How to Overcome Self-Sabotage From Lack of Self-Belief and Arrogance 

A Simple Lesson to Help You Be Both Confident and Humble 

Resources to help you self-direct your WorkLife learning
Learning Resources From School of WorkLife. Resources to help you self-direct your WorkLife learning.

“You Sabotaged Yourselves Through Whatever It Was That Was Going on Within Each of You”

Samantha and Josh’s Dreams Were Crushed When They Heard These Words

Samantha and Josh had been working at A-Z Advertising Agency for 2 years. Both had joined as college graduates. As part of their graduate programme, they’d both worked for six months at a time in different functions across the company. This was a requirement designed to allow them to understand all aspects of the business more broadly.

The next part of their development plan was to have the opportunity to be part of the team working closely with, and being mentored by, Caitlin, the company’s Creative Director. This was an opportunity that was offered just once a year. To be accepted onto her team, they were each required to present their ideas for a new campaign for a long-existing client.  

How did they do? 

They both failed. 


Because they both sabotaged themselves.

But in very different ways:

Samantha allowed her negative self-talk to impact her self-belief in her own ability. She doubted every single idea she had, and came across as insecure and needy.

Josh believed his ideas were the best ideas, and the only ideas that would work. He came across as arrogant and closed-minded.

As part of the process in preparing their presentation for Caitlin, they had first pitched their ideas to focus groups. These groups were made up of experienced professionals across the company. The groups had given feedback on what they liked and didn’t like.

Samantha homed in on what they didn’t like, completely blanking what they liked, which led her to not believe in herself or her ideas. Her belief was that everyone else’s ideas were better than hers.

Josh homed in on what they liked, completely blanking what they didn’t like, which led him to believe in himself and his ideas. His belief was that his ideas were better than anyone else’s. 

For them to be considered for the opportunity the following year Caitlin gave them both feedback.

Sage Wisdom

She told them that the focus groups were impressed with both of their ideas, and that the feedback was given to help their ideas to be even better. She said: “Instead of listening to hear and understand what was being said and learn from that, you both got in your own way. In effect, you sabotaged yourselves through whatever it was that was going on within each of you.”

She went on to say that a stipulation for them to be considered next year, would be for them to present back to her what they’d learnt from this experience, and how they’d used this to set themselves up for success in the next opportunity. She told them she wanted to see confident presentations that demonstrated both humility and self-belief. She said she’d meet with them in nine months to hear what they have to say. 

She left them with these parting words of wisdom: “Listening to the right people, and this includes listening to yourself, is a gift, a chance to learn about how to do better. Listening to the wrong people, and this includes listening to yourself, particularly the early critics, is a trap. If you’re not careful, it can become a place to hide.” 

She proposed a question to ask themselves by way of reflecting on their experience. The question she said that will serve them well in this moment, and will stand them in good stead throughout their WorkLife, is to ask:

“How am I complicit in creating the conditions that I say I don’t want?”

She finished by suggesting they read Timothy Gallwey’s work on The Inner Game.

Nine months later, helped by the book wisdom of The Inner Game of Work, this is what Samantha and Josh presented to Caitlin:

Book Wisdom

Samantha: The greatest challenge and consequently the greatest possibilities, lie in overcoming the self-imposed mental limitations which prevent the full expression of my ideas and subsequently my potential. 

Through self-feedback I realised I need to monitor my negative self-talk, because my mind is always listening, and If I talk about all my perceived limitations, if I argue for them, they’re mine, if I fight for them, I get to keep them, and so I always have to be careful of my negative self-talk. 

My self-image can be an obstacle, probably the greatest obstacle to my growth, by believing my ideas are not as good as other people’s, I limit how well I will let myself draw on other people’s ideas to develop my own thinking.  

Acknowledging my weaknesses, has allowed me to behave differently in response to what I’ve acknowledged. I’ve taken my inner voices on a journey with me to highlight challenges and obstacles. This allows me to be my own fiercest opponent, other opponents will be small compared to the expectations I have for myself. 

