The Art of Making (and Not Making) Plans

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Cultural Studies

Adult life is full of commitments: bills to pay, family to see and a job you probably have to show up for. But in a world where many of us complain of being overscheduled, there’s something uniquely depressing about having no control over the time once quaintly called “personal” and “free.”

A recent study by the Olin Business School at Washington University in St. Louis found that scheduling leisure time with friends — for movies, drinks, bike rides — can make these otherwise enjoyable activities feel like chores, which is often why we cancel them.

The New York Times covered the culture of plan-canceling as early as 1986. (“Those who cancel do so for widely varying reasons that range from failing to write down lunch dates to psychological problems,” the article said.) The topic has more recently been given new life thanks to the advent of efficient if impersonal modes of communication like text message and email.

But if technology has made bailing on commitments too easy, how about a radically different approach? Make fewer to begin with.

This doesn’t mean becoming a hermit — as tempting as that is in chilly weather or when there’s a new season of “Transparent” to watch — but, rather, scheduling your time more deliberately so you can be a better friend or family member. Consider it a mindfulness approach to socializing.

Out of my own personal antipathy to making plans came an ironclad rule: I don’t schedule more than two in a given week. Which means that, yes, I am frequently that person suggesting a date one or two months in advance. But it also means that the majority of my free time is open for spontaneous plans — actually doing what I feel like doing — which most often happen with my closest friends. Like airlines and frequent fliers, I give people who are important to me priority booking.

On its face, the act of making plans shouldn’t be stressful. We’re lucky to have people to make plans with, right? But it can be loaded, particularly for people who have lifelong friends and family close by.

“You naturally have a larger network,” said Kathryn Ebner, 33-year-old employee at a start-up in Manhattan who grew up in the New York City area. “That means more milestones — weddings, baby showers, birthdays — that you want to say yes to. But if you say yes to everything, you inevitably reach a point where you realize you don’t have any time left for yourself.”

Amy Astley, the editor in chief of Architectural Digest and someone with a reputation for very rarely canceling plans, explained her strategy.

“I start by asking myself if I really want to go,” she said. “Is there an actual reason for me to attend? A business reason? A personal reason? And if I decide I really want to be somewhere, I commit to it. I’m not going to accept a so-called better offer or cancel, because I’ve already thought about why I was committing in the first place.”

If you’re dragging your feet, it may be worth evaluating why. If there is no real reason for you to engage (and no real repercussions if you do not), just say no and move on. The only thing worse than turning someone down is having to do it over and over again.

Which brings us to arguably the most awkward part: how to say no graciously.

“I personally don’t believe you have to justify yourself to anybody,” Ms. Astley said. “Except maybe your mother or your best friend. Just say, ‘I’m so sorry, I have a prior commitment.’ Or: ‘I’m sorry I can’t be with you that day. Hopefully next time.’”

Yet many people engage in what one friend called “polite flakiness,” refusing to nail down a time or not following up to confirm. Others, like Roberto Rhett, a real estate broker in New York, simply plead work. “This is New York City!” Mr. Rhett explained. “Everyone is always working.”

But what about when work itself is the problem? Bill Shapiro, the director of editorial and new business enterprises at Fast Company magazine, has his own tactic for managing the professional influx.

“My response is often the same and turns out to be very effective,” he said. “I just say, ‘You know, I can’t meet with you now, but I’m happy to talk on the phone for a few minutes.’ That actually eliminates a lot of people who never take me up on it.”

When there are people you genuinely want to see, or can’t escape anymore, but you’re wary of committing to an all-evening event, try finding another activity. Ms. Astley often suggests a yoga class. “You can still be together,” she said. “You can chat before and after.”

Or, use the same technology that allows us to so easily cancel plans to stay in touch instead. I take advantage of my extra-long commute by skipping the bus, getting some exercise by walking instead, and using the time to call and catch up with family or friends I haven’t seen in a while. Bonus: An unexpected phone call in this day and age generally makes people feel extra special.

Still, lack of time is a common refrain.

“I was so overwhelmed by how many plans I had in New York that I moved to San Francisco,” said Gaia Filicori, a publicist who grew up in Manhattan, only half-jokingly. “Here, I’m scheduled the same way I was New York — still going to yoga, still going to events — but I look forward to my weekends now.”

Ms. Ebner had a similar experience after moving to London for professional reasons a few years ago. “I really enjoyed having zero obligations in a city where I didn’t know anybody,” she said. “It was freeing! But then I found myself constantly flying to New York for weddings and other things I didn’t want to miss. So I moved back.”

Who can blame her? As the comedian John Mulaney put it, “In terms of, like, instant relief, canceling plans is like heroin.”

And you can’t cancel plans if you don’t have any in the first place.