The Creative Entrepreneur's Guide to Diverse Thinking Styles (6 Types for Increased Creativity)
Box Cutter Free Issue No. 55
Ever been told, “Don’t Overthink It!”?
It’s a far too common expression — and also one that proliferates in schools. As in:
“Don’t overthink it because I’m the authority, I know best, and here at school you’re not permitted to think for your Self — AND! you must cite references for any sources of thinking.”
For the most part, Overthinking is a myth. Plus… it’s in danger of grouping all ‘thinking’ into one box suggesting:
“You know that thinking thing… nope… don’t do that, at least not for, or by, your Self.”
Thinking (in its many, many forms) can be a Superpower
Think about “empathy” for a moment. It’s a term with varied and sometimes nuanced meanings.
Merriam-Webster defines it as: “the action of understanding, being aware of, being sensitive to, and vicariously experiencing the feelings, thoughts, and experience of another.”
The ability to engage in perspective-taking is called “cognitive empathy”. It’s linked to our ability to identify and understand what other people may be thinking and feeling (without necessarily sharing those thoughts or emotions).
This requires thought… and thinking. (And critical thinking is probably not going to assist).
If you’ve experienced any post-secondary (“higher”) education you have probably heard the great bastion of universal (e.g. university) thinking — Critical Thinking.
It’s often hailed as the pinnacle of intellectual achievement, the cornerstone of academia, and the lifeline of any serious profession. Critical Thinking is repeatedly identified as a ‘top five trait wanted by employers’.
But… critical thinking is NOT the only way to tackle problems, decisions, challenges, and, especially creativity and idea generation.
It's just one way of thinking.
The over-focus on ‘critical thinking’ in schools and academia overlooks many other valuable ways of thinking. It also frequently leaves a negative stigma for many — especially those who want to write digitally and publish online.
“Oh well… I can’t do that, I’m not RRREEEAALY an expert”.
And, thus, for many the scourge and mantra of ‘critical-thinking-only’…
…gives rise to impostor syndrome, feelings of “I’m not expert enough”, and fear and anxiety around being ‘called out’ for posting on specialized (and even general) topics.
To get us started, here are just a few other types of thinking (just as important as ‘critical thinking’):
Thinking about Thinking (metacognition)
Creative Thinking
Abstract Thinking
Concrete Thinking
Convergent Thinking
Lateral Thinking
Divergent Thinking
Reflective Thinking
Holistic Thinking
Analytical Thinking
Systematic Thinking
Problem-Solving Thinking
Intuitive Thinking
Deductive Thinking
Inductive Thinking
Synthesizing Thinking
Adaptive and Flexible Thinking
Resilience Thinking
Procedural Thinking
and more…
Our brains are wired for more, much more. Our brains (and minds) are also highly complex. And, really important to keep in mind that this isn’t only about our ‘brains’ and our ‘minds’.
Our brains and bodies are deeply intertwined and connected. For example, we think with our guts and our brains are impacted by our guts.
We think with our hearts, and our brain are fed and impacted by our hearts.
We even think with objects outside of us—extensions of our bodies. From those with artificial limbs to those who are experts with hockey sticks, racquets, chainsaws, bats, bows and arrows, swords, pens, paintbrushes, and more.
(How we think with things is such a fascinating area of thought, thinking, and creativity — a topic for a future issue).
As creative entrepreneurs, we're not just thinking, we're meta-thinking. It's like having a bird's-eye view of our thought processes, constantly analyzing and adapting. This isn't just thinking outside the box, or inside the box — it's about understanding the box itself, what’s in it, around it, influencing it, and more.
In this issue - I explore six types of thinking that I find critical for creative entrepreneurs. Including those who think in creatively entrepreneurial ways within their professions, careers, and families.
6 Types of Thinking to Leverage in the Creator Economy (and Life)
Let’s take a little trip through a spectrum of thinking styles that will assist in the art of digital entrepreneurship.
1. Thinking about Thinking (Metacognition): Insight, Choices, Strategies, Decision-making
This is our cornerstone, our foundation, our launching pad for all things: Thinking.
‘Thinking about thinking' — referred to as metacognition by academics — is the process of being aware of and understanding our own thought patterns and cognitive strategies.
It involves monitoring and regulating how you learn, unlearn, solve problems, and make decisions (to name a few). Essentially, it’s our oversight of personal mental operations — like you are looking down from above into your mind and how it thinks.
Thinking about Thinking is the most important kind of thinking — and all other thinking emanates from here. That’s why, in the diagrams above, I place “thinking about thinking” at the core and start of any reflection on thinking processes.
2. Parallel Thinking: Encouraging Diverse and Non-interfacing Viewpoints
Parallel thinking refers to people thinking alongside each other in the same direction. Each person approaches a problem, issue, or decision from their perspectives at the same time (from their life experiences, perspectives, etc) — rather than confronting each other with opposing views.
In Canada, where I live, many early treaties with Indigenous peoples and communities were signified by a Two-Row Wampum Belt. These would often display two parallel tracks running alongside each other. A lane (so to say) for each distinct community — in parallel.
