Remember the Why

It is easy to forsake honesty for programming and forget the ‘why’ behind the ‘what’. When presentations are intentioned as marketing ploys rather than authentic expression, the why is forsaken.

Why Aren't There More Designer Founders?

We’re supposedly in the midst of a design renaissance, where beyond the cliché Steve Jobs and Apple ecosystem example, we see a design-centric focus in everything from soap (Method) and thermostats (Nest) to email (Mailbox) and even baby food (Plum Organics).

And yet, there’s a dearth of designer founders.

At this point, the technology tools for design — enabled by the web — have evolved to a point where good design is accessible and scalable. Before, even design-centric product companies had to be founded by technical founders because of the narrow expertise required by the tools, not to mention the lack of user experiences and context at the time. But that’s no longer the case, and hasn’t been for a while.

So why then, in this Golden Age of Design, don’t we see more designers transitioning into entrepreneurship?

To be clear, I’m not saying there aren’t a healthy number of designers out there freelancing or starting design agencies; that is certainly entrepreneurial. What I’m talking about here is the type of entrepreneur where the designer is not an agent or service provider, but rather, part of the founding team that leads and drives the vision for the entire company’s spawning of innovative products.

It’s difficult to find the exact percentage of entrepreneurs that claim design as a primary skill set. But if I draw on the data of applicants to FounderDating, a network of entrepreneurs ready to start their next side projects or companies, there are far fewer designer founders relative to other skill sets. Using this data as a proxy, it’s around 15 percent; after correcting for people who are more design-appreciators than designers, it’s probably closer to 6 percent.

It was only when the question of “where do you find more designers that want to be entrepreneurs” came up that I realized the real asymmetry in this market: lots of demand for designer founders, not enough supply of them. (It’s telling when you compare the ratio of engineer founders, which is at 50 percent). That’s a problem when trying to build well-rounded founding teams.

The answer to the question of why there aren’t more designer founders partly lies in examining what entrepreneurs are good at.

Designers want to design. They are passionate about and “driven by their craft,” as Eric Ryan of Method explains. They obsess over pixels and details. This is how they rise up in the world of design. (I was initially concerned about presenting this hypothesis to designers. But literally every designer I’ve spoken to — and I’ve spoken with many both over the course of my career and in exploring this question recently — agrees. Sometimes it takes a few seconds — a tilt of the head, a pensive pause; but sure enough, along comes a nod.)

A single-minded dedication to craft is one reason why so many designers flock to design and advertising agencies: They can stay focused on their craft. And what could be better than doing so while surrounded by a like-minded cohort of other designers?

At other companies — especially startups — designers are often the lone designer for years. Sometimes that’s because startups have limited resources and can’t afford more designers; other times it’s because they can outsource or feel that others can pick up slack on the design side of things.

Most entrepreneurs, in contrast, are actually not amazing at any one thing. People may see them that way, especially given the media narrative of how we depict entrepreneurs and startups, but founders are typically just “good enough” at a slew of things: fundraising, product, partnerships, etc. Good enough to get things rolling and faking it until they make it — that is, can hire people that are better than them in most areas.

A founder’s job is to lead. Their job is to be ready with a shovel, filling the holes, often doing the work no one else is excited to do. One day you’re working on product and fundraising, the next you’re recruiting and doing the dishes. There is no “typical day.”

Designers want to design. Most entrepreneurs, in contrast, are actually not amazing at any one thing.

On the surface, there seems to be an inherent tension between what makes a good entrepreneur and what makes a good designer. For example, an entrepreneur’s job is to figure things out as they go — iterate and problem solve. It’s not just about a craft: It’s about what the market wants. Entrepreneurs walk a delicate balance between the needs of their customers, teams, and investors.

But if you think about it, this characteristic is true of designers too. A great designer excels at iterating and problem solving. At walking a delicate balance between the needs of their audiences, colleagues, and funders. Design is not just a service industry, but a cross-functional way of thinking that is invaluable in starting innovative companies. Yves Behar (Jawbone, Ouya, August) told me he thinks designers could be great entrepreneurs because they “are uniquely suited at solving problems on multiple dimensions without losing sight of the big opportunity to wow the customer.”

