Published on November 3, 2025

Have you ever seen the show “Love It, or List It? It features homeowners whose homes no longer fit their needs, either because they’ve outgrown them or because years of DIY projects have failed to turn their money pit into their dream house.
The show presents owners with two options: invest in a makeover and keep the house, or sell it and buy a house that fits their needs. Invariably, the makeovers fall short, running into unexpected problems or going over budget. Yet some homeowners choose to stay, reasoning that they’ve already invested so much, they must be close to making it work for them.
This is a classic example of the sunk cost fallacy. And it doesn’t just happen to homeowners; we see it a lot when digital leaders start looking at new digital experience platforms (DXPs).
In this post, we’ll look at why some companies keep limping along on legacy platforms when modern DXPs offer so much more.
The sunk cost fallacy is the belief that you’ve invested so much time, effort, and money into something that it's only going to take a little more to reach your goal. In the world of technology decisions, it looks like this:
Digital leaders will explore modern platforms that offer all of the creative possibilities that are currently out of reach and then conclude that replatforming is more effort than it’s worth. They’re used to the foibles of their existing platform. They know what the workarounds are. They’re sure that with just a little more investment, their current platform will meet their needs.
A year later, they’re still stuck. And the new investments they’ve made make it even harder to cut their losses and replatform. Targets and KPIs are missed for another year.
It's a logical disconnect. They’ve spent so much money that they feel like they’ve got to be close to making it work. So they keep sinking money in that they’ll never recoup.
The reality is that no amount of money will turn an aging platform into the modern DXP they need.
The false assumptions that keep teams chained to a platform long after they outgrow it are insidious. They start with a grain of truth, but they lead to the wrong conclusion.
This is probably true, but are they skills like knowing what workarounds to use, fixing glitches, and troubleshooting problems a new platform won’t have? Instead of thinking of those skills going to waste, think about what your marketers and developers could accomplish on a platform that works like it should and requires less maintenance just to keep the lights on.
If you’ve been on the same platform for the last five or 10 years, you probably have a good relationship with the account executive. There’s a personal aspect to ending that relationship, but this is a business decision that should be in your best interests, not theirs.
Legacy platforms are notorious for painful upgrades. They’ve conditioned users to expect that any upgrade or major change is an expensive 18-month project with questionable results. Often, the new features hardly seem worth the effort.
I’ve seen some teams hold off on upgrading for years, which works in the short term, but eventually they become “version locked,” where upgrading is no longer viable and they need more than an out-of-date platform can provide.
The good news is that modern technology vendors release upgrades in small slices, introducing new features at a fairly painless pace. Think about new iOS versions. When you first install one, you're like, “What is this mess? I don't know where all my buttons are. I preferred it like it was before.” But within a couple of days, you're enjoying new features and you can't even remember what it was like before.
That’s the kind of bliss you can expect from a modern SaaS platform. Frequent enhancements and new features with zero effort from you..
“I'm staying where I am, because I can't even comprehend what moving 150 websites to a new website platform would look like.” That’s a fair argument, but what if you start with one site that’s high impact, but low risk? If that went well, could you move another and another? You would have to run two platforms side by side, but before you know it, you’re on a modern DXP with all the benefits that entails. No more sleepless nights before a big launch; no more unplanned downtime due to high load at a critical moment.
Moving, whether you're moving to a new house or moving to a new platform, is often easier than you think. It’s a short period of disruption with a big payoff. And with a modern content platform, like Contentful, the disruption is minimal.
At its core, Contentful is a composable platform with a huge amount of common integrations out of the box. It’s inherently flexible, designed to meet brands where they are and scale. That means migrating away from your legacy platform can start with a single page and move at a pace that works for your business.
Dipping your toe in without committing to replatforming eliminates the risk of a big decision with a lot of unknowns. You can see for yourself how much effort is involved and what return on investment you get.
Choose a first step that’s big enough to deliver measurable results, but isn’t business critical. For example, a corporate website that’s a jumping-off point into other parts of your user experience. You can migrate that to a new platform with minimal risk and measure the impact.
Ask yourself: How quickly were you able to migrate the site? How much faster does the site run? Were you able to improve the user experience? Are performance numbers up? Do people enjoy using the platform? Did they need a lot of training? Is this something you do with another slice of the business, and another?
This approach, sometimes called the salami-slice strategy, makes a big migration manageable. With each slice, you add value and get more comfortable with the new platform. Instead of dreading the migration, people have a chance to get excited about using the old platform less and less.
Before you know it, all of your business is on a modern platform that everyone — developers and marketers alike — love. And you get to feel like a hero.
Sounds a lot better than literally paying to be stuck on the same old platform with the same old problems a year from now, doesn’t it?
When Docusign realized their legacy CMS wouldn’t keep up with modern business needs, they did their research and decided to pilot Contentful.
The team developed a marketing website and an ecommerce experience with reusable components. Then used Contentful’s orchestration capabilities to establish self-service workflows, reducing bottlenecks that were common prior to Contentful.
The results were dramatic.
“Before Contentful, it took Docusign an average of two weeks to push out website updates. After adopting Contentful, the website takes just five minutes to update."
— Andy Rossi, Senior Product Manager, Docusign
With Contentful, Docusign could now offer constant updates for users. And that was just the beginning.
Since that pilot, Docusign expanded its use of Contentful. They used Contenful’s localization and translation features to translate 7,000 pages into 60 languages. Now they’re automating translation and SEO with Contentful AI Actions.
A team of three is using Contentful Personalization to run personalized home page experiences for 20 different audience segments and planning to extend personalized content to every market Docusign serves.
These are the results you can get when you step outside the familiar comfort of a legacy CMS and see what a modern DXP has to offer.
Moving forward and changing platforms is an uncertain thing. But embracing that uncertainty and challenging the assumptions that are holding you back can help you see the benefits of a modern DXP.
If the idea of re-platforming is marred by your experiences with past upgrades, remember that you're comparing the move to a new platform with the maintenance of an old platform. Yes, you know how to work around that platform’s failings, but wouldn’t it be nice to use a platform where everything works the way it’s supposed to?
Playing it safe is a fallacy. Progressive companies embrace uncertainty and become their own disruptor. Remember, if you're not your own disruptor, someone else will be.
Be brave, be bold, and look at your aging platform with fresh eyes. Is it really going to bring your business into the future, or is that just wishful thinking?
Ready to see the value a modern platform can bring? Let’s make this the year you invest in a platform built for the future. Contact us now.
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