If Leadership Feels Worse, You’re Probably Doing It Right
The first leadership role feels harder not because things got worse, but because you finally see how much is broken—and you’re now responsible for it. You lose control, gain pressure from both sides, and have to deliver through others instead of yourself. If it feels uncomfortable, that’s not a problem—that’s leadership.
Carter Cathey
4/1/20262 min read
The first time you step into leadership, something strange happens. It doesn’t just feel harder. It feels like the entire business suddenly got worse.
It didn’t. You just started seeing it differently.
As an individual contributor, problems come and go. Some days are smooth. Some aren’t. There’s an ebb and flow.
As a leader, that disappears.
Your team brings you their problems. Constantly. You stop seeing what’s working and spend most of your time inside what’s broken.
If you’re not ready for that shift, it can make everything feel a lot darker than it actually is.
At the same time, you start doing less of what made you successful. You were promoted because you were great at something—selling, building, executing. Now you do less of it. Instead of doing the work, you’re enabling others to do it. And if you were a “super-doer,” that’s a tough adjustment.
Because jumping in is still the fastest way to solve the problem…but it’s the wrong move. Every time you take over, you get the result—and your team loses the opportunity to grow.
The tradeoff isn't obvious at first.
Then there’s the pressure.
As an IC, it comes from one direction. As a leader, it comes from both.
Your team pushes up.
Leadership pushes down.
You’re not on one side anymore. You’re the point where it all meets.
And no matter how hard you work, there will always be more problems than hours. So you start making tradeoffs—knowing full well that some real issues are going to sit unresolved. That’s new. And it’s uncomfortable.
This is where a lot of new leaders get it wrong. They interpret the discomfort as a signal that something is off. So they soften feedback. They avoid hard conversations. They jump in and do the work themselves. They try to make the role feel like it used to. It doesn’t work. Because the discomfort isn’t a warning sign.
It’s the job.
And if you're trying to eliminate it, you're probably avoiding the work that actually matters.
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About Carter Cathey
Carter Cathey is a sales and revenue leader with more than 20 years of experience helping market research, technology, and private-equity-backed businesses scale revenue, improve operations, and build predictable growth systems.
Throughout his career, he has led sales transformation initiatives, pricing strategy projects, subscription business model transitions, operational redesign efforts, and commercial growth programs.
He writes about leadership, organizational design, business systems, data-driven decision making, and the challenges companies face as they scale.
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