Stewart Butterfield believes that building a great product starts at the tilt of an umbrella.

I discovered the meaning of this when I listened to the co-founder of Slack recall on a podcast that in the early days of the company, he and the (then) head of product design were walking on a narrow pavement in Vancouver when, “as it does in Vancouver”…

It started to rain.

Neither of them had umbrellas.

But as the more prepared Vancouverites began to walk towards them with their umbrellas, Butterfield observed something that fascinated him.

Now everyone knows that any good umbrella has only two jobs: it has to keep you dry, and its metal pointy-ends have to stick out directly at eye-level to those around you.

But what Butterfield observed was that most people seemed to forget the latter fact, and would end up forcing the pair to step off the pavement to avoid going blind.

Being the positive souls that they were, Butterfield and his colleague took turns guessing whether the next person in their game of chicken would tilt their umbrella out of the way so the pair could pass without being shunted off the pavement.

In the end, they reckoned only one in three did.

But what was going on with the other two-thirds?

Why did they not tilt their umbrellas?

Butterfield suspected that this had to be for one of three reasons.

The first was that for some people, the opportunity to exert power by maintaining umbrella stiffness was too good to pass up. For them, the game of chicken was real — and they were looking to win.

The second: the umbrella wielder saw the impending collision they were about to cause, but could not, for the life of them, think of a way to stop it.

And the third reason was that perhaps the person had no such awareness — it had never even occurred to them that they, lethal umbrella in hand, could be the cause of a problem.

Well, as cynical as it sounds, Butterfield came to feel that this observation applied more broadly; that most people are oblivious to the problems others face—and when they do notice them, they either can’t come up with a solution or choose to waste the chance to have a positive impact for the small satisfaction of feeling powerful.

Interestingly, this anecdote came in response to the question of how someone building a product could develop taste—implying that taste was an edge.

And whilst Butterfield agreed with that notion, he was more certain that the more reliable advantage for product builders came from being observant of other people’s problems and finding small ways to tilt your umbrella.

Echoing Bezos’ infamous line, ‘your margin is my opportunity,’ Butterfield notes his alternate mantra: “Tilting our umbrella is our opportunity”.

Naturally, this seems the opportune moment to discuss the meaning of life.

Do you have a moment to talk about our lord and saviour Bret Victor?

I believe that I am an incredibly lucky person, in that on most days, joy and optimism both seem to come naturally to me, leaving me uninterrupted by doubt to do what I think is right, and faith that what I do matters.

But even I, mortal as anyone, experience days you could define as ‘existential’, where I feel I’ve been pulled out of the carriage and off the train I thought I’d always have a seat on.

And as I demand that the train conductor let me back on, he asks not for a ticket, but a purpose.

Some have told me that the purpose of living is in the name: to live.

But somehow I’ve never found that to be satisfying enough to sustain me—is it perhaps too directionless and passive to give me that meaningful sense of drive?

And so on those harder days, I’ve usually looked to who I can be in order to align my actions—to rewrite the journal entry of my life titled: ‘Identity’, to find the calm needed to return to normalcy.

Maybe this comes from the memetic compulsion I heard Founders Podcast’s David Senra articulate when he expressed that the best founders were those who made themselves “easy to interface with”—the idea that, by labelling your work, and even yourself, in a way that can be easily understood, you can move through life more smoothly.

And this makes sense. Abstract it to the business-level, and you quickly see that of course you’re going to get quicker sales by being clearer about the problem you solve.

Unless you’re selling the iPad. No one understands what the iPad solves.

The only problem is that there’s something awfully limiting about your identity being your job title. I wouldn’t be the first to say that.

Whilst moving through the world, saying “I’m a Product Designer” makes it much easier for society to hire, fire, or maybe even admire me, it’s also not really the whole garden of who I am.

At least it’ll earn me a living.

Wait… but will it, you know, earn me a living sustainably?

Even that title, “Product Designer” is relatively new: popularised in the 2010s¹, and often used as an umbrella over what used to be split into “UX Designer” and “UI Designer”—and, earlier still, roles like “Information Architect” and “Web Designer.”²

Which means the label won’t last. I’ll rewrite it again when the world changes again. AI, I’m looking at you.

