your full attention to form, inform, and re-form who you are. Not what someone told you. Or what your social media persona aspires to be. But you. The real you.

So create a map for your journey. No great trip or path goes straight. It must meander, traverse, and respect the landscape, the territory, the ecosystem, the weather and is filled with detours. You discover new paths that intrigue, inspire, or just raise your curiosity. You get glimpses of you, your inner light breaks through a few cracks in the armor that you have formed to protect your soft underside of doubt, uncertainty, and fear, but also of your raw potential. There is a big difference between a trip and an adventure!

Checkbox lives are a one-dimensional fantasy leading to a mirage.

Years later I was invited to my cousin’s second wedding. She had forgiven me for my outburst and we put it into a time capsule and never spoke of it. I was sitting at the reception after a beautiful ceremony, when my cousin asked me to dance! Sarah looked at me and I knew I needed to keep my big mouth shut. So, I averted my eyes from my cousin’s gaze as we swayed to the music. She grabbed my face! She smiled and said in a forceful but peaceful voice, “Not a day goes by when I don’t think of what you said! I have no plans! I love my life and this moment!” She was still holding my face like a ripe melon and I looked back at her and smiled. “It’s a beautiful day. I am so happy for you.”

Today she has three healthy and exceptional children, a strong marriage, a ceiling shattering career, and is enjoying the light she shines. She started with a set of checkboxes to happiness and lived a happy life instead.

Stuff will happen and can happen if you let it.

Thanks for reading. John