What is the one book that has had the biggest impact on you?

A colleague of mine suggested that I listen to the Tim Ferriss podcast episode with Naval Ravikant, who is an entrepreneur, investor and CEO of AngelList.com. Before I get to the point of this post, I highly recommend this podcast episode. It really made me think long and hard about my own philosophy, the books I read, and on my approach to some important things in life. While I didn’t agree with everything said, I thoroughly appreciated the conversation.

Many of the questions Ferriss asks Ravikant are consistent with the ones he asks in his book, Tribe of Mentors. Towards the end of the episodeFerris asks, “What is the one book that has had the biggest impact on you?”.

ProfilesMy own answer to that question is not hard. For me, the book that has had the biggest impact on me is Profiles in Courage by President John F. Kennedy, which he wrote when he was serving as a United States Senator representing Massachusetts.

This 1957 Pulitzer Prize winning book profiles eight United States Senators who, in their time, demonstrated courage by going against the grain of their party or popular opinion to stand up for their beliefs. My edition of the book (a used copy and a priceless gift from my father) has a powerful forward by Robert F. Kennedy and a rich introduction by the author.

In the introduction, President Kennedy explores the differences in between delegation and representation in government. A delegate’s job is simply to reflect the popular opinion of his constituents in legislative discussions. Representatives are elected to bring their judgment and opinions into legislating. Prior to reading the book, I believed firmly in the “delegate” point of view. Reading it changed my perception entirely to the “representative” camp.

Since reading Profiles in Courage, I have not read anything that so fundamentally changed my understanding of leadership and my expectations for leaders. There are many lessons in the book about the commitment it takes to lead in opposition to popular opinion. It is a nuanced view of how leaders stick to their opinions for better or worse and the consequences one might face for doing so.

For example, President Kennedy quotes Senator Daniel Webster’s last words to the U.S. Senate:

I shall stand by the Union…with absolute disregard of personal consequences. What are personal consequences…in comparison with the good or evil which may befall a great country in a crisis like this?…Let the consequences be what they will, I am careless. No man can suffer too much, and no man can fall too soon, if he suffer or if he fall in defense of the liberties and Constitution of his country.

Concepts like the one explained by Senator Webster in the book were my first exposure both to the notion of serving a greater cause as well as to servant leadership and its true, non-rhetorical, non-clichéd implications. Profiles in Courage is both inspiring and and a healthy warning to aspiring leaders. On the one hand, it praises instances where leaders stood up for their convictions and discussed them openly. On the other hand, it outlines the career, health, and general welfare risks of doing so.

Leadership can be both public and deeply isolating. It can give privilege and freedom, while also limiting rights. The bottom line is that leadership is not an easy or simple endeavor and those who do not want to lead and are not prepared for those dichotomies, probably should not.

When I was in school, I felt like leadership was over-emphasized. While anyone can lead, everyone shouldn’t lead. Leader-follower dynamics are important and followers are far more important in actually making change happen. This is the concept behind the social contract, which inherently produces equally important leaders and followers in a society. “Followership” can be learned too and should be discussed and explored along with leadership in academic settings.

Profiles in Courage inspired me to engage in rigorous reflection and questioning to decide whether I really wanted to live the life of a leader who was willing to stand up in the face of public opinion. Thinking about it during my formative years, I knew that I wanted to be a leader that was principled and values-driven and accept the consequences from there. Being secure, self aware, and not taking things personally are all important tools on the way to our own chapters in Profiles in Courage.

KEY TAKEAWAY: Leadership is a challenging proposition filled with dichotomies and, at times, obstacles. Values-based leaders who possess certain qualities, learned over time, can prepare for these challenges. Profiles in Courage is both an inspiring and cautionary book that I recommend highly to all leaders and aspiring leaders.

Profiles in Courage is available for purchase on Amazon for $24.83 (does not include Prime discount)

No vision, no mission

We choose to go to the moon. We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard, because that goal will serve to organize and measure the best of our energies and skills, because that challenge is one that we are willing to accept, one we are unwilling to postpone, and one which we intend to win, and the others, too. –President John F. Kennedy speech at Rice University September 12, 1962


That quote from President Kennedy is one of my absolute favorites. The reason why is that in this quote (and the entire speech), Kennedy lays out the case for human space travel and does it extremely effectively. Setting aside the rhetorical expertise for a moment, Kennedy’s biggest impact is his vision: “We choose to go to the moon”.

Think about that for just a minute.

Leaders have problems getting followers, employees, even those closest to them to join them in going just about anywhere. Have you even been a part of a new system implementation, a go live, or even an office move? It’s hard to get people aligned to a vision of moving across the street let alone sending a man TO THE MOON!

In this speech, actually in this quote, Kennedy succinctly tell us “where” we are going and “why” we are going there. He articulates a vision that we will go to the moon, because it is a challenge that we are up for and need to meet, even though it is hard.

This quote was my first lesson in the power of vision and how having one is supremely vital in any organization. Leaders must articulate a vision and convince people that it is the right way to go and that they should be a part of it.

A popular saying in the non-profit world is, “no margin, no mission”. In other words, if your organization is not financially sustainable, it is not in a position where it can actually work to fulfill that organization’s mission. In my mind, the same lesson is true for a vision: “no vision, no mission”.

Without a clear vision, the organization is similarly not positioned to fulfill the mission. Without a vision, organizational alignment is nearly impossible to achieve. Lacking a clear vision allows everyone to interpret and act on the mission independently, not collaboratively with other team members. One employee may define an activity that advances the mission far different than another employee or even the way the “big boss” defines it. This is where organizations tend to drift, when the future is opaque and the bridge describing “how” we get from today’s reality to accomplishing the mission is undefined.

Groups of people, being countries or organizations, like to know where we are going. It is not only comforting, but helps people make sense of the actions you take as a leader. It changes the conversation from, “I don’t know why the boss is doing this. Maybe just to make my life more difficult” to “I can see how what the boss is doing fits into where we are going”. It gives purpose to work and an important destination to focus on.

There is popular literature on whether a vision should be for 6 months, 1 year, 5 years, 10 years, etc. There is also much discussion of whether the vision should be attainable or aspirational. My advice: Don’t over-think it. Start with the ideal state. Define when you may realize that ideal state and the work backwards from there to create a strategy to attain it.

Success in leadership requires defining a vision of an inherently uncertain future to create meaning and alignment in an organization. Without those elements, organizations (countries, even) tend to drift. Do the work to create a vision and tell everyone about it. Don’t be shy. The next step is finding people to help bring it to reality. When you do that, then you will truly be a leader.

The very essence of leadership is that you have to have a vision -Theodore Hesburgh

KEY TAKEAWAY: Creating a vision of the future is a vital tool for leaders to add meaning and alignment for daily activities. Don’t overthink creating a vision, do your best work to develop an ideal state in the future and then create a map to achieve it. Work collaboratively to reach it. Good luck!