How I Negotiated a Sweet Salary


Back in the day I used to be incredibly shy. Like, so shy I wouldn’t even be able to talk to my friends’ moms growing up just to ask for a darned juicebox. As I grew up, though, something changed. Not just puberty, and not just “coming out of my shell,” but eventually I just sorta “got over it.” I wasn’t exactly a social butterfly, but I loved talking to people and learning more about their lives and I never had a problem playing the clown.

But when I graduated college and started going after my first big-boy salaried jobs, I felt like I was being ushered back into my my previous form. I had to ask my parents how the heck negotiation worked. I had gotten a degree in music business and was going after a job that wasn’t entry level and pretty prestigious — and I had no freaking clue how to negotiate the potential salary.

Nevermind the fact that it had taken more than a year for this promised job to finally come through as a legitimate offer. That was the hard part. “What? Getting paid? I don’t care... I’m just glad I get to work for you guys,” was my attitude. I sometimes am hard to read thanks to an upbringing that forged my personality in the white-hot fires on deadpan sarcasm, and that can be a negotiating upperhand, to be sure. But it had to have been obvious that I was checking with my parents to see what they’d advise — like one of those Facebook whiz kids did to each other to give the appearance they knew what they were doing — because I could only nudge the conversation forward one notch whenever we talked to haggle.

Even if you’re saying the right things, if you aren’t able to “seal the deal” and massage the conversation along, you’ll lose the upper hand. This isn’t so much about my specific experiences, per se, but I say that knowing that in the time that has past, as I have embarked much much more along my career, I have a better sense of my goals, where I want to go and, most relevant here, what I’m worth.

I say all of this because we all need to go on journeys to get a sense not just of self-worth, but also knowing what we’re worth roughly in a dollar amount. has a pretty cool five-item list of how to better negotiate a salary equivalent to that number, and I think the ones you should mainly glean from are Nos. 4 and 5: Never name the first number because “the first number... has a profound impact of the rest of the conversation.”

I think if you’ve gone down enough roads you’ll be able to handle the other rippling impacts that first number has. But remember: It’s only money. And money isn’t everything. Nevertheless, try making a go in this world without much of it.

That said? I’ll see you at the winner’s table in the millionaire’s mansion! 

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a comedy-writing instructor for Second City. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. When not playing video games for work he's thinking of dashing out to Chicago Diner, Pizano's, or Yummy Yummy. His first career aspirations were to be a game-show host.

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