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The Most Significant Award I’ve ever Received : Part 2 The Pit of Despair

Updated: Aug 27, 2022

In part 1 of this series, I talked about my life leading up to becoming a traveling consultant. This post picks up just after walking through the portal to this new life.

The best way to describe my first year of Microsoft Consulting Services is that it was periods of technological euphoria, punctuated by moments of absolute terror. I joined the company as a remote employee in 2008, before working remotely was cool. I flew to Minneapolis to onboard to the company and then started working from home. I was with Microsoft for two weeks before my boss called me on a Monday and said, “I need you to go to Microsoft Services University for three consecutive weeks in Seattle. You leave tomorrow.”

Hearing those words were a complete shock to my system, despite knowing it was a possibility. Was I really going to leave my family behind for a full three weeks on short notice? It took a bit to process, but then I recognized that this is exactly what I signed up for, so if I was going to put my best foot forward I needed to jump on the opportunity.

I quickly made arrangements and headed off to Seattle, leaving my bewildered family behind. The training ended up being a mix of a Tony Robbins seminar and some of the best professional development training I’ve ever taken, but it was grueling. At the time, Microsoft was known for training that lasted from around eight in the morning to eight in the evening, and we had Saturday work too. Plus, I was now on Pacific Time, and my family was on Central. So, I sweated having to navigate the schedule to still connect with my wife and kids.

Then disaster struck. In the middle of the coldest February in decades, our furnace caught on fire. My wife was overwhelmed by the enormity of the emergency. Years later, I still remember her desperate cries on the phone and being powerless to help her. Luckily, her parents lived in town, so they had a place to stay while it got sorted out, but that kind of event wasn’t something I had even considered when I took the role.

When I finally got home after a couple of the longest travel days of my life, we were all so happy to see each other. Words can’t describe it. That weekend was far too short, though, because the next week, I was off to my first customer for four days on-site and three nights in a hotel.

If you’ve never lived this lifestyle, here’s a taste of what my week looked like. Monday would begin by 5:00 am with travel, hoping to get to my client by 1:00 pm for an afternoon of meetings. Then the evening was spent catching up on the four hours of work missed due to travel. Tuesday and Wednesday, the goal was to squeeze in twelve or more billable hours both days, getting to 32. Thursday, I would jam another 10 hours in before my late flight home. Finally, with 42 hours billed, there was time on Friday to attend mandatory corporate meetings and training and still squeeze in another four billable hours. Then maybe I would only have to work four more hours on Saturday if it was a light week.

As brutal as this may sound Fridays at home was a progressive move on Microsoft's part and I had a better boss than most of the people I knew in the consulting industry. I had friends who's clients demanded Fridays on site, and being back first thing Monday morning. So in some ways I had it easy.

Behind the schedule was a goal to reach 110% attainment on my billable hours to avoid the dreaded “meets expectations” rating and minimal bonuses that come with it. To be clear, I knew that’s what I was signing up for when I started. I knew that there were consequences of my travel that my family and I were going to have to adjust to. But there was one hazard of my hectic schedule that I never saw coming.

There was a pattern that had developed when I would call home. One of my kids would get on the line and I would hear,

“Daddy, what did you do today?”


I had nothing. I was literally out of words. After a brutal travel day, verbally jousting with customers, and the challenge of managing corporate expectations, there were just no more words in my brain. Plus, my kids didn’t actually want to hear about how I spent my day discussing the comparative encryption strength of RSA vs. AES algorithms.

So, day after day, I found myself in the same place…leaving my family hanging on the end of a dead phone line because I'd run out of words. On more than one occasion after the call ended with a weak "Love you." I just sat there alone in my hotel room completely broken with grief.

What kind of father can't even hold a five minute conversation with their family?

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