Soapbox: Building Career Courage

3 tips to help you start acting with more courage today.

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 I’m not courageous. One can be simultaneously afraid and courageous. The presence of fear is the most basic hallmark of courageous behavior. When you are engaged in a courageous act, you are fearful, not fearless. The trick is to act despite the fact that you’re afraid.

The First Virtue

Courage, according to Aristotle and others, is the first virtue because it makes all the other virtues possible. Outside of work, courage has been viewed as the most essential ingredient to living a meaningful, fulfilling, and moral life. It’s also the premier virtue of work. Think about all the important workplace situations that connect directly to courage. It is courage that helps you “step up to the plate” and take more initiative, embrace change more enthusiastically, and assert your opinions with more force.

So how can you start acting with more courage? Start with the recognition that you already are courageous. It is important that you absorb this fact. You were courageous when you learned how to drive a car, asked someone out on a date, and went on your first job interview. At work, you were courageous when you took on a role that eclipsed your skills, gave a presentation to your boss’ boss, and asked for a raise.

Tip 1: Strike Out Fear

One useful exercise was taught to me by Sara Blakely, the founder of SPANX shapewear. The exercise involves assessing your courage history by writing down career moments when you were full of fear but kept on moving forward. In every instance where you see the word, “afraid,” or “scared,” replace it with the word, “courageous.” As Sara related to me, she was full of knee-knocking fear when she traveled around to buyers to get them interested in selling her new footless pantyhose, and when she went on the QVC network, and when she was a guest of The Oprah Winfrey Show. Working with fear, instead of running from it, is what makes Sara courageous. And it has advantages. She graced the cover of Forbes magazine as the youngest self-made female billionaire.

Tip 2: Establish an Anti-Brownnosing Agreement

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 their bosses more freely. The courage of assertiveness (what I call Tell Courage) seems to be the most avoided form of courage at work. Probably because our earliest lessons deal with learning to bite our tongue and “respect our elders.” But lack of assertiveness in the workplace can equate to lack of relevancy and power. So gaining Tell Courage is important for any aspiring career.

One way to honor your boss’ legitimate desire to be respected is to clarify his (or her) expectations about how assertive he expects you to be. Directly ask, for example, whether or not your boss wants you to be a brownnoser. The boss nearly always will respond with something such as, “No! I need people who provide me with the information I need to know, not just what I want to hear.”

Once you’ve established the “no brownnosing” ground rule, get your boss’ coaching about how to approach him or her with difficult feedback or information. Say, “You have my commitment that I won’t be a yes-person. To help me, can you give me some 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.”

After this ground rule has been established, you can refer to it when you have to deliver tough messages, saying, “Remember our ‘no-brownnosing’ commitment? Well I’m going to honor our commitment by giving you the feedback I’d like to share with you now…”

Being able to give your boss the feedback he or she needs to be an effective leader and becoming a trusted confidante will be a lot easier if you’ve created an agreement that supports courageous conversations.

Tip 3: Do Your Lead-Ups

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 to a customer that you made a mistake. Big courage feats come on the heels of many little courage acts. Lead-Ups, as I call them, 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 national construction company who was intimidated by 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.

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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” and “Courage Goes to Work: How to Build Backbone, Boost Performance, and Get Results.” His clients include Saks Fifth Avenue, Accenture, CNN, UBS Bank, 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.