I’ve never been particularly good at negotiating. This is a bit ironic, given I’ve covered personal finance for over 10 years, but it doesn’t come naturally to me. It’s not that I don’t think I deserve more money, but I’d rather my work speak for itself. Of course, that’s not how the real world works.
But when I was a novice reporter at Money Magazine, I wrote a story on salary negotiation and heard a piece of advice that’s stuck with me to this day: Asking for more money might be uncomfortable in the moment, but that lasts maybe five to 10 minutes at most. In any other context, would you sit in an uncomfortable silence with someone for five to 10 minutes if you knew you’d be paid, potentially, thousands of dollars at the end of it?
That thinking has helped me in many situations, including when, a couple years ago, I worked up the courage to ask for a raise and a title change that I felt better reflected the work I was doing and value I was bringing to the organization. I did end up getting the raise and the title change, but only after bringing my editor a competing job offer. That was another uncomfortable conversation and a course of action I didn’t particularly want to take, but it got me what I did want. That is, more often, how the real world works.
I’m sure you all have stories like these—about taking risks, realizing your worth, and learning hard lessons along the way. That’s what we’re exploring in Work History, our new series detailing women’s salary and career trajectories. Yes, the salary disclosures are juicy, but it’s the advice and insights these women share that make this series really valuable.
We’re kicking things off with a high earner, but today’s writer wasn’t always banking six figures—or even close to it. She started her career as an account executive for a PR agency in Detroit in 2005, earning just enough to pay her $400-a-month rent and fill up her gas tank to make it to work.
There are a number of ups and downs throughout her 21-year career, which makes for a gratifying read. If you’d like to submit your own anonymous Work History, you can do so here. We have a lot of great submissions, but we’re looking for more from women earning less than $100,000 per year.
The responses below have been lightly edited and condensed.
Age: 43
Location: Detroit
Current industry and job title: Communications, founder and principal
First salary: $27,000 in 2005
Current salary: est. $250,000 in 2026
Biggest salary drop and reason for the drop?
My biggest salary drop was $70,000. In my experience, insecure leaders are generally the reason for big salary drops that leave women laid off while pregnant, traumatized about corporate politics, and scared to speak up.
Conversely, a woman hired me while pregnant (the week I was due), became my first client, and advocated for me by sending more referrals my way when I created my own business.
Biggest salary jump and reason for the jump?
My biggest salary jump was $100,000, which came from making my own company with my own rules and no insecure leaders in my way. Now I make more money on my own terms doing work I consistently love with clients I like.
Best salary-related advice you’ve ever received?
Call a male peer, give him the job description, and ask what he’d ask for. Add $10K and send.
Another awesome piece of advice a dear friend gave me was to advocate for yourself in these negotiations like you’re sparring on behalf of your best friend. Sometimes dissociating can help remove ego from the narrative.
Biggest salary or pay-related regret?
Not asking male counterparts what they make sooner. I lost hundreds of thousands of dollars trying to fly in the middle of the pack financially with a top-tier skillset. Confidence ain’t easy.
Anything else you’d like to share?
Dear new grads: Really think about what you want in life. Not stuff, but how you want to feel. What makes you afraid? What makes you cringe. Try to spot those things in hiring managers. Turds always smell. Gems can grow. And ladies, please say nice things about women in the workplace while squashing anyone who does otherwise. It hurts all of us in the end.
Work History
First job: Account executive for PR agency
Starting salary: $27,000
Year: 2005
In this role, I pitched media news for clients and worked 50 to 60 hours per week grinding away on phones, writing pitches, tracking progress, and doing all the awful tasks generally relegated to 22-year-old college graduates.
I’ll never forget the call where I was offered the job and fumbled my way through asking for more money—like $30,000—and the HR person told me, “Yeah this isn’t that kind of chat. If you want the job, here’s what it pays.” So I took it and looked up ways to cut costs.
The wild part is that three years later, I married my then-boyfriend, who is a teacher, and he still made $5,000 more than me for a couple years. We both saved our offer letters. I did get bumped up to $30,000 two years later. Thank god my apartment only cost $400 per month.
Departing job title and salary: Account executive earning $30,000 in 2009.
Second job: Social media coordinator for professional sports team
Starting salary: $35,000
Year: 2009
I was a professional sports team’s first social media person and managed fan engagement globally. It was a cool job where I came up with web content, traveled globally, and worked with the league on setting standards for online fan engagement.