Of course I can’t demonstrate I’m right for the project if I only focus on my inadequacies, I have to project confidence, and this is a confidence that I can learn to develop myself and my ideas through other people and their ideas. I can do this by accepting feedback objectively, making my judgement by observing the facts, and from this making my decisions.

When I engage in self-sabotage through negative self-talk, then my self-confidence suffers. This leads to a cycle of self-interference, and one that I haven’t yet learnt to overcome, but I have learnt how to deal with it and to manage it. 

I do this by asking myself the question: “Do I want to do this badly enough, or do I want to give into the notion that I’m not good enough?” To be part of your team, to have the opportunity to work closely with you, and to learn from you, is my heart’s desire, this is an amazing opportunity, and it’s my opportunity. So yes, I do want it badly enough, I have to do it, and I am good enough. 

Success for me is walking into a room, believing in myself and what I do. Presenting my best self in the knowledge I’ve put everything I can into my work, and being happy with the result.

Josh: I can be my own worst enemy, and I need to get out of my own way, and start developing patience. To be patient with myself, to accept that I don’t know everything, and my ideas are not the only ideas or necessarily the best ideas. 

Self-feedback has allowed me to know that the mental interference that is keeping me from being my best right now, will also make it more difficult to acquire new skills. I needed to find a better way, and to make a change.

To do this I looked to behaviours and tactics of people I admire in the world of sports. I posed questions to myself about; how they keep their minds quiet and focussed to manage the impact of inner dialogue on their performance. I discovered the art of relaxed concentration to trust my mind’s potential to learn and perform.

This practice uses the unconscious rather than the self-conscious mind, it helps to unlearn or suspend the habits and concepts which interfere with my natural learning ability and to trust the innate intelligence of my mind. 

I want to be good at my job, and I want to find solutions, I want to find a way to become good. I recognise now that there is no instant solution, I will learn through experience, I will make mistakes, working with and listening to experienced professionals who are passionate about their work, will allow me to learn though these experiences and mistakes.

I need to let go of what I think I know because learning any new skill is about the process of discovery which comes primarily from the experience itself. By letting go of my preconceived notions, by not resisting new experiences I can learn far more. I can learn how to deal with the unexpected whenever I encounter it. I’m discovering I can adapt to strange or different concepts only when I’m willing to let go of dependence on old concepts.

George F. Kneller said: “To think creatively, we must be able to look afresh at what we normally take for granted.” 

I believe there’s a way to be humble and confident. Success to me is to turn up in life with humility, confidence, authenticity, with fun and to be myself.


Caitlin was impressed, by the sincerity of their self-reflection, and what they learnt from this. She gave them both the opportunity to present their ideas for this year’s campaign. She asked that they work together on their presentation, saying they each had something different and unique to bring to their work, that they could both learn from and challenge each other.

Samantha and Josh were both relieved and excited to have been given the opportunity again. They agreed to be their own and each other’s biggest critics and champions, to hold themselves to the highest standards. To work to come up with new ideas to challenge their excellence.

It worked. They were both successful in Caitlin accepting them onto her team, to work closely with her on the new campaign. Their unique WorkLife stories continue.

Words of Wisdom

Taking a long hard look at how you are self-sabotaging is both insightful and painful. It requires you to look in the mirror at who you are, and what you do that at its worse is destructive or at its  best is slowing you down, preventing you from fully being who you should be. Master your inner dialogue: What you say to yourself matters more than what the entire world together says about you. 