The key trade of both designers and entrepreneurs is therefore problem solving. Both in being obsessed with a problem (note, there’s a difference between being obsessed with a specific problem and entrepreneurship, as Anil Dash pointed out here in WIRED) — and in how to solve it. One obvious example of the latter is IDEO’s popularization of ‘design thinking’ as a repeatable process for such problem solving.

The key trade of both designers and entrepreneurs is problem solving.

It’s not enough to just love to design. It’s about loving the process so much that you want to design your company from the ground up. As Gentry Underwood, former IDEO-er and co-founder of Mailbox explained to me, “thinking like a designer means being better suited for the open-ended ambiguous problems that epitomize the startup journey and having the skills needed to iterate towards product-market fit.” You’re excited to apply the design mindset to rethinking organizational structure, go-to-market strategy, and the many other challenges that inevitably get thrown your way — “opening the aperture to what it is they are designing,” is how Neil Grimmer, co-founder/CEO of Plum Organics put it.

Pushing entrepreneurship on people that live only for designing interfaces, products, or logos is therefore not a good use our time. If someone just loves to design for design’s sake, or is focusing on just that when designing a product, then maybe he or she shouldn’t start a company. I’d say the same for people who just love to code or just love to sell.

But if what they really love is the process around designing — around solving problems they are passionate about — then they are well-suited for entrepreneurship.

Many designers don’t even know they want to go out for entrepreneurship or that it’s a possibility. Evan Sharp of Pinterest admitted in Designer Founders that he’s “not much of an entrepreneur. I hate to say it…I actually don’t hate to say it. I’m totally fine saying it. I fell into this thing, in a good way. I think I’m more of a builder, not to be too ideological about it.” Many need to find their complement to feel fully confident. In describing the partnership with his Behance co-founder Scott Belsky, Matias Corea noted that “when I met Scott, I was just a designer… I turned Scott into a designer, he turned me into an entrepreneur.”

Design is not just about how it works, it’s about the process of how you get it to work. 

For some this lack of awareness or exposure is the fault of education. For too long, designers have been trained to be agents: working at the will of someone else’s vision. It’s true at design or advertising agencies. And it’s true at larger companies; even corporate design or UX departments often act as an internal services arm, working on projects requested by others. These services firms and departments are fed young talent by design schools who, with the occasional exception, sprinkle rather than embed entrepreneurship into their programs. (For others, the issue is funding. John Maeda, RISD head and former associate director of the MIT Media Lab, calls for more ways to crowdfund “artrepreneurs.” As for the VC industry … that’s for another piece.)

For me and many of the designers I know, though, it’s a terminology and mindset issue. Steve Jobs pointed out that “Design is a funny word. Some people think design means how it looks. But of course, if you dig deeper, it’s really how it works.”

Actually, it goes a level deeper. Design is not just about how it works, it’s about the process of how you get it to work. And that’s what founding a company, what entrepreneurship is all about.

The Art of Doing

“You are what you remember — your very identity depends on all of the events, people and places you can recall.”

In The Art of Doing: How Super achievers Do What They Do and How They Do It So Well - A compendium of pragmatic advice on such modern fixations and timeless aspirations as how to create a great company culture (courtesy of Zappos CEO Tony Hsieh) to how to be funny (courtesy of Alec Baldwin) to how to fight for justice (courtesy of Constance Rice) — neurologist, neuropsychiatrist, and prolific brain book author Richard Restak offers some vital tips on how to optimize your brain, central to which is honing the capacity and performance of your memory:

"On a very basic level, you are what you remember — your very identity depends on all of the events, people and places you can recall. Improving your memory will help you develop a quicker, more accurate retrieval of information that will increase your intelligence. Sharpening your short-term or “working” memory requires concentration. For instance, study four unrelated words for 15 seconds, then set an alarm for five minutes. Pay attention to another activity until the alarm sounds. Then try to remember the words. As you get better, change and add to the number of words and increase the amount of time. You can do similar exercises with numbers, visual designs, spoken words or even try to recount the scenes of a television show you just watched."

But this, Restak cautions, can be physically taxing:

"When you do these exercises your brain will require extra oxygen, blood and glucose. Just as with physical exercise, this can tire you out. Many “tricks” to sharpen your recall use memory pegs, systems to attach an association or meaning to what you desire to remember. There are visual and story memory systems, some dating back to Ancient Rome. One of these systems is called, "the memory palace" in which you associate the things you want to remember with vivid mental pictures, which you then imaginatively place in a familiar setting such as your living room. Later, you can “tour” in your mind the living room to observe the remembered objects in their familiar places. This technique can be so effective it is often used by memory contest champions."

