The Fatal Flaw of Highly Successful People (and How to Avoid It)

The shadow of ambition leaves you feeling empty and driven by an inner tyrant attempting to achieve the impossible — perfection.

Dr. Matthew Jones
Better Entrepreneur
4 min readFeb 16, 2021

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Photo by Stefano Pollio on Unsplash

Ambition is one of the best assets an entrepreneur can possess. The motivation to achieve one’s dreams and resilient, resourceful attitude are requirements of building a profitable company, but most people fail to realize the shadow — or dark side — of this mindset.

The shadow of ambition is chronic unhappiness.

When people are so focused on their future goals and aspirations that they prevent themselves from being fully present — focusing on their lofty exit, their next business, or their $100 million mansion in the hills — they create a negative inner climate that inevitably detracts from all aspects of their lives, including workplace performance.

Working towards your future goals with the intensity required to manifest them prevents your ability to appreciate the gifts already present in your life.

You’re so focused on buying a Ferrari that you can’t appreciate your BMW. You’re lusting after multiple millions and can’t appreciate the savings and investments hovering around $900k. And while you think you can both appreciate what you have and push yourself towards the grand vision of your future, your lived experience shows otherwise.

Many successful people find themselves feeling an inner emptiness after achieving their dreams because once their pursuit falls away, they are left with nothing — confronted with the same aimlessness and inner distress they avoided through their relentless work ethic.

All of the money and success in the world mean nothing if you feel empty inside.

If what you have is never enough to bring you a sense of fulfillment, then you will continue down a lonely, shallow road.

Measuring success by counting dollars in the bank or material possessions alone exclude more enriching life experiences, such as meaningful relationships, which are consistently rated as the single most important thing on your deathbed.

The biggest mistake that highly successful make is attaching themselves to an idealized image rather than staying grounded in their true selves.

As a young child, a grandiose over-estimation of your strengths is adaptive. It helps you build self-esteem and fill in emotional gaps that your environment fails to provide.

Unfortunately, if you are confronted with the reality of your limitations too quickly or not quickly enough, children become overly attached to and identified with their idealized image: The inner image of perfection encompassing all that they should become. And once you become overly identified with your idealized image, you start holding yourself accountable to unrealistic standards and expectations — you berate yourself for not living up to this inner image of perfection.

Karen Horney, a prominent American psychoanalyst, discussed this topic in her book Neurosis and Human Growth: The Struggle Toward Self-Realization. She described how the inner critic ruthlessly attacks the individual when they fail to achieve the unrealistic standard set by their idealized self.

Horney noted that this inner critic often voices what one should do, feel, know, as well as the taboos on how or what they should not experience. She called these expectations the shoulds. Because the shoulds originate in the idealized, rather than the actual or true self, they are unrealistic, overly demanding, and too rigid to be achieved.

The shoulds often have a disregard for the conditions or contexts within which they take place.

Instead of taking the environment or unique situations of an individual’s life into account, the shoulds are unforgiving and lack a healthy adaptive quality. Just as they disregard context, they also neglect psychic conditions.

These should-thoughts ignore the individual’s present abilities and care only for the idealized self’s absolute perfection. Therefore, when individuals experience shortcomings, the inner critic relentlessly torments and punishes the individual for not attaining the idealized standards.

Horney argued that the purpose of the shoulds is to maintain the idealized image at all costs, by eliminating the perception of imperfections and giving the impression of perfect attainment. This negative self-dialogue has a coercive tone that punishes the individual when one fails to meet their unrealistic standards.

Most people lack full awareness of the impact or nature of the shoulds, which Horney believed is the inner tyranny that causes depression and anxiety. This inner tyranny is often the shadow of success, in that it lurks in the shadows of the psyche, only observable in moments of intense frustration with oneself.

The cost of success

In building a perfect company or a spotless appearance, many successful individuals rely on their ambition and ruthless self-criticism to manifest their dreams. However, such perfection comes at a cost.

When you lack awareness that the very voice that drives you towards achieving success is also detrimental to your emotional wellbeing, you remain unbalanced and unhappy, leading to greed, jealousy, and ruthlessness hidden through the socially-rewarded outlet of materialistic achievement.

Avoid the mistake of attaching to your idealized self so that you can achieve success and experience a deep sense of fulfillment.

Discern the difference between your image of perfection and your true self. Know when you are being led down a false path of materialistic success and inner emptiness.

Expand your sense of self and your definition of success by integrating more non-material and non-status items.

Work with an entrepreneur psychologist to accelerate your inner growth so that you can connect to gratitude and experience more fulfilling relationships. You deserve it.

(A former version of this article first appeared in Inc. Magazine)

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