This story has been adapted from chapter 25 of my book: Your WorkLife Your Way: Self-Sabotage. It also featured in the School of WorkLife book, How To Overcome Self-Sabotage. I developed it further for WorkLife Book Club

Today’s featured book is: The Inner Game of Work by Timothy Gallwey 

WorkLife Book Wisdom Stories:

The intention of the stories I share is to inspire you through people’s stories of their WorkLife experiences. Through these stories, you will learn about people’s dreams and ambitions, along with the challenges, obstacles, failures and successes they encountered along the road of their WorkLife journey. And how they used the power of book wisdom to help them find the inspiration and guidance to navigate their path to live their WorkLife with passion, purpose and pride.

My hope is that these book wisdom stories will help you throughout the chapters of your WorkLife Story.

I believe stories are a powerful mechanism for teaching, a powerful medium to learn through, and a powerful way to communicate who you are and what you stand for.



This story was originally published on 12/4/21. I needed to republish it to add updates and also to tell you

… The Continuing Story …

The pandemic brought about a change in my WorkLife from delivering in-person individual coaching sessions and group workshops to creating resources to help people self direct their WorkLife learning.

In the last three years, I’ve published 30 books and over 200 stories.

Each book and each story is based on real life struggles and successes that people have encountered in their WorkLife. They also detail the exercises that helped navigate through these situations, which are set as assignments for readers to adapt to their WorkLife situations and learning needs.

I believe stories are a powerful mechanism for teaching, a powerful medium to learn through, and a powerful way to communicate who you are and what you stand for.

My inspiration for creating my work comes from a lifelong passion for learning. My work has taught me that the one thing in life that can never be taken away from you is your learning. 

School of WorkLife Guiding Statement: To create resources that are helpful, insightful and inspiring in helping people to pursue their WorkLives with greater clarity, purpose, passion and pride by creating continuous WorkLife learning programmes and resources that are accessible to everyone.

The resources I create will help you take ownership of self directing your learning in your own space and in your own time.


School of WorkLife helps you self-direct your WorkLife learning through resources that have been created to help you to take ownership of your learning in your own space and in your own time. 

What is Self Directed Learning? 

Self-Directed Learning is when an individual is motivated to take the initiative and responsibility on decisions related to their own learning. It is a series of independent actions and judgements free from external control and constraint. 

Resources to Help You Self-Direct Your Learning 

You may find the books below from The School of WorkLife Book Series helpful in meeting your learning needs as a self directed learner. Tap the book title to see a preview of what’s inside each book.

How To Get To Self-Realisation and Self-Acceptance 

How To Overcome Self-Doubt Through Self-Appreciation 

How To Be Vulnerable and Courageous 

Tap The School of WorkLife Book Series to view the complete collection of books. From here, you can tap on each individual title to see a preview of what’s inside each book.

Carmel O’ Reilly is a learning practitioner and writer. She creates resources to help people self-direct their WorkLife learning
Carmel O’ Reilly is a learning practitioner and writer. She creates resources to help people self-direct their WorkLife learning

Carmel O’ Reilly is a learning practitioner and writer. She creates resources to help people self-direct their WorkLife learning.  These include a Collection of Books which originated from her first book, Your WorkLife Your Way and a  Learn Through Reading Series of Case Studies.  which originated from her latest book WorkLife Book Club. 

That’s the power of writing (and reading, which is an integral part of the craft for writers). It helps you find, develop and tell the right story at the right time in all WorkLife situations – in day-to-day communication: WorkLife and feedback conversations, presentations, talks, and negotiations, at interviews, and when socialising and networking in building and maintaining good relationships. The practice of writing helps you to tell the stories that express who you are in an interesting and engaging way.

Published by Carmel O' Reilly

Carmel O’ Reilly: WorkLife Learning Practitioner & Writer Author of WorkLife Book Club, Your WorkLife Your Way and The School of WorkLife book series. Created to help you manage your WorkLife Learning. Blogger & Podcaster: Telling people’s powerful stories about WorkLife challenges & successes Founder of My guiding statement is to help people pursue their WorkLives with greater clarity, passion, purpose and pride by creating continuous WorkLife learning programmes that are accessible to everyone.