Thinking Sideways
The Joys of Lateral Thinking
Sideways Theology
Lateral thinking jumps is not linear. It jumps across conceptual boundaries. Often it is provocative, or funny, or both—using surprise and playfulness to disrupt expectations and make space for fresh ways of seeing. It is not opposed to logic; it complements it. Whereas logic refines ideas, lateral thinking creates the conditions for new ideas to appear in the first place.
Many of the world’s sages—Jesus, Lao Tzu, Francis of Assisi, and the Buddha—were lateral thinkers. So, too, were women whose voices often challenged orthodoxies from the margins: Hildegard of Bingen, Julian of Norwich, Teresa of Ávila, and Dorothy Day, among many others. All thought outside the inherited boxes of the political, religious, and cultural orthodoxies of their times, often unsettling their contemporaries while opening new moral and spiritual horizons. Thinking beyond patriarchy is an act of lateral thinking.
But lateral thinking is not reserved for sages and prophets. We, too, can think laterally—and often we do—whenever curiosity, playfulness, and imagination interrupt habit and invite us into new ways of understanding ourselves, one another, and the world. Mothers and fathers think laterally when they improvise responses to a child’s needs, find unexpected ways to comfort fear or encourage growth, or reimagine what love looks like in changing circumstances. Friends and neighbors think laterally when they step outside roles and routines to repair a strained relationship, welcome a stranger, or discover creative ways of caring for one another beyond what rules or expectations prescribe. Lateral thinking, even when provocative, even when shocking, is often rooted in love.
It is possible—and perhaps even probable—that the very soul of the universe is a kind of divine laterality: experienced as an inwardly felt lure to move beyond settled patterns, to risk the unexpected, and to imagine possibilities not yet realized. Perhaps it is not from necessity alone, but from the very heart of the universe itself, that we are beckoned to dream up—and to work toward—what has not yet been realized, and what can seem “unimaginable” to more statically inclined minds: world peace, universal love, and communities organized around compassion rather than fear, cooperation rather than domination, and care rather than exclusion.
- Jay McDaniel
Many of the world’s sages—Jesus, Lao Tzu, Francis of Assisi, and the Buddha—were lateral thinkers. So, too, were women whose voices often challenged orthodoxies from the margins: Hildegard of Bingen, Julian of Norwich, Teresa of Ávila, and Dorothy Day, among many others. All thought outside the inherited boxes of the political, religious, and cultural orthodoxies of their times, often unsettling their contemporaries while opening new moral and spiritual horizons. Thinking beyond patriarchy is an act of lateral thinking.
But lateral thinking is not reserved for sages and prophets. We, too, can think laterally—and often we do—whenever curiosity, playfulness, and imagination interrupt habit and invite us into new ways of understanding ourselves, one another, and the world. Mothers and fathers think laterally when they improvise responses to a child’s needs, find unexpected ways to comfort fear or encourage growth, or reimagine what love looks like in changing circumstances. Friends and neighbors think laterally when they step outside roles and routines to repair a strained relationship, welcome a stranger, or discover creative ways of caring for one another beyond what rules or expectations prescribe. Lateral thinking, even when provocative, even when shocking, is often rooted in love.
It is possible—and perhaps even probable—that the very soul of the universe is a kind of divine laterality: experienced as an inwardly felt lure to move beyond settled patterns, to risk the unexpected, and to imagine possibilities not yet realized. Perhaps it is not from necessity alone, but from the very heart of the universe itself, that we are beckoned to dream up—and to work toward—what has not yet been realized, and what can seem “unimaginable” to more statically inclined minds: world peace, universal love, and communities organized around compassion rather than fear, cooperation rather than domination, and care rather than exclusion.
- Jay McDaniel
Lateral Thinking
What Is Lateral Thinking?
Lateral thinking is a problem-solving approach that deliberately moves sideways rather than straight ahead. Instead of progressing step by step within established assumptions—as in logical or analytical thinking—it seeks to reframe the problem, challenge habitual patterns, and generate novel perspectives that may initially seem unconventional or even counterintuitive.
Origins of the Concept
The term was introduced by Edward de Bono,* who argued that many problems persist not because they are inherently difficult, but because human thinking becomes locked into familiar pathways. According to de Bono, creativity requires techniques that help the mind escape these grooves.
