Being a polymath, I loved that environment.
It's hard to imagine a workplace where the IT Director does a huge amount of developing, network administration, logo designing and client meetings.
In the wise words of Marco Silva I was the CWO - Chief Whatever Officer in a 1,5 million euro / year company for more than a decade and enjoyed it.
It all started in the brink of the year 2000 and the world was ready to implode with the millennium bug (link to Y2K). People were expecting planes to fall from the skies, computers to burst into flames and half the world's money to disappear into digital sinkholes. Yes, it was fun. Most of it never happened and if anything, the whole situation ended up being a perfectly good excuse for me to spend some time on code refactoring.
A lot happened in that decade: created and managed the IT Dept. for a company of 25 people, developed a system for the interchange of information to legalize motor vehicles according to Portuguese ever changing laws. And did all that maintaining an impressive quality of service if I may say so myself.
My daily routine was filled with development in SQL, VB6, custom controls playing a great part in every solution, resorting to tricks like webscraping to bridge the gap between non cooperative government systems, killing off obsolete systems, coming up with custom document management systems and supporting the Quality Management System after we got our ISO9001 certification.
No man is an island and I had the privilege of working with some fine professionals that came and went through the years:
João Quaresma, a quiet and methodical programmer with a warm sense of humor. Always dependable, day in day out he teamed up to code the foundations of an application for the company's core business and the whole experience reminds me that although some jobs will be long and boring, in the end you'll have something solid to build up from. Having done it with a long time friend was just an unexpected bonus.
Later I met Nuno Mendonça. He's part geek, part scout, a bit of an undercover evil master and a great friend to have around when in trouble. He was my guide into the early years of all things cloud and with great PHP, WordPress and craftsmanship skills. Alongside some soldering we came up with all kinds of unexpected solutions for everyday problems like intranet dashboards, temperature control, automated data backups and network management. He's the reason why I insisted my two daughters should be in the scouts as a way to build a strong and versatile human being.
When you get to work with great people, team management ends up being a great job: you just do your best to keep your team happy and everything works out. Major lesson learned there, as IT Director I would always take the blame for everything in management meetings. If something didn't happen as expected there was no point in trying to deflect responsibilities, we would do our jobs until we found a solution. And we did it in the best work environment possible.
When information technology becomes a great part of a small company, the IT guy plays a big role in corporate client meetings and working with giants like Vodafone, Mitsubishi Motors and Mercedes-Benz really gives you some nice negotiations skills. Be kind and assertive and when in doubt ask. In the end I still believe "under-promise but over-deliver" pays every time.
Building the IT software for medium sized company is not just about technology, it is about making sure a company is efficient and effective at all levels. These are the reason of why I loved being the CWO.
If you have read up to here, you know what I learned along almost two decades working in a enterprise environment. Since 2012 I've been self employed doing mostly outsourcing task. Still fun, just a different flavour of fun.
(XKCD, a weekly companion for more than a decade.)