Picture this: You’re driving to the most important meeting of the quarter. You’ve ignored that check engine light for months—after all, the car still runs fine. Then, on the motorway, in the rain, running late, your engine seizes.
You’re stranded on the hard shoulder, watching your competitors zoom past, all because of preventable maintenance you postponed.
This is exactly what’s happening with your “stable” software.
The £500,000 Oil Change
Last month, I watched a the colour of CEO’s face drain as I explained why their “quick software update” had turned into a six-month nightmare:
- 20 systems needing emergency fixes
- 140 engineering days of unplanned work
- £70,000 in direct salary costs
- 3 months of delayed features
- 2 major clients questioning their renewals
- 5 senior developers updating their CVs
All because they treated software maintenance like that blinking check engine light: ignorable until it wasn’t.
Your Software Isn’t Wine, It Doesn’t Improve with Age
Here’s what business leaders often misunderstand: software isn’t like a building that stands still. It’s more like a car in constant motion:
- The road (technology landscape) keeps changing
- Traffic laws (security requirements) get updated
- Other vehicles (integrated systems) evolve
- Weather conditions (cyber threats) worsen
- Fuel standards (industry standards) advance
Standing still means falling behind. And unlike wine, software doesn’t improve with age, it rots.
The Compound Interest of Neglect
Let me show you how postponing updates compounds costs:
Year 1: “It’s working fine”
- Cost: £0
- Risk: Minimal
- Developer opinion: “We should update soon”
Year 2: “We’ll update next quarter”
- Cost: Security monitoring increases
- Risk: Known vulnerabilities appearing
- Developer opinion: “This is getting concerning”
Year 3: “It’s too risky to change now”
- Cost: Can’t hire senior developers (“I won’t work on that ancient stack”)
- Risk: Security patches no longer available
- Developer opinion: “I’m looking for a new job”
Year 4: “We need to maintain what we have”
- Cost: Premium support contracts, specialist contractors
- Risk: Compliance failures, security breaches
- Developer opinion: Already left
Year 5: “We need a complete rebuild”
- Cost: £2 million+ and 18 months
- Risk: Business continuity threatened
- Developer opinion: Replaced by expensive consultants
The tragedy? Year 1 updates would have taken 2 weeks and £15,000.
The Hidden Costs You’re Already Paying
Think you’re saving money by not updating? You’re already paying, just invisibly:
Recruitment Nightmare: “We use cutting-edge technology from 2018” doesn’t attract top talent. Good developers have choices, and they choose modern stacks.
Feature Delivery Molasses: Simple changes take weeks because developers navigate around limitations, create workarounds, and test manually what modern tools automate.
Security Roulette: That stable system? Hackers have had years to study its vulnerabilities. You’re not stable, you’re a stationary target.
Innovation Paralysis: Your competitors leverage AI, cloud scaling, and modern architectures while you’re stuck explaining why “our system can’t do that.”
The Maintenance Schedule That Saves Millions
Just like your car needs regular servicing, software needs planned maintenance:
Quarterly Reviews (Like Oil Changes)
- Security patches
- Minor version updates
- Performance tuning
Annual Upgrades (Like MOT Tests)
- Framework updates
- Dependency refreshes
- Architecture reviews
3-5 Year Overhauls (Like Major Services)
- Platform migrations
- Fundamental modernisation
- Strategic re-architecture
Ignore this schedule, and you’ll find yourself broken down at the worst possible moment.
Warning Signs Your Software Is About to Leave You Stranded
Technical Check Engine Lights:
- Developers saying “we can’t do that with our current setup”
- Security team raising frequent concerns
- Simple changes taking disproportionate time
- Difficulty recruiting quality developers
- Increasing bug rates despite fewer changes
Business Impact Indicators:
- Competitors releasing features you can’t match
- Customer complaints about performance
- Compliance auditors raising eyebrows
- IT costs increasing despite doing less
- Key technical staff leaving
If you see three or more of these signs, you’re not maintaining stable software, you’re ignoring a crisis.
The Investment Formula That Actually Works
Here’s a formula for technology maintenance investment:
Annual Technology Maintenance Budget = 15-20% of Development Costs
Sounds expensive? Let’s compare:
Option A: Planned Maintenance
- Annual cost: £150,000
- Business impact: Minimal
- Risk level: Controlled
- Team morale: High
Option B: Emergency Rebuild
- Crisis cost: £2,000,000+
- Business impact: Devastating
- Risk level: Extreme
- Team morale: Destroyed
Which looks expensive now?
What Good Maintenance Actually Looks Like
I recently worked with a company that gets this right:
- Quarterly update cycles planned in advance
- 20% of engineering time allocated to maintenance
- Business stakeholders involved in planning
- Clear metrics on technical health
- Regular investment in team learning
Their results:
- 50% faster feature delivery than competitors
- 90% developer retention rate
- Zero security breaches in 5 years
- 40% lower total technology costs
They spend more on maintenance but less on everything else.
Your 90-Day Action Plan
Days 1-30: Assessment: Get an honest technical health check. How old are your frameworks? What security risks exist? What’s your actual technical debt?
Days 31-60: Planning: Create a realistic maintenance schedule. What needs immediate attention? What can be planned? What resources do you need?
Days 61-90: Implementation: Start with the highest-risk items. Quick wins build momentum and trust. Show the team this is a priority, not just talk.
The Conversation with Your Tech Lead
Share this article with your technical leadership, then ask:
- “What’s our current technical debt situation?”
- “What would a proper maintenance schedule look like?”
- “What resources do you need to keep us current?”
- “How can we make this sustainable?”
ℹ️ Note
Your tech lead has probably been wanting this conversation for years. There’s a companion piece written specifically for them: Why ‘Upgrade and Pray’ Cost My Client 140 Engineering Days
The Competitive Truth
While you debate whether to update, your competitors are:
- Shipping features faster
- Attracting better talent
- Spending less on maintenance
- Sleeping better at night
Don’t let them leave you stranded on the hard shoulder of digital transformation.
Choose Your Future
You have two choices:
- Continue ignoring the check engine light until catastrophic failure
- Implement regular maintenance that keeps you competitive
The choice seems obvious, yet I keep meeting CEOs dealing with preventable crises.
Which CEO will you be?
Ready to understand your true technical position and create a sustainable maintenance strategy? I provide Strategic Technology Consulting that helps business leaders make informed decisions about their technology investments.
Simply use the contact form below, and I’ll be in touch as soon as possible to arrange a free 30-minute discovery session at your convenience.