Plan to Pivot

An essay by Austin Knight

Summary

Some of the most iconic products in history started as something else entirely. Slack began as a chat tool for a failed video game. Twitter was a side project inside a dying podcasting platform. Instagram emerged from a bloated check-in app. The world’s most popular smartphone chip architecture came from a forgotten British computer company. And frozen peas? They owe their existence to an Arctic fishing expedition.

Great products rarely arrive fully formed. They’re discovered, hidden inside something that didn’t work. Teams that succeed aren’t just persistent. They notice when something unexpected works and have the discipline (and conviction) to follow it. Success doesn’t come from sticking to the roadmap. It comes from knowing when to change it.

Slack wasn’t supposed to exist. In 2011, Stewart Butterfield and his team at Tiny Speck were building Glitch, a whimsical multiplayer online game. It had style, charm, and a devoted community. But not product-market fit. The game was shut down in 2012.

While building Glitch, the team had created an internal chat system to coordinate their work. It was fast, searchable, and met their needs better than anything else on the market. After Glitch failed, they looked at that chat tool and realized it might actually be better than the game they had tried to ship. That internal tool became Slack.

The product launched publicly in 2013. Within two years, it was one of the fastest-growing B2B software products in history. In 2021, Salesforce acquired it for $27.7 billion.

That kind of turnaround isn’t just a lucky break. It’s a reflection of leadership that knows how to read the room, see what's interesting to people, and most importantly, walk away from what had already been built. Pivoting from a video game to enterprise software isn't a minor course correction. I can only imagine how tense and entertaining some of those internal conversations must have been at the time. But it worked.

What Is a Pivot?

A pivot isn’t a flinch, or a surrender, or an admission of failure. It’s strategy. Maybe a bit improvised at times, but a strategy nonetheless.

At its core, a pivot is a shift in direction based on new evidence. A feature becomes the product, a side project becomes the business, a failure becomes the foundation for something better.

Good pivots don’t start from scratch. They start with something that’s already working (usually something unintended). That’s the key: pivots aren’t guesses. They’re observations followed by bold decisions.

CASE STUDY

Slack & Flickr: Two Pivots, One Entrepreneur

Butterfield’s story is remarkable because he did it twice.

Before Slack, there was Flickr. In 2002, his team was working on Game Neverending. Once again, the game fizzled. But inside it was a lightweight photo-sharing feature that was getting some real traction. That internal tool was spun out into its own product in 2004. Flickr became one of the first major social photo platforms and was acquired by Yahoo in 2005 for $25 million (that was a huge exit at the time).

Two games. Two internal tools. Two global products.

To me, this is a sign of exceptional instinct. Butterfield empowred his team to build the tools they needed, then paid attention to what actually worked, and then wasn’t afraid to throw away the original plan when a better one emerged.

That's some serious conviction, courage, and even clarity of mind. A pivot like that means abandoning months or years of work, facing uncertain markets, and risking your team’s trust. Most leaders just aren’t willing to do that. Butterfield was, twice.

CASE STUDY

Twitter: From Podcasting to Microblogging

In 2005, Odeo was a podcasting startup led by Evan Williams. Then Apple added podcasting to iTunes, and obliterated Odeo’s reason to exist. Rather than wind things down, the team held a hackathon to explore new ideas. One of them, prototyped by Jack Dorsey, was a simple status-sharing tool via SMS. Internally, it clicked. People used it constantly. That tool became Twitter.

The pivot wasn’t obvious. The product was strange, minimalist, and hard to explain. But real usage beat theoretical elegance. Twitter launched in 2006, and by 2009, it was reshaping global communication.

That’s exactly why we run regular Hack Weeks at Square. They’re more than just a morale boost; they’re a deliberate space for discovery. Cash App itself was born from a Hack Week in 2013. What started as an experiment quickly evolved into a unicorn with over 57 million active users and more than $5 billion in annual gross profit.

The lesson: if you create time and space for exploration, and take what you find seriously, you’re more likely to uncover your next breakout idea.

CASE STUDY

Instagram: From Feature Bloat to Focus

Burbn was a mess.

It was a location-based check-in app with too many features: social sharing, gamification, photo filters, messaging. The founders, Kevin Systrom and Mike Krieger, watched users carefully and noticed something. People didn’t care about the check-ins. They just liked the photos.

Instead of refining the product, they cut everything. They rebuilt it around one thing: fast, beautiful photo sharing. Instagram launched in 2010. It hit a million users in two months. Facebook acquired it in 2012 for $1 billion.

The lesson here isn’t just about simplification - it’s about listening. The pivot didn’t come from a brainstorm. It came from paying attention and having the conviction to commit to a singular idea.

CASE STUDY

ARM: From Computers to the World’s Chips

In the 1980s, Acorn Computers was building personal computers in the UK. To power its machines, the company designed a lightweight, power-efficient chip architecture.

The chips were so good, they outshined the computers they were meant to support.

