Why Success Can Keep Us Too Busy to Question What Really Matters
The Boy Who Wanted to Become a CEO
In 1982, I achieved what might be described as my first moment of fame. I appeared on the front cover of the Select Sires directory, a publication devoted to dairy cattle breeding. I was probably six or seven years old, wearing blue dungarees and standing beside a young calf. It wasn’t exactly the front cover of Vogue, but everybody has to start somewhere.
What interests me most about that photograph today isn’t the magazine appearance. It’s what was going on in the mind of that young boy. From an early age, I dreamed of becoming a CEO. I was fascinated by successful businesspeople, how they made money, built organisations and reached positions of responsibility. As I grew older, that childhood ambition became an increasingly important part of how I imagined my future.
Over the following decades, I built a successful career in commercial leadership, managed substantial businesses, led large teams and accepted increasingly demanding responsibilities. Yet something interesting happened along the way. I became so accustomed to pursuing that ambition that I rarely questioned whether it was still what I genuinely wanted. It took working with my own executive coach to begin examining whether the dream I’d carried since childhood still reflected the person I’d become.
That experience raises a question I now frequently encounter in my coaching work. How many high achievers spend their professional lives answering difficult questions for everybody else, while rarely making time to ask the questions that could fundamentally change their own direction?
When Success Leaves Little Room for Reflection
Doctors, lawyers, CEOs and founders are generally rewarded for their ability to solve problems, exercise judgement and make decisions. Their professional value frequently depends on being the person others turn to when situations become complicated. The more successful they become, the greater the demands on their time, attention and expertise. Over time, responding to those demands can become so normal that creating space for personal reflection begins to feel almost indulgent.
Yet being exceptionally good at solving problems doesn’t necessarily mean we’re asking ourselves the right questions. We might spend hours examining commercial strategies, patient outcomes, legal arguments or organisational challenges while giving comparatively little consideration to our own priorities. We become increasingly effective at managing the responsibilities we’ve accumulated without necessarily questioning whether those responsibilities still align with what matters most.
In Harvard Business Review, Jennifer Porter explored why leaders often resist meaningful self-reflection despite its potential benefits.[1] Some struggle to know where to begin, while others find it uncomfortable or believe they have more pressing demands. Research by Giada Di Stefano and colleagues also suggests that deliberately reflecting on experience can improve learning and subsequent performance compared with experience alone.[2]
That resonates with my own experience. During my corporate career, there were periods when the workload appeared endless, yet I continued operating effectively because that was what I’d trained myself to do. The danger wasn’t necessarily that I was making poor decisions. It was that I could become so absorbed in making decisions that I neglected to examine whether the direction behind them still made sense.
The Ambitions We Continue Without Questioning
Ambition is something I’ve always valued. It has driven much of what I’ve achieved in business, education and endurance sport, and I have no intention of suggesting that successful people should become less ambitious. However, I increasingly believe that ambition needs to evolve alongside the person pursuing it.
A goal established at 25 might be entirely appropriate at that stage of life. By 45 or 50, circumstances may have changed considerably. Family responsibilities, personal experiences, financial security and our understanding of fulfilment can all influence what we value. Yet we sometimes continue pursuing earlier ambitions because we’ve invested so much time and energy in them that reconsidering their relevance feels uncomfortable.
Psychologists Kennon Sheldon and Andrew Elliot explored the importance of self-concordant goals, those aligned with an individual’s values and developing interests.[3] Their research associated these goals with sustained effort and greater wellbeing benefits when achieved. Related research by Carsten Wrosch and colleagues examined how adjusting commitments to unattainable goals can support wellbeing.[4] Neither finding suggests that changing direction is always desirable, but both reinforce the importance of the relationship between our goals and our circumstances.
In my earlier article, The Second Half of Ambition, I explored how my understanding of success has evolved as I’ve grown older. The distinction here is slightly different. Before we can decide whether an ambition needs to change, we must be prepared to question it in the first place. And that can be surprisingly difficult when the ambition has become intertwined with our identity.
