Images and sound, which respond to our touch, create the feeling that we are interacting with something that is actually there. We talk about going to a web site. We tap buttons, open folders, and select choices from menus, and aren’t bothered by the inconsistency with real world analogs as we drag windows and surf the web.


I don’t know the story behind this image sent to me via Twitter by “Brett” — is it an original in drawing or native digital creation? or were 140 characters too short for attribution?

There is a strength in the Tim Berners-Lee vision of the web as “always a little bit broken” allowing for us to post these disconnected fragments which cause images and video to act like language, spread virally and owned by no one, in direct contradiction to our copyright laws. I also feel a loss that there was never widespread adoption of the Ted Nelson model that he envisioned when he coined the word “hypertext” — every link could let you dive into its source and references were a “transclusion” — instead of copying, everything would be by reference.

We need to intentionally draw real world connections in this strange, fictional world of software we create. Even the so-called users of software create this world of code and data that we inhabit.

An epic win is an extraordinary outcome that feels impossible, until it happens. What does it take to imagine that epic win? What needs to happen so that we can believe that it is possible, and in creating that belief, we create the space for it to actually happen.


Many steps are hard, and many have significant risk of failure. It is so unlikely that enough things would go right that you will achieve that goal. You try things and sometimes you fail, and sometimes you win, and every win moves you closer to that goal.

When we believe something is possible and desirable, yet uncertain, we want it more. It explains why we like gambling, and (mostly) don’t like to work even though we know we’ll get paid for it. There’s quite a bit of fascinating research that dives into the details. I recently read a really nice explanation:

…making the unknown known — i.e., figuring out what is in a wrapped package or finding out which reward one has earned — is a positive experience. Because people are excited to find out what they can actually get, working for an uncertain reward makes the whole situation more like a game and less like work.

ChicagoBooth report on The Motivating-Uncertainty Effect

It is the uncertainty which makes the epic win so appealing. Persisting through that experience of uncertainty seems to be its own reward. Our human brains release dopamine at these moments — this chemical does not only bring us lovely happy feelings, it’s also correlated with increasing our ability to learn. Of course, we have to win around half of the time, on average, for it to continue to be fun.


In retrospect, we can see a complex feat that has been reduced to a thousand micro-skills, where a human being has learned those skills and applied them in such a focused way that the impossible has not only become possible, it is has become certain.

Witnessing an epic win expands our ideas about our own limits. We can see that another human did this thing that we never imagined was possible.

There is a joy in mastery. We reach a certain level of skill where we can be incredibly good, yet in practicing that skill we become better. Interesting to look at the definition of epic win, as evidenced by epic win video compilations (there are over 50 of these on YouTube) and parkour, Almost all of the videos show solo wins — incredible acts by individuals. I believe the more epic wins are those where we work with other humans to do more than we each could make possible, whether it be an organized team where you know all of the people, or a crowd aligned to a purpose mediated by software or seemingly unconnected individuals who find themselves part of a kurass.

One of my best decisions as CEO of Blazing Cloud was to set a policy that any employee was authorized to spend up to $25 on the purchase of something they needed for their work.

This was intended for things like office supplies and notebooks. Also people were encouraged to buy things for the whele office, not just for themselves when they saw a need. This meant that it wasn’t just the office manager’s job to make sure we had whatever anyone decided they needed. We were a small team and people would look out for each other.

tyraI think someone may have actually asked me about the purchase of a giant inflatable dinosaur, but it was a pretty independent action from the team from my perspective. I arrived back from a ski trip to a new member of the Blazing Cloud family. She was named Tyra, and she would hang out near the entrance or above a conference room. She celebrated Pride with us with her own little rainbow flag and even earned a mention in an NPR story.

She was a part of the Blazing Cloud culture. I used to say that “Blazing Cloud was optimized for fun.” I was often unsuccessful in achieving that goal, but I’m proud of a few things I did that I think helped foster a spirit of joy and delight amongst the creative and talented people who joined me in making that small company happen.

Culture is What You Do

Most people don’t like making rules, but rules can be liberating. It was liberating to have a corporate policy about how money is spent and what does not need approval, followed by examples of people collaborating on shared purchases and individuals buying a favorite (expensive) notebook or pen. I believe that craftspeople need to have the best tools. I don’t need to mediate what kind of pen someone uses, and having them feel a sense of pleasure in their work as their pen slides across paper is priceless.

I don’t have any research to back it up, but I believe that there is a psychology of abundance — this feeling of abundance sparks creativity. I believe that large monitors make us smarter. We need space to think and an endless supply of post-it notes. We need to be surrounded by smart people who value difference — different ideas, different customs, different skills. I don’t care who you are at home, if you show up and are kind to your co-workers, yet don’t back down from speaking truth when you disagree. There’s a whole set of values that I hold and a belief system about what makes a great team, and the seemingly little decisions create an environment to make that happen.

All of the Blazing Cloud culture might not be directly related to that giant inflatable dinosaur, but having rules and precedent that favor independent action and individual choice can foster creative inspiration.