Core Characteristics of Lateral Thinking
Lateral Thinking and Vertical (Logical) Thinking
Vertical, or logical, thinking proceeds sequentially. It evaluates correctness at each step and seeks to optimize solutions within given assumptions. Lateral thinking, by contrast, temporarily suspends judgment, explores multiple possibilities, and questions the assumptions themselves. The two modes are not rivals; they serve different functions in the overall process of thinking.
A Simple Example
If traffic congestion is framed as the problem of “how to move more cars faster,” solutions tend to remain within that logic—wider roads, additional lanes, or improved traffic signals. A lateral shift reframes the issue as “how to reduce the need for cars,” opening possibilities such as remote work, staggered schedules, public transit redesign, or walkable neighborhoods.
Practical Uses
Lateral thinking is widely applied in innovation and design thinking, conflict resolution, organizational change, and education and creative practice. It is also valuable in ethical and cultural reflection, particularly where inherited frameworks limit imagination and alternative futures are difficult to envision.
In short, lateral thinking is not opposed to logic; it complements it. Logic refines ideas. Lateral thinking creates the conditions for new ideas to appear in the first place.
Lateral thinking is a problem-solving approach that deliberately moves sideways rather than straight ahead. Instead of progressing step by step within established assumptions—as in logical or analytical thinking—it seeks to reframe the problem, challenge habitual patterns, and generate novel perspectives that may initially seem unconventional or even counterintuitive.
Origins of the Concept
The term was introduced by Edward de Bono,* who argued that many problems persist not because they are inherently difficult, but because human thinking becomes locked into familiar pathways. According to de Bono, creativity requires techniques that help the mind escape these grooves.
Core Characteristics of Lateral Thinking
- Pattern disruption: Breaks habitual ways of seeing and reasoning rather than refining existing patterns.
- Openness to novelty: Creates space for new possibilities to emerge.
- Reframing: Changes how a problem is defined, not merely how it is solved.
- Provocation: Uses deliberately odd, playful, or extreme ideas to open new lines of thought.
- Non-linear movement: Jumps across conceptual boundaries instead of following a single, sequential chain of logic.
Lateral Thinking and Vertical (Logical) Thinking
Vertical, or logical, thinking proceeds sequentially. It evaluates correctness at each step and seeks to optimize solutions within given assumptions. Lateral thinking, by contrast, temporarily suspends judgment, explores multiple possibilities, and questions the assumptions themselves. The two modes are not rivals; they serve different functions in the overall process of thinking.
A Simple Example
If traffic congestion is framed as the problem of “how to move more cars faster,” solutions tend to remain within that logic—wider roads, additional lanes, or improved traffic signals. A lateral shift reframes the issue as “how to reduce the need for cars,” opening possibilities such as remote work, staggered schedules, public transit redesign, or walkable neighborhoods.
Practical Uses
Lateral thinking is widely applied in innovation and design thinking, conflict resolution, organizational change, and education and creative practice. It is also valuable in ethical and cultural reflection, particularly where inherited frameworks limit imagination and alternative futures are difficult to envision.
In short, lateral thinking is not opposed to logic; it complements it. Logic refines ideas. Lateral thinking creates the conditions for new ideas to appear in the first place.
Whitehead's Philosophy of Novelty
Some degree of lateral thinking is present in everyday life. We encounter it in humor, where an unexpected twist disrupts ordinary expectations; in creative problem-solving, where a fresh angle suddenly reveals a way forward; and in art, where surprising contrasts invite us to see the world differently. In each case, lateral thinking creates a pause in habitual perception, opening a space in which new meanings, responses, and possibilities can emerge. We also see it in children, whose outlooks on life have not yet been canalized and who readily—and often effortlessly—“think outside the box.”
To be sure, lateral thinking is not the only important mode of thought. In many contexts there is a genuine need for logical thinking, managerial thinking, and analytical thinking, each of which plays an essential role in organizing, evaluating, and implementing ideas. We humans cannot live on lateral thinking alone.
Yet in societies and groups where predictable forms of thinking have hardened into orthodoxies that suffocate or oppress—and where lateral thinking is ignored or dismissed as “illogical,” “childlike,” or even “crazy,” there is a clear and urgent need to reclaim and highlight its importance. Lateral thinking does indeed open up space. It brings with it a sense of freedom and joy that is otherwise lacking, releasing thought from rigid pathways and reopening the playful, exploratory dimensions of human creativity.
