Confessions of a Workaholic: The Wake-Up Call

When I was working for a fast-growing company a few years back, I was placed in a position of leading a large team. 

One of the main reasons was because we needed to build out new courses /products and I had the mind of a teacher. I also had a great understanding of the audience we were serving and what they needed to succeed. I could project manage, I could work with designers, I could create collaborative teaching arrangements. If I didn’t know something, I had a few great people to lean on who knew even more. Together, we’d release 12 products over 12 quarters together.

A great fit on so many levels!

The only problem with being in the position was that I would also be the direct manager of approximately 12 people. That’s 12 one-on-ones every week (as an introvert). Leadership experts say the right number of people for a single person to manage is 5, if you have creative or complex roles. I was managing 2.5x that and releasing a product every quarter. 

Manage isn’t quite the best word here either. These people were absolutely amazing. They needed very little oversight. They coached or supported people, day in and day out. If they ran into a crazy situation, or needed a sounding board, they could vent to me. I could ask our team what the clients were experiencing as challenges. If that was all it was, it would have been simple.

But…I was also supposed to add all this extra structure and expectations around their role. Frankly, it made me cringe. It felt restrictive and prohibitive. I didn’t like it.

But…the person paying my paycheck wanted these standards, expectations, and the structure in place, so I felt the responsibility to make it happen. Obligated. I felt obligated to make it happen.

We didn’t have middle managers fully installed yet, so I had to lead that charge. I felt so uncomfortable.

These were people I respected, people I admired and saw their brilliance. I felt like we should let them do their thing. Hire great people, get them the tools they need, then get the heck out of the way. That was my philosophy. But that wasn’t my boss’s philosophy. He wanted a replicable system that anyone could be plugged into and do that role.

I can articulate that now; I couldn’t articulate that then.

So I lived in this terrible, gut-wrenching discomfort. I worked pretty much every waking moment of a day. I neglected my family 90% of the time. My wife handled everything. I threw myself into this work. I wasn’t emotionally healthy enough to see the problems arising. Or maybe I saw all the problems, heard all the problems, dealt with all the problems — all day, every day — and just thought I could plow through them. I was strong. If I just weathered the storm, handled the next person leaving, getting the next person hired and trained, getting the next product released, it would all be ok. That’s what I told myself.

Looking back, I felt caught in the middle of a terrible circumstance. Sure, I weathered the storm. But the collateral damage was significant.

Family damage at home. Lost great people at work. Lost friendships for a time. My respect for my boss dropped a notch.

The company was “winning!” We were “growing!” Growth! Growth! More growth! We were launching new courses and products every quarter to help more people. Boss was happy because he had a replicable system that anyone could be plugged into and do that role.

But I couldn’t feel the excitement. I couldn’t celebrate the wins. Because I was stuck. Emotionally depleted. Relationally bankrupt. I didn’t feel like I was actually helping the people on my team I knew and cared about. And I certainly wasn’t helping my own wife and kids at home.

After we “turned around that team”, meaning 75% of the people on the team left the company and we hired all new, I was given badges of honor (awards and a small raise). I was then moved over to another role to improve another area of the company. The stakes were even higher. But that’s another story for another time.

Let me stop this one here. If the lessons haven’t been explicit yet, let me state some: 

1. Never sacrifice your family for work. You’ll have a lot to apologize for and a lot to fix. Much of that damage is irreversible.
2. You’ll also live with that remorse for the rest of your life (missing parts of your children’s childhood, losing friends), so the sooner you catch it, the better.
3. If something feels like it’s going against your conscience, if something isn’t settling well, get curious about it. Ask why and do the work to get clear on why.
4. If your management philosophy doesn’t align with your boss’s, work to sort that out early, find a new position within where you’re not managing, or find a way to exit graciously.
5. Embrace the times when work feels fun, when coworkers are great, when you’re doing things in your wheelhouse. It is a great joy! At the same time, remember it’s work and that’s one piece of the puzzle that is life.

This is also part of the Failure series, Entry 2. You can read Failure, Entry 1 for a more humorous account.