If You Want to Make Everyone Happy, Sell Ice-Cream

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Over the course of eighteen-plus years in leadership, I've been fortunate to make an impact on the careers of many. It's been an honor and a privilege to be trusted with the careers of others, helping them to develop, grow, and succeed. Many of the people who have worked for me are still in touch, and as the years go on, getting those random texts from those from the past is always a joy.

Of course, not everyone has liked working for me. I mean, let's be honest, I can't be everyone's favorite, and amidst having to make difficult decisions and delivering difficult feedback, at some point, someone is bound to dislike me.

My favorite story, though, comes from early in my career when I was in the process of exiting a particular individual. She knew it. She hated me as a result. I was a new leader who had just taken over a severely underperforming team. I had six people, and it was clear that four of them needed to go quickly in order for me to rebuild.

This particular individual, we'll refer to her as Kara. Kara was condescending to me every chance she got. She wasn't performing, and hadn't long prior to me arriving, and was sort of one of those individuals who had skirted the system for a while.

Kara knew I was zeroing in on her, and when I put her on a performance improvement plan within weeks of arriving at the job, she really started to turn her hate on me.

My favorite story to tell is when I asked to attend a client meeting with her. She sent me the address, rather than offering to do a ride-along together. Which was frankly fine, I didn't want to spend that much time with her anyway, but it was apparent she was trying to do everything she could to avoid me. We met at the client's office for the meeting, and when we walked out, it started pouring like I hadn't seen before. We were standing in the parking lot trying to recap the discussion, and Kara pulled out an umbrella and covered herself up to avoid the rain. I had no umbrella, which was only my fault, but as I stood there getting soaked, Kara continued to smugly hold the umbrella over her head, just staring at me while I spoke.

Kara knew exactly what she was doing. It was almost like a power move on her part to watch me get soaked, never offering to cover an inch of my jacket up. By the time we got done, I was drenched, and Kara was untouched by the water. I still choose to think today that she got into her car that day feeling like it was a win.

Somewhere in the next two weeks, we decided to part ways. I bet she still has that umbrella.

Look, leadership is tough, and in addition to that, being at the top of anything is hard. The higher up you go, the more success you have, the more eyeballs are on you, and with that comes more judgment. Judgment of everything you say, you do, you don't do, and more.

People have opinions and lots of them, and they tend to follow the people who deserve the most attention. You just can't make everyone happy, and if you're trying to make people happy, then you're doing it wrong.

The saying goes, "If you want to make everyone happy, then sell ice cream."

If you're a leader, you're going to have people who both admire you and want to bring you down. If you're number one in your field, you'll have people who want to take you down. If you have attention on you, you'll have people who want to take you down.

The moment you start making decisions that actually matter, decisions that impact people, outcomes, and direction, you stop being universally liked and start being respected, challenged, questioned, and sometimes flat-out resented. That shift can mess with your head if you're not ready for it. You start to wonder if you handled things differently, said something softer, or gave it more time, maybe you could have kept the peace.

The truth is, peace was never the job. Progress was. And progress almost always comes with friction, uncomfortable conversations, and yes, moments where you're standing in the rain while someone else stays dry.

So you have to make a choice. Are you here to be liked, or are you here to lead? Because those two things will not always coexist.

The best leaders I've ever seen are the ones who can sit with that tension and still move forward anyway. They don't chase approval; they chase outcomes. They don't avoid hard decisions; they lean into them with clarity and conviction. And over time, something interesting happens. The same people who questioned you, doubted you, or even disliked you start to respect you. Maybe not all of them, maybe not right away, but enough to know you did it the right way.

So yeah, Kara probably still hates me. But I walked away with something a lot more valuable. I learned that leadership isn't about staying dry; it's about being willing to stand in the storm when it actually counts.

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