History demonstrates many examples of where these agreements were run over rough-shod. Yet, parallel thinking can still be a powerful process.
It can facilitate understanding, respect, and empathy. It can also be very valuable to implement and utilize in business enterprises within the Creator Economy. It can support different approaches to business and creativity, which can coexist and thrive without needing to converge.
In our little educational startup and social enterprise — Humanity Academy — my wife, Lisa, and I have adopted the tagline: “There is no one right way to live”.
This is immersed in a multiplicity of methods and ideas, recognizing that there's not just one way to success, living, thriving, or going about things. Often this can mean things moving along on parallel tracks that do not need to merge, converge, or diverge.
This kind of thinking supports the notion of a 'Box Cutter Philosophy' by encouraging alternative perspectives and acknowledging the validity of endless approaches to digital entrepreneurship and content creation.
3. Holistic Thinking: Understanding Complexity
Holistic thinking— in many ways, speaks for itself. It’s about exploring and thinking deeply about the bigger picture (or pictures). It’s often about seeing how all the pieces might fit together in a puzzle. But… it can also be about how pieces that appear to fit in the puzzle — actually don’t.
Many might suggest that holistic thinking is akin to systems thinking. And, it may very well be. It involves recognizing interdependencies and how changes in one area can ripple through others. This type of thinking will often support building and thinking about more comprehensive strategies.
Thinking about where decisions are made and putting that into the context of considering the entire system rather than isolated elements. This often requires deeper thinking that engages reflection (looking back), introspection (looking in), and prospection (looking forward).
[Stay tuned for a future issue on this trifecta]
4. Adaptive Thinking: Navigating Change
Adaptive thinking is all about fluidity, flexibility, responsiveness, and resiliency in the face of change. And remember… change is the one constant in life. No matter what, time forges on.
In the Creator Economy, the ability to shift strategies, embrace new ideas, and learn from experiences is crucial. Plus, it's not just about reacting to change, but:
proactively seeking it,
understanding its implications, and
leveraging it for personal, creative and business growth.
Adaptive thinking is such a key part of entrepreneurship — and thus digital entrepreneurship, solopreneurship, and life in general. An Adaptive Thinking mindset can be critical in anticipating shifts, adapting, and turning challenges into opportunities for growth, learning, and unlearning.
In the Creator Economy, this will continue to play out as social media platforms change algorithms, change hands (e.g. X Twitter), become obsolete, and/or new ones come online. (And, especially, as the Creator Economy is forecast to continue to grow at 30% per year from its current $250 billion annual output in value.)
5. Counterfactual Thinking: Exploring Alternative Realities
Counterfactual thinking is — in many ways — the heart of a Box Cutter philosophy.
It goes beyond just being a powerful tool for creative entrepreneurs, encouraging innovation and problem-solving — it’s an excellent tool to engage in life.
If you ever disagree with someone and really want to understand their arguments — then break them down bit by bit. Not in dialogue, but through thinking and potentially a Learning Journal.
Taking this approach means considering different perspectives by imagining alternative outcomes or scenarios. This process will reveal underlying assumptions, weaknesses, or strengths in an argument — and not just the other person’s, but yours too.
By exploring "what if" situations, you can gain a deeper understanding of the reasoning behind the arguments (and positions) and potentially develop more robust, well-rounded counterarguments or insights. And, often, your own perspective will change too — as you identify your own biases, assumptions and weak logic.
Imagining "what if" scenarios are invaluable in business — and in thinking through digital writing and content creation. It involves considering alternative realities and outcomes, asking questions like, "What if things had happened differently?"
This type of thinking stimulates expanded creativity and opens new possibilities. It also encourages thinking outside conventional boundaries, leading to unique and original content…. like a Box Cutter.
Key here is to do this exploration without shame or blame — of you or others.
6. Synthesizing Thinking: Integrating Diverse Ideas
This is one of my absolute favourite kinds of thinking. Synthesizing.
I’m of Gen X, meaning I grew up with 1980s music. Anyone who did similar, or listens to 80s music, will remember the sounds of the “Synthesizer”. Essentially, keyboards combined all sorts of sounds and rhythms to create innovative (yet sometimes awful) music.
In many ways, these are the roots of various music genres now, where beats and sounds and auto-tune churn out music from people’s laptops and devices — and then are distributed across the world wide web.
Or a solo lounge singer or street busker can produce background beats and sounds that support their playing guitar and singing.
Synthesizers from the 1980s and 90s are a great metaphor for articulating Synthesizing Thinking, as they blend different ideas and perspectives to form new thoughts, concepts and solutions.
When skillfully combined, Synthesizing Thinking can produce harmonious and deeply varied output, much like synthesizers in music can pull from varied sources and produce all sorts of rhythms, sounds and effects. And, do this in highly creative and innovative ways.
Music was never really my strong point — even though I played the alto saxophone in high school band from grade 8 through 12. However, synthesis and Synthesizing Thinking have been a big part of my life for decades.
I love synthesizing. My main tool for doing and tracking this is in Learning Journals. I am constantly capturing snippets, thoughts, ideas, quotes, and all sorts of other bits-and-pieces.