Whitehead offers a metaphysical framework in which lateral thinking appears as natural rather than unnatural. His philosophy of organism understands the universe as intrinsically creative, animated by an impulse toward novelty that operates at every level of reality, from the subatomic to the stellar. The universe itself is, in Whitehead’s well-known phrase, a “creative advance into novelty.”
Within this ongoing advance, forms of order play an important role: they stabilize experience, enable coordination, and make complex achievements possible. Yet order can also become rigid. When it does, it risks stifling the deeper aim present in all living beings—the aim toward satisfying richness of experience, a richness that includes contrast, intensity, and the interplay between the expected and the unexpected.
From this perspective, novelty is not an occasional disruption of an otherwise static cosmos; it is the very heartbeat of reality. New forms of feeling, action, and understanding are continually being evoked into existence. Lateral thinking, understood in this light, is not a quirky human deviation from rationality but an expression, within human consciousness, of the universe’s own creative movement.
Whitehead further invites us to think of the mind of the universe as a whole—otherwise named God—not as a distant ruler or external designer, but as an inwardly felt lure toward novelty. This lure is both cosmic and individualized: cosmic in that it operates everywhere, offering fresh possibilities to the entire universe, and individualized in that each moment of experience feels this lure in its own way, shaped by its particular situation and history. Rather than coercing outcomes, this divine influence works persuasively from within, inviting each subject toward richer, more harmonious, and more intense forms of becoming.
Indeed, and provocatively, Whitehead suggests that the very being of any and every actuality is itself an expression not of neutral “stuff,” or of a more substantial Being (with an upper case B) that is the ground of all that is, but of an ultimate reality he calls Creativity—of which even God is an expression, along with all other actualities. Creativity, in this sense, is the groundless ground of all that is, actualized only in and through its concrete instantiations in God and the world. In these ways, Whitehead offers a metaphysics—or cosmology—that naturally lends itself to the kind of creative thinking so important to Edward de Bono and to advocates of lateral thinking more generally.
Edward de Bono adds an important practical dimension to this metaphysical vision. Where Whitehead articulates the cosmic conditions that make novelty possible and meaningful, de Bono shows how lateral thinking can be cultivated as a deliberate human practice. He demonstrates how consciously disrupting habitual patterns of thought, reframing problems, and experimenting with provocative ideas can serve not only individual creativity but the well-being of societies and institutions. In this sense, lateral thinking becomes a disciplined way of cooperating with the universe’s creative advance—helping individuals and communities loosen rigid assumptions, imagine alternatives, and respond more imaginatively to complex, entrenched problems.
To be sure, lateral thinking is not the only important mode of thought. In many contexts there is a genuine need for logical thinking, managerial thinking, and analytical thinking, each of which plays an essential role in organizing, evaluating, and implementing ideas. We humans cannot live on lateral thinking alone.
Yet in societies and groups where predictable forms of thinking have hardened into orthodoxies that suffocate or oppress—and where lateral thinking is ignored or dismissed as “illogical,” “childlike,” or even “crazy,” there is a clear and urgent need to reclaim and highlight its importance. Lateral thinking does indeed open up space. It brings with it a sense of freedom and joy that is otherwise lacking, releasing thought from rigid pathways and reopening the playful, exploratory dimensions of human creativity.
Whitehead offers a metaphysical framework in which lateral thinking appears as natural rather than unnatural. His philosophy of organism understands the universe as intrinsically creative, animated by an impulse toward novelty that operates at every level of reality, from the subatomic to the stellar. The universe itself is, in Whitehead’s well-known phrase, a “creative advance into novelty.”
Within this ongoing advance, forms of order play an important role: they stabilize experience, enable coordination, and make complex achievements possible. Yet order can also become rigid. When it does, it risks stifling the deeper aim present in all living beings—the aim toward satisfying richness of experience, a richness that includes contrast, intensity, and the interplay between the expected and the unexpected.
From this perspective, novelty is not an occasional disruption of an otherwise static cosmos; it is the very heartbeat of reality. New forms of feeling, action, and understanding are continually being evoked into existence. Lateral thinking, understood in this light, is not a quirky human deviation from rationality but an expression, within human consciousness, of the universe’s own creative movement.
