Having Fun in the Pit of Despair

Many spiritual teachers advocate the principle of detachment, which means being unattached to outcomes. The reasoning is that attachment to outcomes creates unnecessary suffering. Life is full of surprises, and if you become overly attached to specific outcomes, you’re likely to create extra stress, frustration, worry, and disappointment for yourself. So why bother with this needless suffering?

Dispassionate detachment is a popular idea, especially in Buddhism. It claims to help people transcend neediness and clinginess — if they practice this principle enough. But for many people, it’s impractical to consistently apply this principle in real life.

On one level it seems clear to me that people suffer some emotional distress when they become overly attached and clingy to specific outcomes. I’ve received dozens of emails from people asking me how they can capture and secure a specific relationship partner who doesn’t reciprocate their feelings. I’ve also received abundant emails from people asking how they can let go of such clinginess because it’s eating them up inside, and they really want to stop obsessing.

I’ve had my own challenging lessons with attachment to deal with, especially in my first several years as an entrepreneur. I set specific and measurable goals, and I became attached to them. I grew increasingly frustrated when I had to deal with setbacks. I tried not to let the setbacks bother me, but they did. Even when I did achieve my goals, the stress created along the way made the accomplishments feel bittersweet.

I tried the Buddhist approach and found that it gave me some temporary comfort, but the results were inconsistent. On the one hand, it helped lower my stress levels for a short time, but on the other hand, if I didn’t care enough about my goals, I often felt like I was using meditation and detachment as justifications for laziness and procrastination. Practicing detachment actually increased my stress in the long run because it postponed real growth and progress. I felt better when I confronted my challenges head-on, regardless of how attached I felt to the outcomes. I’d often experience a queasy feeling in the pit of my stomach while practicing detachment, and that became one more feeling I wanted to transcend. Detachment had all the telltale signs of a partial match, so I knew there had to be a better approach.

Moreover, I didn’t like feeling so aloof. It was just too Vulcan for me. It made me wonder, Why bother doing anything at all? I might as well sit around doing nothing. This practice encouraged me to check out of real life and to ignore my goals and ambitions. Why bother helping people? Why bother writing? Why bother living? None of it matters anyway.

Swami Vivekananda, a Hindu Vedanta evangelist, stressed that any good philosophy should satisfy our reason as well. The Buddhist notion of detachment failed this test for me. It didn’t satisfy my reason. And it didn’t feel intuitively right to me either.

Exaggerating Attachment

My eventual solution — and one that has served me well for years — was essentially to do the opposite. Instead of stepping back into detachment, I stepped further into attachment. I adopted a more playful mindset and looked for ways I could increase and exaggerate the feeling of attachment. More Klingon. Less Vulcan. This approach has worked beautifully.

Some friends have been staying at my house for the past few weeks, and we occasionally play the game Carcassonne together — a competitive strategy game. If I practice the Buddhist version of detachment, the game isn’t as fun. If I don’t get attached to the outcome, then what’s the point? The degree of fun depends on how attached the players are to the outcome. So instead of trying to step back and be detached and objective, I immerse myself in the necessity of victory and the horrible threat of defeat.

Sometimes I’ll say things like this to my friends as we begin a game:

I subscribe to the Gul Dukat standard of victory, so my goal isn’t just to defeat you. A true victory is to make your enemy see that they were wrong to oppose you in the first place — to force them to acknowledge your greatness.

Occasionally I’ll quote The Princess Bride:

Your ears you keep and I’ll tell you why. So that every shriek of every child at seeing your hideousness will be yours to cherish. Every babe that weeps at your approach, every woman who cries out, “Dear God! What is that thing,” will echo in your perfect ears. That is what “to the pain” means. It means I leave you in anguish, wallowing in freakish misery forever.

You can imagine what effect this has on my friends. On the mild side, it elicits a collective groan. Sometimes it encourages them to gang up against me. Either way it raises the stakes of an otherwise mild-mannered activity. When I express my attachment to winning, my friends become that much more attached to my defeat. This has the effect of making the game more emotional and immersive. If one of them wins, they relish the win that much more. But if I win, it’s all the more glorious a victory. Suffice it to say that I’m no stranger to having both expletives and game pieces hurled at me. As I see it, this is just my opponents’ way of acknowledging that they were wrong to oppose me in the first place. 😉

When I lose a game, I don’t try to pull back from disappointment — I wallow in it. I curse my foul luck, re-analyze the critical moves, and grudgingly congratulate the victor. I allow the defeat to sting, and I vow vengeance at the next rematch.

