Last week we saw two significant, public system outages, one belonging to NYSE because of a “configuration issue” and the other to United Airlines because of a “router issue”. This week, the news is on OPM’s  data breach of 21 million users and their lack of investment and follow through on resolving security issues identified by auditors.

My first thought on seeing these failures is that CIOs have little hope in achieving 99.9%+ uptime, fifteen minute or less recovery times, and secure perimeters when the world’s greatest organizations suffer from what looks like basic IT 101 issues. Though I am certain the issues are far more complex in reality and fixing them a significant challenge to their IT staff, I think about how many times CIO walked into a Board room with their head tucked in because of similar issues? A critical operational outage because of some preventable infrastructure, operational, or software issue?

But my second thought turns to our roads, bridges, highways and infrastructure. At the bottom line, the US would have to invest $3.6 trillion to bring it all up to snuff by 2020. That’s some technical debt and we’re lucky that there isn’t infrastructure related catastrophes reported on a frequent basis. But what you may not see in the numbers but people feel on a daily basis is the negative impact poor infrastructure has on growth. Stuck in traffic because a highway needs expansion? Subway delays because of a switching issue? How about that high speed rail that would be faster, cheaper, safer and more environmentally friendly?

Over the past five years, businesses have been smarter about investing in innovation and digital capabilities. We’ve been enabling analytics and data driven decisions, adjusting to a user driven mobile workforce, and insuring we can personalize and improve customer experiences.

But have we attacked the IT legacy and technical debt with the same enthusiasm let alone internal celebration? Are you still running Windows 2003 even though Microsoft will end extended support for it this week? Will you upgrade that .Net application on V3.5 or that Java one on V7? Will you connect and secure your data sources, or continue to run them as inefficient data silos?

Lots of work to do, but before you spend hours reviewing, debating, and blaming what to do when you hit your next outage, I suggest spending a greater amount of energy, funding, focus and celebration on where you will attack your technical legacy.