My Worst Professional Day

I’ve been asked before to outline my work habits and productivity system, and I recently set out to do just that. But as I started writing those posts, I realized that I probably first had to explain why such a system was even needed.

And to explain the need for the system, I need to tell you about the worst day in my professional life. I need to tell you about a memory that still makes me cringe even to this day.

The Catalyst

A few years back, the group I worked with was just about to start a big, brand-new project, one that I was personally very excited about. We were meeting with both the head of the group and her boss, the big boss, to discuss the project’s kickoff.

I was on an unrelated call that went right up to the start of the meeting, so I was running a bit late, but I still managed to get to the tiny conference room in time to take the last seat and make the start of the meeting.

The big boss kicked off the meeting as soon as I sat down.

“Great, we’re all here. As you know, we’re about to commence a very big undertaking.”

We all nodded along.

“To get us moving on initial steps and planning, Dan is going to present an overview of the project and lead us today in planning initial steps.”

I froze.

The group all turned to me as I felt my entire chest tighten. I had nothing prepared. I wasn’t even aware I was supposed to prepare anything, let alone lead the meeting!

I nervously cleared my throat and tried to stammer through an explanation.

“I, um, thought this was just an initial kick-off meeting and, uh…”

The big boss interjected. He wasn’t a beat around the bush kind of guy.

“Did you not prepare anything for this meeting?”

I must have looked completely flustered, pale and with a gaping jaw. There was no point in trying to come up with an explanation. “I, um, no. I haven’t.”

“Ok,” he concluded, “let’s reschedule this for next week then. Dan, mind sending the invite? Thanks everyone.”

He got up and left. The rest of the group collected their papers, stood up from the table, and followed, mercifully downplaying this complete embarrassment.

Only my manager and I remained. I felt awful.

“Listen, it’s ok, it happens to everyone. Don’t worry about it,” she very kindly reassured me. She stood up to leave, “Let me know if I can help with the prep for the meeting next week.”

She walked out. To everyone else, this was no big deal, but to me, my career was over.

The Aftermath

As I sat alone in that room, one question kept circling around and around in my head.

How could this have happened? How could this have happened??

Did my leading this meeting come up in a previous meeting? I felt like I would have remembered that.

Had an email come through about this? My inbox was fairly under control, so I felt somewhat confident something this big wouldn’t have slipped through the cracks.

Maybe my manager or her boss had mentioned it to me in passing in the hallway, or after some unrelated meeting?

I felt suddenly aware of just how many cracks existed in my system, and how painful something slipping through those cracks felt.

I panicked as my mind went through every other upcoming meeting on my calendar. Were there others that I’d be totally unprepared for?

How could this have happened???

The Old System

At the time, I really prided myself on being a fairly organized person.

Even more, though, I prided myself on something else, something really dumb: my memory.

This sounds crazy to even admit now, but at the time of this disaster meeting, I didn’t take notes in meetings. And I was proud of this! I thought this was impressive.

I thought it was something people noticed and respected, maybe even admired, like a parlor trick. “Oh, don’t worry, I’ll remember it.” I’d say with a smile when people asked if I was taking notes.

And maybe some people did notice and respect it, I don’t know. No one ever commented on it positively, at least.

But I’ll tell what people did notice: when I dropped the ball on my responsibilities.

My manager certainly noticed when she had to check in on a follow-up task that I hadn’t done.

My coworkers certainly noticed when they had to prod me on an email they sent that I hadn’t read.

And I had certainly noticed right then and there when everyone turned their eyes to me and expected me to start presenting for a meeting I was completely unprepared for.

My “impressive” short-term memory wasn’t some parlor trick that impressed people, it was a system of disorganized chaos. And it had to stop.

The Better System

I knew I needed a better system, and whatever it ended up looking like, this system would need a few critical features.

- Broad Application — I wanted this system to handle every type of input thrown at me at work: emails, meetings, calls, one-off conversations by the coffee machine, everything. I wanted a single procedure for handling all the ins and outs I experienced at work.

- Fast to Update — Last thing I needed was another full-time job managing an overcomplicated, bloated system. This needed to be seamlessly integrate into the way I interacted with and thought about business.

- Simple to Understand — I wanted this to be as intuitive to me as possible so that I never had to second guess the structure. The goal of the system would be to act as an automated extension of myself.

- Reliable — This system had to work without hiccups, plain and simple. I didn’t want to work with a system I’d need to ditch if I didn’t have my computer, my phone, or a pen and paper with me.

So I had the needs, and I was definitely motivated. As I slowly slunk out of that meeting room, my face still pale, my chest still tight, I promised myself I’d never feel that feeling again. And to this day, I haven’t. All thanks to the system I’ve built up. Tomorrow, I’ll start by explaining the critical core at the heart of it.