FileMaker9 min read

Your FileMaker app works fine. Here's why that's a problem.

"If it ain't broke, don't fix it" sounds like wisdom. It's actually a slow-motion disaster.

FileMakerLegacy SystemsStrategyRiskCompetitive Advantage
A frog sitting comfortably in a pot of water on a stove, unaware of gradually rising temperature

"It works fine."

Three words that have killed more businesses than any recession. Three words that feel responsible and prudent. Three words that are slowly, quietly strangling your competitive advantage.

We get it. Your FileMaker application runs. Orders get processed. Reports get generated. Nobody's screaming. In a world of constant tech disasters and failed implementations, "works fine" feels like a win worth protecting.

Here's the uncomfortable truth: "works fine" and "serves us well" are not the same thing. Not even close.

The seductive comfort of "fine"

Let's be honest about why businesses cling to legacy systems that technically function. It's not stupidity — it's actually rational, at least on the surface.

Replacing a working system involves risk. It costs money. It disrupts operations. It requires retraining. And for what? To fix something that isn't broken?

This logic makes sense right up until you realize that Kodak's film business "worked fine" in 2005. Blockbuster's stores "worked fine" in 2008. Your competitor who ate your market share last year? Their old system probably "worked fine" too — until they replaced it with something that actually gave them an edge.

The "if it ain't broke, don't fix it" mentality assumes that the only purpose of technology is to not break. It completely ignores whether that technology is helping you grow, compete, or even just keep up.

What "works" is hiding from you

Here's an exercise: walk through your office (or hop on a video call with your team) and ask people how they actually use your FileMaker system. Not how it's supposed to work. How they really use it.

You'll hear things like:

"Oh, I export that to Excel first, then clean up the data, then import it back..."

"Yeah, that field doesn't really work, so we just put the notes in a different field and everyone knows to look there."

"The report takes forever to run, so I kick it off before lunch and check it after."

"Only Janet knows how to do that. We're all terrified of what happens when she retires."

These workarounds have become invisible. They're just "how we do things." But each one represents a tax — a tax on time, on efficiency, on your ability to scale, on your employees' sanity.

According to workplace productivity research, the average employee loses more than two hours daily to inefficient processes and workarounds. That's not a rounding error. That's 25% of their productive capacity, vanishing into the gap between "works fine" and "works well."

The boiling frog problem

You know the metaphor: drop a frog in boiling water, it jumps out. Put it in cool water and slowly raise the temperature, and it boils to death without noticing.

Your FileMaker app didn't start out with seventeen workarounds and three fields that nobody uses correctly. It degraded gradually. Each limitation got accepted. Each workaround became "just how we do it." Each frustration became background noise.

The system you have today isn't the system you built. It's the system that emerged from years of accumulated compromises, each one too small to trigger action, but collectively creating a Frankenstein's monster of technical debt.

And here's the really insidious part: you've stopped noticing. Your team has stopped noticing. The pain has become normal.

What your competitors are doing (while you're maintaining status quo)

Here's a question that should keep you up at night: what are other companies in your industry doing with their technology?

While you're celebrating that your 15-year-old system "still works," your competitors might be:

  • Automating processes you're still doing manually
  • Getting real-time insights while you wait for overnight batch reports
  • Serving customers on mobile while you're still desktop-only
  • Integrating with modern tools while you're copying and pasting between systems
  • Scaling effortlessly while you're hitting performance walls

McKinsey research consistently shows that digitally mature companies outperform their peers by 20-30% on profitability and revenue growth. That gap isn't because their systems "work" — it's because their systems enable things that yours can't.

"Works fine" is table stakes. It's the minimum. It's not a competitive advantage — it's a competitive anchor.

The employee perspective you're not hearing

Want to know a secret? Your employees have opinions about your legacy system. Strong ones. They're just not telling you.

Why? Because they've learned that complaining about the system leads to one of two outcomes: nothing changes, or they get voluntold to lead the replacement project. Neither is appealing.

So they suffer in silence. They build their workarounds. They grumble to each other. And when recruiters call, they mention the frustration with outdated tools as a reason they're open to new opportunities.

