How I Tried (and Failed) to Negotiate My Pay

We’ve all read the listicles. We’ve read the articles in Forbes and Fortune. We know we need to have more conversations about being paid appropriately, and negotiating for higher rates. In theory, we know how to negotiate for higher pay.

I had never had a job where I even considered negotiating, up until I learned an acquaintance of mine had an opportunity on her team. She ran a content creation and event planning company in my hometown and was looking for an assistant to help her with a busy season.

“How do you feel about it?” a friend of mine texted me. She worked freelance gigs like this all the time, and she had experience setting up contracts.

“I don’t know much about independent contracting, so I’m researching,” I told her. “The money is good though — $19 an hour.”

“That’s actually kind of low,” she typed back.

Having never worked for more than $15 an hour previously, $19 an hour initially sounded great. Another friend of mine, however, reminded me that freelancers have to save at least 35 percent of their earnings for taxes. So, after savings, I was realistically only looking at $13 to $14 an hour.

Through several more conversations with peers, I realized I was being underpaid for this gig, and I was terrified at the idea of negotiating. The friends I had talked with had experience and talent. They knew their worth and weren’t afraid to ask for it. While I always loved and appreciated them for it, I wasn’t entirely sure if I was that same kind of woman. Sure, I had a bit of success in previous career opportunities, but what did I know about this very specific business? At the same time, my gut was telling me not to push. This potential boss was a one-woman business, not an agency or firm. She was just one human, and it was possible $19 an hour was the best she could afford.

My friends convinced me to negotiate anyway. As a young professional, fresh out of college and hot off the heels of a fantastic New York City internship, I couldn’t deny I wanted the chance to shine. This was my chance to prove I was the kind of woman who could walk into a room, know her worth and demand to be paid appropriately. Armed with my friend’s encouragement and a slightly inflated ego, I set up another meeting with my potential boss.

This is the part where I wish I could say: And you know what? It turned out great!

Spoiler: it didn’t.

A few days after our meeting, my potential boss called to inform me she had decided not to hire me. I was crushed. Not only did I feel I had let all my female freelancer friends down, I felt embarrassed and ashamed. I pushed too hard. I ignored my gut. I lost out on what could have been an incredible learning opportunity. I spent days wondering if this was the painful piece of humble pie I needed, or if I had just blazed into that meeting so hard, I left any chances I had in flames. Was this just a case of business as usual, or was I victim to the same demise of so many other women before me?

I let my bruised ego heal and found a job at a coffee shop while I continued job-searching. A few weeks later, I checked in with my almost-boss, letting her know I was considering writing about the experience. Being a writer herself, she understood this and did me one better: she offered to meet and explain her reasoning for rescinding the job offer.

Truthfully, this was the last thing I wanted to do. It was going to be awkward and painfully humbling to hear her list all the things I did wrong in that initial meeting. Just the thought put a hard rock of uncomfortable embarrassment in my stomach. Ultimately, that’s exactly why I agreed to meet with her. She was giving me an invaluable opportunity.

Bythis point, I had a few theories about why she decided the way she did. For all my apprehension, I was still immensely curious. Was my earlier assumption right? Since she ran a small business, was it more likely she realized her business couldn’t even afford an employee? Was it better to reconsider now, before she hired me, rather than discover three months after the fact that it was a mistake?

“Your instinct was right,” she told me that night. “It’s not because you negotiated. I can’t stress that enough. I would never tell a woman to not negotiate.”

At a cozy little wine bar downtown, she shared that when she called me that Monday morning, she hung up the phone feeling in her gut exactly how I must have felt that day, and knowing she was the one who caused it. She told me a story about how she had similarly applied for a job, only to be absolutely crushed when it didn’t pan out. She shared her negotiation advice, and how I could improve the next time around; stressing again and again, that my negotiation wasn’t the reason she didn’t hire me. Ultimately, my theory about the state of her business was an accurate one. She realized her company wasn’t as ready for another employee as she initially thought. We both agreed it would be far better for her to realize this then, rather than later.

When I lost the job, I thought I had missed out on an incredible learning opportunity. I thought that by not successfully negotiating, I was somehow less of a professional and that it reflected poorly on my character. This entire experience though, from the research to the negotiation, was the real learning opportunity. Having the chance to sit down and discuss my almost-boss’ reasoning at length not only gave me a powerful insight to her thinking, but it also provided encouragement in the aftermath. I learned that, as they so often say, sometimes it’s just business.

She did ask me one question that caught me off guard during our meeting, though: “What did you learn from all this?”

I sipped my wine and was silent for a moment. “I need to trust my gut more,” I finally said, setting my glass down. “I knew, instinctively, that you couldn’t afford the rate I was asking.”

She nodded. When she hadn’t trusted her gut, she said, it “completely screwed her over.” I appreciated the bluntness.

My friends weren’t wrong for encouraging me the way they did. Their advice came from experience and time. These were the tactics they used to find success in their own lives, and it’s worked well for them. Just because it didn’t work this time, doesn’t mean it won’t work the next. I know I’ll be playing numbers chicken again some day, this time with experience that should lead to better success. All the listicles and friendly advice, however, can’t give you one of the strongest tools in your arsenal: intuition. I didn’t trust myself in that initial moment, and I lost a job. I trusted I could learn from the experience by meeting with the successful businesswoman who turned me down, and I did. Now, instead of an almost-boss, I have a mentor and friend. I walked away from that wine bar feeling encouraged and inspired.

It’s rare to get the chance to know exactly why something didn’t pan out the way you thought it would. Too often in life we’re stuck with the crappy outcomes, and none of the explanations. Sitting down with her has become one of my favorite moments in my (relatively) short career.

Regardless of where the rest of my professional life takes me, I know this: trusting myself is the best negotiation tool I have.

Originally published at