I started my career on Freehand and Photoshop. Back then, the designer-versus-art-worker divide was real. Designers loved the freedom of Freehand. Art workers complained every time we sent them Freehand files because they lived in Illustrator. It was messy, but the tools were ours and we loved them.

Then Adobe did what monopolies do. They bought everything they could. Killed the competition they couldn’t. Consolidating the market. For two decades, they owned us. And for a while, it was fine.

Then it wasn’t.

The Slow Erosion of Trust

Adobe’s move to Creative Cloud subscriptions made perfect business sense. Predictable revenue. Reduced piracy. Delighted investors.. But somewhere along the way, Adobe stopped asking if creatives loved it.

The subscription costs kept climbing. The software got bloated. Features nobody asked for kept appearing while bugs lingered for years. Customer support became a maze. And the message was clear: you need us more than we need you.

This is what happens when you make business decisions instead of brand decisions. Adobe optimised for financial efficiency, forgetting about the people actually using their tools. They treated a captive market with contempt. And in doing so, they created the exact conditions for disruption.

Enter the Challengers

Canva saw an opening. Not by building a better Photoshop, but by asking a different question: what if design didn’t require years of training? They democratised creativity for the 99% of people who just needed to make something look good quickly. Adobe dismissed them as a toy for amateurs.

Figma saw a different gap. They recognised that design isn’t a solo sport—it’s collaborative. They built a tool that let teams work together in real time, with handoffs between designers and developers that actually made sense. Adobe scrambled to catch up with XD, but it was too late. The workflow had already shifted. Then tried to buy Figma, but this time governments stepped in.

Here’s what both challengers understood that Adobe forgot: people don’t just buy tools. They buy relationships.

Change from the ground up

A member of our team recently pitched moving part of our workflow to Figma. The presentation was delivered in Figma—sharp, collaborative, alive. At the end, I sent Figma a note asking for a call. Within hours, I was speaking with someone who listened, answered every question with care and respect for our workflow, and genuinely excited me about the change.

That’s brand building. That’s what brand trust feels like. That’s what happens when you treat customers like partners, not prisoners.

Now contrast that with trying to cancel an Adobe subscription or get support for a persistent bug. The difference isn’t just operational, it’s philosophical.

The Free Forever Gambit

Now, Canva have made their boldest move yet. They acquired Affinity, the beloved Adobe alternative that professionals respect—and made it free. Forever.

Not a free trial. Not freemium with crippled features. Actually free.

This isn’t charity. It’s good strategy. Canva knows that if they can get professional designers into there ecosystem—the collaboration, the scalability, the AI integration, many will upgrade to paid plans. But more importantly, they’re making a statement: we respect you and want to earn your business.

Adobe’s response? We will see. When you’ve spent years optimising for lock-in rather than loyalty, you don’t have a playbook for genuine competition.

AI Changes Everything (Again)

We are in a time of fundamental change, and AI might make all of these tools less relevant anyway.

Adobe built Firefly for enterprise safety. Canva Ai is automating entire workflows. Figma Ai is accelerating UI generation. But a real disruption is happening outside these platforms with AI generating creative work without opening any design software at all.

In this new landscape, brand loyalty matters more than ever. When the tools become commoditised, the relationship becomes the differentiator. Who do you trust? Who treats you with respect? Who’s building with you?

Adobe’s years of customer contempt are now a strategic liability.

The Lesson for Every Category Leader

This isn’t just a story about design software. It’s a cautionary tale for any market leader.

When you dominate a category, you face a choice: invest in brand trust or optimise for short-term business metrics. Adobe chose extraction over relationship. They raised prices, bloated products, and ignored feedback because they could. They made business decisions when they should have made brand decisions.

And now? They’re fighting a multi front war against challengers who are younger, hungrier, and more responsive. Canva has 260 million users. Figma is the default for product design teams. Adobe still has the revenue and the install base, but they’ve lost something harder to measure and harder to rebuild: enthusiasm.

What Comes Next

I’m genuinely excited about this battle. Not because I want Adobe to fail, but because competition makes everyone better. Already, we’re seeing faster innovation, better pricing, more respect for users. Adobe is being forced to remember that customer relationships matter.

As an agency owner, I’m less excited about ballooning software subscription costs across multiple platforms. But as a creative professional, I’m excited. The market feels alive. Tools are improving. Service matters. Creativity is being respected, and users are treated like humans again.

Brands need to be found, understood, lived, and loved, because in the long run, brand decisions beat business decisions every time.

You can extract value from a captive market for a while.

But eventually, someone comes along who actually gives a damn about the people using their product.

And when they do, the monopoly crumbles faster than you think.

The Bottom Line

Adobe didn’t lose ground because its tools stopped working. They lost ground because they stopped caring. In any category, customer contempt creates opportunity. The question for every market leader is simple: are you building trust or exploiting it?

Because someone, somewhere, is watching. And they’re building the thing your customers wish you still were.