5 Obstacles Introverts Must Overcome to Become More Strategic

In the coming years, the importance of strategic thinking will surpass the popularity of critical thinking.

Although the ability to analyze and evaluate facts will always be necessary, the ability to outcompete and outthink others will be even more vital.

Strategic thinking is much more action-oriented in maneuvering around problems than critical thinking.

In the article “Three Types of Thinking and Why They’re All Important,” Krista Gerhard said:

Strategic thinking is a mental process that is applied when one is trying to achieve some goal or set of goals. Whereas critical thinking is all about analysis, logic and reason, strategic thinking is about planning. It involves being able to understand cause and effect and seeing several steps ahead in order to achieve some desired outcome. *

Traditionally, introverts have thrived in the realm of critical thinking. After all, they are the ones who are academically inclined and curious about how the world operates and why it operates as it does.

They play by the societal rules of comportment and civility, sometimes at the behest of passive-aggressive behavior.

And often, playing by societal rules may hinder introverts from becoming better strategists.

Abiding by governmental laws fundamentally differs from following societal rules. Violations of legislated laws have stricter penalties than mere rule infractions.

Thus when introverts are rule-bound, competitors will consistently beat introverts by thwarting the rules through creative maneuvering.

Introverts are not encouraged to break the rules but are inspired to align their interests and goals to optimal results.

If rules disfavor introverts, they should be broken because they serve to sabotage the efforts of introverts.

There are five obstacles introverts must overcome to become more strategic.

Adopting philosophies and ideologies before testing

Like many people who accept clichés and trite statements without putting them to the test, introverts can fall prey to them also.

Years ago, talk show host Phil Donahue interviewed philosopher Ayn Rand. During the interview, a woman from the audience shared that as a young, single woman, she embraced Ayn Rand’s philosophy of the virtues of selfishness. But, as she got older and had children, she felt that Rand’s philosophies endangered her children because of its contrarian approach to social engineering.

Rand pushed back, suggesting she didn’t care what the woman believed. It was her choice to decide what was best for her.

The issue isn’t that people’s ideas may change as they age or that philosophies are impractical in everyday life. It’s that many people never attempt to evaluate if specific doctrines work.

Untried and untrue concepts must be set aside when becoming strategic.

As intellects, introverts must ensure that any philosophy they adopt has stood the test of time and resonates with their current reality because they’ve used it and found it compelling.

Practical philosophies are experiences people have lived as a basis for establishing facts.

Untried and untested ideologies can’t be the basis for strategic thinking because facts and data are critical for effective planning.

Playing to survive instead of playing to win

It has been said that courage is feeling fear and acting despite it.

Introverts who don’t operate to gain optimal results instead of merely avoiding adverse outcomes are not acting strategically.

There are no guarantees in life, but research, due diligence, and best practices allow introverts to gain greater assurances that a strategy has a probability of success.

And introverts must maneuver with a high degree of assurance and probability to experience desired outcomes.

Otherwise, an insecure and shortsighted mindset is oppositional to practical strategic thinking.

Acting in the self-interest of others

Conventional wisdom suggests that people operate in their self-interest for survival.

Consequently, accepting that people act intentionally against their self-interest is irrational.

So if one is not acting in their self-interest, they are operating in the self-interest of others.

Suppose introverts can’t achieve results that operate in their favor or are mutually beneficial for all parties. In that case, they should reject any notion where the scales consistently tip favorably towards the interests of others.

Introverts must see themselves as solid and free agents in any endeavor.

Otherwise, introverts allow other parties to leverage power and authority against them, which can only lead to an unfair advantage.

Failing to adopt a dominant, driven mindset

In my article, How Introverts Can Overcome Barriers to Strategic Thinking, I share how my inability to say “no” to people led to a life of disempowerment until I changed my way of thinking.

As an introvert, I have always had nervous energy and played by the rules ensuring that I didn’t hurt or offend anyone unintentionally.

The barrier for me was the fear and unwillingness to say “no.” I felt “no” would be met with disapproval, and I would stop gaining favor with people I liked and respected.

Their approval allowed me to enter and remain in spaces restricted to others.

Although I was aligning my interests with those within these social circles, I was giving up my identity for the opportunity to exist among them.

I would have been better served if I had built my own structure and network, which would have given me power and authority.

As a result, I would have communicated with members of these inner circles differently (from a position of strength) and traded my value more effectively to become a true partner in a project or venture.

Introverts should grow their power and align with like-minded people with shared interests.

Believing that human nature is benevolent

Many people view themselves as warm, generous, and altruistic despite the potential for human nature to be diabolical.

A study conducted years ago asked serial killers if they thought of themselves as bad people.

Overwhelmingly, these serial killers did not see themselves as bad people. But as good people who did terrible things.

Indeed, people can rise to the ideals of their higher angels when needed. But they also have the same capabilities to descend through the gates of Hades in their wickedness.

Swiss psychiatrist Carl Jung spoke of the dark side of human nature being the part people don’t want others to see.

Jung said:

Unfortunately, there can be no doubt that man is, on the whole, less good than he imagines himself or wants to be. Everyone carries a shadow, and the less it is embodied in the individual’s conscious life, the blacker and denser it is. At all counts, it forms an unconscious snag, thwarting our most well-meant intentions. **

Jung postulated that the shadow was the unconscious part of the personality that individuals did not desire public viewing.

Many introverts are hypersensitive and attach negative thoughts to their self-image.

Consequently, by not allowing their shadow to operate in draconian ways when necessary, they short-circuit a tool that could serve to attain their goals.

Political strategist Niccolò Machiavelli believed that gaining and maintaining power required individuals to act according to the situation’s needs.

Applying the required panacea to a problem entails individuals having various tools in their arsenal.

To become more strategic, introverts must embrace the ideals and darkness of their personality to be agile and flexible.

In the coming years, introverts overcoming the obstacles to becoming more strategic will allow them to maneuver quietly and clandestinely in a high-stakes world where winners take all.

Not only will introverts be able to win based on their self-described success, but they can also win on their terms.

—Jane Woodard


* Gerhard, K. (2019, Nov.6). Three types of thinking and why they’re all important. Salience Learning. Retrieved from:  https://bit.ly/3x7xdzs.

**Weaver, T. (2022, Nov. 29). Embracing the shadow-Carl Jung. Orion Philosophy. Retrieved from: https://bit.ly/3REPNIN.

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