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Develop Your Courage. And Seize Your Opportunities.

(Photo by Sasint on Pixabay)

A crowd of people. Everyone looks around. No one steps forward.

I think, “I can do this. I’d like to try it.” I start to raise my hand.

But then I hear,

“Why would anyone follow you?”

“You can’t do this, you don’t have any experience.”

“You’re not good enough yet, why not wait for now and let someone else take this one.”

No one else hears it. Just me. It’s all in my head. But the words are all the more powerful because of it.

So I lower my hand. I let self-doubt quiet my voice. I let fear rule the day. And yet another opportunity is lost.

What Are We Waiting For?

How often do we find ourselves in this trap?

We have ideas but we keep them to ourselves.

We have thoughts but we stay quiet.

We have interests and passions and contributions but we hold back. We hesitate. We wait for permission.


We never used to have this problem. If you watch a group of kids, there’s never a shortage of leaders. Kids are inquisitive, and curious, and willing to be different just for the sake of being interesting. Anyone who’s tried to convince a toddler to behave in public knows how much kids care about “fitting in” among the group. And every parent knows that kids aren’t shy about putting forth any ideas or thoughts that occur to them.

And then somewhere along the line it became safer to keep these ideas to ourselves. Maybe it all goes back to middle school — when it was much simpler to just fit in with the social group and not risk being ostracized.

At some point we realized that standing out is to be vulnerable. Offering new ideas invites criticism and leading brings insecurity.

At some point we realized that to bring our best work is to expose our true self and be willing to see that we’re not as good, or as talented, or as strong as we hope we are.

So we wait. We wait for the time that we’ll no longer be vulnerable. We wait until we’ve perfected our craft to the point that no one could criticize or disagree with us.

Except this day never comes. So we keep waiting.

Confidence is Overrated

“No problem can be solved from the same level of consciousness that created it.” — Albert Einstein

A common belief is that we’re waiting for confidence. How confident are we that we’ll be successful in this new role?

So we develop confidence through repeated success in a specific role. More success equals more confidence for next time.

Sounds good, right?

But relying on confidence limits us. It keeps us in the same silo. It prevents us from branching out and trying something completely new.

If we let confidence drive our decision to step forward, we’ll only lead in situations where we’ve already proven ourselves. If we’re looking for confidence, it’s no wonder we hold back when we’re in a new situation. We’ve never given ourselves a chance to develop any.

So the answer can’t be confidence. It needs to be courage. We need courage to take that uncertain first step.

Because that first step will always be uncertain. No amount of confidence will give us the security that it will turn out alright. We need to decide if we want this badly enough to risk that.

As writer Dani Shapiro told Debbie Millman on her podcast, Design Matters, “I’ve got to dive in. Only by diving will there be water underneath me…hopefully. And there’s no way of knowing until you do it.”

(Photo by Bryce Evans on Unsplash)

Give Yourself Permission — Take Action

“We are all capable of everything.” — Virgil

It’s courage that helps us step forward without permission. It’s courage that lets us take that first step into uncertainty. And it’s courage that let’s us move forward when there’s no guarantee of safety or security.

Throughout my career managing people and reviewing companies, I’ve seen a wide range of methods that people use to build up this level of courage. But I think the most effective can be summarized into the following five areas.

So here’s my challenge to you today. Pick one that suits you. Pick a method that will help you overcome that hesitation. And take that first step of uncertainty.

Stop waiting for perfection. You’re ready now. We need you.

Pursue What Gives You Meaning

“…any attempt to restore a man’s inner strength in the camp had first to succeed in showing him some future goal. Nietzsche’s words, ‘He who has a why to live for can bear with almost any how,’ could be the guiding motto for all psychotherapeutic and psychohygienic efforts regarding prisoners.” — Viktor Frankl, Man’s Search for Meaning

Viktor Frankl, in one of the best books of all time, wrote that “suffering ceases to be suffering at the moment it finds a meaning.” It was this reason, and the thoughts of behaving in a manner in which their loved ones would be proud, that helped him and his fellow prisoners survive the deplorable conditions of multiple Nazi concentration camps. It was this meaning that urged them to continue to fight for survival. It provided the daily courage to brave a set of horrors that I can’t begin to imagine.

Extreme example? Perhaps. But if this path helped Frankl and his fellow prisoners then it should do wonders in helping us through our issues.

