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When to Say When: 6 Signs That It's Time to Make a Leap

How do you know when it's time to say yes to a call?

According to the mythologist Joseph Campbell, who popularized the “hero's journey,” Phase 1 of responding to a calling is running from it.

A perfect example of this was captured in J.R.R. Tolkien's The Hobbit, when the wizard Gandalf visits the peaceful village of the Shire and knocks on Bilbo Baggins' front door, slyly telling him of his search for “someone to share an adventure.” Bilbo's response was classic Phase 1: “We're just plain quiet folk and have no use for adventures. Nasty disturbing uncomfortable things! Make you late for dinner!"

This response is actually universal and inevitable, and as such may be of some consolation if you find yourself deep in Phase 1 behavior in relation to a calling. I myself took five years to respond affirmatively to the call to leave employment for self-employment as a writer, and it took that long in part because I knew there was something trying to come through me but I was simply too scared to step aside and let it through, too scared of the pain of dissolution and uncertainty, too afraid—in that anthropologically deep way that humans naturally are—of The Unknown.

I'm often struck by the fierceness with which people (myself included) cling to the status quo even when it no longer serves them, or when it long ago turned into diminishing returns and left them feeling out of whack with themselves and transfixed by their fears like deer caught in the headlights, unable to move.

A calling, though, is an organism, a living entity, with an animus all its own. It exerts a centrifugal force on your life, constantly pushing out from within, or perhaps pulling at you the way a character in a novel- in-progress might strain at the leash, demanding to go her own way. And if you're at all faithful to your calls, they'll eventually lead you to a point of decision, and here you must decide whether to say yes or no, now or later, ready or not. And they'll keep coming back until you give them answer.

But a call isn’t something that comes from on high as an order, a sort of divine subpoena, irrespective of your own free will and desire. You have choice. You have a vote! And when to say yes is entirely up to you.

Letting go of what's familiar—a job, a relationship, a lifestyle, or a mindset—isn't something to take lightly. I don't belong to the sink-or-swim school of thought on making change, and therefore don't generally recommend that people just up and quit the status quo, unless the prospect of turmoil is preferable to the psychological death you're experiencing by staying put, in which case I say let 'er rip. But as Henry David Thoreau once said, “The mass of men lead lives of quiet desperation, but it is a characteristic of wisdom not to do desperate things.”

There were many times when I came a hairsbreadth away from quitting my job as a reporter out of desperation or frustration and just starting up my freelance career, but fortunately my survival instincts kicked in, or more likely I was talked out of it by someone who knew better, who knew that if I leapt at freelancing without properly preparing for the rigors of that business (as well as starting a new venture in the emotionally shell-shocked aftermath of quitting a job in desperation or anger) I'd likely drown. One friend, an environmental writer, pointed out to me that in nature, sudden transitions tend to be catastrophic—earthquakes, eruptions, flash floods, tsunamis.

But preparation can easily devolve into procrastination. With any significant transition, there's no end to the rehearsals you can make, the questions you can ask yourself, the experts you can consult, the classes you can take, the wayward ducks you can continually attempt to line up. And it's depressingly easy to get stuck in a kind of chronic vacillation, a neverending “maybe” that can steal decades from your life. At some point you just have to take a leap.

There's nothing so powerful, they say, as an idea whose time has come, but how do you know when an idea's time has come—or not arrived yet, or come and gone, or isn't in the cards at all? It's generally harder to find the perfect moment to act than the imperfect moment. It's a guessing game, but you want your guess to proceed as much from logic as passion, and with a firm eye on the signs.

Here, then, are some suggestions for gauging when it's time to make your necessary leaps of faith (or when you're overdue for one):

  1. When the pain of staying put becomes greater than the fear of leaving. Or to borrow a bit of cowboy wisdom: When your horse dies, get off.
  2. When you've traded off passion for security for so long that it's sucked the life force out of you, leaving you numb, depressed or indifferent.
  3. When whatever calling you've been running from suddenly turns into a wakeup call. Wakeup calls are calls that, from neglect, have become desperate to get your attention. They don’t generally start out that way. They start as polite requests, gentle taps on the shoulder and whispers in the ear, but they tend to increase in volume and voltage (and occasionally violence) the longer you ignore them. Sociologist Gordon Allport calls this the power of the fait accompli. The done deal. The career disaster that blows a hole in your hull below waterline. The accident or illness that suddenly changes your priorities. The partner who leaves you for someone else. The case of burnout that lands you in the hospital. The addiction that lands you in the courtroom or the newspaper.Your soul will speak as softly as it can, but as loudly as it has to.
  4. When the decision to say Yes migrates from up in your head to down in your gut. This is a felt shift, and you'll feel it, because it's the difference between if and when. In an interview on 60 Minutes some years ago, journalist Dan Rather asked the political commentator/comedian Jon Stewart what he considered his “big break.” Stewart's answer: “When I made the decision this was the life I was going to live," i.e., it was an inside job.
  5. When you've spent some concerted time becoming a student of the life you want to live, studying it in detail, conducting informational interviews with people who are doing what you feel called to do, and doing some of the pick-and-shovel work of self refection. In preparing for the freelance life, I spent two years of Thursday nights (3 hours a week at the public library) becoming an archivist of its details: reading up about it, querying editors, writing stories, rewriting stories, and interviewing freelancers of every stripe. When I finally made the leap, I leapt into work, not into an abyss.
  6. When there are no more appeals. When you can't go any further with only, say, changes in job description or cosmetic readjustments to your lifestyle. When you know that what you need is a tectonic change, and that what the life you dream of for yourself needs is a Yes and not a No or a Maybe. “Your life mirrors what you put into it and what you withhold from it,” say the authors of Art and Fear. “When you hold back, it holds back. When you hesitate, it stands there staring at you with its hands in its pockets. But when you commit, it comes on like blazes.”

For more, visit gregglevoy.com

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