Throughout the majority of my career I’ve been fortunate to be in a position of a certain degree of creative control, working on novel solutions to problems. This path was at least somewhat self-determined, as I chose to pursue early stage startups where I could scratch this itch. Consequently, a question I often get asked is ‘how did you make that?’
I am first and foremost an intuitive product maker, preferring to feel things out rather than following a well-defined process. This post is an attempt to distill my intuitive method into something clearer than the often chaotic, freeform, and not-entirely-conscious set of things I deploy while working out a problem.
I say ‘working out a problem’ because as a product maker and entrepreneur I’m tasked with making things that are functional, that have a clear use to others and a business model attached. However, as you’ll see below, the inputs and process I use draw from both practical domains like business and user research and the wildly impractical world of artistic expression - specifically an over-reliance on exploring emotion and managing motivation. Over time, as I’ve matured, gained mastery in certain domains, and perhaps gotten a bit bored of making yet another CRUD UI, I’ve shifted my perspective to pursue problems where I can engage both practical and artistic sensibilities. I haven’t yet determined how helpful or not this is in my career, but it does keep things interesting.
Finally, I hesitate to write this as a guide for anybody else, because I find most advice to be too prescriptive or confident in its broader applicability. I’d like to approach this with more humility, so I’ll only deign to write in the second person (“you” / “we”) for things that I’m pretty sure are more broadly applicable. In all other cases, I’ll stick to writing in the first person.
A Quick Note on Making Things
Making anything is the product of motivations, experiences, and skills collected, cultivated, and transformed over time into your own personal approach.
Many of these are additive, where you get objectively better at your work as you gain wisdom and learn the underlying patterns of an industry or function.
Some of these simply change as you grow as a person, like an artist that enters a new life phase or has a particularly profound experience and changes the focus of their expression.
And every once in a while these can make you worse off, as you get less sharp or have traumatic experiences that block your ability to see certain approaches to problems.
This post is an exploration of each of these inputs. I’ll start with motivations, as these are the root of all work, and guide the deployment of energies and focus.
The following motivations are either part of my personality or things I try to cultivate in order to do better work. Unfortunately I have no idea how to explain how to cultivate motivations, other than to be curious, open-minded, self-aware, and caffeinated. The following are what motivate my output:
Raw Creation - the desire to make and see something exist that didn’t before. This excites me to no end, and is further fueled by learning new skills / gaining new powers / seeing new opportunities.
Evocation - the desire to make things compelling, beautiful, and sublime; to tap into something deeper. This has always been of interest to me and is why I started my career in video game design, where the goal is to drive a player’s emotional state. Evocation is an important motivation if you are exploring the boundaries of the functional and the artistic in your work, as I attempt to do in mine.
Cleanliness - the desire to make things consistent and clean for its own sake. I grew up in an artistic household that cultivated a sharp eye for perfections and imperfections, which seems to have developed in me a (mostly) productive from of OCD. Though as motivating as this is, it can sometimes be distracting. I find it best deployed midway through the messy creative process, when it’s time to focus some after flaring out.
Problem solving - the desire to really nail the problem the user has. I almost wrote this as empathy; to deeply understand and feel someone’s problems, but that alone is not satisfying enough. I want to understand and solve things. A great solution feels like a lego brick that slots perfectly into a gap where a problem is.
Novelty - the desire to find a new insight into a problem or new solution to a problem. I love it when in the course of creating I stumble upon a different way to do things, and just the possibility of stumbling on these moments is very motivating.
Meaning - the desire to have positive impact on others. I will only be satisfied that I’m doing something meaningful if it mixes the highly individual emotion of empathy and the intellectual appreciation of doing things at scale, so that I know my work has maximal impact. This is also what drives me away from a particular strain of the artistic persona that is excessively navel-gazing. I leave it to my weird artistic side hobbies to process my own emotion, and keep my main work focused on maximum positive impact to others.