When we’re doing something that we believe truly matters, we’re driven by something that’s bigger than ourselves. We recognize that this pursuit is too important to be waylaid by our feelings of insecurity and we gain the strength to forge ahead.

A strong sense of meaning helps us understand that we have limited time and we cannot afford to be distracted and deterred from our mission. It helps us focus our time and energy on what truly matters and ignore that which isn’t aligned with our purpose.

What mission gives your life purpose? What meaning gives you the courage to overcome the uncertainty of that first step?

When we’re pursuing our why, we can handle almost any how.

(Photo by Greg Rakozy on Unspash)

Commit to Continuous Growth

“Learning and innovation go hand in hand. The arrogance of success is to think that what you did yesterday will be sufficient for tomorrow.” — William Pollard

I wanted to start writing for some time before I had the courage to finally hit “Publish.” I was in a perpetual “Save as Draft” do-loop, constantly refining words to get things perfect.

It took far too long before I realized that it didn’t need to be perfect. And it never would be. But the important first step was just starting.

So what finally kicked me into gear?

Some inspirational quote on living bravely? Eh, not really.

The dawning realization that the world needed to read my brilliant thoughts? Not quite.

It was the thought that by writing, I’m improving. By researching topics and trying to communicate ideas in a concise and hopefully entertaining method, I develop much greater knowledge of a subject area. And the process of getting feedback on each piece has helped me to improve.

My writing still sucks. But it sucks a little less each day.

When we understand that we’re not a final product, every experience becomes a step towards improving. Every piece of feedback is an opportunity to refine our craft.

When we can see each experience as a development tool, we change our criteria for success. In this way, simply doing is succeeding.

What can you learn through this experience? How will it help you develop and grow?

As novelist and poet Louisa May Alcott wisely put it, “I’m not afraid of storms, for I’m learning how to sail my ship.”

Help Someone Else

“…we’ve made leadership about changing the world and there is no world. There’s only six billion understandings of it. And if you change one person’s understanding of it, one person’s understanding of what they’re capable of, one person’s understanding of how much people care about them, one person’s understanding of how powerful an agent for change they can be in this world, you’ve changed the whole thing. And if we can understand leadership like that, I think if we can redefine leadership like that, I think we can change everything.” — Drew Dudley

In his TEDx Talk, Drew Dudley encourages us to celebrate leadership as the daily actions we take to improve others’ lives.

We underestimate the impact these moments have, but we all have them. That day we’re feeling low and a kind word lifts our spirits. Or when we’re feeling disconnected and a genuine concern helps us understand that people care. Or those times we feel lost, and overwhelmed, and scared and someone takes the time to help us find our way.

And just as we benefit from these moments, we’re also contributing them to others. We just don’t recognize them as anything special. Why would we? To us, they’re just second nature.

But when we take these moments to help someone, we’re contributing to the community. We’re reinforcing our value and reminding ourselves that we belong.

When I was a junior in college, I was struggling to find an internship. The clock was winding down and panic mode was setting in. Looking for advice and help, I sent out an email to a number of alumni.

And I was overwhelmed with the positive response. Dozens of replies with different advice on how to develop a career, find a position where I could excel, and secure a job that I’d find meaningful. It was these responses that pulled me out of my panic state and helped me focus on finding a solution. They made all the difference to me.

After I saw Drew’s talk, I went back and reviewed those thirteen-year-old emails. One was actually sent from a girl that I’d been working with for the past couple years. Not surprisingly, she had no recollection of sending me that email. To her it was a trivial moment, quickly sent and quickly forgotten.

In that moment she was a leader. She just didn’t realize it.

So let’s take the time to consciously celebrate these moments. When we can help others, it brings a wealth of positive energy to us. And it reaffirms our identity as a leader.

And when we see ourselves as someone who positively impacts the world, it gives us the courage to keep doing so.

Share Your Knowledge

“Give what you have. To someone, it may be better than you dare to think.” — Henry Wordsworth Longfellow

Francesca Gino is my favorite researcher. Partly because she covers practical topics that are actually useful, but mainly because she shares all of her research. She posts all of her issued papers, for free, on her website. She actively shares her knowledge and lets anyone interested benefit from her research.

