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Embracing Optionality: 8 Reasons to Base a Plan on Flexibility Instead of Prediction

Embracing Optionality: 8 Reasons to Base a Plan on Flexibility Instead of Prediction

February 26, 2024

President Dwight D. Eisenhower once famously said that “plans are worthless, but planning is everything.” Despite the apparent paradox, he was right.

Planning for things to unfold in a certain way, and single-mindedly acting as though they will, is likely to lead to disappointing or even catastrophic results in a real world that’s inherently unpredictable. In fact, you likely don’t even know who you will be in the future, let alone the conditions surrounding you.

That said, the act of planning allows a person or team to work out exactly what their intentions are, what factors matter, what can and might go wrong, what risks they can and can’t allow for, and what contingency plans should be in place.

It’s this level of thoughtfulness in the creation of a robust plan that ultimately allows one to act effectively even when the environment and circumstances have shifted. At its best, preparation leads to high-quality positioning, which gives us not just the insight but also the capability to do what needs to be done.

So, it's better to create a plan than to go without one, even if you don't expect reality to match the map. But why go through the step of adjusting the plan on the fly when surprises happen, when you can just make the right kind of plan in the first place? 

Taking this all a step further to its logical conclusion, the best starting point is to plan for optionality, and not for a single desired path and outcome.

"Optionality" is the quality of being available as a choice, but not obligatory. To plan for change and optionality means to prepare yourself to be able take a large number of potential courses of action depending on the circumstances, but not being forced to take any in particular.

Predicting what you think will happen and aligning your course of action as though that will actually happen is a fool's errand, and it's an avoidable mistake.

With that in mind, here are eight reasons why the best plan is often a plan for optionality.

  1. Adaptability in a Dynamic World

The world is in a constant state of flux. Markets shift, technologies evolve, and unexpected events occur. In such a landscape, rigid plans can quickly become obsolete. A flexible approach allows you to adapt to changing circumstances, seize new opportunities, and mitigate potential risks. 

  1. Resilience in the Face of Uncertainty

Uncertainty is inherent in life. In personal goals, professional endeavors, and external conditions, unforeseen challenges and disruptions are bound to arise. A plan designed with maximum future options equips you with the resilience needed to weather storms and navigate through uncertainty with grace and determination. 


  1. Maximizing Opportunities

Roman philosopher Seneca once said, “Luck is what happens when preparation meets opportunity.” Opportunities may not always align perfectly with your initial expectations. By embracing optionality as a cardinal value in your preparation, you position yourself to recognize and capitalize on unexpected opportunities that may lead to growth, innovation, and fulfillment. 


  1. Embracing Continuous Learning

Flexibility encourages a mindset of continuous learning and adaptation. When plans change, there's often a wealth of insights to be gained from the experience. Embracing flexibility means embracing the opportunity to learn, evolve, and refine your approach based on new information and experiences. 


  1. Fostering Creativity and Innovation

Rigid plans can stifle creativity and innovation by limiting your ability to explore alternative paths and think outside the box. Flexibility fosters a mindset of innovation by encouraging experimentation, embracing failure as a steppingstone to success, and encouraging creative problem-solving. When the future inevitably arrives in a way that doesn’t fit with any of your initial conceptions of possible outcomes, you yourself will have practiced and become ready to meet the challenge.


  1. Enhancing Relationships and Collaboration

In both personal and professional settings, flexibility strengthens relationships and promotes collaboration. Being open to alternative viewpoints, accommodating the needs of others, and adapting to changing circumstances can build trust, promote teamwork, and cultivate strong, resilient relationships. 


  1. Reducing Stress and Anxiety

The pressure to adhere to rigid plans can often lead to stress and anxiety, especially when faced with unexpected setbacks or deviations. Flexibility allows for a more relaxed and adaptive mindset, reducing the negative impact of stress and empowering you to approach challenges with clarity and composure. Calm and peace don’t come from knowing what will happen, they come from knowing that whatever happens, you’re ready.


  1. Achieving Sustainable Long-Term Success

In the pursuit of long-term success and fulfillment, adaptability is key. A flexible plan allows you to stay true to your overarching goals and values while remaining responsive to the ever-changing landscape of opportunities and challenges. By embracing flexibility, you set yourself up for sustainable growth, resilience, and success in the long run. 


Embracing flexibility is often the key to navigating life's twists and turns with resilience, creativity, and grace. By cultivating a mindset of adaptability and openness to change, you empower yourself to thrive in an ever-evolving world. So, dare to plan, but don't base it on your best guess of what will happen. Plan for change and optionality. Your future self will thank you for it.