How to Survive Your Relationship with Your Boss

Why you can never build trust and how you’re always bound to talk about the damn weather.

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The most complicated relationship in my life isn’t with a partner or a soulmate. It’s not with family, friends, or anyone I recently met. The most complex relationship in my life is the one I have with my boss.

The problem isn’t that we don’t click. In a lot of ways, my boss gets me. She knows my strengths, and my weaknesses. She knows what I like doing and what’s considered a favour when it travels down the pipeline and finally lands on my plate.

She knows to say please and thank-you when she asks me to train an intern. That kind of patience sits on the far edge of my personality. My boss knows that I need long stretches of time with no calls. If I skip a meeting, she understands that she’s gone too far. She automatically clears my schedule for the following week, or I just might quit.

The company likes to say that they’re all about transparency, but my boss knows I’ll take that too far. I’ll say all the “wrong things” to big clients and screw up major business, knocking us off track to meet revenue targets. And I’ll be completely oblivious to everything that happened.

Business speak is so beyond me.

So, it’s not that we don’t jive.

It’s just that, it’s complicated. It’s more complicated than dating.

When you date, you’re looking to build something with someone. You’re hoping to do that relatively constructively, harmoniously. Peacefully? You’re looking to grow old, together. Happily ever after. At some point, you might even create joint bank accounts — the pinnacle of trust. I could never do that with my employer.

If I’m wrong about all this, you’ll forgive me? I’m single.

I’m also constantly in the market for a job. Even if I have a job, I’m looking for a job. When I have ten offers lined up, I’m in the market for a job. When the ink is still wet on the contract I just signed, I’m looking for a job. When I have a job, and a side gig, and a part-time swing, I’m in the market for a job.