The Mind of the Design Entrepreneur
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In my last post, we explored how Design entrepreneurship combines science, culture, and values.  This has led me to conceive a new approach that we can only call ‘designerly ways of venturing’, one that involves mindsets, human sense perception, cognition and reasoning. This harkens back to Nigel Cross’ original terms ‘designerly ways of knowing’ in 1981.[i]

In the present blog essay, I explore the mental side of design entrepreneurship by looking at designerly mindsets, the designerly sense of human perception, and finally that special kind of designerly intelligence that only entrepreneurs seem to have. Design entrepreneurs seem to find their own personal entrepreneurial ecosystem.

We should speak more properly of mindsets in the plural.  The mindsets of the design entrepreneur include enterprise, empathy, critical thinking, and logic.

The enterprising mindset

The ‘Starship Enterprise

Many people misinterpret the word ‘enterprise’. Rather than being some firm or company, today the word enterprise (or enterprising) is used as an ‘attitude to life, an attitude of exploring, of developing, of leading and of taking initiatives’.[ii] It is no accident that the Star Trek crew commanded the ‘Starship Enterprise’ using such entrepreneurial traits as: 

  • ‘Boldly go where no [one] has gone before’.
  • ‘Space… the final frontier’
  • ‘To explore strange new worlds, to seek out new life and new civilizations’.

Enterprise—as in an ‘enterprising personality’—is the process of identifying, developing and bringing a vision to life, be it an innovative idea or simply a better way of doing something, in all fields of human endeavour. Think of how many self-employed professions there are—artists, photographers, musicians, designers, writers, financial advisors, analysts and interior designers. Beyond this, think of the creative and innovative people in arts, civil society, not-for-profits, community trusts and social enterprises.  From artist to zoologist, some people have the enterprising mentality.

An enterprising mindset is marked by imagination, initiative and readiness to undertake new endeavours; by a confident focus on a particular opportunity and by the ability to quickly act – all the while experimenting how to shape the opportunity within an social enterprise or business model.

From the perspective of trait theory, the behaviours of taking initiatives, seeking opportunities, taking responsibility, taking risks beyond security, and having the tenacity to push an idea through to reality combine into a special perspective that permeates entrepreneurs from all walks of life.[iii]

Starting a venture or any kind of (ad)venture — be it social, business, community, or environmental – requires an enterprising mind-set. Here is a list of competencies of an enterprising mindset:

  • Self-efficacy—‘I can do this, and I can make a difference.’
  • Collaboration—‘I know how to build a team and share roles.’
  • Identify opportunities—‘I can spot and validate problems and solutions.’
  • Empathy—‘I can stand in the shoes of another and see their perspective.’
  • Design perspective—‘I am a master of human-centered design.’
  • Communication—‘I can tell a compelling story about an opportunity.’
  • Representation—‘I can build what I can imagine and get feedback from others.’[iv]
The enterprising mindset
The enterprising mindset

The empathic mindset

Human empathy image
‘Empathic’ means having a sensitivity to other people’s emotions

The designerly mindset is based foremost on empathy, namely, the ability to put yourself into your customer’s/client’s/stakeholder’s shoes to understand problems from their perspective, to uncover their pains and problems (including some that they didn’t even know about), and to generate unexpected solutions (including ones that they had not thought of). ‘Empathic’ means having a sensitivity to other people’s emotions.[v]

Traditional business management processes do not typically overlook empathic engagement with customers. Design entrepreneurs take the opposite view to the manager’s data-driven analysis because empathy means a focus on the human angle. Managers pay little attention to how to use customer co-creation and feedback to turn their new ideas into a business model that can be shared with a larger group.[vi]

Empathy is made up of the following entrepreneurial mindsets. This is especially true when you do empathy mapping. Empathic entrepreneurs have the capacities to:

  • Understand real human needs, fears and desires. The entrepreneur/designer must have a deep empathy for what motivates people who make up the social or business world.
  • Be relentlessly optimistic. Design entrepreneurship relies on creative confidence and self-effectuation – a belief that you have the tools and capacities to create change, no matter how wicked the problem or how pressured you are.
  • Tolerate ambiguity. This means being comfortable with a problem-solving process that is liquid and open, and celebrating unexpected alternative solutions.[vii]
  • Collaborate positively. Two plus two is greater than four. When great minds get together, the outputs are always stronger and more impactful than if each person worked on the problem alone. You use your own creativity, to be sure, but multiple creativities and perspectives strengthen the positive effect of the solution.
  • Experiment joyfully. An experimental and explorative mindset is a seen as key to design entrepreneurship. Mistakes are a natural part of the process. Using the methods of hypothesis-driven entrepreneurship, you will have fun in failing and learning from the stumbles that you make.
  • Serve the world. Empathy means being the servant of the customer. You do not design solutions on the basis of ‘build it and they will come’. Human-centred designers see the world, and all the opportunities to improve it, through a new and powerful lens.
  • Immerse themselves in other peoples’ lives. The empathic mindset forces you to immerse yourself in another’s world and to leave behind your preconceptions. The Field Guide to Human-Centered Design states that ‘[e]mpathizing with the people you’re designing for is the best route to truly grasping the context and complexities of their lives. But most importantly, it keeps the people you’re designing for squarely grounded in the centre of your work.’[viii]
  • Have self-aware meta-cognition. Research has confirmed that some of us are more aware and have a better understanding of our own thought processes than others, and this is connected to the development of empathy. There is a ‘step-like’ pattern in empathy development and even in the neurobiological mechanisms associated with empathy.[ix]
  • Visualise new scenarios. The empathic mindset is future oriented and seeks to improve an existing situation into a preferred one. Using intuition and vision, this means having the urge to challenge the norm and to boldly go where no one has gone before.[x]

Designerly perception

Human perception image
Designers must take all human sense perception into account

To be a good empathic designer, you must understand how people see and how the brain interprets stimuli.[xi] Here are some common examples.

  • Most mental processing is unconscious, and people use their peripheral vision to get the ‘gist’ of a scene or situation.[xii]
  • People do not like too many choices.[xiii]
  • People can retain only 3–4 items in working memory.[xiv]
  • People prefer curved objects to straight.[xv]
  • Men prefer symmetry but women not as much.[xvi]
  • The brain processes information best when it is in a story format.[xvii]

Familiarity with this type of research helps entrepreneurs build websites, apps, products, and brands. Weinschenk says there are ten important things you need to know about people.[xviii]  You need to know:

  • How people see. This relates to user interfaces, hot maps, optical theories, pattern recognition, people’s expectations of graphic communication, and visual impairments.
  • How people read. This involves typography. Why are all-caps harder to read than lowercase? Why do people prefer hard copy to a computer screen?
  • How people remember. Do they like chunks, bits, or long form? Do they remember more or less when they are moving the knobs and features?
  • How people think. Research suggests that ‘progressive disclosure’ rewards users for their gradual efforts. Using stories in the communication design breaks up the factual information.
  • What motivates people. Do they love achieving goals or being rewarded for loyalty? Do they like progress indicators for user tasks?
  • That people are social animals. How does the innovation fit into their social environment? How do they interact with their friends and peers? Do they freely give social feedback or word-of-mouth feed-forward?
  • How people feel. Can you read their body language when collecting user feedback? Does graphic design/content affect your trustworthiness (credibility)? Do they have relationships with you?
  • People make mistakes. How can you learn from the mistakes and errors in your communication design and software?
  • How people decide. What do they think about when they buy a product? Do they like more or fewer options?

Designerly cognition

Design entrepreneurship involves a set of cognitive processes that are in some ways different from those in other disciplines. Cross calls this ‘design intelligence’. Design intelligence is associated with abductive reasoning, critical thinking, intuitive thinking, reflective reframing, holistic viewing, integrative thinking, and divergent/convergent thinking. ‘Designerly intelligent’ individuals can plan, review, reflect, adapt and, above all, create novel solutions. Like other forms of intelligence and ability, design intelligence is not simply a given talent or gift, but can be trained and developed.[xix]

How do we normally decide if something is true or false? Most of us are only familiar with two kinds of logic: inductive and deductive.

Deductive logic reasons from the top down, or from the general to the specific, by making references to a generally accepted theory or law. ‘If all crows are black, and I see a brown bird, it cannot be a crow.’ Inductive logic reasons from the bottom up, from the specific to the general. ‘Every time you eat peanuts, you get hives. So, you must have what doctors call angioedema.’

The trouble is that new ideas do not emerge from these conventional logics. New ideas come into being not by deduction or induction but through ‘logical leaps of the mind’. New ideas arise when a thinker observes facts that do not fit existing conceptions. This process starts not by observing but by wondering. The goal is not to decide true or false.

You have to make what American philosopher Charles S. Pierce called an ‘inference to the best explanation’.[xx] Design entrepreneurship uses this third kind of logic. Abductive logic is what you use when you are confronted with an incomplete set of observations. You make hypotheses using the best information available, which often entails making an educated guess after observing a phenomenon for which there is no clear explanation. Then you test your hunches until you have the likeliest possible explanation for the group of observations.