And so this is where I need someone much wiser than me to intervene, to keep this train of thought from riding into the abyss.

Enter Bret Victor.

Victor once held the title ‘Human-Interface Inventor’ at Apple, which is interesting because it’s a title I’ve never heard of before—

—But I’m fairly sure he’d be disappointed that I’ve introduced him with a label at all.

I say this because, over Christmas, I stumbled on an absolutely wonderful talk he gave in 2012.

It’s called ‘Inventing on Principle’, which starts by him presenting a collection of the engineering outputs he had crafted that demonstrated his desire to enact what he deemed as his principle. His principle for inventing.

To him, this was the principle that: “creators need an immediate connection to what they’re creating.”

This principle influenced every micro-decision within his projects.

From giving engineers a live-preview of their codebase that reacts in real-time to code changes, to providing a scrubbing interaction to dial up and down every numeric value; Victor gave users of the tools he built to step aside from working in the code blindly or do mental simulations to predict the outcome of their creation, and instead, be fascilitated to work in a way that allowed them to converge on what feels right purely artistically, by receiving instant feedback.

Again, Victor’s principle was that “creators need an immediate connection to what they’re creating.”

And he felt strongly about this because he observed that “without an immediate connection, many great inventions and theories will not emerge,” that “so much of art, so much of creation is discovery, and you can’t discover anything if you can’t see what you’re doing.”

This conviction meant that to Victor, building something that did not commit to enact his principle: violated it, and was wrong.

Wrong, not in the sense of having made a mistake, but in the moral sense.

This was his duty. And his work was a vessel to fulfil that duty.

Victor then spends the rest of his talk highlighting inventors such as Larry Tesler, who pioneered the concept of software user studies whilst working at Xerox PARC, and observed that people’s inability to become fluent with software of the mid ’70s lay in the hands of the then interfaces which were being designed around modes.

So if you were in a text editor for instance, you couldn’t just type and have what you were wanting to type just appear on screen — no, you would be in ‘command mode’, and if you wanted to insert text, you’d first have to press ‘I’, which would take you into ‘insert mode’, before then needing to exit the mode to do anything with it. If you wanted to move the text, for instance, you’d need to hit ‘M’ to go into ‘Move mode’.

To Tesler, this was a wrong.

It was a complexity, a barrier, that prevented people from ever truly becoming the native computer users that was necessary to unlock new ways of thinking and living.

And thus, “no modes” became the monocle that Tesler invented with: eventually inventing ‘Gypsy’, the text editor that formed the behaviour around text editing “as we know it today”.

Typing produced words on the screen. To select text, Tesler invented the ‘click and drag’ interaction. Even this idea of ‘drag’ was spawned from this invention. To move text around, he invented the commands Cut, Copy, and Paste. And of course, all of this required… no modes.

Victor also outlines the leading principles and defining ‘inventions’ (which are really just the manifestations of changes made) of the likes of Richard Stallman, Doug Engelbart, and Alan Kay.

Each of these people, as Victor notes, “dedicated their lives to fighting for a particular ideal with a very clear sense of right and wrong.” They were engineers, but lived like activists.

But where social activists “fight for their cause by organizing. Technologists fight for their cause by inventing.”

Victor’s empowering speech reminds us that no matter how small our domain of current skill may feel in comparison to what was seemingly required to bring about the great movements we learn about in history, it’s actually having first defined a principle that will guide us to finding the skills, tools, and ideas necessary to bring about one ourselves.

And that, better still, we likely have many opportune moments where we can enact this principle already.

And to me, this might just be the most meaningful (and actionable) way to live that I’ve ever heard of so far.

I’m reminded here of a sign you might see in common public spaces, like that of a bathroom or changing room. One that might advise us: Leave this place better than you found it.

Or like this one I found online, which I tweaked slightly:

If we return to the story Stewart Butterfield told, the one where he had encountered his own principle on the pavement that one rainy day—

You can see how what Butterfield had really stumbled across was a purpose.