Whitehead further invites us to think of the mind of the universe as a whole—otherwise named God—not as a distant ruler or external designer, but as an inwardly felt lure toward novelty. This lure is both cosmic and individualized: cosmic in that it operates everywhere, offering fresh possibilities to the entire universe, and individualized in that each moment of experience feels this lure in its own way, shaped by its particular situation and history. Rather than coercing outcomes, this divine influence works persuasively from within, inviting each subject toward richer, more harmonious, and more intense forms of becoming.
Indeed, and provocatively, Whitehead suggests that the very being of any and every actuality is itself an expression not of neutral “stuff,” or of a more substantial Being (with an upper case B) that is the ground of all that is, but of an ultimate reality he calls Creativity—of which even God is an expression, along with all other actualities. Creativity, in this sense, is the groundless ground of all that is, actualized only in and through its concrete instantiations in God and the world. In these ways, Whitehead offers a metaphysics—or cosmology—that naturally lends itself to the kind of creative thinking so important to Edward de Bono and to advocates of lateral thinking more generally.
Edward de Bono adds an important practical dimension to this metaphysical vision. Where Whitehead articulates the cosmic conditions that make novelty possible and meaningful, de Bono shows how lateral thinking can be cultivated as a deliberate human practice. He demonstrates how consciously disrupting habitual patterns of thought, reframing problems, and experimenting with provocative ideas can serve not only individual creativity but the well-being of societies and institutions. In this sense, lateral thinking becomes a disciplined way of cooperating with the universe’s creative advance—helping individuals and communities loosen rigid assumptions, imagine alternatives, and respond more imaginatively to complex, entrenched problems.
Generous Provocation
Confessions of a Kindly Troller
Sometimes I say crazy things—online and in person. I guess you could say I have the spirit of a troller in me. A friend calls it healthy mischievousness. I like to stir the pot, to say what’s unexpected, to nudge people off balance.
But my aim isn’t malicious. I don’t want to hurt people or humiliate them. I want to wake something up—to loosen what’s become too tight, too certain, too sure of itself. And, to tell the truth, I want others to do this to me, too. I want them to say things that stir my pot.
I want to be interrupted, unsettled, and occasionally confused. Not humiliated or harmed, but challenged in ways that help me see what I’ve been taking for granted. I want to discover where my own certainties have quietly hardened into habits, and where my best ideas have become a little too comfortable.
I trust that there is more going on in people—including myself—than our first reactions. I trust that a little disruption, offered and received with care, can open a door. I think Jesus worked this way, telling strange stories, answering questions with riddles, blessing outsiders, unsettling the pious. And I think the Buddha did something similar, using paradox and silence to interrupt our habitual ways of clinging. The Buddha's Flower Sermon was a kind of troll: holding up a flower instead of saying anything. And the idea that this Very World is Nirvana is a kind of troll, too. It unsettles the idea that Nirvana and Samsara are distinct.
Sometimes I even wonder if the soul of the universe has a bit of the troller in it. If God—him or her or it or they—isn’t interested in keeping us comfortable, but in keeping us alive, awake, and open. Maybe the divine lure itself comes with a kind of holy and loving mischievousness, gently undermining our certainties so that something new can be born.
I think Jesus revealed this divine trolling and became a window through which people around him could feel its energies. He was, as John Cobb puts it in "Christ in a Pluralistic Age, the Spirit of Creative Transformation at work in the world. And sometimes this spirit comes to us precisely through constructive trolling—or, perhaps better, generative and generous provocation. It doesn’t arrive to shame or coerce, but to unsettle us just enough to make room for love, truth, and new possibilities.
But I see lots of generative and generous provocation in others, too. Certainly in some Buddhists, and in trickster figures, and in poets, artists, and storytellers. A Zen koan is a kind of troll—posed to interrupt habitual patterns of thought. A paradox from Daoism does something similar, quietly undermining the mind’s urge to settle too quickly into fixed distinctions. In Judaism, a sharp question from the Talmud or a mischievous Hasidic tale can work the same way, unsettling certainty through argument, irony, or holy humor. And in Islam, especially within Sufi traditions, paradoxical sayings and startling reversals are used to crack open the ego and loosen the grip of conventional understanding. Each of these traditions trusts that wisdom does not always arrive by smoothing things over. Sometimes it arrives by gently—or not so gently—disrupting the mind’s desire for premature closure.
