My Voyage to the Cloud

I wish more of my friends and colleagues in the Information Technology field would share their stories.


There’s a vast, hidden treasury of insight locked away in our heads – and not about technology alone but also, how organizations use and adapt to technology (or don’t).

This recently came to mind (and inspired this post) as I reviewed the last few years of my career over a few glasses of wine. During this brief time, my entire point of view about the purpose and future of IT has dramatically changed.  I’ve travelled the path from cloud skeptic to cloud enthusiast.  What transported me from one pole to the other?

That’s the story I’m going to tell.

A Sense of Dread



My career in Information Technology – which started well over a decade ago – was practically an accident. After leaving college, I worked in banking in a very entry level position.  It was a tedious job that involved the manual reconciliation of account data (i.e., did deposits match withdrawals? …and other minutiae).  Hour after hour of eyeballing columns of information searching for inconsistencies inspired a sense of ennui.

Wasn’t there a better way?  Wasn’t this a perfect job for software?  Surely there was an algorithm that could accomplish this.  I’d worked extensively with computational methods in college, solving statistical problems using the resources available in the computer lab so I knew there were powerful alternatives to this drudgery.

I presented my ideas to management who, with one notable exception, politely thanked me and promptly returned to their 1950s mental cocoon. Until, that is, the FDIC came along.

Mechanization Takes Command

Modern Times
Modern Times

Without going into deep detail I’ll say that when the bank was audited it received a failing grade for the lack of investment in Information Technology (among other sins).  Suddenly, there was a mandate to modernize the organization’s minimal IT infrastructure.  A VP with whom I was friendly pointed towards me and said: ‘that’s the guy who will make it happen’.  As a professor of mine often said, ‘repetition is the key to learning’ – my mantra about the need for IT, combined with a government directive and the sponsorship of a mentor had changed my career, almost overnight.

Welcome to the Present – and Future

MCQ-cloudcityThis ushered in an exciting time; network cables were laid, a data center was made, a client server infrastructure was built and methods were created to import data from offsite mainframes into on-premises servers for real-time analysis by financial personnel, all coordinated by me.  It was a whirlwind of activity that completely transformed the way the bank operated.  And yes, the account reconciliation process – tailor made for automation – left human hands and became the work of algorithms.

The Age of Consultancy

Style: "Mad Men"

Eventually, there were ‘no more worlds to conquer’ at the bank and I found myself growing restless – a not uncommon condition of people in our field.  A friend suggested I interview with a consultancy start-up he’d recently joined – a firm composed of a combination of young hotheads looking to dive into the world of client server development and older, infrastructure veterans, weary of the politics and mission silos of corporate IT.  I was impressed by this group of visionaries and made the leap.

This started the next phase of my career, defined by a sort of creative chaos as I was sent from one assignment to another with only the vaguest idea of what I was supposed to be doing.  One moment, it was writing transact SQL code and the next, it was acting as a sysadmin for a massive farm of Solaris servers.

Despite the uncertainty, I learned three valuable lessons from this time:

  • To be open minded and technology agnostic
  • To cultivate a spirit of constant learning
  • To think of myself as a technologist first and not as the champion of a particular company’s stack

These lessons would serve me well as the next chapter began.


The Importance of Deep Knowledge

20053772190_6606a23662_zBy now, I was comfortably operating as an IT generalist, working under the umbrella of the consulting firm whose business was growing at a rapid pace.  An encounter with a seasoned professional however, would shake my confidence in future prospects and reorient my thinking towards deeper topics.

While engaged on a lengthy project, one with a heavy emphasis on Tru64 Unix, I had the pleasure of working with a man whose knowledge of that platform was profound.  He took me under his wing, stressing one important message: ‘it’s good to have a wide range but you must possess deep knowledge in at least one area to be a serious professional.  Pick something you love and make it a part of you.  If you do that, and it’s critical to business, you’ll always excel.’

I knew what I needed to do: I would become a messaging expert.

You’ve Got Mail

microsoft-exchange-logoThis turned out to be precisely the right decision as Microsoft Exchange – once a ‘toy’ product – was coming into its own as a robust messaging platform.  Integration with Active Directory and the publishing of an API that programmatically extended the platform and broadened the amount of knowledge required to truly be considered a subject matter expert.  With the introduction of versions 2007 and above, Exchange graduated to enterprise class.  And also, the foundation for SaaS versions of the product were laid.

Messaging is the SaaS Gateway for Many Firms

Having established myself as a messaging SME focused on MS Exchange, it was only a matter of time before Office 365, the mature successor to what was once known as the Business Productivity Online Suite (or BPOS) entered my life.  My first encounter with BPOS left me cold – I was firmly rooted in the world of data centers you could touch, bare metal and virtual machines you owned and the illusion of control.

Of course, along with that supposed control there came a host of challenges that often wrecked weekends and ruined sleep: server malfunctions, active directory issues, VMWare host or VDI problems, network communication challenges, firewall configuration mysteries and on and on.

Despite this nearly constant churn of drama – even in well-designed and reasonably well behaved infrastructures – I was deaf to the potential of (then nascent) cloud technologies.


But all that was about to change.


forbidden-planet (1)I accepted a position with a firm that had gone all in with AWS and Office 365: AWS on the PaaS and newly created DevOps side of the house and Office 365 on the SaaS/back office side (oh and of course, the nearly ubiquitous SalesForce SaaS was heavily in-use).  Office 365 was adopted, it was hoped, as a way to eliminate the expense and infrastructural complexity of on-premises Exchange – the theory was that less knowledge would be required to manage these cloud technologies.  Of course, this turned out to be wrong but what was discovered along the way was the scalable power, flexibility and velocity made possible by leveraging the public cloud.

My discovery was that by letting go of an attachment to legacy practices – of a fixation on ‘owning’ the infrastructure – I could explore the use of computing power as a utility and change my career direction from being part of a cost center, often beset by crises, to crafting solutions and actually being the business.

Through Office 365, I reoriented my thinking away from isolated areas (i.e., the ‘messaging’, or SharePoint, or IM silos as separate areas of expertise) and towards SaaS as a collaboration tool set that enabled the organization to become nimble.  Through AWS (and a little later, Azure) I learned to rethink my relationship to server assets from the pet to cattle model.

This has reinvigorated my career and opened an exciting new chapter.

So much so, that I’ve become an unabashed enthusiast and ‘evangelist’ for cloud technologies.