Types of Logic
Jokhio, Iffat, and Ian Chalmers. “Using Your Logical Powers: Abductive Reasoning for Business Success.” User Experience Magazine, 2015.

For example, imagine you enter the living room where the dog has been alone all day and you observe strips of papers all over the place. You ‘abduce’ that the dog tore them up. But unbeknown to you, your roommate has decided to move out and tore up the paper in preparation for moving out. The dog theory was the likeliest until you had more information.

Abductive reasoning gives us testable hypotheses that are suggested by facts. It is useful in design entrepreneurship because it is the logic of what could be. It complements deductive and inductive reasoning because the designer wants to move from what is known to what could be, to say, ‘What is something completely new that would delight us if it existed but doesn’t now?’ As Martin says, designers use abduction to generate ideas, challenge accepted explanations, and infer possible new worlds.[xxi]

Designerly thinking

Critical thinking is another important design entrepreneurship skill. ‘Critical thinking is the intellectually disciplined process of actively and skilfully conceptualizing, applying, analyzing, synthesizing, and/or evaluating information gathered from, or generated by, observation, experience, reflection, reasoning, or communication, as a guide to belief and action’. Critical thinking is especially important when we want to solve wicked problems. A well-cultivated critical thinker:

  • Raises vital questions and problems, formulating them clearly and precisely;
  • Gathers and assesses relevant information, interprets it effectively, comes to well-reasoned conclusions and solutions, and tests them against relevant criteria and standards;
  • Thinks open-mindedly within alternative systems of thought; and
  • Communicates effectively with others in figuring out solutions to complex problems.[xxii]

Other cognitive skills include intuitive thinking (generating solutions with using the power of reason) and reflective reframing (imagining new ways of viewing a problem in the first place). While developing solutions to design problems is a well-recognised design skill, the ability to think up new ways of looking at the problem in the first place is what really matters.[xxiii] Design thinkers are constantly questioning how a problem is represented, and they look ‘outside the box’ not only at solutions but also to see if the right question is even being asked in the first place. The skill needed is to identify, frame, and then reframe the problem. This demands a holistic view, a 360° perspective that starts with the customer’s needs, including social, emotional and cultural factors.[xxiv] A holistic view allows us to visualise the customer’s ‘pain’ as a system, with all its patterns and events, rather than just seeing the isolated picture.

Divergent and convergent thinking

All of this demands integrative thinking, which means bringing together competing, even clashing, ideas to form a better model, which might keep the superior parts of each model, all the while seeking a balance in the human and technical dimensions.[xxv]

It also requires divergent and convergent thinking. Divergent thinking involves widening your perspective to explore as many ideas and solutions as you can muster, while convergent thinking reduces these down to the ‘good’ or ‘best’ possible solutions. First, we go wide and explore the multiplicity of possible solutions in a free-flowing, spontaneous manner, where multiple creative ideas are engendered and evaluated. Then we narrow the scope of possibilities usingconvergent thinking to devise the most effective answer to a problem.[xxvi]Over time, as the funnel narrows, so too do the design possibilities; the designers eliminate unfeasible paths and refine the design, converging upon the best possible solution for implementation. In practice, design entrepreneurship involves a constant balance between divergent thinking (creating choices) and convergent thinking (making choices); see Figure 6.2 for a visual representation of this.

Divergent and convergent thinking images
Divergent and convergent thinking

Design thinking is the opposite of analytical thinking, where all proof comes from the past and from historical data. Most business schools teach young managers to examine what has already happened before deciding on a course of action and to protect the organisation from the ‘randomness of intuitive thinking[xxvii] This is not to say that analytical thinking is unimportant; it is essential when exploiting an opportunity. Intuitive creativity leads to breakthrough concepts, which analytical implementation can then exploit.


We can approach design entrepreneurship through mindsets, human sense perception, addressable problems, and cognitive and reasoning perspectives, not to mention tools and practices. We call this ‘designerly ways of knowing’. The designerly approach means using enterprising and empathic mindsets. Powerful human perceptions and cognitive abilities affect how we use design and how we interact with end products. We use hypothesis-driven entrepreneurship to test and validate assumptions concerning our proposed solutions to wicked problems. ‘Design intelligence’ means using reasoning and intuition to frame and reframe alternative solutions. Especially important is abductive reasoning, using the best information available (often making an educated guess) after observing phenomena for which there is no clear explanation; then testing your hunches until you have the likeliest possible explanation for the group of observations. Bringing it all together are divergent and convergent thinking, where you widen and then narrow your scope.