Indeed, I see generative provocation in ordinary people—friends, critics, students, strangers—who say something that catches me off guard and won’t quite let go. Often they don’t intend to be provocative at all. They’re just being honest, or curious, or playful, or stubbornly themselves. And somehow that’s enough to disturb the surface and let something deeper show through.
Sometimes it comes from people I disagree with, or from voices I would rather not listen to. Sometimes it comes from those closest to me, who know exactly where to poke. Sometimes it comes from people who lack the language I would prefer, but carry a wisdom I still need to hear. And, I have to admit, sometimes it comes from my cat, Rollie, who is clearly a troller in his own right.
In each case, the provocation doesn’t arrive polished or pure. It arrives mixed with ego, clumsiness, emotion, and limitation—like everything else in a human world. It seems to me that we need to be open to this side of life: the side that is gently, generously, and generatively provocative. When called for, we need to do our best to become cooperative agents of its holy mischief—and humble recipients of its transformative power.
As agents of holy trolling, we are sometimes called to be disruptive, annoying, confusing, or irritating - whatever is called for in the moment. And we need to have the humility to receive the same from others, and be transformed by their gifts of generative provocation. The world becomes more beautiful, when we welcome it with provokable hearts.
But my aim isn’t malicious. I don’t want to hurt people or humiliate them. I want to wake something up—to loosen what’s become too tight, too certain, too sure of itself. And, to tell the truth, I want others to do this to me, too. I want them to say things that stir my pot.
I want to be interrupted, unsettled, and occasionally confused. Not humiliated or harmed, but challenged in ways that help me see what I’ve been taking for granted. I want to discover where my own certainties have quietly hardened into habits, and where my best ideas have become a little too comfortable.
I trust that there is more going on in people—including myself—than our first reactions. I trust that a little disruption, offered and received with care, can open a door. I think Jesus worked this way, telling strange stories, answering questions with riddles, blessing outsiders, unsettling the pious. And I think the Buddha did something similar, using paradox and silence to interrupt our habitual ways of clinging. The Buddha's Flower Sermon was a kind of troll: holding up a flower instead of saying anything. And the idea that this Very World is Nirvana is a kind of troll, too. It unsettles the idea that Nirvana and Samsara are distinct.
Sometimes I even wonder if the soul of the universe has a bit of the troller in it. If God—him or her or it or they—isn’t interested in keeping us comfortable, but in keeping us alive, awake, and open. Maybe the divine lure itself comes with a kind of holy and loving mischievousness, gently undermining our certainties so that something new can be born.
I think Jesus revealed this divine trolling and became a window through which people around him could feel its energies. He was, as John Cobb puts it in "Christ in a Pluralistic Age, the Spirit of Creative Transformation at work in the world. And sometimes this spirit comes to us precisely through constructive trolling—or, perhaps better, generative and generous provocation. It doesn’t arrive to shame or coerce, but to unsettle us just enough to make room for love, truth, and new possibilities.
But I see lots of generative and generous provocation in others, too. Certainly in some Buddhists, and in trickster figures, and in poets, artists, and storytellers. A Zen koan is a kind of troll—posed to interrupt habitual patterns of thought. A paradox from Daoism does something similar, quietly undermining the mind’s urge to settle too quickly into fixed distinctions. In Judaism, a sharp question from the Talmud or a mischievous Hasidic tale can work the same way, unsettling certainty through argument, irony, or holy humor. And in Islam, especially within Sufi traditions, paradoxical sayings and startling reversals are used to crack open the ego and loosen the grip of conventional understanding. Each of these traditions trusts that wisdom does not always arrive by smoothing things over. Sometimes it arrives by gently—or not so gently—disrupting the mind’s desire for premature closure.
Indeed, I see generative provocation in ordinary people—friends, critics, students, strangers—who say something that catches me off guard and won’t quite let go. Often they don’t intend to be provocative at all. They’re just being honest, or curious, or playful, or stubbornly themselves. And somehow that’s enough to disturb the surface and let something deeper show through.
Sometimes it comes from people I disagree with, or from voices I would rather not listen to. Sometimes it comes from those closest to me, who know exactly where to poke. Sometimes it comes from people who lack the language I would prefer, but carry a wisdom I still need to hear. And, I have to admit, sometimes it comes from my cat, Rollie, who is clearly a troller in his own right.