Digitally, if a thought comes to mind, I quickly start a ‘draft’ article. Either here on Substack, or on Medium, and even on social media. “Save as Draft” can be a very powerful function. I also use the Notes app on my iPhone — especially on walks. I’ve come to love the voice memo functionality.
That way, I always have some ‘irons in the fire’ 🔥 — so to speak. And, as these begin to collect, I find that one set of notes or drafts from one spot begin to interface and mesh with thoughts from another spot.
Let the Synthesis begin!
In Box Cutter Co.'s journey (now over one year), synthesizing thinking has played a pivotal role — merging creativity with strategy; adaptability with creativity; and flexibility with learning.
Synthesis is the art of integrating diverse ideas, concepts, and perspectives to create a cohesive whole. This process is crucial in entrepreneurship (especially digital), where combining various elements from different sources can lead to innovative solutions, authentic and creative writing, and unique content.
Synthesizing Thinking is all about zooming out to consider the bigger picture, starting to zoom back in and connecting the dots between seemingly unrelated ideas, and crafting something original and impactful.
And, then, zooming back out again. And rinse and repeat as needed.
As Box Cutter Co. (and my other digital ventures) continue to evolve, Synthesizing Thinking will be key in continuing to weave together (and pull apart) insights from various thinking modes, ensuring a multifaceted, creative, and flexible approach to problem-solving, problem-identifying, digital writing, and content creation.
Thinking Does Not Stop Here
As this issue comes to a close, try to keep in mind that the realm of thinking is vast and varied — and that Overthinking is often bullshit.
In my varied personal and professional experiences, I’ve often found that when I start accusing myself of overthinking — or, I hear it from others — I realize it’s a process of looking for shortcuts. For quicker gratification.
Of, trying to get easy, quick wins. Of, the classic bureaucratic bullshit statement “low-hanging fruit”. (I learned the hard way while picking fruit in Australia that those low hanging fruit are often where the big spiders are hanging out… 😱)
And, yes, absolutely, there comes a time for action. But to everything it’s season — and rushing the season will often result in something that is not wanted or required.
In my journey of establishing digital writing and content creation businesses over the past 20 months or so… I (and we, my wife and I) have taken slow, steady, mind-full approaches to building.
We’re not interested in the “10K Followers in 60 Days” approach. Or, posting writing and content in search of virality. We’re focused on building businesses that support and suit our lifestyles (now and desired in the future). And in many ways, what we’ve built thus far — is a key part of our lifestyle!
Now, there’s a deadly combination. As in deadly-cool… not… deadly, kill ya. :)
Engaging the hundreds (if not thousands) of different modes of thinking can enhance our creativity, decision-making, choices and problem-solving skills —with added bonuses of enriching our understanding of the world and our Self.
And, yet, building Thinking about Thinking skills is the key foundation to all of this.
Want to Explore Some?
Grab your Learning Journal — or start one. (This can be as simple as grabbing a piece of paper and a pen)
Thinking about Thinking: Reflect on a recent decision you made. What thought processes led you to this decision? How could you improve this process in the future?
Parallel Thinking: Think of a current challenge. How would someone with a different background approach this issue in parallel to your approach?
Holistic Thinking: Identify a complex problem and map out how its different elements are interconnected.
Adaptive Thinking: Recall a significant change you navigated successfully. What adaptive strategies did you employ? Maybe you live in an area that has a growing threat of wildfire, flood, or other climate change threats.
Counterfactual Thinking: Consider a post, article, situation or story in which you feel you completely disagree with someone. Think counterfactually about their position and argument— break it down. Then… do the same for your position. How did this change your current situation or position?
Synthesizing Thinking: (first try and say this 5 times fast)… Then combine two seemingly unrelated ideas or concepts to create a new approach or solution. ChatGPT can be awesome at this. For example, take three thinkers or experts from three different disciplines and ask ChatGPT to mix-and-mash. (It often blows my mind with what it comes up with.)
In addition to using these as prompts for thinking — you can also use these as prompts for writing. These could be social media posts, Medium stories, newsletter issues or otherwise.
That’s it for this week. Thanks for reading this ‘thinking about thinking’ Issue.
Would love to hear your questions (or disagreements) — drop a like, a comment, or re-post on channels you navigate. Thank you to those who do this regularly.
Watch for the next Free Issue of The Solopreneur Series coming shortly.
Great take and for shedding light on a topic that deserve way more attention.
Overthinking is probably misconstrued with cognitive overload, which will lead to worse judgment compared to simply relying on heuristics for example. Ironically, I think I had a slight dose of cognitive overload after combing through this piece (in a good way).
I've always contemplated whether to rank metalearning ahead of metacognition in a tier-list of future-proof skills. Interested to see how you would compare these two skills head-to-head.
Wow. This is a cool different perspective.
Perhaps "overthinking" isn't as bad as I thought. Something to ponder on.
I agree on the danger of the "easy thinking": the low hanging fruit can easily hide a big huntsman ready to jump at you!