Fearless Creative Leadership Charles Day

Which two things are true at once?
Robbie Kaplan is a lawyer and the founding partner at Kaplan Hecker & Fink LLP.
Robbie is best known for successfully challenging a key provision of the Defense of Marriage Act. Today, gay marriage is legal in America because Robbie Kaplan stood in front of the Supreme Court and argued for it.
Recently, she was E. Jean Carroll’s lawyer in both of her successful lawsuits against Donald Trump.
And among Robbie's many awards is one from The Financial Times, which named her the “Most Innovative Lawyer of the Year”.
People that know her, say about Robbie Kaplan, “she just sees things from a thousand different angles all at once, it’s hard to keep up with her thought processes. She’s not afraid, if she sees a problem, to go figure out some law that’s going to allow her to fix it.” 
Others say she is “a lawyer that you don’t want to see opposing you.” 
They say, “she’s brilliant, she’s unrelenting, she can’t be intimidated and she’s not going to back down. She eats bullies for lunch.”
And the Washington Post has described Robbie as “a brash and original strategist, a crusader for underdogs who has won almost every legal accolade imaginable.”
Which may make this admission surprising.
Not everyone doubts themselves. 
But many people do. 
If you are one of those people, if sometimes feeling that you are an imposter is holding you back, is preventing you from unlocking the potential of the people around you, as in yourself, then let me offer you this.
Two things can be true at once.
You can feel like an imposter and achieve extraordinary things at the same time.
You do have to be clear about the extraordinary things, and why they matter to you.
But then that’s what leadership is all about.

What is your leadership for?
Senator Kirsten Gillibrand is the Junior Senator from the State of New York.
Running for public office places you in a spotlight that is white hot. Being clear why you’ve made the choice to run in the first place is table stakes for creating the life you want to live and the legacy you want to leave behind.
In too many companies and for too many people, leadership is seen as the thing that comes next for those who are willing to stick around. The inevitability of rising up the org chart into a role that comes with more everything is too rarely challenged by company or individual.
Leadership is a privilege. An opportunity to make the biggest difference for the most people, that most of us will ever have.
Marty Baron of the Washington Post described it as a responsibility.
Mark Thompson, when he was at the New York Times, described leadership as the act of running towards the gunfire.
Cecile Richards, formerly of Planned Parenthood, described herself as blessed to have been one of the really privileged few that could do what she thought needed doing.
In industries where awards, wins, and results are to the fore, and success is often measured by how many and how much, I’m hoping that some of these conversations will also stir thoughts of what.
What do I want to make better? What do I want to change? What difference do I want to make for the people around me?
Because, as my work continues to evolve and my understanding continues to deepen, what I increasingly know to be true is that the awards, the wins, and the results are directly connected to the whats.
That the leaders who are clearest about what difference they want to make are the ones who have the most evidence of having made it.
Literally and figuratively.
So, what is your leadership for?

Edited highlights of our full length conversation.
What is your leadership for?
Senator Kirsten Gillibrand is the Junior Senator from the State of New York.
Running for public office places you in a spotlight that is white hot. Being clear why you’ve made the choice to run in the first place is table stakes for creating the life you want to live and the legacy you want to leave behind.
In too many companies and for too many people, leadership is seen as the thing that comes next for those who are willing to stick around. The inevitability of rising up the org chart into a role that comes with more everything is too rarely challenged by company or individual.
Leadership is a privilege. An opportunity to make the biggest difference for the most people, that most of us will ever have.
Marty Baron of the Washington Post described it as a responsibility.
Mark Thompson, when he was at the New York Times, described leadership as the act of running towards the gunfire.
Cecile Richards, formerly of Planned Parenthood, described herself as blessed to have been one of the really privileged few that could do what she thought needed doing.
In industries where awards, wins, and results are to the fore, and success is often measured by how many and how much, I’m hoping that some of these conversations will also stir thoughts of what.
What do I want to make better? What do I want to change? What difference do I want to make for the people around me?
Because, as my work continues to evolve and my understanding continues to deepen, what I increasingly know to be true is that the awards, the wins, and the results are directly connected to the whats.
That the leaders who are clearest about what difference they want to make are the ones who have the most evidence of having made it.
Literally and figuratively.
So, what is your leadership for?