So given the choice of following her research or paying $38 to read another professor’s study that concludes with a ground-breaking recommendation for further research, it’s not much of a choice.

We’ve all encountered people who hoard their knowledge. Or those who always want to profit from every interaction.

This group lives in a zero sum world. If exclusive knowledge is an advantage, it can only remain so if its kept secret. But this mentality is destructive. It reinforces a behavior of selfishness and disconnection. Any advantage that it gains someone is temporary and fleeting.

In 2010, Dr. Jay Bradner’s lab discovered a molecule that, in mice, appeared to trick certain cancer cells into becoming normal cells. And in an age when most pharmaceutical companies would have brought in the lawyers and kept everything secret, Dr. Bradner did the opposite. He gave it away. He published a paper that detailed the molecule (JQ1) structure and told people how to make it. He mailed samples to other labs and pharmaceutical companies.

And the results brought new insights beyond what they could have accomplished on their own. Bringing this open source mentality to science has let people collaborate and build with far greater resources than any individual lab could manage. As Dr. Bradner put it, it felt like “the more efficient way to do science — and maybe the more honorable way.”

The act of sharing is one of generosity. It doesn’t matter if it’s behavioral economics research, or cancer-fighting molecules, or simply a practice that helps you to be a more successful version of yourself. When we share our work, we’re using our work for the betterment of the community. We’re recognizing that our ideas and creations are valuable to others and we have an obligation to teach people what we’ve learned.

And as Austin Kleon writes in Show Your Work, “When you teach someone how to do your work, you are, in effect, generating more interest in your work. People feel closer to your work because you’re letting them in on what you know.”

So let’s share our work. Because as we continue to contribute to the community, we continue to give ourselves permission to lead.

Let Discomfort Be Your Guide

“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.” — Tim Ferriss, The 4-Hour Workweek

We’re naturally drawn to behaviors that make us feel comfortable. It’s the reason that gym attendance drops off in February and why people spend eight hours a day checking their email.

Comfortable feels safe. It’s familiar and predictable.

But it’s not safe. Not in the long-term. It creates mediocrity. And it makes us invisible.

Growth is uncomfortable. Learning is uncomfortable. As I tell my employees, “if you’re not uncomfortable, then I’m not challenging you enough. So tell me, because I’m selling your future short.”

And it’s uncomfortable to lead others. It’s uncomfortable to challenge the status quo, and bring up new ideas, and maintain high standards in the face of adversity. But it’s this discomfort that let’s us know we’re on the right track. To quote Seth Godin, “if you’re not uncomfortable in your work as a leader, it’s almost certain you’re not reaching your potential as a leader.”

It’s the discomfort that makes growth valuable. It’s the discomfort that weeds out the vast majority of the population and makes exceptional performers so valuable. Because if everyone did it, then it wouldn’t be valuable.

When we lean into discomfort, we’re leaning into growth. If we can recognize and push towards discomfort, we push towards excellence. And we leave behind everyone who settled for the path of least resistance.

It’s your career. And your life. Isn’t it worth more than mediocrity?

(Photo by Annie Spratt on Unsplash)

Choose Courage

Through it all, the allure of waiting for perfection is seductive. It offers the illusion of safety and protection.

The alternative is to put ourselves out there. To expose ourselves to criticism and vulnerability.

The first path leads to a lifetime of waiting — of a slow descent into mediocrity. The latter leads to a lifetime of daring greatly — of living courageously and seeking connection.

And as we struggle with these decisions on a daily basis, I’ll borrow words from Brene Brown’s final thoughts in Daring Greatly.

“In a world where scarcity and shame dominate and feeling afraid has become second nature, vulnerability is subversive. Uncomfortable. It’s even a little dangerous at times. And, without question, putting ourselves out there means there’s a far greater risk of feeling hurt. But as I look back on my own life and what Daring Greatly has meant to me, I can honestly say that nothing is as uncomfortable, dangerous, and hurtful as believing that I’m standing on the outside of my life looking in and wondering what it would be like if I had the courage to show up and let myself be seen.”

I hope you choose courage. We need you.

If you enjoyed this or have any suggestions, please let me know your thoughts. I’d love to hear from you. And if you found this helpful, I’d appreciate if you could clap it up 👏 and help me share with more people. Cheers!

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Jake Wilder

Jake Wilder


I don’t know where I’m going. But at least I know how to get there.