How You Feel About Taking a Sick Day Tells Me Everything I Need to Know (About Your Boss)

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In my late 20s, back when I worked a corporate job, I once called in sick early in the morning with a wicked migraine.

The sort where you can't have your curtains open. Where your head feels like someone has tied a thick elastic band around it, pulling tighter by the minute. If you know, you know.

So I made the call, told my boss briefly what was happening. She said "no problem." I went back to bed, relieved.

By 11 AM, I hear my phone (which shouldn't have been anywhere near me) go ding, ding, ding.

And of course, against my better judgment, I checked.

And of course it was her.

"Please urgently review this file and let me know."

I felt crazy. It was like our morning conversation never happened.

I didn't reply. I couldn't.

An hour later, another alert.

"Did you get my last text?"

So I (painfully) typed: "I can't. I have trouble with screens since I have a migraine. I'll review this when I'm better."

And then I turned the phone off.

She wasn't happy about it when I got back to work.

The Red Flags I'll Never Ignore Again

Here are a few things I'll never understand about some leaders, and refuse to accept anymore in my thirties:

1/ The Complete Lack of Empathy

Health is more important than any document. Period. And guess what? It wasn't urgent anyway. She sat on it for two days before sending it out.

When a leader can't extend basic compassion to someone who's unwell, it reveals something fundamental about their character. They see you as a resource to be extracted from, not a human being who occasionally needs rest and recovery.

2/ False Urgency as a Management Style

If everything is urgent, nothing is.

Also, if one person is the only one who can review a document, you've got a leadership problem. Build your team better. Cross-train people. Create redundancies. That's what strong leadership looks like—not frantically texting your sick employee because you failed to plan ahead.

False urgency is often just poor planning dressed up as dedication. And it burns people out faster than anything else.

3/ No Respect for Basic Boundaries

To this day, I'm triggered when people send me work on WhatsApp. A quick question is fine. Sharing a win is great. But anything else? I'm too old for this now.

Honestly, it used to be the most boundary-crossing communication channel in my life. There's something about the casualness of messaging apps that makes people think they can reach you anytime, anywhere, for anything. And leaders who exploit this? They're telling you loud and clear that your personal time means nothing to them.

4/ When You Have More Emotional Intelligence Than Your Boss

This is the killer. You won't stay with them long because you'll burn out trying to compensate for their lack of this all-important form of intelligence.

You'll find yourself managing their emotions, smoothing over their mistakes with the team, and constantly making excuses for their behavior. That's exhausting work, and it's not your job.

If you're lucky, the company will recognize this and change the leadership. This was the case for me. But if not? The answer is clear. Low-key seek greener pastures.

What Taking a Sick Day Should Feel Like

Here's the thing: how you feel about calling in sick is a perfect litmus test for the quality of your leadership.

If you feel guilty, anxious, or stressed about taking a sick day- if you find yourself checking your phone "just in case" or apologizing profusely for being human- that's not a you problem. That's a leadership problem.

In healthy work environments, taking a sick day looks like this:

• You inform your manager

• They say "feel better" and mean it

• Your team covers for you (because that's what teams do)

• You recover without interruption

• You return when you're actually better

No guilt. No texts. No "just checking in" messages that are really thinly veiled requests for work.

The Culture Question

Leadership isn't about squeezing more out of people. It's about building a culture where they don't feel like they have to choose between their health and their job.

And let's be real- when leaders ignore boundaries, manufacture urgency, and treat sick days like personal inconveniences, what are they really saying? That loyalty is a one-way street. That your value is purely transactional. That you better not be human on their time.

The best leaders I've worked with since that experience? They've been the ones who actively encourage rest. Who tell you to close your laptop when you're unwell. Who say things like "your health comes first" and actually mean it.

Because they understand something my old boss didn't: burned-out, resentful, boundary-violated employees don't produce great work. They produce turnover statistics.

Final Thought: You Deserve Better

If you're reading this and thinking about your own workplace, ask yourself: What would happen if I took a sick day tomorrow?

Would you feel supported, or stressed? Trusted, or guilty? Like a valued team member, or like you're letting everyone down?

Your answer tells you everything you need to know- not about you, but about your boss.

And if the answer makes you uncomfortable? Maybe it's time to start looking for a leader who actually knows how to lead.

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