Edited highlights of our full length conversation.
What is your leadership for?
Senator Kirsten Gillibrand is the Junior Senator from the State of New York.
Running for public office places you in a spotlight that is white hot. Being clear why you’ve made the choice to run in the first place is table stakes for creating the life you want to live and the legacy you want to leave behind.
In too many companies and for too many people, leadership is seen as the thing that comes next for those who are willing to stick around. The inevitability of rising up the org chart into a role that comes with more everything is too rarely challenged by company or individual.
Leadership is a privilege. An opportunity to make the biggest difference for the most people, that most of us will ever have.
Marty Baron of the Washington Post described it as a responsibility.
Mark Thompson, when he was at the New York Times, described leadership as the act of running towards the gunfire.
Cecile Richards, formerly of Planned Parenthood, described herself as blessed to have been one of the really privileged few that could do what she thought needed doing.
In industries where awards, wins, and results are to the fore, and success is often measured by how many and how much, I’m hoping that some of these conversations will also stir thoughts of what.
What do I want to make better? What do I want to change? What difference do I want to make for the people around me?
Because, as my work continues to evolve and my understanding continues to deepen, what I increasingly know to be true is that the awards, the wins, and the results are directly connected to the whats.
That the leaders who are clearest about what difference they want to make are the ones who have the most evidence of having made it.
Literally and figuratively.
So, what is your leadership for?

What do you think and why?
Tom O’Keefe and Jeff King are two of the four partners who have just merged their respective businesses, OKRP and Barkley.
Mergers are a forcing function for open-mindedness. And for doing things differently.
The ability to accept the need to do things differently, to truly change perspectives, is a never ending leadership challenge.
In my experience, you have to be pretty clear about your own point of view in order to embrace new ones.
Worry too much about providing strong leadership, and the temptation to stick to our beliefs — even in the face of evidence or views to the contrary — becomes almost like a drug. An addiction to being right or first or better.
This is perhaps the most damaging characteristic that any leader can possess. And too much of it will ensure you’re not a leader of very many or very much for very long.
When we are clear about why we think what we think, when we are free of insecurity or hubris or ego, then we can assess an alternative path with an open mind.
Mergers provoke the need to lead through this lens. Tom’s outline for unleashing the creative potential of the newly formed business is filled with best practice.
But regardless of external forcing functions — like mergers — being clear about why we think what we think is table stakes for the most fearless leaders.
So what do you think? And what will it take for you to see things from a different perspective?

Edited highlights of our full length conversation.
What do you think and why?
Tom O’Keefe and Jeff King are two of the four partners who have just merged their respective businesses, OKRP and Barkley.
Mergers are a forcing function for open-mindedness. And for doing things differently.
The ability to accept the need to do things differently, to truly change perspectives, is a never ending leadership challenge.
In my experience, you have to be pretty clear about your own point of view in order to embrace new ones.
Worry too much about providing strong leadership, and the temptation to stick to our beliefs — even in the face of evidence or views to the contrary — becomes almost like a drug. An addiction to being right or first or better.
This is perhaps the most damaging characteristic that any leader can possess. And too much of it will ensure you’re not a leader of very many or very much for very long.
When we are clear about why we think what we think, when we are free of insecurity or hubris or ego, then we can assess an alternative path with an open mind.
Mergers provoke the need to lead through this lens. Tom’s outline for unleashing the creative potential of the newly formed business is filled with best practice.
But regardless of external forcing functions — like mergers — being clear about why we think what we think is table stakes for the most fearless leaders.
So what do you think? And what will it take for you to see things from a different perspective?