The Future

“[The fragilista] defaults to thinking that what he doesn’t see is not there, or what he does not understand does not exist. At the core, he tends to mistake the unknown for the nonexistent.” - Nassim Taleb 

“The third condition, unknowing, means acknowledging the limitations of what we can know at all, and treating with respect those aspects of the world which are beyond our ken, rather than seeking to ignore or erase them.” - James Bridle 

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Jacques Derrida, the late French philosopher, distinguished the future in two ways. That which will be “predictable, programmed, scheduled, foreseeable,” and the future to come, what he called l’avenir, and “whose arrival is totally unexpected.” Beyond the future that will be is the real future, Derrida argued, unforeseeable and without anticipation or foreknowledge save the sense that this is the Other to come. 

Compare l’avenir to Ray Dalio, whose company, Bridgewater, was one of the first investment consultancies to computationally model market futures to develop trading strategies. “As I wrote in a December 1981 article, I believed (and still believe) that ‘theoretically … if there was a computer that could hold all of the world’s facts and if it was perfectly programmed to mathematically express all of the relationships between all of the world’s parts, the future could be perfectly foretold.’” 

The synthesis to strike our third point of view on the future is delivered by Nassim Taleb. “Man-made complex systems tend to develop cascades and runaway chains of reactions that decrease, even eliminate, predictability and cause outsized events. So the modern world may be increasing in technological knowledge, but, paradoxically, it is making things a lot more unpredictable. Now for reasons that have to do with the increase of the artificial, the move away from ancestral and natural models, and the loss in robustness owing to complications in the design of everything, the role of Black Swans is increasing.” 

History, for Taleb, and therefore the future, is shaped by the improbable. The “Black Swan” is an outlier of an event where nothing in the past convincingly points to its future possibility, and whose arrival carries massive impact, changing everything, and is only rationalized after the fact in the stories we tell, which then, in present tense, make the once-unknowable catalysm appear obvious and inevitable, when really we’re always blind to the randomnness that eventually intrudes as “necessary” to the development of “history, technology, knowledge, everything.” 

Brand strategy is—for all its math and data, pomp and circumstance—just a decision that a brand makes about its direction and thus a judgment about the future. It’s a wager, much like an investment in the stock market. Many brands position themselves for the future that will be, rather than for the Other to come, and without the rigor and humility of Dalio’s meritocratic, first-principles objectivity that he deployed to shape culture at Bridgewater. “Rather than argue about our conclusions, my partners and I would argue about our different decision-making criteria. Then we resolved our disagreements by testing the criteria objectively. The rapidly expanding power of computers during that era was like a constant stream of gifts from the gods to us.” 

I’m guilty of researching and writing a brand’s strategy, positioning, and values as if the future is linear, an extension of today’s preferences, with just enough trend data to make it look evolved. I assumed tomorrow will be shaped by what’s programmed and already proven to work. Pure fragility. 

Brands that endure are structured to expect volatility and even, if rigorously framed, thrive in l’avenir, with an evolving but articulated strategy for how to behave, communicate, and adapt when the maps break. 

Fragility

Fragile brand positions are modeled on stability or transient conditions, aligning with, say, trends over conviction, making them especially vulnerable to market shifts, platform volatility, and replication from competitors. 

Casper was built during the golden era of Facebook ads and DTC virality. The brand scaled quickly on paid acquisition and soft lifestyle storytelling, but lacked repeat purchase behavior, profitability, or real differentiation. When CAC spiked and the category crowded, Casper couldn’t hold its ground. The IPO underperformed by 50%, the business model broke, and, not long after, the company was taken private. A few takeaways:

• Depended on DTC unit economics remaining viable (cheap CAC, millennial loyalty).

• Rose on the tailwinds of the “mattress-in-a-box” boom and the golden age of Facebook ads.

• Framed itself as a lifestyle brand, but lacked a durable philosophy beyond “better sleep.”

• Vulnerable to shifts and competitive pressures as CAC rose, repeat rates were low, and Amazon and Purple outperformed on margin and logistics

Quibi launched with $1.75B in funding, a Hollywood pedigree, and a big bet: that people wanted premium, short-form, mobile-only content consumed in life’s in-between moments. But the launch collided with the pandemic, which erased commutes and casual downtime. TikTok, YouTube, and Instagram already owned mobile attention, and they were free, participatory, and culturally fluent. Six months later, Quibi was gone. 

• Assumed a future where users would pay for tightly produced short-form video consumed during daily micro-breaks.

• Over-indexed on tech optimism and built for behaviors that proved ultimately ephemeral (e.g., commute-time entertainment).

• Marketed itself as revolutionary, but lacked a core belief beyond format; there was no emotional or cultural gravity.

• The pandemic led to shifts in behavior, erasing use cases and redirecting attention to user-generated, shareable, and socially native platforms. 

Robustness 

Robust brand positions are designed to withstand volatility with strong category fortifications. These brands grow large and dominate through investment, M&A, and consistent, heavily funded advertising. They become, over time, legacies. And legacies grow, over time, stagnant. 

Burdened by bureaucracy and corporate bloat, they stop taking chances. They tinker at the margins. And they begin, over time, to atrophy and decay. Think of Nike, Adobe, and Oracle. Consistent. Dominate. And saturated with a prosperity ripe for disruption. 

Antifragility 

Antifragle brand positions strengthen under stress because, like Bridgewater, they’re commonly established on meaning and principles instead of market trends. These companies interpret change through a consistent lens and can assimilate l’avenir without losing coherence. 

Figma’s early thesis as “a real-time, multiplayer design in the browser” was a structural commitment to open, collaborative problem-solving. As distributed teams and cross-functional workflows became the norm, Figma’s core belief system allowed it to expand naturally into new use cases, like FigJam. Each market shift didn’t require a brand reinvention, but instead added meaning to the existing one. A positioning that metabolizes shifts in organizational culture and workflows into growth.

Notion built its brand around a syntax of flexibility.  Docs, databases, wikis, and calendars, all in one space. But Notion’s real power lies in the user’s ability to shape the platform to their needs. That use-agnosticism created a platform that adapts rather than dictates. As teams change, Notion expands with them, often starting bottom-up and scaling across departments. The brand grows stronger as new use cases emerge.

From the start, Snowflake rejected the idea that data lived in silos or single clouds. It positioned itself not just as a faster warehouse, but as multi-cloud, collaborative, and secure by design. That framing anticipated the future of governed data sharing across companies and platforms. So when AI, zero-ETL architectures, and app frameworks started to reshape data infrastructure, Snowflake absorbed the shift. Its brand became more coherent as the world caught up to its vision.

Canva began as a prosumer tool: clean, accessible, and social. But in 2021, it formalized its enterprise strategy, launching features like Brand Kits, admin controls, and security protocols—a reframing of its core principle. Canva scaled accessibility, shifting from “anyone can design” to “everyone can stay on-brand,” and thus turned the decentralization of design into a defensible advantage. 

Giving Up the Ghost of Prediction 

Brand strategy is a decision we make about the future. The trick is to hold two things in mind. One, a decision must be made. Two, whatever we think about the future is not what the future will be. And thus, a good brand decision is based, at best, on what might happen rather than what will. 

Or, as Taleb puts it, “to make a decision you need to focus on the consequences (which you can know) rather than the probability (which you can’t know).” 

And if you focus on consequences, you begin to think differently. About what you believe, why you believe it, and how that belief might hold when the Other we can never name finally arrives.