The Enlightenment Test

Home for the holidays and why the tennis analogy beats ego dissolution

Ram Dass remains one of my favorite spirituality writers. At times of confusion or pain, his words uplifted me and helped me find peace of mind.

One of his better lines that stuck with me was always:

If you think you’re enlightened, go home for Thanksgiving

—Ram Dass

A while back I saw a chart showing the amount of time most of us spend with our parents. As you might guess, it drops precipitously after the age of 18. By the time we’re in midlife, the number is close to zero.

Image from Romit Kuhar

That chart hit me like a ton of bricks the first time I saw it because it felt so real, so pertinent to my life. In my mid-20s I left Philadelphia to try my hand at making it big in New York City. I landed a job at a large advertising agency while most people my age were struggling to find any job in the midst of the Great Financial Crisis. Making the most of NYC’s networking opportunities I landed another, higher paying, role at a boutique agency. Then I caught the entrepreneurship bug and decided to take a shot at the VC startup route, and, somehow, pulled that off.

Before I knew it, a whole decade had passed and I had become a startup founder in New York City. Not too far from family, but enough distance to forge my own path. Along the way I started a VC-backed business, studied at MIT, married, divorced, then re-married and had a beautiful baby girl.

12 years had passed since spending a lot of time with my parents to almost no time at all. Except now, I was married with a child. To make up for lost time, we would try to make visiting family a priority around the holidays.

Our family’s tradition the last few years has been to go visit my mother, who lives in a beach town year round, for the Fourth of July. Independence Day has become a time when my sister and I make use of mom’s proximity to the beach to gather. My kids, my sister’s kids, it’s a packed house. There’s only one problem.

Let’s just say the relationship between me and my mother’s husband (they married when I was in my thirties, so it’s always been a bit weird for me to call him ‘stepfather’), hasn’t always been smooth. He’s a tough personality to deal with. They seem to get along fine when it’s just the two of them but the moment her family (us) comes by, something changes in him.

Unfortunately, the trip ended in a fight. Not with me directly, but I got caught in the middle of it. There was yelling, crying, and table slamming. In an effort to shield my kids from family drama, I quickly packed our bags, loaded the car, and rushed us back home.

On the drive back, stuck in traffic, I thought “how did I let it get to that point?” Given everything I know, and teach, about mindfulness and unity consciousness, how could I allow myself to get sucked in to someone else’s vortex of aggression? Isn’t that what I spend so much time reading, writing, and coaching others about? Aren’t we all one essentially? Why are we bickering, in the family no less?

And how do I square this desire to raise a conscious family that is grounded in peace, kindness, and love with family drama.

My first instinct was to run— to move our family away, as far as possible from this madness. But as the miles passed and traffic jam cleared, Ram Dass’ words replayed in my head.

It’s easy to be ‘enlightened’, however you define it, while living an ascetic lifestyle. Cut off contact from the outside world, meditate for hours on end, eat vegan and drink smoothies, and do some yoga stretches for good measure. But that isn’t life, not for most of anyway. We live in the real, messy world. Not everyone is ‘conscious’ or even desires to be. We are forced, in this lifetime, to interact with fellow human beings.

If you’ve ever spent a bit of time around someone getting into meditation for the first time, or someone coming back from a psychedelic retreat, there is a whole lot of excitement, optimism, and deep-dive head first into the “pure bliss” that awaits us all once we grasp the elusive ‘enlightenment’. Most though have a harsh crash landing back in the real world. Which got me thinking—what if we're approaching this all wrong?

Instead of chasing pure bliss and 24/7 enlightenment, a lofty but mostly unrealistic goal for the vast majority of us, what if instead we chose to live a life of understanding, compassion, and patience—starting with ourselves. To accept our ego, not seek its destruction. “Ego Death” is possible with enough psychedelics or meditation, but even the best trips end at some point. Then what?

Between “we are all one” and “dog eat dog” there exists a third path. The path of the collaborator. The path of the tennis match.

To play tennis with another human is to enter, collaboratively, onto the court and agree, together, to provide a competitive experience for one another. To stare across the court with loving eyes because “we are all one” and refuse to serve the ball would make for not only a dull game experience, it will likely annoy your counterpart to the point of never wanting to play with you again. But just because you decide to take it seriously and try to beat them, doesn’t mean you are enemies off the court.

It’s interesting how you play, like when you play Monopoly, if you play the game Monopoly, which is a board game in which there are thimbles and hats and irons. And you pick a thimble, a symbol, and you move it around the board, and you go to jail or you win Park Place or the utilities and so on. If you and I played Monopoly together, the game requires we play fiercely, that we compete. But you and I collaborated to sit down and play the game. We are collaborators to compete.

— Ram Dass

That is the level I try to attain. To remember that life is one big tennis match. We aren’t enemies of one another, but while we’re here we have roles to play and sometimes that means being competitive, but as collaborators in a game. Not adversaries.

No one is perfect, and I’m far from it. But if there’s one thing I learned over many years, it’s to take time to reflect on the day, the week, the month, the year and ask myself to learn the lesson. To show up and be a high quality collaborator without identifying with the emotions of the ego.

This doesn’t mean you need to keep toxic people in your life, even family.

But it does mean we owe ourselves a path to engage with the world, even when the experiences are less than pleasurable. True enlightenment isn't found in the absence of conflict, but in how we navigate it. The tennis match continues and we get to choose how we play.