Trying Too Hard

It's Doing Too Much of a Good Thing

You never get enough of what you really don't want. Most of us do too much of something: if we're a Six, we worry too much, if we're a One, we scold too much, if we're a Two, we please too often -- each style has something it overuses.

The Sufis have a saying that Jesus stands by the river and sells river water. What they mean by this lovely aphorism is that Jesus tries to convince us that God is in the ordinary and we don't have to look for him any place but in ordinary reality. It's easy to find God, it's easy to please Jesus. It's sort of an anti-mystical statement. And in the gospels, whenever people marvel at Jesus, it isn't long before they turn on him. His opening statement of mission in Luke 4:14-30 is a good example.

In both Sufism, a possible source of Enneagram wisdom, and in Christianity, the understanding is that we try too hard. Trying too hard is a subtle perversity. If we're accused of it, we are taken aback -- it's like being told we're too smart or "overqualified." Trying too hard baffles us. It's almost like an oxymoron, a successful failure. In the spiritual life, how can the Enneagram be against trying hard.

Can we understand the earnest young American student who went to the guru in India and asked him how long it would take to reach enlightenment. The guru said it often takes three or four years, but "because you are working so hard at it, it will take ten."

In Parables and the Enneagram this insight is repeated for each type. The parables presume a world of abundance. Trying too hard presumes a world of scarcity. That's the rub. In our Enneagram trance, we're wrong about the way the world is. It isn't the act of trying hard that annoys both human and divine love, it is the underlying assumption that a) you won't love me unless I do these things and b) if I do these things, I can earn your love. Both of those presuppositions are emotionally destructive to a relationship. It is insulting to a lover to say you can earn their love and it is arrogant to think I can do anything that will "make" you love me. Love is radically free on every level.

Grace Is Free

In traditional Christian theology, it is always taught that grace is free. We are loved as sinners. That goes down smoothly enough, we've heard it a lot of times. But the Enneagram really makes that teaching emotionally dramatic. If I am a Two, my attempts to earn love by emotional investment are sick, counterproductive and offensive. If I'm a Three and I think my achievements will earn love, that too is sick, counterproductive and offensive. In America, where "We Try Harder" is respected, that goes down hard. But the Enneagram is clear: our chief feature, our major fault, is the overdoing of whatever it is that we do best. Nobody outperforms a type Three. But let the Three push too hard and you can see it is compensatory. Threes try so hard because they feel bad about themselves inside. They look so good because they feel so bad.

Remember the essay on polarization. Let me push that a bit. When we try too hard, we intensify the polarization. The dog most afraid barks the loudest. The biggest bully is the biggest coward. And the highest performing Three says that despite the medals, money and magnificence, they feel like an inadequate child inside. When we dissociate from our feeling unlovable, we intensify our search for love. But all religions and Jesus in the parables says it doesn't work that way.

That's why Enneagram work, in my opinion, starts with work on our perceptions. We don't have to "do" a lot of things, we have to do those few things that will alter our perceptions. Then our activities will flow naturally from a less distorted view of the world. One way to define the Enneagram is the nine wrong ways we see the world and the strenuous efforts we make to get that wrong world to work.


Parables and the Enneagram, Clarence Thomson; The Dynamic Enneagram (In this video, Condon works with a type Three that acts out this polarity dramatically).Sufi literature has wonderful stories that boggle your mind. They can weaken our distorted model of the world.


  1. Trying too hard is always done rigidly. Instead of adjusting to reality, we repeat the patterns of our childhood. Ask yourself: "How old is the behavior I do too much of?" (Some things, like eating and drinking too much are of varying ages, but temper tantrums or pouting or "showing off" can be approximated).
  2. Can I get in touch or have others help me see what I do that doesn't work? (Healthy people do what works, unhealthy people do what used to work...) When I'm doing something that doesn't work, it's a clue I'm dealing with a world that exists only in my mind.
  3. If you really want to test your talent, watch the upcoming campaign and see if you guess the developmental age of the Enneagram styles of the candidates.