Just as important as working memory, Restak argues, is emotional memory — an essential psychological tool that has found creative expression in everything from sentimental cartography to object-based storytelling to wearable personal histories. Restak writes:

"Another aspect of recall is emotional memory, when we relive how we felt at moments in the past — elated, sad, depressed, or angry. When we lose emotional memory of our own youth, we find that we no longer understand young people. If this forgetting progresses, we begin to lose touch with ourselves. And if we allow our emotional memories to disappear, as happens with Alzheimer’s patients, we will find a stranger staring back at us from the mirror."

He recommends an exercise for reacquainting yourself with your emotional memory, one practiced by cultural icons in their letters to their younger selves and embedded in the heart of the It Gets Better project:

"Find a picture of yourself in which you are half of your present age. Stare at the picture for a while. Then write a letter to your older self from the perspective of the younger you in the photo, expressing all of the younger self’s hopes and concerns about the future. Follow this with a letter back from the present self to the younger you, telling that younger self about all the things they will do in their future and who they will grow into. Hopefully you will uncover feelings and memories of things you haven’t experienced for years."

Restak reminds us of the multi-sensory dimensions of experience:

"The olfactory nerve links directly to the emotional centers of the limbic system, so the scents of your past — such as mowed grass, crayons or perfumes — can also bring back emotionally charged memories. Think of Proust and his madeleine."

Website Info Architecture In 4 Steps

When a website or web application is planned properly the project is more likely to run smooth and profitable. One way to effectively plan a site or application is to have good techniques when you are planning the website’s information architecture. 

Step 1: Interview your customer

This step is obvious, but surprisingly it can be overlooked and mishandled. The goal is to have a casual conversation with the client or stakeholder to understand how they operate their business and how they make money. An effective way to do this is to use a website planning checklist. A good set of questions to use in your website planning checklist are as follows:

1. Who are your customer segments for each product/service line?
2. How does each customer segment buy from you?
3. What are the operations behind delivering your product and/or service?
4. List products and/or services from most important to least important.
5. What are your measurements for a successful website?
6. What type of information would like to capture from site visitors?
7. What geographic regions do you want to target?
8. How would you like each customer segment to use your site?

It’s important to help the parties involved seriously think about these questions and answer them accurately. From these questions you can start to write your functional specification, which is a document that lays the foundation for the website.

Step 2: Write your functional spec

The functional specification is where the majority of the website’s information architecture is formulated.

The beginning of the document addresses the business case for the website and clearly defines the customer segments, methods of reaching those customer segments, and website metrics.

The next part of the document explains functionality and illustrates the global navigation, site sections, site pages, page functionality, workflow, and information flow using process and hierarchical diagrams.

The last part of the document specifies the technology needed to support the proposed architecture such as: server stack, security protocols and certifications, and the content management system.

In order to define a good website information architecture the components of your specification should include:

1. Objective of the website
2. Functionality overview
3. Define customer segments
4. Identify goals and key metrics for each goal
5. Global navigation diagram
6. Diagram each site section with their respective child pages
7. Diagram workflow and information flow for forms and applications (shopping cart/checkout, log in, etc…)
8. Complete sitemap diagram
9. Technical requirements (server stack, content management system, security)

Step 3: Build your content survey

Once your functional specification document is complete you can begin to develop content surveys based on the information. The most effective way to do this is to use your complete site map that you developed in the specification and use it as a guide to enter the content elements into a table for each page in your site map.

For ecommerce sites, real estate sites, and other dynamic content heavy sites its wise to use page types for each table. An example would be to develop a content survey table for all category pages and a content survey table for all product pages. The columns of a basic content survey table should contain the following information:

1. Content Element (e.g. logo, site navigation, image slider,)
2. Content type (e.g. branding, informative, navigation, section)
3. Section ( e.g. site-wide, page, category)
4. Priority (comes in handy for tablet and phone layout when elements need cut out)

Step 4: Mock up your templates with Adobe Reflow

Once all of your content survey tables are built you can start grouping together similar page types in order to create page templates. You can end up with 4 page types or as many as 15 depending on the size of the site and its required functionality. The page templates make it easy for the development team to build out the frame work of the site, and also visualize the different layouts for tablet, phone, and desktop devices.

