Soapbox: Career Courage

Courage-building lessons from a big メfraidy cat.

By Bill Treasurer, Founder, Giant Leap Consulting

I am a big ’fraidy cat. From my knee-shaking fear of heights to my tongue-stammering fear of authority figures, I live a life that seems imbued with fear. You may find it surprising, then, that I am a professional courage-builder. My personal mission, and the mission of the courage-building company I founded a decade ago, is to help people and organizations be more courageous.

Now don’t get me wrong, just because I’m a fraidy cat doesn’t mean that I’m not courageous. One can be simultaneously afraid and courageous. They are not mutually exclusive concepts. In fact, they are wholly enmeshed concepts. The presence of fear is the most basic hallmark of courageous behavior. That is, when you are engaged in a courageous act, you are fearful, not fearless.

I suppose there are two kinds of ’fraidy cats, those who become dominated or controlled by fear, and those who, like me, try to find a way to act despite being afraid. The latter get to experience their courage. The good news is, having led courage-building workshops for thousands of executives throughout the world, I am convinced anyone can be the latter.

The First Virtue

Courage, according to Aristotle, is the first virtue because it makes all the other virtues possible. The great theologian and writer C.S. Lewis went further, saying that courage isn’t just a virtue; it is all of the virtues taken to the testing point. Outside of work, great thinkers and philosophers long have held the virtue of courage in the highest regard, seeing it as the most essential ingredient to living a meaningful, fulfilling, and moral life. My question is: If courage is the premier virtue outside of work, shouldn’t that hold true inside of work, too? I believe the answer is a resounding “Yes!”

Think about all the important workplace concepts that connect directly to courage. Leadership, for example, involves rendering bold decisions that some people are going to disagree with, and withstanding the turbulence the decision may cause. Leadership requires courage. Innovation involves creating ground-breaking ideas, and that often involves defying deeply held traditions or conventions. The greatest ideas always start out as blasphemy. Innovation requires courage. Entrepreneurship requires taking risks to capitalize on opportunities, combined with sales hutzpah. Entrepreneurship requires courage. Courage is essential to concepts such as leadership, innovation, and entrepreneurship.

Just as it is outside of work, courage is the most important virtue inside of work. It’s surprising then, that there has been almost no attention paid to building people’s courage at work. That’s too bad, because it is courage that is needed when you want workers to “step up to the plate” and demonstrate more initiative. It’s courage that’s needed when you want workers to embrace change more enthusiastically. It’s courage that’s needed when you want managers to give more direct feedback. And it’s courage that’s needed when you want salespeople to be more aggressive. When each person is showing up to work each day with just a little bit more courage, the entire organization can be transformed for the better.

Now Hear This: You Already Are Courageous!

Start with the recognition that you already are courageous. You are biologically equipped to act with courage. Just as there is a place that lights up in your brain when you’re afraid (the amygdala), MRI studies have shown that there’s also a place in your brain that lights up when you’re acting with courage. It’s called subgenual anterior cingulate cortex, or what I call the Courage Button. This region of the brain becomes activated when you intentionally subdue your fear in order to act with courage. Before offering tips for how to do that, it’s important to absorb, acknowledge, and embrace the fact that you already are a courageous person. You were courageous when you learned to ride a bike. You were courageous when you told spooky stories with the Girl Scouts or Cub Scouts and weathered a night of camping. You were courageous when you learned how to drive a car and went on your first job interview. And at work, you were courageous when you took on a role that eclipsed your skills, gave a presentation to your boss’ boss, gave constructive feedback to a peer, and asked for a raise.

Courage-building is about activating and strengthening the courage that already exists inside of you. It’s about helping you do more courageous things more often.

Tip 1: Strike Out Fear

One useful exercise was taught to me by Sara Blakely, the founder of SPANX body shapers. Sara wrote the forward to my book, “Courage Goes to Work.” The exercise involves assessing your courage history by writing a page or two about career moments when you were full of anxiety or fear but kept on moving forward. After you’ve done that, in every instance where you see the word, “afraid,” or, “scared,” replace it with the word, “courageous.” Reflecting on her own life, Sara said, “In every situation where I was ever afraid, but kept on moving, you could substitute the word, ‘courageous’ for ‘afraid.’ I was afraid, for example, when I started SPANX with $5,000 in savings. I was afraid when I knocked on the doors of textile mills begging them to manufacture my prototype for a new footless pantyhose (for which I had written and earned a patent). I was afraid when I stood in front of the hot TV cameras on the QVC network for the first time. I was afraid when I traveled to Dallas with my lucky red backpack to meet the buyer at Neiman Marcus to interest her in selling SPANX products. I was afraid when I did the same thing at Saks, Nordstrom, and Bloomingdales. I was afraid the first time I was a guest on The Oprah Winfrey Show.”

Sara would tell you that there are definite advantages for acting with, and persisting through, fear. She was on the cover of Forbes magazine as the youngest self-made female billionaire.

