Wholesome Guide to Misbehaving

Running a company did not leave much time for relaxation, and Jonathan Christian Hudson, a 30-year-old New Yorker and founder of a social coaching start-up, hadn't taken a real vacation in more than two years. But last winter, during dinner with a group of friends at a Mexican restaurant, someone made an outlandish suggestion: Why not go to Mexico? Why not go, like...right now?

The friends headed to their apartments to grab passports and flip-flops and met back up at JFK airport. "I had a lot of trepidation going into it," says Hudson. "I try to be logical about the decisions I make, but this was highly emotionally—and alcoholically—driven."

The group purchased tickets on the spot ($250 apiece) and boarded a flight to Cancun. There, they lay on the beach and partied with the spring-breakers. The experience was "absolutely amazing," says Hudson. "I had more fun in those five days than in two years of living in Manhattan."

The spirit of misbehavior stayed with him when he returned to New York and his business obligations. "Yesterday I bought a skateboard," he says. "I haven't skateboarded in 15 years."

Misbehaving, or acting in ways we'd normally deem improper, can be good for our souls. It can boost our mood, leave us with a sense of liberation, get our creative juices flowing, and make for great memories. Although some people may misbehave too often, or even construct truly transgressive "double" lives, the rest of us are often overly fearful about breaking behavioral boundaries. For routine-oriented types in particular, modest misbehavior can have some very positive results. By exposing us to new and different ways of doing things and of presenting ourselves to the world, it can start a chain reaction resulting in more success and happiness.

The healthy approach to misbehavior, experts agree, is to occasionally break rules, norms, or expectations in ways that don't cause any serious harm. By doing so, we can test out roads not normally taken, and make sure we're on the path that's right for us. Misbehavior usually reaffirms our established ways just as it provides a refreshing break from them. But it sometimes reveals an even better direction in which to steer our lives. If we never misbehave, we'll never know what we're missing...and it could be something great.

Revise Your Rule Book

Our own guidelines mingle with the official laws and regulations imposed on us to influence almost everything we do—from what time we get to work, to how far over the speed limit we drive, to what kinds of white lies we tell. Since such guidelines vary from person to person, so do definitions of misbehavior.

We start developing our idiosyncratic behavioral codes when we're young, in part by registering the disapproval we get from parents when we do something they deem inappropriate, says Leon Seltzer, a clinical psychologist and the author of Paradoxical Strategies in Psychotherapy. Peers, teachers, and coaches also contribute to our early socialization as we soak in their perspectives on what is the "right" way to act. We're also born with raw personality material that inclines us to either comport ourselves badly (in the case of sensation-seekers) or too well (as with people-pleasers and conformists.) "Some people have inhibiting elements in their personalities that forbid them to go outside the box," says Seltzer. For many of us, boundaries have always been comforting. Still, it's important to figure out if those self-imposed limitations are squashing our potential and keeping us from leading a more fulfilling life.

As adults, we absorb even more behavioral expectations when we take on new roles as employees, neighbors, spouses, and parents. Problem is, adhering to others' expectations can keep us away from harmless natural tendencies that can help us flourish as individuals. The next time you find yourself suppressing the urge to strike up a conversation with a stranger, or to don a platinum wig, you might ask yourself why. If the answer is that the behavior might cause some eyebrows to rise, but there's nothing inherently wrong with it, try it anyway. You might make a new friend, or learn that you look fantastic as a blonde.

Paul Draper powered his way through a Master's program in anthropology and scored a professorship at UNLV, "to please my mom," he says. But a few years into his job, he butted heads with a senior colleague and decided to leave teaching to pursue his childhood passion. "I was performing magic tricks for my classmates when I was 8," he says.

He launched a career as a magician, losing his apartment and his girlfriend of five years in the process. "My mom's reaction was terror," he says.

"You need to come into your own authority," says Seltzer. "The great paradox is that in going beyond your self-imposed boundaries, you may get more in touch with who you actually are in the first place."

Step Away From Yourself

Simple misbehavior is a reprieve from the self, relieving the tension that builds up from an unrelenting focus on aspirations and duties. Hence the holidays, feasts, and other celebrations that most cultures and religions build in as a break from day-to-day difficulties.

"If you're working very hard toward a goal, you're going to want to let off steam now and then," says John Portmann, a professor at the University of Virginia and editor of In Defense of Sin. "It's better to do that every weekend or so, rather than refuse ourselves for too long and then explode."

There are lots of fairly safe ways to open the valve. Some people have a boys' or girls' night out, filled with drinking and dancing. Some gamble (it's OK, if you know your limits). A lot of people use fantasy. "That explains Internet pornography," says Portmann.

We act a bit naughty because it feels nice, and we usually know where to draw the line. "I think most of us are pretty good at letting ourselves out of the cage for a little while, and then getting back in and resuming our normal duties as people, parents, and workers," says Portmann.

Temporarily stepping outside our normal behavior gives us a taste of another lifestyle, but also helps us understand that it might not be sustainable for the long term. We realize we'd feel sick and die young if we pounded tequila every night; we'd be broke if we went on a shopping spree every weekend; and we'd get really bored (and sunburned!) if we had to lie on a beach all day, every day.

The downsides of our misbehavior—the hangover, the empty wallet, the guilt we feel after flirting with someone behind our partner's back—also remind us why we typically choose the alternative.

Be Less Angelic And More Innovative

For those not naturally inclined to naughtiness, most psychologists encourage the occasional foray. "When I work with patients who are unhappily rigid and rule-bound, I have sometimes said, 'I hope you don't take this the wrong way, but I think it would be good for you to break a rule every once in awhile,'" says Seth Aronson, a psychologist with the William Alanson White Institute. "It's one thing if living within your rules makes you happy. If not, why are you adhering to them?"

