My friends and I like to play a game we call "pennies from heaven." It's very simple: Pinpoint a sum of money you believe could come to you out of the blue, with no effort on your part, from a source you don't expect, within the next month. You could find a nickel on the sidewalk. A kindly billionaire might stroll up and cut you a check. Write down the amount, then forget about it until a month later—at which point you should see whether your heaven pennies have arrived.

One of my friends, Claire, didn't want to play the game. "This is silly," she said. But after some cajoling, she decided she could just barely imagine $1,000 floating her way. Three weeks later, Claire received a letter saying that her company had miscalculated her 401(k) withholding. Along with the letter was a check for almost $800. It wasn't a thousand bucks, but hey—$800 is nothing to sneeze at. "Told you this game works!" I said to Claire. "Well," she said, "I'm never playing again. I know better than to tempt fate."

This reaction may seem bizarre: She won the game! And she didn't want to play again? But her refusal is more typical than you might think. Most of us are comfortable only if we have a certain amount of money, health, love, and promising opportunities in our life. When we fall short of these targets, we almost always find ways to improve our circumstances until we're back in that sweet spot. But weirdly, we often also feel uncomfortable when things get "too good." We have a sort of happiness set point, and if we exceed it, we may, like Claire, discount or even sabotage our good fortune in order to feel normal again.

Why on earth would we do this? Well, one reason is simple anxiety about anything unfamiliar (this is why people who receive fashion makeovers often freak out and immediately return to their Sasquatch ways). Another is social conditioning. Mom, Dad, and Nana may have always reminded you not to expect much. They did this out of love and the hope that you'd never feel the pain of disappointment or loss. But obviously, this is self-defeating: It ensures the very thing we fear. That is, very little that's good ever enters our life. Yet many of us prefer a mediocre, even miserable, existence to the possibility of loving and losing.

And we find so many fun and interesting ways to bring that miserable existence into fruition. When something good happens to you, maybe you immediately remind yourself that it's only temporary, or look for some catch that you're sure will ruin everything, or tell yourself you don't deserve it, or focus on any tiny flaws you can find in this happy turn of events. Whatever your approach, I'm sure it's very effective—and if you never want to feel better than you do already, you should definitely keep using it. But if you'd like things to improve, you need to change the pattern.

You might assume you can take the logical approach and reason with yourself—the way my friends and I all tried to convince Claire that if the wildly illogical pennies-from-heaven game worked once, it might work again. You may have read inspirational books, chanted affirmations, attempted to white-knuckle your way toward optimism. Unfortunately, when we try to force the most timid parts of our psyche to feel safe, they tend to feel only the force, not the safety. Then we get the whiplash effect as our brains belch up a double dose of pessimism.

The key is to accept loss without resistance. It might seem that leaning straight into sadness would leave us in a welter of fear and disappointment. Paradoxically, the opposite is true. Nonresistance can actually help us raise the ceiling on our happiness level while reducing the pain we feel when things don't go our way. Learning the art of nonresistance means distinguishing between enjoyment, which leads to happiness, and attachment, which doesn't. We tend to conflate these phenomena, though they're actually very different. Enjoyment is present-moment delight with pleasurable circumstances. Attachment is the wretched cluster of emotions that go with fear of loss—anxiety, clinginess, neediness, sadness, flat-out panic. All creatures, so far as I can tell, seem able to enjoy. But only humans become attached, obsessing about potential future loss even in the best of circumstances.

Animals are experts in enjoyment without attachment. I once watched four lionesses spend half an hour sneaking up on a warthog, moving at about the speed plants grow, displaying incredible patience. Then—boom—the warthog saw them and dashed off. Immediately, all four lionesses dropped in their tracks and fell sound asleep. No moaning, no agony, no rage about their mistakes or their missed opportunity. The lionesses weren't attached to the object of their desire. They lost out on that dinner, but knew another opportunity would come along. And in the meantime, they were going to get the most out of the here and now. They decided that if they couldn't enjoy a warthog, they'd enjoy a nap.

I learned how to stop puncturing my own happiness from my first dog, an abused pound puppy I named Mei-Mei. When I brought her home, I could practically hear her thinking, What fresh hell is this? She wouldn't eat, drink, or lie down. When I fell asleep that night, she was still sitting bolt upright, trembling, waiting for the other shoe to drop. But the next morning I awoke to find Mei-Mei lying beside me in bed, her head on the pillow, snoring blissfully. In one night, she'd allowed her happiness set point to zoom upward. She accepted her good fortune without wondering whether she deserved it or being afraid that relaxing would jinx the deal.

It occurred to me then that I could raise my own set point if I could be like a pound dog. I decided to train myself with the most basic doggy instructions: "Here," "Sit," and "Stay." This approach has worked amazingly well for me and for many of those I've advised. I'm hoping it will work for you, too.

The first command—"Here"—is simple enough. It means going to the place where you expect good things to happen. You could, for example, play pennies from heaven. Or spend a few minutes counting your blessings. Notice anything positive at all. Make a list. Then tell yourself that these things will keep showing up, and that even better things are coming.

If this makes you uncomfortable, practice the next command: "Sit." When you feel yourself drifting back toward your happiness set point, sit still and watch your inner turmoil of fears, memories of past losses, and catastrophes you're already imagining. Let it all float by and then gently bring your attention back to the present moment. Many people who meditate simply call it sitting, and like a meditator, you may find that focusing on your breathing as you ride out the emotional storm is blessedly grounding.

Once you're sitting, go to the final and most challenging step: "Stay." Buddhist nun Pema Chödrön teaches "learning to stay" as the central skill in personal transformation, the humble but royal road to equanimity and acceptance. Staying in an openhearted place of nonattachment is the best way I know to raise our happiness set point and allow better and better circumstances to flow to us, even as we depend on these circumstances less and less. Here are some helpful hints to use as you gradually teach yourself to stay in hope and enjoyment:

• As you train your "puppy," be kind. Notice how from a position of power you can feel a calm intention to care for and protect her. Ponder the notion that the universe may feel the same way about you.

• When you train a puppy, you have to reinforce good behavior—gently, firmly, repeatedly—until that good behavior becomes ingrained. You've done this for yourself dozens of times in your life: When you first learned to tie your shoes, write in cursive, or drive a car, you probably felt unsure and nervous, but you persisted until these skills felt natural. Think of enjoying good fortune as one more skill you can master with practice.

• Look back over your life and notice how things have floated through it, arriving, often without your intention, then leaving, making way for new things. Notice that while things come and go, the flow of them is inexhaustible. You don't need to rely on any one thing; you can rely on the flow, which never ends—maybe (who knows?) not even at death.

Eventually, Claire went on to play many more rounds of pennies from heaven. (And guess what? Sometimes it worked. Sometimes it didn't.) But the pennies weren't really the point. The point is that hope isn't dangerous; good fortune doesn't portend bad fortune; and enjoyment and nonattachment, used together, reliably decrease your fear of loss. Luck comes and goes, but those lessons are permanent, and they can hugely increase your overall happiness. But don't take my word for it. Just walk into a place of hope and enjoyment, and follow three little suggestions: Here. Sit. Stay.