Thinking about what could go wrong is just as important–and perhaps even more so–as thinking about what could go right.

Catori, 45, a Native-American freelance writer, has been brainstorming about how she can build multiple writing revenue streams while developing her “authentic voice” and sense of belonging in the local community. She moved to the area a year ago from her native Oakland, California, longing to make a fresh start in completely new surroundings while working for the only person she’s ever wanted to work for: herself.

One morning at the office complex cafe where Catori does most of her writing, she was fine-tuning her list of writing revenue goals when Elizabeth stopped by to see how Catori was doing. Elizabeth, 71, is a retired African-American school teacher who works part-time running the complex’s resource center, and is an informal mentor to many of the professionals who work in the complex. Catori showed her the list of goals, and the writer’s voice was energetic and excited as she expressed hope about achieving them.

“I’m not trying to burst your bubble,” Elizabeth said after listening intently to Catori for a few minutes. “But have you considered jotting down what might hinder you from reaching those goals? What might go ‘wrong?'”

Objectivity and Resilience

Catori looked puzzled. “No, I haven’t thought about doing that. I’m just trying to stay positive. My negativity has always gotten in my way in the past, so i’m trying to uproot it from my life.”

Elizabeth smiled. “I get that. Toxic negativity certainly gets in the way.” She leaned closer to Catori. “But I’m not talking about negativity; rather, I’m talking about being objective and strategic, thinking through the possible obstacles before you encounter them. So that, if and when you encounter them, you’ve already got a game plan to keep them from throwing you off course.”

Catori reflected for a moment. “That makes sense,” she said. “I’ve really never tried that kind of an exercise. How would you suggest I get started?”

“Well, here’s something I’ve done many times,” Elizabeth said. “Keep your list of goals in front of you, and get out a second sheet of paper. Write each goal down along the left side of the paper, in a single column. Then draw three to four additional columns. And in each of those columns, jot down potential obstacles you could face for each goal. Be as thorough as possible, and don’t over-think anything. Just get it all down.”

“And what do I do after I’ve jotted all that down? Have a stiff drink?” Catori smiled.

“Maybe,” Elizabeth said, laughing. “And, while sipping that drink, you could get out another sheet of paper, and begin to write out action steps you could take to neutralize each of those obstacles. Again, write down as much as comes to mind, without spending much energy evaluating whether something is right or wrong. Before you know it, you’ll start to have even more confidence behind achieving your goals because you’re thinking ahead about what you’ll do to course-correct if you need to.”

Catori took a deep breath. “I’m still processing all of this,” she said, “but I think i’m going to try it. Well, I’m going to do it.” She smiled. “It doesn’t feel nearly as fun as jotting down my goals and thinking about success, but who knows; I might find it energizing.”

“You just might,” Elizabeth said. “And you just might even be mo;re resilient than you’ve already shown me during the time I’ve known you.”

“Do you really think I’m resilient?” Catori asked, and felt tears forming in the corners of her eyes. “That’s a quality I’ve always wanted in myself. One that I’ve always thought eluded me.”

“You’re more resilient than you think,” Elizabeth said; and as she stood to leave she embraced Catori, whose eyes stayed moist long after Elizabeth had left the cafe.

Learning Agility

Thinking through what might hinder you from reaching your goals is a practice of learning agility. Learning agility is regularly seeking new experiences, applying feedback, and reflecting on lessons learned. It’s a strength that you can continue developing across your career and life, and can set you apart from the crowd.

The more you practice defeating obstacles before they arise, being as objective as possible without tunnel-vision toward the positive outcomes you’re eager to achieve, the better you’ll get at predicting such obstacles while yo