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A 30-Day Challenge for Entrepreneurs: Tap Into Your Courageous Leadership What you do these next four weeks can make all the difference.

By Gail Angelo

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.


As the economy continues its rise out of its previous slump, a couple of things can happen.

One: We can live in fear that it will happen again.

Two: We can learn from the past and continue to make bold, confident decisions to do things differently in a way that supports long-term sustained agility and success.

Related: 4 Great Non-Business Role Models for Entrepreneurs

Organizations that choose option 2 -- to focus and invest in talent, innovation, and leadership during a downward spiral -- demonstrate the one thing that will continue to be required going forward: courageous leadership.

So, what is courageous leadership? A state of mind? A virtue? A set of behaviors and actions? A critical part of your brand? It is all of the above. And, for you, as an entrepreneur, your courageous leadership starts . . . now.

While there are many behaviors that support the growth of courageous leadership, there are four questions we can ask ourselves to amplify its development and impact on results. So, as an entrepreneur, solopreneur, start-up executive or maybe someone working through the night to carve out a new, fresh idea, seize the opportunity each week -- for one month -- to get clear on your courageous leadership. Then, use it. Here's how.

Week 1: Promote Self-Awareness.

Know who you are, what you are afraid of, what you are inspired by and what your patterns of resistance look like. Self-awareness puts us in the seat of choice. Once we become aware, we have the power to choose consciously and take responsibility for our choices. As we grow increasingly aware of our strengths and gaps, we can surround ourselves with talent that complements our skills and attributes.

Knowing how we typically respond under pressure gives us the power to make a different choice if our traditional approach is not constructive. Maintaining clarity about our fears and patterns of resistance allows us the choice and opportunity to feel the fear and do it anyway -- to choose an alternative behavior that moves us through our resistance, versus burying our heads in the sand. After all, it is our places of resistance that hold the greatest potential for growth.

A direct correlation exists between this vulnerability and courage. Our willingness to admit that we don't have all of the answers makes us real and consequently builds trust. It provides an opportunity to ask big things of our teams and give them the chance to be more than they thought they could be.


  • Observe yourself throughout the day and notice when you feel strong and energized. Then reflect on how you are creating a life and environments that support your strength . . . or not. What changes might you need to make?
  • Notice what you keep putting off. What is getting in your way? What does your resistance look like? What are the patterns you have taken on that are causing this resistance? How are these patterns serving you? What are they costing you? What do you need to let go of to move forward?
  • Set aside 15 to 30 minutes each day just to be still. As entrepreneurs, we are often in the doing phase, fearing that if we're not, nothing is happening. Nothing could be further from the truth. Reflection is the seat and engine of growth and innovation. Make is a daily practice.

Week 2: Meet reality.

There are times where our resistance keeps us from seeing the reality of our situations. It is one thing to be optimistic and tenacious. But sometimes that optimism crosses the threshold into denial. Once there, we find ourselves in a position where we have to react versus respond.

Think about gardens. There are times where they are at their peak. Suddenly, one day, we see only dead flowers, overgrown bushes and dry grass. We wonder how that happened without our noticing. A good gardener will go out and prune the overgrowth, pinch off the dead blooms and water the grass. Courageous leaders are willing to do both the pruning and watering in order to prepare for new growth.

Courageous leaders are also willing to see things for how and what they truly are and have an inner circle that supports their ability to do so in a balanced and informed way. Once they accept reality, courageous leaders are poised to inspire action in others that leads to a future distinct from the past.


  • Identify a "board of directors" for yourself that is willing to help you ask the hard questions and will give you the real picture.
  • Consider joining a group in your community of leaders across industries that can function as a peer advisors for you.
  • Talk with people in your organization. Set a tone and expectation for balanced feedback from all levels of your organization
  • Send a three-question survey to teams and clients periodically, asking:
  1. What can we do more of?
  2. What can we do less of?
  3. What are you noticing that we may be missing about leadership, innovation, service?

Related: 7 Ways to Create an Inspired Team

Week 3: Inspire Innovation

When we take the time to look at the horizon line, to anticipate changes in the marketplace, in our clients and in the degree to which business is getting done, we create a culture that is quick, agile, and innovative -- in other words, a courageous culture.

Courageous leaders do not simply lean into change and innovation. They understand deeply that change and innovation are the life blood of sustainable success. Courage supports the ability to consistently ask the question, "what if?" Courageous leaders encourage experimentation, take calculated risks and allow for failure by focusing on the learning that comes from the experience.

As organizations move out of the slump, it is easy to remain fearful, which often leads to our playing smaller than we are capable of playing. Courageous leaders focus on possibility versus fear. They are bold and willing to take calculated risks to continue to explore what can be done versus what can't be done.


  • Start meetings with a review of the purpose statement and ask: What are we doing in alignment with our purpose? What is not in alignment? What constitutes a bold decision in this situation? What is stopping us from making that decision?
  • Where you focus is what you get. Make innovation a value and priority in all aspects of the way you do business.
  • Reward calculated risk taking.
  • Make reflection a core business best practice. Reflect on insights and learnings from day-to- day experiences, i.e., What are the patterns we are noticing? What can we learn from these patterns? What is different as a result of different actions taken? How might we apply learnings in other situations?

Week 4: Stand up and make it happen.

Courageous leadership is not for the faint of heart.

It may require stepping beyond your fear of rejection to raise difficult issues, provide balanced feedback, have challenging conversations and make decisions that may not always be popular. It may often require going against the tide or tradition or "the way we have always done it" for the greater good. It is holding up the mirror to help others see what they have been unwilling to see or hear. It is challenging people to try a different approach -- asking, why not?

Courageous leaders make choices intentionally and take responsibility for those choices. They step up boldly, lean in, speak the truth, focus on what is possible, make decisions for the highest good and inspire others to do the same.

Leaders have the capacity and responsibility to move forward in courage, particularly as our businesses, communities, country and world continue to become more complex.


  • Ask yourself each day how you and others demonstrated courageous leadership. How might you continue to reinforce courageous leadership as part of the culture of your organization?
  • Ask yourself each day -- what if and why not?
  • Make your choices consciously and take responsibility for the choices you make
  • Recognize that leadership is a team sport. Lead inclusively.

You have a choice. Be bold. Be brave. Step into your courageous leadership to continue to make a difference. It is your time to move purposefully beyond fear into a brave, bold, courageous future.

Related: Wake Up and Get Off the 'Someday Island'

Gail Angelo

Gail Angelo is an ICF certified coach, skillful strategy consultant, and catalyst for personal, professional and purposeful transformations.

Gail Angelo is an ICF certified coach and strategy consultant. Angelo's mission is to empower individuals and companies to recognize their unique purpose while leveraging their greatest strengths for impactful results. Learn more at, or contact her directly at

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