My own coach helped me examine this through relatively simple exercises, including the balance wheel. We explored different areas of my life, how satisfied I felt with them and what mattered most. The real value emerged through the questions that followed. Why had I given something a particular score? What had become more important? Had my priorities changed? Was becoming a CEO still the destination I genuinely wanted, or was I continuing to pursue something because I’d wanted it for so long?
Is Busyness Sometimes a Convenient Distraction?
I understand genuine professional pressure. Having spent nearly three decades in commercial leadership, including responsibility for substantial financial performance and large teams, I know that senior positions can bring relentless demands. Doctors and lawyers face additional responsibilities where the consequences of decisions can directly affect people’s lives. Suggesting that these individuals simply need to make more time for themselves ignores the reality of their working environments.
Nevertheless, I believe there’s another dimension worth exploring. Sometimes we genuinely don’t have enough time to reflect. On other occasions, remaining busy can become a convenient way of avoiding questions whose answers might challenge the lives we’ve created. Those two situations aren’t always easy to distinguish, particularly when being productive has become central to our identity.
Organisational psychologist Tasha Eurich has examined how people can overestimate their self-awareness, even when they consider themselves thoughtful and experienced.[5] Her work highlights the importance of examining our assumptions and seeking perspectives beyond our own. That matters because being successful doesn’t automatically make us more willing to question ourselves. In some circumstances, success can reinforce the very assumptions that deserve examination.
I recently met a senior professional who had spent more than a decade dreaming of opening a florist’s shop. Despite having a genuine passion for the idea, they hesitated because of concerns about how other people might perceive such a significant career change. Eventually, they pursued that ambition, and I was delighted to hear it. What struck me wasn’t the decision to become a florist, but the number of years during which the expectations of others had influenced what this person felt able to do.
It’s easy to dismiss such stories as examples of people lacking courage, but I think the reality is more complicated. Professional identity, financial responsibilities, reputation and family expectations can all make significant changes difficult. The more interesting question is whether we recognise those influences or simply allow them to determine our choices without ever properly examining them.
The Questions Worth Making Time For
One of the things I’ve learned through executive coaching is that the first problem somebody presents isn’t always the most important one. A client might initially want to improve their confidence, make a difficult career decision or overcome a professional obstacle. Those concerns are often entirely genuine, but as the conversation develops, other factors can emerge that influence how the individual sees the situation.
I don’t believe there’s a magical coaching question that works for everybody. Effective questioning is much more about understanding when to continue exploring, when to challenge an assumption and when to allow somebody the space to think. Researchers Alison Wood Brooks and Leslie John have examined how thoughtful questioning, particularly follow-up questions, can encourage learning, trust and deeper understanding.[6]
For somebody who rarely pauses to examine their own direction, I believe six questions provide a useful starting point:
- Am I still pursuing something I genuinely want, or something I once wanted?
- If I were starting again today, would I choose the same direction?
- What am I tolerating simply because I’ve become good at managing it?
- Whose definition of success am I working towards?
- What would I change if I stopped worrying about disappointing other people?
- Am I making meaningful progress, or simply becoming more efficient at remaining where I am?
These questions don’t require somebody to abandon their career, reconsider every decision or make dramatic changes to their life. Their purpose is to create space for examination rather than automatically accept the assumptions behind existing choices. Sometimes the answers will confirm that we’re exactly where we want to be. At other times, they may expose a difference between what we’re doing and what we genuinely value.
The important part is resisting the temptation to rush towards an answer. High achievers are often exceptionally good at reaching conclusions quickly, but self-reflection sometimes benefits from staying with a question longer than feels comfortable.
Why the Right Conversation Can Change Everything
When I reflect on my own coaching experiences, something continues to fascinate me. The conclusions I reached felt entirely my own, which in many ways they were. My coaches didn’t tell me to abandon my ambitions, change direction or establish my own business. Instead, they created an environment in which I could explore my thinking, test assumptions and recognise possibilities I hadn’t previously considered.
Having subsequently trained as an executive coach myself, I understand more clearly what was happening. A seemingly simple question can lead to another, and then another, until somebody begins recognising something underneath their initial answer. Knowing when to continue, when to challenge and when to remain silent is part of the skill. So too is recognising the emotional significance of what somebody is saying, rather than concentrating exclusively on the words.
