THE WISDOM OF PARADOX: HOW TO THINK BOTH/AND!

Ever had a learning moment from childhood that stuck with you, shaping the way you see the world?

For me, it wasn’t a maths formula or a chemistry experiment—it was a mind-blowing concept from a high school history lesson.

That lesson introduced me to the power of paradox, and it’s changed how I approach almost everything—work, relationships, health, and happiness.

What Is A Paradox?

At its core, a paradox is a situation that seems contradictory at first glance but reveals a deeper truth when you dig beneath the surface. It’s the essence of both/and thinking—embracing two seemingly opposing ideas at once.

Paradoxical thinking invites both flexibility and constraint, complexity and simplicity. It’s about holding two conflicting truths together and finding wisdom in the tension.

Imagine two opposing forces coexisting, defying logic yet offering a fresh perspective. That’s the beauty of paradox—it’s not about choosing either/or, but embracing both/and. By approaching life’s challenges through this lens, we open ourselves to new ways of thinking, unlocking fresh insights rather than being locked into polarities.

Let me share two powerful lessons I learned in school that show how embracing paradox can sharpen your decision-making in almost every area of life.

Principle 1 - Extreme Edges Are Almost Always Lopsided

I first glimpsed the paradoxical nature of the world in my late teens.

During a history lesson on Hitler's Nazi Germany (left-wing fascism) and Stalin's Communist Russia (right-wing socialism), my teacher sketched a horseshoe on the board. It illustrated how seemingly opposite ideologies can lead to eerily similar outcomes: totalitarian regimes—one big boss, no personal freedom, and plenty of militarism.

I was fascinated by the idea that as we move toward extremes, whether far left or right, our blind spots grow. We lose the ability to hear other perspectives or engage with real-world nuance.

But this raised a question: Does that mean we should settle for mediocrity, simply straddling the ideological fence instead of standing firm in our beliefs? Surely not.

Principle 2 – ‘Both / And’ Not The Mediocre Middle

My next lesson came in physics, where the concept of paradox became clearer.

Our teacher asked, "Is light a wave or a particle?" Half of us chose wave, the other half particle. It turns out, it’s both! Logically, that shouldn’t be possible, but neither fully explains the properties of light. By holding both ideas in mind, you unlock a paradox that captures the true nature of light.

Fast forward thirty years, and while my light-theory knowledge remains limited, that 'aha' moment stuck with me. What if the big, messy problems in life require more than one answer? What if we need to juggle opposing ideas instead of choosing one side or settling for something 'meh' in the middle?

This is the beauty of paradoxical thinking—to find rich, textured solutions to life’s challenges by holding two opposite truths in balance. Rather than getting stuck in 'progressive' or 'conservative' boxes, what if true wisdom lies in the space between the two?

From my experience, once you embrace this mindset, you’ll start noticing paradoxes everywhere, leading to far more nuanced decision-making.

Paradoxical Thinking In Practice

Nobel Prize-winning physicist Niels Bohr once said, "The opposite of a correct statement is a false statement. But the opposite of a profound truth may be another profound truth."

The key to navigating complex situations is to embrace the wisdom of paradox—holding opposing truths together.

Here’s are three examples:

1. The Productivity Paradox

Running a successful business is both a science and an art.

There’s a science to success—as the maxim goes, ‘if you fail to plan, you plan to fail.’ Business basics like goal-setting, budgeting, and disciplined execution are essential.

But, as many of us know, doing everything right doesn’t guarantee success. Business is also an art, shaped by the unexpected. Reflecting on my decade-long entrepreneurial journey, I’ve found that many breakthroughs came from unforeseen opportunities, chance meetings, and serendipity (see my Kairos moment video series for more). Had I stuck rigidly to the plan, my business wouldn't be as profitable or influential as it is today.

So, study the science of business. Make plans. Set goals. But also go with the flow. Trust your gut. And stay open to the moments of grace that keep you growing. This both/and thinking is the key to building a truly productive and innovative business.

2. The Happiness Paradox

Is happiness shaped by our situation or perspective?

On one hand, our circumstances do affect our wellbeing. We need a certain amount of money, achievements, and physical health to feel content. Take away too many good things or place us in an unsafe environment, and happiness suffers.

Yet happiness is also not solely tied to circumstances—it’s about how we interpret them. Spiritual teachings often highlight that happiness comes from our reactions, not our external conditions. This is why millionaires can be miserable while those living with chronic pain can still find joy. It’s wrong to say our situation has no effect on happiness, just as it’s incorrect to suggest perspective alone is enough. Both matter.

If you believe happiness is purely circumstantial, you set yourself up for misery because life will always involve struggle. If you think it’s only about perspective, you’ll neglect essential things like saving money, fitness, or relationships, and discover that internal focus alone won’t sustain happiness.

Wisdom lies in balancing these truths—sometimes working to change our situation, and sometimes learning to accept it. Happiness is a both/and paradox.

3. The Relational Paradox

Lastly, let’s look at how paradoxical thinking can transform a marriage.

Healthy marriages are often said to rely on unconditional acceptance—embracing your partner, quirks and all, without trying to ‘change’ them. Love is for better or worse, richer or poorer, and all the idiosyncrasies in between.

Sounds right, but without both/and thinking, it’s incomplete.

That’s because healthy marriages also require growth. We need to lovingly encourage our partner’s development and set healthy expectations for change—just as we should expect of ourselves.

As relational expert Jaemin Frazer puts it, “‘Don’t change the people you love’ may be the single worst piece of relational advice ever given... If you don’t find a way to change those you love, there’s a high chance your needs won’t be met. You'll be left feeling resentful and frustrated, and what started out as a loving partnership will deteriorate into a managed arrangement." ¹

It’s a strong statement, but it holds truth. To stay connected, intimate, and aligned, both partners need to communicate the need for, and willingness to change for the good of the relationship.

The solution isn’t to ‘find the middle ground’—a half-hearted approach where you ‘half’ accept and ‘half’ communicate your unmet needs. Instead, embrace the paradox of relationships—be fully committed to unconditional acceptance while also encouraging and expecting change.

Learning to Navigate ‘Both/And’

As Parker Palmer wisely said, "Look at life not just as 'either-or' but also as 'both-and.'" ²

This is the essence of making day-to-day choices through the lens of paradox.

Our culture loves to think in black and white—left or right, this or that. But wisdom isn’t found in extremes or playing it safe in the middle. It’s about living fully, moving between opposing truths, and making decisions that sometimes draw on seemingly contradictory logic, depending on the context.

At work, we must plan, yet remain open to serendipity. Sometimes we need to change our circumstances, and other times, we need to accept them. In relationships, we embrace our partners unconditionally, while also setting healthy boundaries and encouraging growth.

That’s the magic of paradox—the brilliance of both/and thinking in a polarised, either/or world.

How can you begin to embrace paradox in your life, learning to navigate the beauty of both/and thinking?

[1] Jaemin Frazer (2022) Leverage: How To Change The People You Love For All The Right Reasons And Get The Relationship You Deserve, Major Street.

[2] Parker Palmer (2018) On The Brink of Everything: Grace, Gravity, and Getting Old, p. 65