A meaning to his days.

And due to the nature of his having such influence over the company, even choosing to tell the story of the umbrella in the onboarding process for every new employee, Butterfield had given the entirety of Slack a principle to enact in all that they did.

And you can see this having played out.

‘Tilt your umbrella’, a slogan that featured on internal company merchandise, manifested through empathetic and considered product design, with features such as the “Shouty Rooster”—which showed the illustration of (you guessed it) a rooster shouting, alongside a message which informed the sender of the message that by tagging ‘@everyone’, they were possibly going to notify ‘147 people in 8 time zones’ before asking for user’s explicit desire to do so.

This feature is particularly poignant because it not only enacted the umbrella tilt by acknowledging and protecting those who would have preferred not to be presented with every possible message that could abuse the ‘@everyone’ feature, but it also asked of their users to consider tilting their umbrella also. Both enacting and inspiring empathy with the same feature—a feature that, notably, runs counter to the more widely adopted design mantra across software builders to always remove friction.

After having read Tom Alder’s wonderful breakdown of the company's strategy, I realised that Slack’s acquisitions of companies like Screenhero, which allowed Slack to bring screen sharing and video collaboration into the product, as well as Rimeto, which made finding the right people, especially within larger organisations, particularly painless for Slack users, demonstrated that ‘Tilt Your Umbrella’ wasn’t just a principle that stayed within the confines of the product team—it sat within the company’s collective consciousness and offered everyone who spent their days in its’ office, a principle they could all believe in, fight for, and enact each day.

And as a result, Slack became an irreplaceable tool, one that would be mourned by the individual who moved from one organisation that used it, to one that didn’t.

Please note, I’m not telling you that tilting the umbrella is a perfect principle to invent from. You might even argue that Butterfield’s principle, though tasteful and empathetic, maintains the larger goal of constructing a systematised, well-oiled vehicle for capital gain—and thus, by mentioning it, it dilutes the pure nature of opting to right a social wrong that the likes that Bret Victor mentioned in his talk.

In fact, Bret Victor himself presents his approach to life as an alternative to that of the problem-solver— the archetype most fulfilled by the entrepreneur, or the academic. The one who picks and focuses their efforts entirely on a field, or set of problems, optimising their outputs to match the needs of their uncovered set of opportunities.

Because to Victor, “when I see a violation of (my) principle, I don’t think of that as an opportunity. When I see creators constrained by their tools, their ideas compromised, I don’t say: Oh good, an opportunity to make a product. An opportunity to start a business. Or an opportunity to do research or contribute to a field. I’m not excited by finding a problem to solve. I’m not in this for the joy of making things. Ideas are very precious to me. And when I see ideas dying, it hurts. I see a tragedy. To me it feels like a moral wrong, it feels like an injustice. And if I think there’s anything I can do about it, I feel it’s my responsibility to do so. Not opportunity, but responsibility.”

That said, I still started this blog post with Butterfield’s principle because, for me, at least, learning about it began to highlight the alternative ways in which we can discover things to work on.

By stumbling on this, I was propelled out of my own existentialism, and it gave me a deeper, and simultaneously more freeing approach than I’d ever given myself before.

That the job title, skill set, or problem area matters less when I might have something more important to make right.

So whilst all of us can learn to tilt our umbrellas, the broader question is, what is your unifying principle?

What is the unifying principle that captures the wrong you feel only you have noticed and believe can be put right?

And will you permit yourself to express that which might most sustainably get you out of bed in the morning, despite it not being directly tied to a direction you’ve seen play out in a montetsiable fashion before?

I will.

Because I’ve found my principle now, and perhaps I’ll write about that too one day.

But until then, I’ll leave you with Bret Victor’s own words:

“There are many ways to live your life. That’s maybe the most important thing you can realise in your life, is that every aspect of your life is a choice. But there are default choices. You can choose to sleepwalk through your life and accept the path that’s been laid out for you. You can choose to accept the world as it is. But you don’t have to. If there is something in the world you feel is a wrong and you have a vision for what a better world could be, you can find your guiding principle. And you can fight for a cause.”