In each case, the provocation doesn’t arrive polished or pure. It arrives mixed with ego, clumsiness, emotion, and limitation—like everything else in a human world. It seems to me that we need to be open to this side of life: the side that is gently, generously, and generatively provocative. When called for, we need to do our best to become cooperative agents of its holy mischief—and humble recipients of its transformative power.
As agents of holy trolling, we are sometimes called to be disruptive, annoying, confusing, or irritating - whatever is called for in the moment. And we need to have the humility to receive the same from others, and be transformed by their gifts of generative provocation. The world becomes more beautiful, when we welcome it with provokable hearts.
Varieties of Healthy Trolling
1. Benevolent Trolling
This form uses surprise or mild contradiction to loosen rigid thinking, but does so with evident goodwill. The aim is not to score points but to open space. One can feel the difference: the provocation lands, but it does not wound.
2. Socratic Provocation
Here the provocation takes the form of feigned ignorance, ironic questioning, or deliberate naïveté. Assumptions are surfaced not by assertion, but by invitation. Like Socrates, the provocateur does not claim superior knowledge, only curiosity sharpened into a tool.
3. Playful Provocation
This form relies on humor, exaggeration, or absurdity. It lowers defenses and invites lateral thinking. Playful provocation says, in effect: let’s not take ourselves quite so seriously.
4. Generative Disruption
Some provocations are less conversational and more structural. They interrupt settled patterns—of language, framing, or expectation—so that something new can appear. The goal is not chaos, but creative friction.
5. Affectionate Contrarianism
This is disagreement practiced within relationship. It challenges ideas while honoring persons. It presumes mutual intelligence and shared concern for truth, or at least for depth.
6. Trickster-Style Provocation
Drawing on ancient and cross-cultural traditions, this form teaches through mischief. Like Zen koans, prophetic parables, or indigenous trickster tales, it destabilizes in order to reorient. Wisdom arrives sideways.
7. Productive Irritation
Finally, there is provocation that mildly annoys—but only enough to awaken attention. It resists the narcotic comfort of consensus. The irritation is proportional, and its purpose is insight, not exhaustion.
This form uses surprise or mild contradiction to loosen rigid thinking, but does so with evident goodwill. The aim is not to score points but to open space. One can feel the difference: the provocation lands, but it does not wound.
2. Socratic Provocation
Here the provocation takes the form of feigned ignorance, ironic questioning, or deliberate naïveté. Assumptions are surfaced not by assertion, but by invitation. Like Socrates, the provocateur does not claim superior knowledge, only curiosity sharpened into a tool.
3. Playful Provocation
This form relies on humor, exaggeration, or absurdity. It lowers defenses and invites lateral thinking. Playful provocation says, in effect: let’s not take ourselves quite so seriously.
4. Generative Disruption
Some provocations are less conversational and more structural. They interrupt settled patterns—of language, framing, or expectation—so that something new can appear. The goal is not chaos, but creative friction.
5. Affectionate Contrarianism
This is disagreement practiced within relationship. It challenges ideas while honoring persons. It presumes mutual intelligence and shared concern for truth, or at least for depth.
6. Trickster-Style Provocation
Drawing on ancient and cross-cultural traditions, this form teaches through mischief. Like Zen koans, prophetic parables, or indigenous trickster tales, it destabilizes in order to reorient. Wisdom arrives sideways.
7. Productive Irritation
Finally, there is provocation that mildly annoys—but only enough to awaken attention. It resists the narcotic comfort of consensus. The irritation is proportional, and its purpose is insight, not exhaustion.
Edward de Bono
Wikipedia Page
Edward de Bono (1933–2021) was a Maltese psychologist, physician, author, and international authority on thinking, creativity, and innovation. He is best known for introducing the concept of lateral thinking, a systematic approach to breaking habitual patterns of thought in order to generate new ideas. De Bono argued that human thinking is largely pattern-bound: once we learn a particular way of seeing a problem, our minds tend to follow the same tracks repeatedly. While this tendency is efficient, it also limits creativity. His life’s work was devoted to developing practical tools that enable individuals, organizations, and societies to think differently—not merely more intelligently.