None of this works particularly well without trust. In Trust Is the Bedrock: Why Coaching Fails Without It, I explored why people need to feel safe enough to be genuinely honest before meaningful challenge becomes possible. Research published in Human Relations, examining more than 3,500 coaching processes, found a consistent positive association between the quality of the coaching relationship and client outcomes.[7]
That connection between trust, curiosity and questioning is fundamental to how I approach executive coaching. Successful professionals rarely need another person simply telling them what to do. Many already have considerable knowledge, judgement and experience. What can be missing is an independent perspective from somebody prepared to challenge their thinking without bringing their own agenda to the conversation.
I explored a related challenge in Why People Who Don’t Think They Need Coaching Often Benefit Most. Some of the most capable people I’ve encountered initially questioned what coaching could possibly offer them. Yet their willingness to remain curious and examine their own assumptions often revealed opportunities they hadn’t anticipated.
Making Space for the Questions That Matter
Looking back at that photograph of myself beside the calf, I still recognise the ambition of the young boy who wanted to become a CEO. I don’t regret having that ambition, nor do I regret the opportunities and experiences it encouraged me to pursue. But I’m grateful that, eventually, somebody helped me question whether the destination I’d imagined decades earlier still reflected what mattered to me.
I now have a different understanding of success, one shaped by family, experience, personal growth and the opportunity to make a meaningful difference through my work. That doesn’t make my childhood ambition wrong. It simply means that the person asking the questions today is no longer the boy who first dreamed of becoming a CEO.
High achievers will always have problems to solve, decisions to make and responsibilities to fulfil. The challenge is ensuring that somewhere among those demands, they create enough space to question their own direction, rather than allowing yesterday’s ambitions to determine tomorrow’s decisions.
Sometimes the greatest breakthrough isn’t finding another answer. It’s finally asking yourself the question you’ve been too busy to confront.
What question have you been putting off asking yourself?
References and Further Reading
- Porter, J. (2017). Why You Should Make Time for Self-Reflection (Even If You Hate Doing It). Harvard Business Review.
https://hbr.org/2017/03/why-you-should-make-time-for-self-reflection-even-if-you-hate-doing-it - Di Stefano, G., Pisano, G.P. & Staats, B.R. (2015). Learning by Thinking: How Reflection Aids Performance. Academy of Management Proceedings.
https://doi.org/10.5465/AMBPP.2015.12709ABSTRACT - Sheldon, K.M. & Elliot, A.J. (1999). Goal Striving, Need Satisfaction, and Longitudinal Well-Being: The Self-Concordance Model. Journal of Personality and Social Psychology, 76(3), 482–497.
https://pubmed.ncbi.nlm.nih.gov/10101878/ - Wrosch, C., Scheier, M.F., Miller, G.E., Schulz, R. & Carver, C.S. (2003). Adaptive Self-Regulation of Unattainable Goals: Goal Disengagement, Goal Reengagement, and Subjective Well-Being. Personality and Social Psychology Bulletin, 29(12), 1494–1508.
https://pubmed.ncbi.nlm.nih.gov/15018681/ - Eurich, T. (2018). What Self-Awareness Really Is (and How to Cultivate It). Harvard Business Review.
https://hbr.org/2018/01/what-self-awareness-really-is-and-how-to-cultivate-it - Brooks, A.W. & John, L.K. (2018). The Surprising Power of Questions. Harvard Business Review, May–June.
https://hbr.org/2018/05/the-surprising-power-of-questions - Graßmann, C., Schölmerich, F. & Schermuly, C.C. (2020). The Relationship Between Working Alliance and Client Outcomes in Coaching: A Meta-Analysis. Human Relations, 73(1), 35–58.
https://doi.org/10.1177/0018726718819725
About Laurence Loxam
I’m Laurence Loxam. I’ve pushed limits in business, on mountains and at the finish line.
Now I help high achievers do the same, pushing past the point most people stop. I coach doctors, lawyers, CEOs and founders who’ve achieved success but still feel there’s more.
Together, we unlock clarity, sharpen confidence and lead with conviction.
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