Fun - the desire to enjoy the moment and the journey. I’m often jumping or skipping around the office, making a passionate case for a particular course of action, or just basking in the afterglow of a particular insight or possibility. I try to cultivate this child-like motivation, because the null hypothesis of adulthood is that it is not fun, and I’ve already had my fill of several very extended periods of un-fun in my life.
Expression - the desire to pull complex representations out of myself in an attempt to be understood. In some ways this motivation is a motivation of exclusion - I am really motivated to not be misunderstood. I often find myself in complex or nuanced problem spaces where the truly sublime and beautiful solutions are not always obvious at first blush. I want people to see these ideas and creations for all they’re worth.
Flex - the desire to show off a bit. No list of motivations is complete without at least some degree of pride in work and going a bit above-and-beyond just because you can. Most of my motivation is intrinsic, but sometimes to get proper attribution I have to make myself stand out a bit.
Instead of focusing on my own variety of experiences which may or may not have any relevance or replicability for anyone else, I’d like to focus on an approach I take with experiences: Strategic Ignorance.
This is sometimes called “Beginner’s Mind”, but I find that to be a bit too koan-y and philosophical, rather than a more tangible tool to deploy. It’s also sometimes called “First Principles” but that suggests a more process-driven approach and doesn’t address the importance of the psychological state of naïveté. As I am an intuitive creator, I concern myself first with psychological state.
The basis of strategic ignorance is about pursuing something without the burden and limitations of other’s thinking. Once you learn something you’ll know it for the rest of your life, but in doing so you can never return to the state of not knowing again. Ignorance (on a given topic) is therefore a useful resource at the individual-level, despite it being in quite troublesome at the population-level. And there is a strategy to using this ignorance to build great product.
The Risk of Learning Things
In the context of product and design, spending a lot of time reading about how others frame/define problems and looking at competitor’s products can suppress creative output, especially novel output, and especially in complex domains. We all have a strong bias to over-value anything that provides framing or definition to the unknown, and we’re least sure of ourselves when we are presented with a big domain that lots of other smart people have worked in and that we know we know nothing about.
This means the risk of being negatively influenced by other’s thinking is high. Simply being presented with visible solutions, with clear lists of features and tangible UIs, reinforces any ideas we have that match with the solutions we see, and immediately begin to push out or extinguish non-conforming ideas, hunches, and possibilities. Suddenly our solution space narrows and everything else is shoved over into the subconscious or surrounded with doubt, making non-conforming ideas more difficult to discuss or give proper consideration to. This is especially true in team contexts where politics and risk management take over, but it happens first in ourselves.
An Approach to Ignorance
When I approach new domains and hear of new problems where I am rather unfamiliar with the typical way of doing things, there is always a decision point I have to make about whether to utilize strategic ignorance or not.
Strategic ignorance is a slower process used specifically to root out upside potential in a given domain. I only deploy when I want to have the opportunity to make something wholly new. If I need to solve a problem in relatively well-understood and limited domain, I instead go immediately to a more standard problem solving process of getting a handle on the problem and looking at others solutions.
When I deploy strategic ignorance
• When I think the problem is meaty and complex enough that there may be novel ways to solve it.
• When I want to focus innovation in a particular area
• Only after I understand my own ignorance. Knowing absolutely nothing is too early to deploy strategic ignorance - I need to at least have some handle on a problem.
How to deploy strategic ignorance
• I start by collecting basic info on the problem I'm solving, coming up with my own hunches, ideas, and opinions.
• I frequently bring in ideas from other domains outside the one I'm in as a point of comparison.
• I check in with myself pretty frequently to make sure this approach is valid. If I discover that the problem looks a lot like another problem I've seen and that has clear solutions, I will abandon the strategic ignorance approach and decide to solve it that way.
• I also check in to determine the point at which I think other’s thinking is going to add something, rather than narrow my viewport. This typically happens when I've either a) setttled on one solution, b) have a few solutions where I don't know which to pick, or c) stuck or out of ideas.
