If you’ve ever found yourself asking this question internally, you’re not alone. Whether you’ve been a CEO or MD for months, years or decades, what keeps us challenging ourselves is our underlying ambition to succeed, usually combined with a healthy dose of self-doubt. Whatever the size of this fear (rational or irrational) it’s often the driving force behind our on-going desire to grow, accept bigger challenges and push ourselves and our business forward. If we fail to recognise and acknowledge self-doubt as a real fear, it can often dominate our lives but also overshadow our personal and professional relationships.


As leaders we need to ask ourselves difficult questions about what drives us and how important the ‘need to arrive’ is, as a motivation.

Do you consider yourself competitive, wanting to display your success with the latest status symbols, or having the biggest house, or the most expensive car on your street? If there was little money during your childhood, do you still have a continual fear that your wealth may disappear?

Examining what motivates you and how you define yourself as successful can be a really useful exercise to better understanding yourself.


  • Financial Security Do you need a certain amount of income to feel secure and retain the life-style you aspire to?
  • Fear Are you afraid of losing everything financial or personally important to you?
  • Achievement Will you only be satisfied and consider yourself ‘to have arrived’, if you achieve all your personal and work-related goals?
  • Status How important is it for your position to be acknowledged and recognised by your peers, family and friends?
  • Autonomy Is it important to be in charge and set the agenda and culture in your organisation?
  • Responsibility and Power How important is it for you to call the shots and how do you react when someone else tries to control certain parts of your business?
  • Respect Are you proud of the distance you have covered from the beginning of your career to now?
  • Passion Do you still firmly believe in your business, service or product and are always looking for ways to develop it further?


Be Objective

Once you’ve asked yourself these questions, ask a mentor, close friend or trusted business partner for their answers to the same questions about you. An independent point of view may reveal different answers to your own and highlight areas you may not have considered.

Psychometric evaluation can also shine a spotlight on behaviours that are often unconscious and can therefore provide greater self-awareness and identify patterns of behaviour.



Proving to yourself that you have ‘arrived’ can be simplified by asking three key questions:


Do I need to prove to myself, peers, bosses or family that I have ‘arrived’?

Will I become complacent after I believe I have ‘arrived’?

What happens next, if I achieve my goals and ambitions?


Key Take-Aways

Recognising our ambitions and motivations is a vital step to developing ourselves into inspiring leaders, capable of driving ourselves and our businesses forward. Setting targets and achieving them, is often the process that we enjoy most as CEOs and MDs. If the financial rewards from these successes leave us feeling dissatisfied, the reality could be that we will only feel like we’ve ‘arrived’ when we have a meaningful purpose, that takes us onto our next challenge.



Jeremy Thorn is a Mentor, qualified Business Coach and Non-Executive Director of many businesses. A frequent Guest Speaker at the Academy of Chief Executives, he’s also the author of several prize winning business books including; ‘How to Negotiate Better Deals’, ‘The First-Time Sales Manager’ and ‘Developing Your Career in Management’.