Of course I know that the outcome of a game of Carcassonne doesn’t actually matter. But I practice this kind of over-attachment for two key benefits. First, it makes a relatively mundane experience so much more lively and fun. Second, this practice helps me have more fun and avoid unnecessary stress when the stakes are higher.

Turning Stress Into Fun

When I face circumstances where I’d have a tendency to create extra stress or set myself up for disappointment, I use the same strategy of overplaying my attachment. I don’t try to stave off disappointment. I deliberately overact the potential upside as well as the potential downside. I make the stakes seem even bigger than they are.

This approach gives me the best of both worlds. I get to enjoy the thrill of taking risks. I get to be passionate, involved, and immersed in the emotional experience of life. I get to savor every drop of juiciness. But I don’t suffer because as counter-intuitive as it may seem, I don’t resist the possible outcomes. By exaggerating my attachment, I encourage the neediest part of myself to fully express itself, which transforms it into fun. I know that when I lose, I’m going to overact the loss just the same as I’d overact the victory. Since I’m going to exaggerate the outcome either way, it’s hard to take either outcome so seriously.

I’d rather step forward into life’s experiences instead of dispassionately retreating from them. I’d rather play Carcassonne like Dukat than like Spock. Spock may win more often, but Dukat will have so much more fun.

Why do we love movies that include passionate, lively, and larger than life characters? I think it’s because they express how some part of ourselves would really like to live. We’re not here to sit on the sidelines of life in a lotus position and be aloof and unattached. We’re here to devour all the tastiness that life has to offer. We’re here to relish the bitterness and the sourness of life as well as the sweetness and savoriness.

If you have a victory, celebrate the heck out of it. Let it be the greatest victory any human being has ever experienced.

If you have a setback, celebrate the ridiculousness of it. Don’t try to be aloof and dispassionate. Steamroll those mild feelings into the most absurdly over-acted tragedy to ever befall a human. Then you’ll grasp just how ridiculous it is to wallow in even mild disappointment. To the cosmos your greatest disappointments are always a joke, so do your best to treat them as such.

Celebrating the Pit of Despair

What if you’re feeling attached to a specific outcome that hasn’t been determined yet, such as desiring a specific relationship partner who may not share your desire?

Go ahead and let yourself feel attached, but get out of that fuzzy gray zone between victory and defeat. Set yourself up for a true victory or a true defeat, just like I do when playing Carcassonne. Raise the stakes even higher.

The way to stop making such a big deal out of defeat is to make defeat an even bigger deal. Stop trying to protect your vulnerable self by over-padding the seemingly safe middle. Delete the margin between a win and a loss. Even if you win or lose by only one point, let it be a tremendous victory or a crushing defeat. There is no other outcome.

A favorite tool of cowardice is indirectness. The coward tries to prevent disappointment by only half risking, half asserting, and half committing. The heart remains shielded from defeat, but a shielded heart cannot emit its radiance. A shielded heart has no creative power.

Drop the shields from your heart, and take some real risks. You’ll soon discover that life jumps at the chance to reward your courage, not necessarily with victory but certainly with fun.

When you dare and win, sing loudly of your glorious victories. And when you lose — and you will lose from time to time — then go ahead and make the sound of ultimate suffering until you’re compelled to laugh at your ridiculousness.

Make no mistake: If you shield yourself from taking risks, then you’re the most wretched and miserable coward to ever walk the earth, and you deserve an S&M lesson from Count Rugen in the Pit of Despair.

After you set yourself up for a true victory or defeat, then play your very best game. Enjoy the full richness of the experience, and revel in the soul-stimulating emotions that follow. Don’t just try to come out ahead. Don your Holocaust cloak, and do your best to infiltrate the castle against insurmountable odds, slay Count Rugen, rescue the princess, and ride off into the sunset. If you succeed, give the princess the most pure and passionate kiss the world has ever known. And if you fail, then go build a summer home in the Fire Swamp.

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