Benefits of strategic ignorance
• Avoid analysis paralysis - I'm researching only when I get stuck
• Opportunity for unconventional, novel, and potentially better solutions
• Builds deeper understanding of a domain
Drawbacks of strategic ignorance
• It takes longer
• It leads you down useless paths you will regret spending so much time on
• It can yield absolutely nothing
My Experiences Using Strategic Ignorance
In my two most recent jobs, I've had the benefit of being an outsider lacking in the typical preconceptions of those in the field, and I was able to deploy strategic ignorance to arrive at solutions others before had not:
OneSignal is a tool for developers to send push notifications via their apps or websites. As head of product and design, I was responsible for the dashboard UI/UX and all related documentation which over a half million developers use. This was initially a big challenge as I am not a software engineer nor a growth marketer, but ultimately my outsider perspective and use of strategic ignorance drove us in a direction that was quite different than others in the market.
Rather than reading a bunch of tutorials and trying to learn how to be a (not good) engineer so that I could just struggle the same way that our customers did, I used my ignorance to root out gaps and assumptions big and small in how we explained and presented functionality in our dashboard and documentation. Since our users were nowhere near uniformly skilled nor as talented as the internal OneSignal team (many users were very new developers, and the majority were not English native speakers) there were tons of places where they got tripped up.
This perspective shift led to a much larger effort of redesigning the entire dashboard experience around an embedded guide and supporting documentation. Concepts were clarified and language standardized, gaps in each implementation step were filled in, documentation was restructured to separate concepts from functionality from implementation, and the distinction between the tool (dashboard) and how to use it (documentation) was minimized.
Had I been an engineer, or had I just looked at other similar products on the market, I would have likely had the same blinders that the rest of the team had around simple concepts, similar-but-not-identical synonyms, 'obvious' steps, etc, and I would have never pursued the degree of changes that I did.
Mindstrong is a mental health services company that monitors the conditions of patients with severe mental illness and provides targeted therapy-like interventions. As a product and design consultant, I was tasked with figuring out these therapy-like interventions and how a product can best facilitate them, including how this is documented. Instead of looking to the traditional patterns of existing electronic medical records or online therapy delivery, I used strategic ignorance to get my own sense for the problem and novel ways to build solutions, and only thereafter looked around at what others had built.
Although I can't talk much about the solutions we arrived at, it was in large part possible specifically because I chose not to do a deep dive into other products or spent much time talking to people about those products pros and cons. Instead, the solution reconceptualizes the whole approach to how therapy delivery is delivered and documented. It integrates and standardizes those to lower the learning curve for therapists, reduce administrative burden, and create a platform for continuous improvement.
When all else fails, fall back on your own personal superpowers. Everyone has their own comparative advantage, things they can do more easily than others. These are mine:
Design - To borrow a turn of phrase, in the land of the abstract whoever can make things concrete is king. I've been designing UI since I was a pre-teen and can make something seem real enough to start to ask interesting questions, to move beyond abstract discussion. I can also work closely with other designers to bring out their best work and get at the heart of the problem. Deep design skill means discovering subtler, more novel, and more comprehensive long term opportunities.
Sensitivity - I'm quite sensitive to when a product or interaction feels off. This could be called detail-oriented, but the place it comes from is emotion, which requires unpacking before the details emerge. A quote I love is "The reasonable man adapts himself to the world: the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man." This sums up the sensitivity superpower well - an inability to accept and ignore bad product decisions, because their flaws are an affront to my sensibilities.
Organizing - I'm a huge nerd in when it comes to capturing and organizing ideas. This superpower helps me navigate novel domains because I can make my own categories and identify the underlying structure of the problem. This also creates a motivation that breaks through boring work.
Connections - I've worked in many different industries and find myself consuming information on just about any subject, so another superpower of mine is to draw from these disparate places to make connections and figure out how solutions in one domain apply to another.
This post roughly captures the motivations, experiences, and skills I rely on to create product. I'm not sure how useful this is to others, but in answering this question, I gained some personal insight into my process. Maybe you should try it too!
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