The cost of a legacy system isn't just measured in processing time or licensing fees. It's measured in employee engagement, retention, and the quality of candidates willing to work with your technology stack.

Ask yourself: if you were interviewing for a job and learned the company ran critical operations on a 20-year-old FileMaker database with no mobile access and manual data entry, would that excite you? Or would it be a yellow flag?

The customer impact you're not measuring

Your internal workarounds don't stay internal. They leak out to customers in ways you might not track:

  • The order that took an extra day because someone had to manually check inventory
  • The quote that was delayed because the sales rep couldn't access the system from the client site
  • The customer service call that took twice as long because the rep was navigating three different screens
  • The error that slipped through because the data validation was someone's memory, not the system

PwC research found that 73% of customers say experience is a key factor in their purchasing decisions. Every friction point in your internal systems has a shadow — a customer experience impact that's hard to measure but very real.

Your system "works fine" for you. Does it work fine for your customers?

Reframing the question

The problem with "is it broken?" is that it sets the bar on the floor. Of course it's not broken. The lights come on. Data gets stored. Reports get generated.

The better question is: "Is it optimal?"

  • Is this system helping us grow, or just helping us maintain?
  • Is it enabling our strategy, or constraining it?
  • Is it a competitive advantage, or just infrastructure?
  • Are we making decisions based on what the system can do, rather than what we should do?

Gartner has predicted that by 2025, legacy systems will consume up to 80% of IT budgets while delivering only 20% of value. That's not a technology problem — it's a strategic problem disguised as a technology decision.

The most dangerous legacy systems aren't the ones that are obviously failing. They're the ones that work just well enough to avoid scrutiny while silently limiting everything you could become.

The strategic question you need to answer

Here's what it comes down to: Is your technology enabling your business strategy, or is your business strategy being shaped by your technology limitations?

If you're making decisions about what markets to enter, what products to offer, what customers to serve, or how to operate — and those decisions are influenced by what your FileMaker system can or can't do — then you have a strategic problem, not a technical one.

"We can't do that because of the system" is a phrase that should terrify executives. It means technology has stopped being a tool and started being a cage.

What "fine" is really costing you

Let's add it up:

Hidden CostHow It Shows Up
Employee timeHours lost to workarounds, manual processes, waiting
Opportunity costThings you can't do, markets you can't enter, customers you can't serve
Risk concentrationTribal knowledge, single points of failure, key person dependencies
Talent costHarder to hire, harder to retain, limited by shrinking talent pool
Customer impactSlower service, more errors, inferior experience
Competitive positionFalling behind while others accelerate

None of these show up on your FileMaker licensing invoice. None of them trigger an error message. None of them cause the system to crash.

They just quietly compound, year after year, while you celebrate that everything "works fine."

The conversation you need to have

If you've read this far and you're feeling a little uncomfortable, good. That discomfort is the first step toward honest evaluation.

The conversation isn't "should we replace our working system?" That framing guarantees the answer will be no.

The conversation is: "Is our current technology enabling the business we want to become, or just maintaining the business we've been?"

That's a strategic conversation, not a technical one. And it deserves strategic thinking, not reflexive defense of the status quo.

Start with a simple exercise: list five things your business would do differently if technology were no constraint. Then ask how many of those are blocked or limited by your current system. The gap between those lists is the true cost of "works fine."

The bottom line

Your FileMaker app works fine. We believe you.

But "fine" isn't a strategy. "Fine" isn't a competitive advantage. "Fine" isn't going to help you grow, adapt, or thrive in a market that's moving faster every year.

The question isn't whether your system is broken. The question is whether it's holding you back. And if you're being honest — really honest — you probably already know the answer.

The frog in the pot doesn't feel the water getting hotter. But the water's getting hotter whether the frog feels it or not.


Not sure what to do about your FileMaker situation?

You don't have to figure this out alone. With 18+ years of FileMaker experience, we help businesses honestly assess their options — whether that means modernizing, migrating, or something in between.

Entvas Editorial Team

Entvas Editorial Team

Helping businesses make informed decisions

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