Negotiation Is Not Rude. It’s Required.

Welcome to the fourth edition of Jobtober! The little tiny pumpkins are taking over your grocery store window display, and for many of us…it’s OPEN ENROLLMENT season! In this five-part series, we’ll explore how to make your job work for you and how to improve your life at work (well, at least the financial part of it). We’ve already covered employee benefits, layoffs, and consulting, so let’s look at how to ask for more money.

Key Takeaways:

• A small gap in compensation at the start of your career grows into a large one over time.

• Make your ask about results, not emotion.

• Preparation, timing, and context make the difference between success and failure.

When I graduated from college, the country was still reeling from the 2008 financial crisis. I had a degree in English from a small liberal arts school and a few internships under my belt. I was excited to snag one of the rare editorial assistant jobs out in the world. When the offer came, I said yes before the email even finished loading. It was a recession, I was lucky to get anything, and I didn’t want to risk looking ungrateful, or worse, risk them giving the job to someone else. That line from The Devil Wears Prada haunted me: “A million girls would kill for this job” and “I can find someone to do your job in five minutes.” Still, at the time, an extra five thousand dollars a year would have covered most of my student loan payment each month. What I didn’t realize in that moment is how painful that lack of negotiation would be in the future.

Let’s look at why.

Raises are usually given as percentages of a salary. A “standard” 3 percent bump each year is called a merit increase, but most of the time it’s just COLA, cost-of-living adjustment. Translation: your boss is helping you barely keep up with the pace of inflation.

Say your starting salary is $30,000. Meanwhile, your colleague negotiates $35,000.

• After one year, with a 3 percent merit raise, the gap between your two salaries is $5,000.

• After three years, it’s about $5,300.

• After ten years of “just 3 percent raises,” your salary will be at about $39,000. But your colleague’s will be at about $45,500. The gap has grown to $6,500 a year.

And that’s before bigger raises, promotions, bonuses, or retirement matches—all of which are calculated as a percentage of your base salary, as well. What starts as a polite silence when you’re 23 years old ends up costing you a decent vacation or the financial freedom to leave a job you hate. Inaction compounds.

I hear excuses for not asking for a raise all the time. A client once told me, “It just feels rude to ask. I like my boss. I don’t want to spoil the relationship.” She’d been promoted twice in two years, managed a team, and directly generated revenue for her department. Yet asking to be paid more felt, in her words, “like crossing a line.”

There was a story that floated around my publishing office, that a woman finally asked for a raise after three years of doing the work of three people. She rehearsed her speech, printed out her wins, and booked a meeting with her boss. He leaned back and said: “Oh, thank God. We’ve been waiting for you to ask.” The budget had been there all along. They just weren’t going to hand it over until she asked. That’s how most workplaces operate. Negotiation isn’t personal, though it feels that way. It’s not about whether your boss likes you. It’s about whether you’ve made a business case. The comps matter—but not all comps are created equal. That salary you saw on Glassdoor might be inflated by a higher cost-of-living city, or a role that demands 60-hour weeks in an office, not a flexible remote setup. You have to decide how much the lifestyle differences are worth to you. Comps are a good guideline.

And then there’s timing. Annual reviews, new responsibilities, or big wins are obvious openings for a raise discussion. But sometimes the best time is off-cycle, when your boss isn’t benchmarking you against everyone else at once. You want to catch them in a moment when they can actually listen.

The hardest part about asking for a raise is taking the emotion out of it. You are not begging for a favor. You are not confessing. You are presenting numbers: Here is the value I bring, here is what the market pays for it and here is the salary I’d like to discuss. Then stop talking. Silence works wonders.

Not everyone gets this right the first time. I heard an anecdote once about someone who walked into their boss’s office and delivered an ultimatum: more money immediately, or they were quitting. They were just fed up and exasperated after a difficult day. They didn’t have any sense of timing; it was just an empty threat. Unfortunately, their role wasn’t deemed essential, and they were let go that week. That wasn’t negotiation; it was an emotional explosion. Those can be dangerous.

The same rules apply when you’re evaluating a new job offer. Salary is one part of your compensation. Don’t get me wrong, it’s the big one. But there’s also vacation, a signing bonus, professional development funds, flexibility, maybe some equity—those all carry weight. Equity especially gets sold like a lottery ticket. But until a company goes public or gets acquired, those shares have only implied future value. You can’t Venmo your landlord with vested options. Take stock options if they sweeten the deal, but don’t rely on them to fund your current lifestyle. Rent is due in actual dollars.

The American workplace is built on a culture of negotiation. It’s not impolite to do it, it’s expected. I didn’t understand that when I started out and it cost me years of compounding opportunity. Negotiation is about making sure your pay keeps pace with your contribution, and making sure the life you want isn’t slipping quietly out of reach while other more assertive colleagues suck up the department budget.

Parting shot: It never hurts to ask.