A great tool to mock up your page templates is Adobe’s new Edge Reflow application. This application allows you to effectively design the user interface for all of your page templates on multiple devices, which is a great boost the workflow between planning and development teams.

If you follow these steps and learn how to manage the process effectively I guarantee your web projects will run smoother, and you will have a website information architecture that provides a great user experience for your users and better search engine rankings. In summary, the four main steps to this process are:

1. Interview stakeholders by using a website planning checklist
2. Write a functional specification
3. Develop content surveys
4. Mock up your page templates with Edge Reflow

Collaboration

The history of art abounds with accounts of gifted individuals, of solitary creators, of geniuses. There are few modes of human existence that fit the mold of individualism more neatly than the idea of the solo artist lost in the pursuit of their own unique creative vision. From the depths of visionary isolation are brought forth all manner of wondrous objects to be emulated and revered by current and future generations. Much art education is founded upon this image of creative individuality and so it is rare to find instances where collective creativity is explicitly required as part of a taught curriculum. Nonetheless collaboration is a common form of art practice in the world beyond art schools – increasingly so - and therefore it is not surprising to detect a subtle pressure upon art schools to address this trend.

Across numerous fields of creative endeavor - the sciences, the arts, business and industry - group work is commonplace. Teams are formed to tackle all kind of difficulties and issues. Teams invariably achieve a great deal more than lone individuals and teams also have the added benefit of strengthening social bonds and colleagueship (though not always with positive consequences). Art schools themselves are organized and run by teams: groups of staff with collective responsibility for the day-to-day support and assessment of students. Teams dominate - indeed govern - all walks of contemporary life.

Teamwork is also increasingly seen as a “life-skill” (educational jargon for something that is frequently needed throughout life and therefore – it is felt - should be widely promoted and taught) and features on many job descriptions across a vast range of careers as a required skill (though how it can be accurately judged from an interview is one of the biggest challenges of any recruitment process).

Setting up collaborations between art students would seem to be an excellent way to encourage the development of these highly valued skills and to maximize the opportunities for both learning and creative production. In practice though, whilst it might look good on paper, obliging art students to collaborate rarely results in anything other than the most hopelessly compromised work, not to mention a lot of disgruntled individuals whose chances of future collaboration are mightily diminished. Undoubtedly the pedagogic benefits of collaboration are potentially much broader than simply the creation of artworks, but if the overriding experience is that such artificially induced collaborations are counterproductive - indeed they invariably dissuade students from future collaboration - then we might justifiably question the pedagogic value of obliging students to collaborate.

In his influential 1762 treatise The Social Contract, Jean-Jacques Rousseau  stated that man must be “forced to be free”. But collaboration, like freedom, tastes sweetest when freely chosen.

Imaginative Minds

In the book Imaginative Minds (Roth 2009) Meme theorist Susan Blackmore presents her view that memes are the evolutionary source of human imagination. The concept of memes is the brainchild of Richard Dawkins who in 1976 coined the term to describe the cultural equivalent of genes. According to Blackmore memes are reproducible instances of culture (ideas, images, slogans, products etc) that, like genes, are propagated through imitation and which are subject to variations in the accuracy of imitation*. These variations frequently render memes useless or meaningless but in rare instances variation brings about alterations (adaptations) that are better suited to their environment and are therefore more likely to survive and to flourish or even supersede previous versions.

Meme theory peaked in popularity in 2002 but has since seen a steady decline in serious academic interest. A wider form of research into the Darwinian aspects of cultural development known as Dual Inheritance Theory continues to garner critical interest, nonetheless there remain pockets of activity in meme theory of which Susan Blackmore’s work is amongst the most prominent.

Blackmore’s contention is that there was a significant turning point in hominid evolution - though she provides no speculative period - when our ancestors became capable of imitation and turned from “gene machines into meme machines”. According to Blackmore, as imitation increased so too did the pressures upon genes to adapt to the resulting social, technical and environmental changes. Ultimately, those individuals and groups most well adapted to the imitation of advantageous behaviours, tool use etc were the most successful. Blackmore extends this theory by reference to what she calls “Memetic Drive”. Memetic drive is a process by which memes precipitate genetic adaptations that favour meme replication which in turn ramps up the co-evolutionary process in an evolutionary feedback loop.

