T is for Succeeding Twice When Tackling A Challenge  


There are many ways to define success. One approach is: a) To succeed by being true to yourself when tackling a challenge; b) To tackle the challenge successfully. You will then have succeeded twice.

It is also possible to fail twice. One leader expressed this in the following way.

It is important to do what you believe in when running an organisation. Some people fail to follow their values and also fail to build a good organisation. They have then failed twice.

Bronnie Ware highlighted the importance of people being true to themselves in her book The Top Five Regrets Of The Dying. She spent many years working in palliative care. You can discover more on her website via the following link.


Many of the people she met found peace towards the end of their lives. The top regret some of them mentioned, however, was:

I wish I’d had the courage to live a life true to myself, not the life others expected of me.

Looking at your own life, can you think of a situation when you were true to yourself and tackled a challenge successfully? You may have chosen to behave in a certain way when following your values, taking a tough decision, leading a project or whatever.

If you wish, try tackling the exercise on this theme. This invites you to do the following things.

Describe a specific situation when you were true to yourself and also tackled a challenge successfully.

Describe the specific things you did to follow your values and tackle the challenge successfully.

Describe the specific things that happened as a result of taking these steps.




Many people feel fulfilled when taking this route, but sometimes things do not always work out. A person can follow certain combinations when tackling a challenge. Let’s explore each of these options.


Being true to yourself
and succeeding

This sounds the ideal and some would say it is quite idealistic. Many people have followed this path, however, to follow their values and also tackle a challenge successfully.

Rosa Parks chose to stay where she was sitting, for example, rather than move to the back of the bus. This sparked a boycott that eventually led to the desegregation of bus passengers in Alabama. Many years later she would say:

I have learned over the years that when one’s mind is made up, this diminishes fear; knowing what must be done does away with fear.

John Wooden, the legendary basketball coach, chose to follow certain principles when working with athletes. He never mentioned winning but his teams won more titles than any other in College basketball history. His view of success was:

Success is peace of mind which is a direct result of self-satisfaction in knowing you did your best to become the best you are capable of becoming.

During his early career he began developing what later became known as his famous Pyramid of Success. This consisted of guiding principles that athletes could follow both on and off the court.

The base of the pyramid consists of phrases such as Industriousness; Friendship: Loyalty; Cooperation; Enthusiasm. Behind each of these words is an explanation. The word Industriousness, for example, is explained in detail. This includes the phrases:

In plain language, I mean you have to work – and work hard. There is no substitute for hard work. None. Worthwhile things come only from real work.

There are several levels to the Pyramid of Success. It culminates in the principle of Competitive Greatness. This is explained as:

Perform at your best when your best is required. Your best is required each day.

You can discover more via the Coach Wooden website. Here is a link to the Pyramid of Success.


Being true to yourself
and not succeeding

There may be times when you follow your values and yet do not tackle the challenge successfully. This can lead to a period of reflection and asking fundamental questions. One approach is to focus on the following themes.

Continuous Improvement

The specific things I did will
when tackling the challenge were: 




The specific things I could
have done better and how were: 




The specific things I can do to keep building on I
did well and keep improving in the other areas are:




Not being true to yourself
and not succeeding

This is the nightmare scenario. One leader described how he had taken this route in a previous position.

Early in my career I led a motivated project team that delivered great results. This led to many of the team being promoted.  

The Managing Director asked me to repeat the good work by turning around a failing department. Several managers had tried to improve the department, but with little success.

My instincts told me that we needed to bring in positive people who would add zest and energy, but there was a limited budget. Bearing this in mind, I tried to motivate the present staff.

The team members were polite rather than aggressive, but they refused to do what was required to thrive in a changing world. Many were customer shy.

They needed to spend more time face-to-face with customers, for example, and help them solve their business issues. They preferred to stay in the office, however, and do everything from their desks.  

I spent six months trying to convince people about the need to change, but it didn’t work. Eventually the department was integrated into another part of the business and I found a job elsewhere.

The lesson I learned was that you have to get the right people in place as quickly as possible. You then have a fighting chance of achieving success.  

Nowadays I set things up to succeed. When applying for a role, I gather information and clarify the picture of success.  

Bearing in mind what I can control, I rate the chances of success. If it is 7+/10, then I look at what can be done to improve the rating. I then decide if I want to go for the role.  

Meeting the prospective bosses, I try to show that I understand the world from their point of view and the results they want delivered. The next steps are:

To reassure them that I can deliver the results.  

To explain how I will get some quick successes and keep them informed about the progress towards achieving the goals. 

To explain the resources required to deliver the results.  

I have learned it is important to reassure prospective bosses, but clear contracting is crucial. It is vital to set things up to succeed, otherwise it is easy to become a victim.  

Not being true to
yourself and succeeding

This is an interesting combination. Some people know how to play the game and succeed, for example, but feel uneasy inside.

A person may take this route to pass an exam, make a sale, win an argument or whatever. They know what is required and know they are good at it. At the same time, however, they may feel empty inside.

Some people start off on this route with the best of intentions. They may aim to get a job with a good income, rise through the corporate ladder or gain recognition from authorities. For some individuals, however, they reach a point where they say:

I am successful, but I am not happy. I want to do things that have more meaning in life.

Not everybody who takes this route feels concerned, of course, but some do. The key lies in how they want to measure their lives.

This is a theme that was highlighted by Clayton Christensen in the book he co-wrote with James Allworth and Karen Dillon called How Will You Measure Your Life? Looking at his own life, Clayton asked the following questions.

Is there something that I can leave the world that is something bigger than me? Something that will help other people become better people? How will I measure whether I am achieving that goal?

Below is a video in which he describes how such questions led to him writing an article for the Harvard Business Review. This then led to producing the book.

Here is an excerpt from the website dedicated to this theme. You can discover more via the following link.


As you may know, in the middle of 2010, I wrote a piece for the Harvard Business Review entitled How Will You Measure Your Life?

The article was the result of a conversation I have with my students at the conclusion of the semester.

On that day, we use the thinking we’ve shared in the course for a powerful purpose – to ensure they are successful not just in their careers, but in their lives as well.

I believe it’s my single most important class of the year.

The reaction to that article was beyond my wildest expectations – it has consistently been among the most read articles on HBR’s website and inspired comments from readers all around the world.

Many of the people who were moved by it asked me to expand my thoughts into a full-length book.

Let’s return to your own life and work. Looking ahead, can you think of a situation where you may be able to succeed twice? This could be in your personal or professional life.

What may be the challenge? How can you follow your values in this situation? How can you also do your best to tackle the challenge successfully?

If you wish, try tackling the exercise on this theme. This invites you to do the following things.

Describe a specific situation in the future when you may aim to be true to yourself and also tackle a challenge successfully.  

Describe the specific things you can do then to follow your values and tackle the challenge successfully.

Describe the specific things that may happen as a result of taking these steps.




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