Cover of Frederick, O'Connor, Kuratko (2019), Entrepreneurship Theory Process Practice (Melbourne: Cengage) Source: Excerpted from Frederick, H. H., A. O’Connor, and D. F. Kuratko. Entrepreneurship Theory Process Practice. 5th Asia-Pacific edition. Melbourne, Australia: Cengage Learning Australia, 2019, pp. 187-197


[i] Cross, Nigel. “Design Thinking as a Form of Intelligence.” In DTRS8 Interpreting Design Thinking, edited by Kees Dorst, Susan Stewart, Ilka Staudinger, Bec Paton, and Andy Dong, 99–106. Sydney, 2010.; ———. Design Thinking: Understanding How Designers Think and Work. 1 edition. Berg Publishers, 2011.; ———. “Designerly Ways of Knowing.” Design Studies, Special Issue Design Education, 3, no. 4 (1982): 221–27.; ———. Designerly Ways of Knowing. Springer, 2006.; ———. “Designerly Ways of Knowing: Design Discipline versus Design Science.” Design Issues 17, no. 3 (2001): 49–55.; ———. “From a Design Science to a Design Discipline: Understanding Designerly Ways of Knowing and Thinking.” Design Research Now, 2007, 41–54.; ———. “The Nature and Nurture of Design Ability.” Design Studies 11, no. 3 (1990): 127–140.; See also Oxman, R. (1999). Educating the designerly thinker. Design Studies, 20(2), 105–22.; Saikaly, F. (2005, March 29–31). Approaches to design research: Towards the designerly way. Paper presented at the 6th International Conference of the European Academy of Design, Design System Evolution. The University of the Arts Bremen, Germany, 2005. Retrieved from ; Stolterman, E., McAtee, J., Royer, D., & Thandapani, S. (2009). Designerly tools. Retrieved from

[ii] Bridge, Simon, Ken O’Neill, and Stan Cromie, eds. Understanding Enterprise, Entrepreneurship and Small Business. Houndmills, Basingstoke, Hampshire: Macmillan Business, 1998, p. 36.

[iii] Quality Assurance Agency for Higher Education. (2018). Enterprise and Entrepreneurship Education: Guidance for UK Higher Education Providers.; see also Bacigalupo, M., Kampylis, P., Punie, Y., & Van den Brande, G. (2016). EntreComp: The Entrepreneurship Competence Framework. Luxembourg: European Union. , p.9

[iv] Plymouth State University, College of Business Administration, (2017), Enterprising Mindset—Habit of Mind—Results of University days workshop, August 2017. Plymouth State University. (n.d.). Innovation & Entrepreneurship – Our Learning Model. Retrieved January 31, 2019, from

[v] We use the word empathic rather than empathetic, which is a counterpoint to the word sympathetic. See WritingExplained (2016, August 24). Empathic vs. empathetic: What’s the difference? Retrieved from

[vi] See Stigliani, I. (2017, June 22). Design thinking – the skill every MBA student needs. Financial Times. Retrieved from

[vii] Bolland, R. J., and Fred Collopy. Managing as Designing. Stanford University Press, 2004.;

[viii] IDEO. The Field Guide to Human-Centered Design, 2015.;

[ix] For more, see Hogan, Robert. “Development of an Empathy Scale.” Journal of Consulting and Clinical Psychology 33, no. 3 (1969): 307–16.; Leonard, Dorothy, and Jeffrey F. Rayport. “Spark Innovation through Empathic Design.” Harvard Business Review 75 (1997): 102–115.; Lovell, Chris. “Empathic-Cognitive Development in Students of Counseling.” Journal of Adult Development 6, no. 4 (1999): 195–203.; Withell, Andrew. “Conceptualising, Evaluating and Enhancing a Design Thinking Curriculum Using a Critical Realist Perspective.” Thesis, Auckland University of Technology, 2016.; Yardley, Susan L. “Response to Lovell: ‘Cognitive Development and Empathy.’” Journal of Adult Development 6, no. 4 (October 1, 1999): 227–29.;

[x] Drews, Christiane. “Unleashing the Full Potential of Design Thinking as a Business Method.” Design Management Review 20, no. 3 (2009): 38–44.;  Junginger, Sabine. “Learning to Design: Giving Purpose to Heart, Hand and Mind.” Journal of Business Strategy 28, no. 4 (July 10, 2007): 59–65.

