Chapter Two:

Surviving Your Boss

Bosses are people, too. They’re just scarier.


What kind of boss do you have?

I’ve had a lot of different kinds of bosses in my career. The office is a microcosm of the rest of the world. There are all kinds of different bosses:

The dreamer

The dreamer is constantly assuring you of imminent success to come. He’s confident, optimistic, positive and sometimes over-bearing. Sometimes his optimism can lend itself to industry buzzwords.

Even though his heart’s in the right place, unfamiliar industry terms can be fodder for your insecurities. What’s a KPI? Does a “happy path” have something to do with McDonalds? Is it “Q & A” or “Q.A.”? And if it’s “Q.A.” then, what the hell is that?

I’m approaching a decade in the industry and only recently realized how common some of those buzzwords have become in my daily lexicon. I caught myself saying the word “deliverable” to my wife just the other day. * facepalm *

If something’s confusing, Google it. If that fails, ask someone. You’re new to this, no one expects you to know all the techno-jargon. It’s actually a little refreshing.

The drill instructor

The drill instructor is not interested in explaining herself. She wants certain things done, in a certain way, usually by yesterday. Do as you’re told, and don’t distract her with “stupid” questions.

The drill instructor can be awesome if you’re comfortable with learning on your own can handle a lot of stress. The problem is, buried in their directives, lies a ton of guesswork. Since you’re just starting out, you’re not going to guess correctly very often. The odds are in the house’s favor, just like Vegas.

Since you’re not able to “pester” (ask) your boss for any guidance and nail down specifics, you’re set up for failure. You might learn a lot very quickly, but eventually you’ll burn out.

The bully

The bully is the king-pen of the start-up scene. Flush with confidence from his last successful endeavor, what he says goes. The bully isn’t interested in nurturing young talent, unless it’s by trial-by-fire.

This bully has left noogies in junior high and favors soul-crushing embarrassment in the office. Always armed with the trump card of a pink-slip, he’s free to do as he pleases. King in the castle. Resident expert. Sooth-sayer.

Bully bosses toss in personal jabs during professional critiques. Maybe 95% of their feedback is constructive, but maybe it was followed by a snide comment about your laziness. Boom, you have a bully on your hands.

For every Steve Jobs, there’s a million wannabes. Leave them to rule their kingdom and go find your own.


The good ones

Good bosses don’t expect fresh hires to know everything right away. They hired you right out of college because, lets’ face it, you’re cheap! And they probably think you can grow into something more worthwhile of their time and money. Pay attention, try hard, make it obvious that you’re trying hard, and be ready to fall on your face.

You’ll eventually mess up. While you wallow in the embarrassment that assuredly ensues after a failure, you may start to question yourself. Don’t. Everyone makes mistakes.

If you find your boss’ expectations cannot be met, try approaching him/her. Bosses are real people. Their capacity to empathize may surprise you.

Dealing with a bad boss

If your boss is a true terror to work with, don’t fret that either. Either push yourself enough to scrape by, or start looking for something else. I have experienced this first-hand (note the “bully” mentioned above).

Generally, people leave their bosses, not their jobs. It can be really stressful to quit. You might feel like this one job is your only chance at a fulfilling career. It isn’t.

There was a time when employees stayed with a company for decades. They slowly climbed the corporate ladder until retirement. For better or worse, those days are gone. There are other jobs out there for you. Better ones.

Sometimes people are assholes. Don’t let that sully your world view. Not all bosses are like that. You can do better.

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