Tip 2: Establish an Anti-Brownnosing Agreement

Having led courage-building workshops for over a decade, I’ve noticed that when I ask people for examples of what they would do if they had more courage, the most common answer has to do with speaking up to the bosses more freely. I’ve also noticed that the courage associated with assertiveness (what I term Tell Courage) is the most commonly avoided form of courage at work. This likely has something to do with the fact that some of our earliest lessons deal with biting our tongue—from “respecting our elders” to the biblical commandment of honoring our mothers and fathers (which mostly means no backtalk!). But lack of assertiveness in the workplace, especially assertiveness that is directed upward, can equate to lack of relevancy and power. If you don’t speak up, you won’t get noticed. If you don’t get noticed, you won’t advance. So gaining Tell Courage is important for any aspiring career.

The reality is, though, unless you gain agreement with your boss that you are expected to speak candidly and assertively, you could do some serious damage to your career. If you give your boss critical feedback, however well-intentioned, it could provoke an indignant who-the-heck-are-you-to-tell-me response. One way to defuse your boss’ defenses while honoring his or her legitimate desire to be respected is to clarify expectations about how assertive he or she expects you to be. During your performance review, for example, ask your boss whether or not he expects you to be a brownnoser. Yes, be that direct. The boss nearly always will respond with something such as, “No! I definitely do not want you to be a brownnoser. I need people who can help me make good decisions, and that means providing me with the information I need to know, not just what I want to hear.”

Once you’ve established this orienting “no brownnosing” ground rule, make sure you get your boss’ coaching about how to approach him with difficult feedback or information. Say, “You have my commitment that I won’t be a yes-person. To support me with this commitment, can you give me a few coaching tips about how to give you upward feedback in a way that will get through to you without putting up your defenses?” Most bosses will say things such as, “Don’t tell me right after the monthly board meeting” and “approach me privately instead of in front of my other direct reports.”

The benefit of setting this ground rule is that after it’s been established, you can refer to it when you have to deliver tough upward messages such as, “Remember that ‘no-browsing’ commitment we made to each other? Well I’m going to honor our commitment by giving you the feedback I’d like to share with you now…”

Becoming a trusted confidante to your boss is a great way to advance your career, but trust is a dividend of shared honesty. Being able to give your boss the feedback he or she needs to be an effective leader will be much easier if you’ve created an agreement that supports courageous conversations.

Tip 3: Do Your Lead-Ups

Earlier I mentioned that I am a big scaredy cat, especially when it comes to my fear of heights. Surprisingly, I am also an ex-high diver. I spent seven years as a member of the U.S. High Diving Team, diving from heights that scaled to more than 100 feet, traveling at speeds in excess of 50 mph, and landing into pools that were only 10 feet deep. It was learning to confront my fear of heights, through the slow and patient persistence of a caring coach, that helped me find my courage. In the extreme sport of high diving, it’s called doing your Lead-Ups. No high diver in their right mind would do one jump from 100 feet before doing 100 jumps from one foot.

In broad terms, there are two kinds of courage; big courage and little courage. Examples of big courage include agreeing to lead a new company division in a different geography, exposing unethical company conduct (i.e., whistleblowing), and quitting a high-paying job to start a business. Little courage examples include asserting an idea that runs counter to the prevailing opinions, attempting a task at which you previously failed, and admitting a mistake to a customer. Big courage feats come on the heels of many little courage acts. Lead-Ups are courage of the little kind.

A good example of doing your Lead-Ups is continuing your education as an adult. For example, I’ve worked closely with the heir-apparent son of a successful Chicago-based construction company who was intimidated at the prospect of taking over the helm from his father. Part of the intimidation was driven by the son’s lack of knowledge when compared to the knowledge of his father, as well as the knowledge of the more experienced senior executive team members. Succession planning, done smartly, should not be a single baton-passing event. Rather it is a Lead-Up process whereby the successor candidate acquires deeper experience, knowledge, and respect in a deliberately planned way. The formal “big courage” baton-passing should be a culmination of many little courage Lead-Ups. In this instance, the son chose to spend time shadowing the company’s division leads and enrolled in business classes at a prestigious Chicago-based university. All of the little courage Lead-Ups served to build the son’s courage capability, as well as his confidence in leading.

Ultimately, courage takes action. It isn’t something that can be delegated away. The courageous acts that will shape, strengthen, and fortify your career will have to be done by you. So start where you are. Start with the goals you’re pursuing or the challenges you’re facing right now. Start by playing it less safe. Above all, if you aim to have a vibrant, meaningful, and fulfilling career, start acting with more courage today.

Bill Treasurer is the founder of Giant Leap Consulting, a courage-building company. He is the author of “Courageous Leadership: A Program for Using Courage to Transform the Workplace” (Berrett-Koehler Publishers, 2008) and “Courage Goes to Work: How to Build Backbone, Boost Performance, and Get Results” (Pfeiffer Publishing, 2011). His clients include Saks Fifth Avenue, Accenture, CNN, UBS Bank, Hugo Boss, and the U.S. Department of Veterans Affairs. For more information, visit

Lorri Freifeld is the editor/publisher of Training magazine. She writes on a number of topics, including talent management, training technology, and leadership development. She spearheads two awards programs: the Training APEX Awards and Emerging Training Leaders. A writer/editor for the last 30 years, she has held editing positions at a variety of publications and holds a Master’s degree in journalism from New York University.