Once upon a time, I threw a massive end-of-quarter celebration party for my sales org. The team was about fifty or so people in total, and we rented out the upstairs of a bar in downtown Seattle. This place had pool tables, ping pong tables, mini-golf, arcade machines, and a fully stocked bar. We had hit a number that was a stretch goal, and they hit it, and as part of it I received a large budget to throw this party and then buy gifts that the team would win as part of a raffle for their achievements.
The night started off normal; we were all hanging out, playing games, having a few drinks, and enjoying the after-work event on this particular Thursday. The team was excited for the celebration and appreciative of it as well. We started giving away items like air fryers, Bluetooth speakers, PlayStations, etc. As the night went on, the drinks started flowing more and more, and at some point, I even held court at the bar, buying shots for all.
Everyone kept hanging around as the vibes picked up; you could feel the energy shift as people laughed, danced, and really enjoyed themselves. Of course, the alcohol started to have an impact on that.
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Then out of nowhere, a disgruntled sales rep of mine decided it was her time to give me a piece of her mind. This individual was on month two of a performance plan and had a real streaky performance over the last several months. Turns out alcohol and an agitated salesperson may not have been a great combo.
She proceeded to tell me everything that was wrong with the situation, my leadership, her manager's leadership, the fact that she was not given fair and equal opportunities, and more.
"And more" is probably a bit of an understatement. She saw a window of opportunity and laid into me. It started inside the bar, it ended outside the bar, and it lasted for what felt like a good half hour. I did my best to let her get her feelings out, as I knew the more I debated it, the more it would escalate.
For years I had hosted events, celebrations, happy hours, and more with my sales teams, and although I have some wild stories from many of those nights, none of them took a turn as this one did for me. I didn't like it. I wasn't a fan of the fact that I had a disgruntled sales rep who couldn't control their emotions as a result of alcohol that I had essentially supplied. I also didn't like that this exchange between the two of us created a dark cloud over what was a fun night for 49 other people. But more importantly, it was a work event, and anything that happened with my staff, even outside of the 9-5, meant I was responsible.
The next day at work, half the team called in sick, which was expected. The night went down as a legendary event, and I learned something important. I had reached a point as a leader where I had to grow up. I had to learn how to step back from these events, and as an individual who was navigating my own career growth, promotions, and taking on more responsibilities in the company, it was time for me to sponsor these events and leave before everyone else. It was almost a sad realization, as it meant I had reached a point in my career where I had to leave the fun behind and start to be even more serious about my leadership responsibilities.
Thankfully, nothing came from it; the event passed, she eventually left the team, and everyone moved on with their lives. Fast forward to when I arrived in Dubai, I told my team before our first major event that they had a two-drink maximum at events. They thought I was joking. I wasn't. When I left that role, they got me a t-shirt that read, "2 drink max."
Your judgment is now part of your brand as a leader, and people are watching how you carry yourself in situations where the lines between work and fun can get blurry.
You see, there's a thing that follows your career naturally if you do it right, and it's how things change as you progress. The young sales manager who was able to take their team out for drinks after work has to eventually grow up at a certain point in time, or you risk being known as that young sales manager with poor judgment for your career.
The further you move in your career, the more you have to understand that leadership changes the rules around you, even when you do not want them to change. There are things you can do early in your career that feel completely normal, but eventually the same behavior gets interpreted differently because the expectations attached to your role are different.
That does not mean becoming boring, stiff, or disconnected from your team. It does mean understanding that your judgment is now part of your brand as a leader, and people are watching how you carry yourself in situations where the lines between work and fun can get blurry. The higher you go, the less room you have to pretend those moments do not matter.
I think a lot of people struggle with this transition because nobody really announces when it is happening. No memo says, "Congratulations, you have officially reached the point where you can no longer act as you did five years ago." You usually learn it through one uncomfortable experience that makes the lesson impossible to ignore.
That night was one of those moments for me. I realized that career growth is not just about getting a bigger title, managing more people, or earning more money. It is also about becoming the person who can handle the responsibility that comes with all of it, even when that means leaving some version of your old self behind.