Surprisingly, for an examination of the evolution of imagination, Blackmore’s essay makes very little direct reference to the imagination and when it does there is little doubt that Blackmore regards it as a minor contributor to memetic evolution. She writes:

“Neither biological evolution nor human creative imagination is a top-down process in which a clever conscious mind thinks up new ideas and puts them into effect; both are mindless processes in which new products emerge because old ones are copied with variation and selection.”

So, according to Blackmore, innovation is the result of “mindless” variation and selection and therefore to exercise a conscious mind in thinking up new ideas and putting them into effect is pointless. We are simply better off imitating old products with occasional mindless variation and selection. Innovation will emerge all by itself.

It seems strange to say it but Blackmore is right – in a very limited sense: mindless variation and selection would almost certainly result in gradual cultural evolution, just as has been the case with biological evolution, but what this theory fails to address is the question of how we appear to be witnessing an exponential memetic evolution that far outstrips the ability of genetic evolution to keep pace. It should also be noted that the logic of Blackmore’s theory leads to the ironic conclusion that it too is a mindless imitation of, in this case, Darwin himself:

“The value of the products of our imagination depends of course on the number, accuracy, and clearness of our impressions; on our judgment and taste in selecting or rejecting the involuntary combinations, and to a certain extent on our power of voluntarily combining them.” -Charles Darwin

In her concluding remarks Blackmore writes:

“Those of us who are most creative are those who are best at accurately copying and storing the memes we come across, recombining them in novel ways, and selecting appropriately from the myriad new combinations created.”

Far more valuable would have been an explanation of how our ancestors might have evolved this alleged ability to select appropriately from the myriad new combinations created, if indeed they ever did. Much of the evidence available to widespread scrutiny supports a contrary view, that in fact human beings are remarkably limited at selecting appropriately and that our insights and innovations are barely more common than would be expected from a purely random process of variation (I’ll come back to this in a moment). Ultimately Blackmore’s conclusions on this subject, and more widely on the nature and evolution of the imagination, can be summed up by another popular meme coined in this case by cartoonist Scott Adams in his 1996 book ‘The Dilbert Principle’:

“Creativity is allowing yourself to make mistakes. Art is knowing which ones to keep.”

Variation (making mistakes) and selection (knowing which ones to keep) are at the genetic – not to say the memetic - core of natural selection. But culture, driven by human agency, introduces a new element: purposeful or guided variation:

"People also occasionally introduce new variants and, because of their intelligence and knowledge, produce innovations that, unlike genetic mutations, are not random but cluster near useful solutions to various problems. This process of intelligent innovation is called guided variation.” - William Irons

Variation undoubtedly makes a significant contribution to cultural change but it would be a mistake to assume that the guiding, selection or knowledge of which variations to keep is something that humans are particularly skilled at. As another contributor to meme theory, Donald Brook, has pointed out; true memetic innovation (The “Art” in art, and all genuine innovation besides) cannot be purposefully marshaled:

“The acquisition of absolutely new memes cannot be counted in any way and exercise of skill. Epiphanies are not more less well-performed actions, at which their users can improve with practice.”

This point deserves emphasis. We cannot know, with any degree of certainty, where or how the next major innovation will emerge and nor can we sharpen our skills at discovering them. True innovations, like epiphanies and revelations are not the product of notable intentions to innovate.

"There may nevertheless be a context that is somehow more propitious than others; a context in which the acquisition of new memes can be eagerly awaited - and may even come to be expected - with a little more than normal optimism." (Brook, 2008)

What we can also do – and do very well - is improve upon newly selected innovations through the application of already accumulated knowledge and technical skill. It is at this level, the level of guided variation - not guided selection - that opportunities exist for exploiting innovation in ways that are significantly more rapid than would be the case if they were simply left to unguided evolution. Cultural evolution is far from mindless and imagination plays an important role in shaping its development.

*This is a common misconception amongst meme theorists. The product of a meme is not a meme, just as the product of a gene is not a gene. A rabbit is no more a gene than a slogan or product etc is a meme. As Brook (2008) points out, it only makes sense to view memes as the repeatable actions that are productive of cultural artifacts such as popular songs or catchphrases etc.