The Challenge of Thinking in Opposites (And Why It’s Worth Mastering)

Illustration by author

Why do so many resist stepping into the discomfort of thinking differently?

Because thinking beyond boxed-in perceptions and biases — built across years of family life, peer interaction, schooling, maybe religion, careers, institutions, media, and so on — is hard, maybe unknown, scary.

The reasons are varied and can cut across evolutionary adaptions to community conformity. For example:

1. Cognitive Biases

Our brains are wired for shortcuts. Our brains use a lot of our daily energy. Thinking eats up even more energy.

Confirmation bias seeks evidence to support our beliefs. Status quo bias clings to the familiar.

If we think differently, it feels like a risk we’d rather avoid. Our brains balk — unless we leverage neuroplasticity (our brain’s innate flexibility and plasticity)

2. Cultural Conditioning

From school to the workplace, we’re taught to look for the correct answers, not wrestle with contradictions or question authorities (who live in their own boxes of perceptions and experiences).

Oppositional and oblique thinking, for example, require tolerance and even appreciation for ambiguity — something many of us were never taught.

3. Fear of Failure

Challenging norms, status quo, and experimenting with unconventional ideas means risking errors. It also risks being ostracized, isolated, and pushed out of in-groups (or the feeling that this might happen, which can sometimes be worse than the actual).

Being wrong can feel like failure — especially in environments where mistakes aren’t celebrated — like many school classrooms, ' exam’ environments, and workplaces exemplify.

Evolutionary adaptations create serious resistance to potentially threatening social acceptance. Throughout most of human history, being a loner meant sure early death.

4. Time Pressures

Thinking differently often takes more time than conformity, questioning, pausing, etc. — time many feel they don’t have.

Under pressure (perceived or actual), most of us default to quick solutions and familiar patterns. Add in the power of Groupthink and other social phenomena.

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The Biggest Mistakes Many Make

Even when we attempt to think differently, we often stumble. Here’s where many go wrong:

1. Overcommitting to One Idea

We get attached to a single solution and shut out alternatives. Oppositional thinking invites us to consider what might work better — or fail spectacularly — in its place.

In creative endeavours and digital business, many online gurus push the apparent importance of “niche-ing down” and focusing on one thing, one audience, or one platform.

Unfortunately, this can often be misguided, leading to quick frustration and fizzle. I’ve seen it repeatedly.

2. Overcomplicating Problems

Complexity isn’t always the answer. Sometimes, the simplest solutions emerge from asking oblique questions like:

• “What would this look like if it were easy?”

• “What would this look like if I let go of perfection?”

• “What’s one of the simplest steps I can take right now?”

3. Avoiding Contradictions

We treat contradictions as problems to solve instead of tensioned spaces to explore. Strategy and chaos, for instance, can coexist and create something entirely new.

Take this illustration below and see how many other points you can identify along this continuum — in the spaces between strategy and chaos.

• Identify where chaos could be beneficial to you

• Identify where strategy may be detrimental to you

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4. Fear of Ambiguity

We rush to resolve uncertainty, even though lingering in it can lead to breakthrough ideas.

For example, I use reluctance as an instigator for creativity. The word's etymology (roots) comes from Latin luctari, which means “to wrestle and grapple.”

When I feel reluctance, I get curious and ask, “why?” It often means I probably need to push against my rational, logical propensity towards certainty and feeling ready.

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In my work as a Solopreneur building creative, largely digital business enterprises — I often swing back and forth on the ambiguous continuum above (and others).

Writing in a “Learning Journal” is one of my key navigation tactics (see link below)

How to Start (or Continue) Thinking Differently

Thinking differently — thinking creatively in contradictions and thinking in opposites — isn’t just a creative flair. They are shapeable and learnable skills.

Our brain is wired to grow, shift, and adapt thanks to evolution. Think about how human groups migrating across vast continents and oceans would have developed brain adaptations for different terrains, climates, and realities.

Neuroplasticity is our brain’s ability to shift and rewire itself. You and I can build new habits of thought and practice at any age.

The more you practice oppositional and oblique thinking, the stronger those mental pathways become.

Like exercising a muscle, your brain responds to repetition and challenge, making approaching problems from fresh perspectives easier over time. (Or at least feeling more ‘natural’)

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Practical Steps

Here are some practical ways to consider building oppositional and oblique thinking skills:

1. Practice Inversion

Flip a problem upside down. Ask,

• “What if the opposite were true?” or

• “What would happen if we did nothing?”

This forces you to challenge assumptions and explore new possibilities. It can also be done in group settings (e.g., families, workplaces, schools).

2. Connecting the Unrelated

Take two unrelated ideas or concepts and force them together. I often use examples from nature and mash them up with human affairs. For example:

• What can the migration patterns of birds teach us about managing remote teams?

• What can the way fungi connect ecosystems teach us about creating resilient communication systems?

• What can salmon's relentless migrations and life cycle adaptations teach us about persistence and navigating obstacles?

This approach sparks unexpected insights and new ways of thinking. AI tools like ChatGPT can be very powerful assistants in this process.

3. Increasing Tension Tolerance

When you encounter a paradox, ambiguity, or great vast gray zones — don’t rush to resolve them. Sit with the tensions. Go for a walk. Write about it. Draw it out.

Often, the most innovative and impactful ideas emerge from contradictions. Added to this, conflict is also an excellent instigator for change and innovation.

The roots of the word conflict mean “strike together.” This also relates to number 2 above.

4. Build Oblique Thinking

The word oblique means indirect or slanted — approaching something from an unexpected angle rather than head-on.

Oblique thinking instigates approaches to break free from habitual patterns by considering problems in unconventional ways. For example, consider the varying tensions in these two entities below.

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Here are some prompts to spark fresh perspectives:

• What if we removed our biggest assumptions instead of our biggest constraints?

• What would happen if we did the opposite of what feels logical?

• How would this look if it were designed for fun instead of efficiency?

• What’s the least obvious approach to solving this problem, and why haven’t we considered it?

• How can we use the limitations of this situation as a creative advantage?

This sort of questioning and curiosity-driven approach creates spaces for surprising, creative solutions to emerge — or at least pathways forward. I use this type of approach in my writing, in facilitating large groups, and in university faculty work.

5. Experiment Relentlessly

Adopt a mindset of trial and error. Research and development. Replace rigid plans with small experiments. Think: “What’s the smallest thing I can test today?”

This is my approach to writing in digital environments. I call my approach ecosystem-based. I write across multiple platforms and in varying formats (short, long and everywhere in between).

Through my 20s, 30s, and 40s, it was also how I approached my ‘career’. A company VP in an interview one time said “Gee, you have an eclectic work history”.

“Yes,” I said. “By design and intent.”

The Pragmatic Payoff

Thinking differently isn’t simply some intellectual or philosophical exercise. It’s a darn practical tool for navigating complexity, swimming in ambiguity, solving challenges, and uncovering opportunities.

But, of course, there’s paradox:

• The messiness of oppositional and oblique thinking can lead to clarity

• The discomfort of questioning assumptions and norms can lead to better decisions

• The willingness to navigate and sit in ambiguity often leads to creative breakthroughs

Sticking to old patterns is the real risk in a rapidly changing world. AI, climate change, and political turmoil are shifting the globe daily — sometimes hourly.

Learning to think differently isn’t just a nice-to-have skill — it’s a survival and adaptation skill. For me, writing is one of the most critical tools in my toolbox to navigate it, record it, and publish it.

How about you?