In 1990, Acorn spun the processor division out into a joint venture with Apple and VLSI Technology. The new company was called ARM. Today, ARM’s designs power 95% of smartphones, and a growing share of everything else with a processor.

The pivot here wasn’t flashy; it was strategic. Acorn didn’t cling to its hardware identity. It followed the signal. The chip was better than the box it came in. So they sold the chip.

CASE STUDY

Birds Eye: From Frozen Fish to Frozen Everything

In 1922, Clarence Birdseye wasn’t trying to launch an industry. He was trying to keep fish fresh. After observing Alaskan fishermen flash-freezing their catches in sub-zero air, he stumbled upon a new method for preserving food.

The product was frozen fish. But the breakthrough was the process: flash-freezing at scale.

Birdseye’s innovation didn’t just stay with fish. It led to the development of frozen vegetables, frozen dinners, refrigerated transport, and freezer aisles in grocery stores. The company pivoted from product to platform, from food to infrastructure.

It all started with a fisherman’s curiosity.

Why These Pivots Worked

Across these stories, a few shared traits emerge:

The original product failed or underwhelmed.
But instead of chasing sunk costs, teams paused and reassessed.
There was something working in the background.
Internal tools, overlooked features, technical byproducts - they all held hidden potential.
Teams paid attention to behavior, not just vision.
Data was the trigger. Real usage patterns pointed toward something better.
Leaders made the hard call.
Pivoting takes courage. It’s emotionally hard, publicly risky, and strategically uncertain. But the upside is there.
They built for themselves first.
Most of these products were internal tools or personal solutions. That mattered. Because when you build for everyone, you often build for no one.

Taste Matters

Allow me a slight tangent that might not make sense at first, but with a bit of consideration, I think will unveil one of the key reasons these pivots work so well.

One of the most damaging fallacies in modern product development is the idea that good design must serve everyone equally from day one. The past decade has seen an overcorrection away from opinionated design: an obsession with covering every use case, accommodating every user, and removing every trace of personal bias. The result is often something neutral, bland, forgettable.

But the best products don’t come from universal consensus. They come from conviction.

Slack was built for Stewart Butterfield’s team, not yours. Instagram was built for people who loved photography, not influencers. Twitter was a toy for employees, not Ellen or Elon. ARM’s chips were designed to solve internal engineering constraints. Birds Eye was built to solve a personal logistics problem.

That clarity of purpose, audience, and taste is what makes great products great. Design requires point of view. And it requires a designer with the conviction to impose their point of view on the design.

If you strive to remove all bias and taste from the process, you remove the value of the designer and the differentiator of the design itself. We don’t need unopinionated designers. Machines can do that. AI can do that: give it a prompt and it will return a neutral, unoffensive design. Probably something flat, based on Shadcn and Tailwind. The kind of thing that nobody dislikes, but also nobody remembers. Designers aren't machines; they have a point of view. And that's precisely the value they bring to the table.

In a world where AI is an excellent executor, the designer with taste and perspective is the standout. We need principled, opinionated builders who know when to listen, and when to lead. Who discern between good and great.

Nail the 90%

At Square, we express this idea in a simple design principle: nail the 90%. Don't get too distracted by edge cases or fringe users until the core of the experience is right. Delight your target user, and only once you've nailed that should you expand strategically to the edges.

This isn't to say you should never build for everyone, or for a highly general and diverse audience. But you typically shouldn't start there. And the threshold to go generic is much higher than most estimate. Even at Google's scale, with its billions of users, I observed that the best designers at the company knew to ignore the corporate build for everyone mantra and start with something unique, inspiring, and opinionated.

Incredible insights lie at the edges, and it's very rewarding to get there. But when pursued too early or without compromise, those edges can have the opposite effect: they water the design down. Design for everyone, and you'll design for no one. To me, these pivoted products worked so well because they started out designing for a very specific audience and use case. They were opinionated.

How to Plan to Pivot

So, now that my tangent is over, how does this all happen in practice? I'd posit that smart leaders don’t wait for pivots. Rather, they actively create the conditions for them.

Encourage internal building.
Your team’s best ideas often come from solving their own problems.
Observe real behavior.
Not what users say. What they do.
Make peace with sunk costs.
Killing something you love is painful. But clinging to it is worse.
Reward principled risk-taking.
Great leaders don’t just execute; they make bold calls when the evidence supports them.
Protect your team’s point of view.
Products need taste, vision, opinion. Don’t compromise that in pursuit of universal appeal.

The pivot isn’t a panic move. It’s a signal that you’re learning.

The Pivot is the Plan

Most companies build the wrong thing first. The good ones admit it. The great ones use it.

What made Stewart Butterfield successful wasn’t just creativity or persistence. It was his willingness to walk away. To build with purpose, observe with clarity, and act with courage. Twice, he chased a vision - and twice, he realized the tool powering the journey was more valuable than the destination itself.

Success doesn’t follow the roadmap. It follows the truth.

So build what you believe in. Watch how it’s used. And when you see something working (something surprising, something different, something small but unmistakably real) don’t ignore it.

That’s your next product. Plan to pivot.