There is a much-quoted moment from Ernest Hemingway’s 1926 novel, The Sun Also Rises, in which a character explains how he went bankrupt. “Two ways,” he says. “Gradually and then suddenly.”

We have all experienced it. Physics calls it the tipping point. A Buddhist proverb says, “When the student is ready, the teacher will appear.” Jesus talked about acquiring “eyes to see and ears to hear.” Lillian Hellman wrote in her 1969 novel, An Unfinished Woman, “Nothing, of course, begins at the time you think it did.” My grandfather, George Randall, laughed about “the last straw.”

If you are like me, “suddenly” can be a quiet dawning or a jarring moment of truth. “Suddenly” can happen in your own awareness, or if you wait too long, it can slam into you from the outside. It can be an epiphany or a moment of dread, or just a quiet conviction that something must change. For example:

• Gradually, I have taken on too much at work, and all of a sudden, (a) I’m mad or (b) things are imploding.
• Gradually, I have wanted to volunteer more, and out of the blue, this non-profit comes looking for me.
• Gradually, I have put on weight, and all of a sudden, my chest hurts.
• Gradually, what I really want to do more of in my work has come into focus.

Recently I heard a common “gradually” from a new coachee: “Gradually,” he said, “I’ve gotten restless in my work. I know I am capable of far more contribution and satisfaction. I’ve thought about hiring you for a while, and this is the right time.”

In the months that followed, I walked with him as he held steady, faced obstacles, and got overwhelmed. He wondered out loud, “Am I doing this right?!” We talked about how his tone of voice sounded as he talked to himself. In each conversation, I’d ask some version of, “What do you want to work on, leave behind, do more of, do less of, or get better at?” Sometimes I heard a hunch that was just forming. We found experiments. If the experiment was useful, then why?

He was brave. Especially as he looked deeply at his own forty-five-year-old life. He pointed out quietly that he’d been thinking about the fact that he was “half-way through.”

I love working with people like him.

Here are some answers that have come in response from others in the beginning of coaching relationships as I’ve asked the “what-do-you-want-to-work-on?” question:

• “I want to be more inspiring as a leader.”
• “I need a new job—maybe find my life’s work.”
• “My leader just doesn’t stop to listen to me—I feel disrespected (and not for the first time). I need to figure out my part in that.”
• “I want to lead my team better—and to see them collaborate better too.”
• “I’m a lawyer, but I don’t want to practice law anymore.”
• “I think I could become the next CEO.”
• “It’s time for me to write something.”
• “I’m ready to find a life partner.”
• “We’re having a baby.”
• “The last baby is leaving home.”
• “I need to make more money without losing my soul.”

Sometimes people hear me talk about “the wilderness.” This is that span of time that usually begins before a clear ending and lasts well into the new beginning. You don’t know how long it will last. It goes something like this (the biblical story of Moses comes to mind): Not only do you have your own disoriented questions, you get some from the people who depend on you, “Where are we going?” “Are you sure you know the way?” “What was so bad about the old situation anyway?” These people will appreciate extra patience and engagement from you. You may think there are more important things to talk about, but they don’t. In the wilderness, I think, you make extra time to keep your followers (and those who love you) well-informed and close to you.

Because the wilderness is confusing, ambiguous, scary, and fluid, we are tempted to hurry through it. But it’s often where many of the biggest breakthroughs and creative opportunities come into focus. It’s not necessarily a horrible place. Like any hero on a quest (even a reluctant one), you will meet with resistance that must be understood, overcome, accepted, or danced with as the transformation becomes irresistible.

Like any hero in the wilderness, maybe you’ll learn things about being resilient when your heart breaks a little. Maybe you’ll learn to be patient, open, willing to repeatedly test and learn, and, through it all, to listen to your life and strengths and values—and to the people closest to you. You will do hard things.

You can tell when you are getting close to “the beginning of the end” of the wilderness when your new direction begins to look like the new normal. You are determined, open, seeking, continuing to make small choices, and you begin to perceive the right direction. You already know that any path through a wilderness is rarely straight and uncomplicated. Relapses, returns to the safety of what you wanted to leave, second thoughts, discouragement, and “squishiness” still happen, but begin to diminish.

In this phase too, I continue to listen deeply, challenging, and supporting. By now we’ll have built trust, and I might become extra direct with a question or with a hard truth. And I’ll acknowledge the character and strengths and values I see.

I know, from my own experience, that this level of courageous growth and sustainable change will affect your life in every way—spiritually, emotionally, physically, socially, and in the way you savor your days and relationships. The people I work with tend to keep it going, both as they work with me over time, and as they find and grow their own coaching voice—the one that will stay with them, after we’ve said good-bye, as they continue their pilgrimage through a cherished, and all-too-short life.