But the drive, pay, and my boss were brutal with a side of misogyny. I learned that by simply treating the players and staff like colleagues instead of celebrities, I could get access and opportunity; one player even told my boss to pay me more. Those guys were the best to me. I think about it all the time.
Departing job title and salary: Social media coordinator earning $35,000 in 2010.
Third job: Brand manager for startup
Starting salary: $60,000
Year: 2010
This was where the magic started for me. The leadership was/are such great people. I thought I swung for the fences and asked for $50,000 per year during the interview process, and my offer ended up being $60,000.
I edged it up to $70,000 per year over four years, and the brand was acquired by a Fortune 500 company. It was the best, most insane wild ride of my career.
I learned that sometimes if you show hunger and talent, a good leader will negotiate pay in your favor. He’s still part of my village today.
Departing job title and salary: Director of marketing and communications earning $70,000 in 2014.
Fourth job: PR manager for online marketplace
Starting salary: $90,000
Year: 2014
After the acquisition, the founders offered me a job in their next startup. As much as I wanted to stay with them, I wanted to become a mom more, so I declined the offer and looked for a remote role. I was hired remotely by an online marketplace and worked with the best team of my career. I worked my butt off and eventually crossed the $100K mark. Magic.
Departing job title and salary: Senior public relations manager earning $102,000 in 2016.
Fifth job: Assistant manager of broadcast at auto company
Starting salary: $132,000
Year: 2016
Through making headlines and auto-show tap dancing, I got close with some of the team at an auto company that eventually hired me. I worked. A lot. Like, a lot, a lot.
The communications leadership was fairly robotic and fear-driven, and after three years, they laid me off while I was four months pregnant.
This happened after six years of trying for a baby (and all of the pain that comes with it) and the general hell of working at a public company during the first Trump administration. Looking back, it was a great thing. But I should have told people to go to hell more often while there.
Departing job title and salary: Assistant manager of broadcast earning $132,000 in 2019.
Sixth job Job: Public relations strategist at lender
Starting salary: $120,000
Year: 2019
After the layoff, I spent a few months looking for the right fit. I went into a final job interview with a very well-known auto supplier whose CEO pointed to my 38-week belly and said, “You think you can do this job and handle all that?” with HR in the room. I said, “Welp, men do it all the time, so it can’t be that hard,” before standing up and saying thank you but no thank you for the opportunity, walking out, and rage crying in my car.
Three months prior, a different company offered me $80,000 for a role. I told HR that at that rate, they probably didn’t want someone at my experience level and recommended a couple junior candidates.
The day after the terrible interview, the other company called to let me know they got the pay up to $120,000 and invited me in for a final interview. They offered me the job on a Wednesday, and I signed the paperwork on Friday while in labor.
In this role, I learned that if you help educate HR on what the rate gets them and help introduce them to candidates who will accept the pay, it might help get what you want in the end.
Departing job title and salary: Director of public relations earning $132,000 in 2022.
Seventh job: Executive director of communications at publicly traded company
Starting salary: $200,000
Year: 2022
I got a bit antsy after a while, and the 100% onsite requirement became untenable once my second child entered the picture in 2022. So I took a remote role with a guaranteed bonus and unlimited PTO.
Amazing, right? WRONG. Week one, the CFO pulled me aside to recommend I find something different. It only got worse from there. They ended up laying me off and completely ignoring the contract we had.
So I sued them. And won a fairly large settlement. In that situation, I learned that you can’t always count on the company knowing your contract, so it’s important to memorize it and push for what’s right, even if they don’t.
Departing job title and salary: Executive director of communications earning $200,000 in 2023.
Eighth job: PR manager at bank
Starting salary: $120,000
Year: 2023
With two kids, it felt pretty scary to be without a job again so I just sucked it up and got a new one—and the company promptly went into free fall. I was there just over a year before being laid off. Whatever, good riddance.
Departing job title and salary: PR manager earning $120,000 in 2024.
Current job: Principal at own firm
Starting salary: $250,000
Year: 2025
My husband encouraged me to start my own agency and just give it a year. No more working for insecure men or worrying about their moods. So I did it. First week: two clients. First month: full client load. Annual salary projection: $250K, unlimited PTO, fully remote, and a much happier life.
Here’s what the past year and a half have taught me about salary, work, and negotiation: Know your worth, demand it, and avoid anyone who will force you to accept anything less.