Even those who are content may be limiting their potential, just like a guy who never leaves the town in which he was born. If you're never willing to step outside the box, think about what it's costing you.

"There's a very important link between risk-taking and creativity," says Portmann. You could still achieve excellence—just like perfectly proficient musicians who never miss a note—but you won't become great. Yo-Yo Ma and other standout players deliberately add imperfections—slowing things down and speeding them up and slurring things. They musically misbehave.

Sure, acting improperly can be a little scary. "Whenever you do something out of your comfort zone, you're going to feel anxiety," explains Seltzer. That doesn't mean it's wrong, just that it's counter to your programming. But if you want to experience personal growth, there aren't any shortcuts to a different understanding of who you are and who you can be. "You have to be willing to face a challenge that is more than you thought you could handle," Seltzer says.

If you never build up the courage to speak out-of-turn at a meeting, your boss may never see you as more than a competent assistant. And if you aren't bold enough to ask for the phone number of the pretty woman on an airplane who just spilled her boyfriend woes, you might miss out on a potential mate.

We can force growth, suggests Portmann, by making ourselves go to intimidating parties, or showing up at events where we think we don't belong. The good news: "Once you've done it a single time, it's easier to do the second time, and the third time," he says. The sense of liberation tends to last much longer than the particular experience, and ultimately you'll be free of any artificial constraints.

DeAara Lewis, an independent filmmaker in Memphis, hit roadblocks every time she contacted a new location to get permission to shoot. "There would be documents to fill out, district managers to call, and other tasks that took an incredible amount of unnecessary time," she says. Finally, she decided to try a different, illicit, approach. When she needed a shot from the roof of a prestigious hotel, she and her cameraman just walked in as if they belonged there. "My imagination was wild with the possibilities of what would happen if we got caught," she says. "But nobody cared about us, and we got the shot we needed. I was elated!"

The lesson? "Sometimes, it's easier to beg forgiveness than ask permission," she says, because while many of our rules are important and necessary, some are not.

"I tell people to think about whatever the rule is and then turn it on its head. What would happen if you did the opposite? Ninety-five percent of the time, you realize you'd have chaos," says Robert Root-Bernstein, co-author with his wife, Michele, of Sparks of Genius. "But the rest of the time, you see that there's no real reason we do what we do. Years ago, someone decided to do it that way and no one ever asked if there's a better way, or a different way." Breaking away from the norm can lead to a real breakthrough.

Expect pushback, though. "People want to go to work and know exactly what they're going to do every day," says Robert Root-Bernstein. And no one should misbehave all the time. "You want to fool around just enough to get good ideas that you then bring back to your problem-solving mode."

Make Memories, Not Trouble

Of course, even light misbehaving can go wrong, especially if it's not well thought-out beforehand. When Lesa Thayer, a senior manager at a nonprofit organization, was called into her boss's office a few years ago, she knew what was coming. "We were having budget cuts, and I took up a large portion of the budget with my salary," she says. When her boss told her she was being terminated, "I basically told her off," Thayer says. "I asked, 'Whose ass can I stick this beeper up?'" Thayer ended up keeping her job, but had to deal with a now-frosty supervisor. "I've learned a lot about communication since then and I should have handled that differently," she says.

If your misbehavior is likely to hurt yourself or someone else, you're going too far. But if no one else is really going to notice or care, go for it. You'll get an immediate adrenaline boost and a vivid anecdote to share. "The more emotions are involved in an activity, the better you remember them," explains Michele Root-Bernstein.

Once a year, on her birthday, Josephine Geraci of Lloyd Neck, NY, pulls her kids out of school for a fun family activity like a Broadway show or a day in Central Park. It's against policy. "We aren't even supposed to take the kids out for doctor appointments," she says. "But my kids still talk about those trips." Geraci herself cherishes the time her aunt took her and her siblings to an afternoon movie, instead of back to class, after their annual dentist appointments. "My mother always said, 'Every day will be ordinary unless you choose to make it special,'" says Geraci. "I think it's so true."

After returning to New York from Cancun, a reinvigorated Jonathan Christian Hudson quickly got his latest business project off the ground. DeAara Lewis, the filmmaker in Memphis, recently finished her first feature film. And Paul Draper, the professor-turned-magician who deviated from an accepted path to success, performs globally from China to Dubai.

"It's the people who are comfortable with risk who go further in life," says Portmann. So get out there and start behaving "badly."—Rebecca Webber

How Dare You?!

If your car tires have worn grooves in the route from your home to your office and you can cook dinner with your eyes closed, you might be stuck in a rut. Try one of these kinda naughty activities to remind yourself that there's more to life:

Play dress up—Dig deep into your closet and find something outrageous to wear to work tomorrow. That tie your Aunt Bessie gave you for Christmas 20 years ago. Or the shimmery bustier you could put on under your suit.

Tell a tall tale—Make up a crazy story for the next stranger you speak with, like the telemarketer who calls after dinner or the guy sitting next to you on the bus.

Crash a party—Don festive attire and head to the fanciest hotel in your town on a Saturday night.

Have sex someplace new—In the car, at the park, under the bleachers. Think like a teenager.

Go rogue at work—March into your boss's office and share your ideas for improving the business.

Attend an age-inappropriate event—Go to senior citizens' bingo at the fire hall, or attend the homecoming game of a local high school.

Go on strike—Tell your family they're on their own for dinner/homework/laundry tonight. Instead, take a bubble bath and crawl into bed at an obscenely early hour.

Say "yes"—Accept an invitation to an event even though you already have plans that night. Cancel them to do what you really want.