[xi] These examples are taken from the wonderful work of Weinschenk, S. (2015). 100 things every designer needs to know about people (2nd edn). Berkeley, CA: New Riders. Retrieved from; Weinschenk, S. (2015). 100 more things every designer needs to know about people (1st edn). Berkeley, CA: New Riders. Retrieved from; Weinschenk, S. (n.d.). 100 things every designer needs to know about people. Retrieved from .

[xii] Larson, Adam M., and Lester C. Loschky. “The Contributions of Central versus Peripheral Vision to Scene Gist Recognition.” Journal of Vision 9, no. 10 (2009): 6–6.

[xiii] Iyengar, Sheena S., and Mark R. Lepper. “When Choice Is Demotivating: Can One Desire Too Much of a Good Thing?” Journal of Personality and Social Psychology 79, no. 6 (2000): 995.

[xiv] Baddeley, A. (1994). The magical number seven: Still magic after all these years? Retrieved from; Broadbent, D. E. (1975). The magic number seven after fifteen years. Retrieved from; Cowan, N., Morey, C., & Chen, Z. (2007). The legend of the magical number seven. In S. D. Sala (Ed.), Tall tales about the brain. Oxford University Press. Retrieved from; Usher, Marius, Jonathan D. Cohen, Henk Haarmann, and David Horn. “Neural Mechanism for the Magical Number 4: Competitive Interactions and Nonlinear Oscillation.” Behavioral and Brain Sciences 24, no. 1 (2001): 151–152.

[xv] Bar, Moshe, and Maital Neta. “Humans Prefer Curved Visual Objects.” Psychological Science 17, no. 8 (2006): 645–648.

[xvi] Shepherd, Kathrine, and Moshe Bar. “Preference for Symmetry: Only on Mars?” Perception 40, no. 10 (October 1, 2011): 1254–56.

[xvii] Singer, Tania, Ben Seymour, John O’doherty, Holger Kaube, Raymond J. Dolan, and Chris D. Frith. “Empathy for Pain Involves the Affective but Not Sensory Components of Pain.” Science 303, no. 5661 (2004): 1157–1162.

[xviii] Weinschenk, Susan. 100 Things Every Designer Needs to Know About People. 2nd ed. Berkeley, CA: New Riders, 2015.

[xix] Cross, Nigel. Design Thinking: Understanding How Designers Think and Work. 1 edition. Berg Publishers, 2011.; See also Cross, A. (1986). Design intelligence: The use of codes and language systems in design. Design Studies, 7, 14–19; Cross, N. (2010). Design thinking as a form of intelligence. In K. Dorst, S. Stewart, I. Staudinger, B. Paton, & A. Dong (Eds.), DTRS8 Interpreting design thinking (pp. 99–106). Sydney. Retrieved from; Cross, N. (1990). The nature and nurture of design ability. Design Studies, 11, 127–40.

[xx] Peirce Edition Project (1998). Pragmatism as the logic of abduction. In Pierce Edition Project, The essential Peirce: Selected philosophical writings (1893–1913), 227. Indiana University Press. Retrieved from 

[xxi] Dunne, David, and Roger Martin. “Design Thinking and How It Will Change Management Education: An Interview and Discussion.” Academy of Management Learning & Education 5, no. 4 (2006): 512–23.

[xxii] Critical Thinking Community (n.d.). Defining critical thinking. Retrieved from 

[xxiii] Dew, N. (2007). Abduction: A pre-condition for the intelligent design of strategy. Journal of Business Strategy, 28, 38–45;

[xxiv] Holloway, Matthew. “How Tangible Is Your Strategy? How Design Thinking Can Turn Your Strategy into Reality.” Journal of Business Strategy 30, no. 2/3 (2009): 50–56.

[xxv] Brown, T. (2008, June 1). Design thinking. Retrieved from; Clark, K., & Smith, R. (2008). Unleashing the power of design thinking. Design Management Review, 19, 8–15; Dunne & Martin (2006). Design thinking and how it will change management education; Norman, D. (2010). Design thinking: A useful myth. Retrieved from ;

[xxvi] Kim, D. K. H., & Pierce, R. A. (2013). Convergent versus divergent thinking. In E. G. Carayannis (Ed.), Encyclopedia of creativity, invention, innovation and entrepreneurship (pp. 245–50). Springer: New York.

[xxvii] Martin, Christensen, & Martin (Eds.). (2013). The design of business, 24; Martin, R. (2010). Design thinking: Achieving insights via the ‘knowledge funnel.’ Strategy & Leadership, 38, 37–41; Martin (2009). The design of business

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Howard Frederick

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