“I’m the Boss, and I’m Sleeping With My Employee”

Money Dilemmas is where we talk about the tricky stuff - the conversations about money that live in the grey area between love, power, fairness, and everything in between.

Each story starts with a real member dilemma, the kind many of us have quietly wrestled with but rarely said out loud.

Because money isn’t simply transactional; it’s about what we value, what we tolerate, and what we’re taught to accept.

And at the end of every story, one of our co-founders weighs in — offering her two cents and best advice on how to navigate the dilemma.

The Dilemma:

I run a small startup with nine employees.

About three months ago, one of my team members and I started seeing each other.

It began in that blurry way these things often do - long nights, drinks after work, inside jokes that started feeling different.

He’s four years younger than me, and I haven’t felt that kind of connection or excitement in years. It’s mutual, discreet, and, for now, fun.

The problem is, I can’t tell how serious it is.

Sometimes it feels like something real, and other times like a fling that just makes the stress of work more bearable. And then last week, during a one-on-one, he asked for a raise.

He said it’s unrelated to us, and to be fair, he’s been doing great work.

But I froze. I couldn’t tell if I was being objective or completely biased.

What’s been eating at me most is the feminism part.

I’ve spent years telling other women to claim their power, build equitable workplaces, hold men accountable — and now I’m the one blurring the lines.

I keep thinking, Have I just undermined everything I stand for? We’re both consenting adults, but consent doesn’t erase power.

And since I’m the boss, there’s no HR, no oversight, no one to reality-check me.

I don’t want to lose something that feels alive and genuine, but I also don’t want to become the cautionary tale.

Do I end it to protect my integrity and my company, or trust that I can keep my personal life separate?

And if I keep it going, does that make me a hypocrite - or just a human being trying to balance both?

Camilla’s Take

You’re not the first woman to end up here, and you won’t be the last.

What makes this so complex is that you’re juggling three conflicting truths at once.

You have genuine chemistry with someone. You’re his boss. And you’re a feminist trying to reconcile desire with ethics. All three can be true, and they can all pull you in different directions.

The first thing I’ll say is this: you haven’t lost your right to call yourself a feminist.

Feminism isn’t about being perfect. It’s about awareness and accountability — and you clearly have both. The fact that you’re even asking these questions means you’re thinking critically about power, fairness, and responsibility.

But awareness doesn’t erase risk.

You said it yourself: there’s no HR department, no one to hold you accountable. That means the responsibility to create a fair environment falls entirely on you.

And the truth is, even if your relationship is completely consensual, the power dynamic will always exist.

He knows you decide his salary, his growth, and his role. That imbalance makes true equality impossible within the company context.

Here’s how I see it: if it’s a serious relationship, it deserves the chance to exist outside of this structure.

And if it’s not serious — if it’s “just” exciting and fun — then it’s simply not worth risking your credibility, your team’s trust, or your company’s stability.

So here’s my advice:

1. Pause, don’t panic. Take a step back to see this clearly. Would you want to be with him if he didn’t work for you? If the answer is yes, help him find a role elsewhere and give this a chance in the open. If the answer is no, end it now with honesty before it turns into something messier.
2. Protect your integrity like a business asset. As a woman in power, people will scrutinise you more harshly than a man in the same position. It’s unfair, but it’s true. You’ve spent years building your reputation - don’t let something casual become the story people tell about you.
3. Reflect on what this reveals about your needs. Sometimes, relationships like this appear when we’re overworked, lonely, or craving connection. That doesn’t make it wrong, but it’s worth understanding what emotional gap it’s filling. You might find that what you actually want is rest, validation, or excitement — not a relationship with an employee.

You’re not a hypocrite. You’re human.

But leadership means making decisions that protect not just your company, but your future self.

You can like him, respect him, even care about him, and still choose to end this.

That’s not repression - that’s power used wisely.

Nothing is ever worth sacrificing your integrity.

What do you think?

Share your thoughts in the discussion thread.