The Examined Life Is Not Worth Living

This piece forms part of a series in collaboration with leadership expert Trevor Waldock.



The cool air that hit me as I emerged from the London Underground station into the sunlight, reminded me that autumn had slipped in unnoticed. I was going to be late for my meeting, so I upped my pace as I climbed the large staircase that would take me over the city’s imposing river. At the top of the steps, a woman was seated on the ground. She was dressed in shabby clothes and was either trying to sleep or was crying, and she had a crumpled coffee cup in front of her, to receive money. I made sure I didn’t catch her eye, walked past her quickly and headed over the bridge. As I descended the other side, a man stood right in front of me holding out a copy of the Big Issue. I sidestepped him, avoided his gaze and headed to my meeting twenty metres away.


What really just happened there? And, why does my inner thoughts and feelings as well as my actions, as a leader, matter in this moment on the bridge?

Because the little things become big things, if you do a lot of them – little thoughts become attitudes, little actions become habits, little decisions become directions and little habits become our character. The big things of my leadership today are made up of the little things I have been doing all day, every day up to this point. I bring myself into every dimension of my life - workplace, family, relationships - and myself is being shaped every day. The little things are the countless thoughts, decisions, actions and conversations that I don’t ever really think about. The moment on the bridge is simply a snapshot, a window, that reveals what kind of person I am.

Clayton Christensen, author of the well-known book The Innovator’s Dilemma, was at business school with Jeff Skilling, former CEO of Enron. Christensen describes Skilling as a good man: smart, hard-working and he loves his family, but Christensen was shocked at what the court cases that followed the collapse of Enron revealed, about Skilling’s character. The man Christensen knew wasn’t the man in the court case, he became the man in the court case. He became that man over many years of practice. Many years of little things led Skilling to the big thing (his central role in the collapse of Enron). Christensen’s conclusion was, “Something had clearly sent him [Skilling] off in the wrong direction.”

I’ve worked with tough leaders who tell me in no uncertain terms that paying attention to the little things that create our character, is introspective nonsense. They believe that Socrates was wrong when he said, “The unexamined life is not worth living”. Instead, their mantra might be, “The examined life is not worth living…… I don’t have time for it.”

Imagine you go into the office early one morning. You have spent long hours creating innovative ideas for a new product, but you now have an over-full email inbox and you want to deal with it while no one else is around. You get to your desk and notice that your boss is already in. She puts her head round the door and asks you if you could bring her your creative ideas.

Freeze-frame that moment.

What will your response be to this request? Exuberant excitement? Nervous anticipation? Give her everything? Withhold, or censor, some key ideas?

The answer will depend on your level of trust in your boss as a leader, which will be based on your experience of them and their character.

Our daily experience of leaders shapes our trust in them. It’s their character that walks into the office, ahead of any job title. And that’s true of us too. People are constantly watching us and making conclusions about us and that affects how much they want to work with us… or not. Character and trust are the bedrock of everything.

young leader



Who we are as leaders is shaped by the little things we do, or don’t do, every day.

The ‘little things’ shape our character as a leader

Character is the basis of all trust

Trust is the foundation of all effective leadership

Two questions:

Who do you want to be in your character as a leader?

What action can you take this week to begin becoming that person?


None of this happens by accident.

Becoming a great leader is the result of intention, not chance.


©Trevor Waldock 2019

This is an adapted extract from Chapter 1: of the book:

Doing The Right Thing – Getting Fit For Moral Leadership by Trevor Waldock 

If you would like a free copy of the pdf version of the book please email [email protected]