I’ve been feeling nostalgic this week. After so many years in ecommerce, supporting catalogers and retailers whose year entirely revolved around the Christmas season, I am almost at a loss for what to do if I’m not running around putting out fires from Thanksgiving weekend up until the week before Christmas.

Strange as it seems to most people, I loved the chaos of the holiday season back in my MarketLive years (2000-2005). I really did. It was high drama, high anxiety and high chaos. All the delicious things that a good single workaholic who lives four blocks from the office craves.

And what was even better was that we knew it was coming, so we got to anticipate it for months before it happened. It was like standing on a beach, watching a huge wave build and build as it rolls towards you and just standing there, bracing yourself, waiting to see if you’re going to be able to keep your footing.

Since so many of my core strengths come to the surface when it’s time to put out fires, it was a natural time for me to hit my stride. In hindsight, I can clearly see that some of the reasons I enjoyed it so much played into some of my less healthy habits. It was still a hell of a lot of fun, though.

Hub in the Wheel
Particularly during my years running point for IT Hosting and Operations, I always got to be in the middle of everything. If I’d had what is euphemistically referred to as “a healthy work-life balance” (a term that makes me crazy), then I wouldn’t have considered that a perk. But, since I didn’t have a life outside of work and since I had a huge ego, being in the middle of everything all the time worked very nicely for me.

Troubleshooting

When things go wrong on an ecommerce site during it’s busiest weeks of the year, any minute of outage is a potential disaster. So every second counts. What I loved about the holiday season is that we ran at a fever pitch, so when anything went wrong, the best troubleshooters in the company were all collected together to figure out what was wrong and how to get it fixed.

At the age of 27, that was one of the greatest experiences I could have asked for. Not only did I learn how to troubleshoot better than almost any professional I have ever worked with since, but I did it with other brilliant, creative, talented people who were also good at it. Part of me wishes I hadn’t taken that skill for granted so much back then. It would be years later before I understood how remarkable a team we had, and how amazingly gifted they were at it.

Making Things Happen

There is nothing I find more gratifying than progress. Like many project managers, I love making lists — simply so that I can cross things off of them. It’s something I find profoundly satisfying. One of the greatest things about the holiday season in my ecommerce days was that suddenly process took a back seat, obstacles were knocked down, priorities were re-oriented and all that mattered was getting something DONE.

Friends

To this day, I have never worked in an environment where I had as many close friends. It was the foxhole mentality. It’s common in the military and political campaign teams. And startups.

Those of us who used to deal with the fires spent insane amounts of time together: we ate together, we argued, we got punchy with each other, we got punch-drunk until we cracked up laughing at 3:00 a.m., we worked 24+ hours straight together, we called each other in the middle of the night to get help with issues. We made each other crazy, we made each other laugh, we made each other smarter. It was awesome, and I’ve missed that rare combination of talent and circumstance ever since.

Like many people, the older I get, the more nostalgic I get about times gone by. I’m lucky that for much of the craziest part of those times, I actually really loved it in the moment — not just after the fact.

It never fails now, though: I see the polished world that ecommerce has become — all marketing and very little tech — and I see the predictions about what kind of sales Cyber Monday is going to see, and I think back to my late 20′s when that was my life.

It makes me proud to think about all the crazy things we managed to pull of with no safety net. It makes me sad that I don’t go to work with those same phenomenal people every day. And it makes me happy, now that I’m a little older and a tiny bit wiser, that I don’t have to be on-call, anymore.