The Raise She Didn't Need to Ask For

She came to our first session with a clear problem: She'd been at her job for 2.5 years without a raise or performance review. She was ready to ask for more money—she just didn't know how.

Should she schedule a formal meeting? Should she ask her boss or go through the Chief of Staff? What if she didn't say the right thing? What if they said no?

These were the questions spinning in her head. They seemed like the right questions. Strategic. Professional. Reasonable.

But within 20 minutes of coaching, we discovered something: She was asking the wrong question entirely.

The Problem Beneath the Problem

Here's what we uncovered:

She'd been making $85,000 for 2.5 years as an Executive Assistant to a CEO—while also doing the work of a part-time paralegal (a role the company eliminated when they hired her). Meanwhile, other EAs at the same company—hired after her, working for non-CEO executives—were making $120,000.

She'd looked at comparable EA roles in her city. Nearly all of them paid significantly more than what she was making. Many required less responsibility than what she was already handling.

And here's the kicker: She didn't even like the work.

The job had shifted from executive assistant work (which she enjoyed) to personal assistant tasks—letting the boss's dog out, picking up laundry, coordinating family logistics. The company's mission (shipping and logistics) bored her. She had zero passion for the industry. She wanted growth, skill development, and work that felt meaningful.

So here's the question I asked her:

"If you ask for a raise and get it, will that make you stay? And if you stay, are you actually getting what you want—or just getting comfortable in the wrong place?"

Silence.

Then: "Oh. I don't want to stay."

The Shift

What started as "How do I ask for a raise?" became "Should I even be asking for a raise in a job I want to leave?"

And suddenly, everything clicked.

She realized she'd been spending all her mental energy figuring out how to negotiate a raise in a role that didn't align with her values, her career goals, or her financial worth.

She was planning elaborate conversations, rehearsing scripts, strategizing who to talk to and when—all to get a pay increase that would only make her feel more stuck.

Her breakthrough (in her own words): "I'm focusing on wanting a raise in a job and position I don't value. If I focus my energy on applying to other jobs, I would get to the place I want to be much faster without the detour of asking for a raise and then feeling more stuck."

That's what coaching does. It doesn't give you the answer to the question you came with. It helps you discover the question you actually need to answer.

The Pattern That Keeps People Stuck

But here's the deeper issue—and this is where the real work began.

She told me: "I work harder for others than I do for myself."

She'd been at this company for 2.5 years, underpaid and undervalued, waiting for someone to notice. She didn't ask for a raise. She didn't set boundaries around personal assistant tasks. She just kept performing, hoping that if she did enough, someone would eventually reward her.

Where did this pattern come from?

The school system.

Think about it: In school, you didn't have to ask for good grades. You earned them, and you were rewarded. The system taught you that performance = automatic recognition. You didn't negotiate with your teacher for a better grade. You didn't advocate for yourself when you thought you deserved more. You just did the work and trusted the system to notice.

That belief gets carried into adulthood. And it keeps people stuck.

Because here's the truth: Workers who perform without asking for more are incredibly valuable to employers—they stay cheap.

Companies don't proactively give raises just because you're doing great work. They give raises when you ask. And if you've been systematically conditioned to believe that asking is uncomfortable, inappropriate, or unnecessary? You stay underpaid.

She wasn't avoiding the raise conversation because she was lazy or scared. She was avoiding it because the system taught her that advocacy wasn't her job. Her job was to perform. Recognition would follow.

Except it didn't.

The Evidence She Already Had

Here's what made this session so powerful: She'd already proven to herself that she could do the hard thing.

A few months ago, her boss kept asking her to watch the family dog. It wasn't in her job description. It was inconvenient. It pulled her away from actual work. But she kept saying yes—because saying no felt uncomfortable.

Then one day, she finally had the conversation: "Hey, I can't keep doing this."

And you know what happened? Nothing bad. The boss said okay. They found someone else. She stopped getting asked.

It was, in her words, "literally so good."

So I kept bringing her back to that moment throughout our session:

• "What happened when you set the dog boundary? Nothing bad."

• "What do you think would happen if you casually mentioned the raise to your boss? Probably nothing bad."

• "What would have actually happened if you left Christmas early when you were exhausted instead of staying until you cried? Probably nothing bad."

She'd been catastrophizing outcomes that, when she actually looked at the evidence, never materialized.

Her own reflection after the session: "Realizing my fears when anticipating 'what will happen if...' I do what I want, and the answer is generally nothing or no big deal yet I fret over it like it's the end of the world."

Your fears are not predictions. They're patterns.

What Changed

By the end of our two-hour session, here's what shifted:

Before:

• Focused on how to ask for a raise in a job she didn't value

• Overthinking scripts, formal meetings, and who to talk to

• Waiting for external validation and recognition

• Prioritizing everyone else's needs over her own career growth

After:

• Clear that the goal isn't a raise—it's a new role

• Committed to updating her resume and applying to 5 jobs before our next session

• Aware of the pattern: she works harder for others than for herself

• Ready to explore how to build internal motivation to advocate for herself

She rated the session 10/10 for value. She said the clarity she gained was a "major breakthrough, everything clicked." She felt heard, seen, and supported at the highest level.

But here's the part that matters most: Her confidence in implementing the action plan? 6/10.

She knows what to do. But knowing and doing are two different things.

That's the work ahead.

The Lesson

If you're stuck in a job where you're underpaid, undervalued, and waiting to be noticed, ask yourself:

Am I advocating for myself, or am I hoping someone else will do it for me?

The system didn't teach you to ask. It taught you to perform and wait for recognition. But that's not how the real world works.

You don't get what you deserve. You get what you negotiate.

And sometimes, the negotiation isn't about getting more money in your current role. It's about having the clarity and courage to walk toward a role that actually values you.

What Coaching Does

Coaching doesn't tell you what to do. It helps you see what you already know.

She knew she was underpaid. She knew the job wasn't fulfilling. She knew she wanted something different. She knew she was capable of difficult conversations.

But she'd been so focused on the question she thought she was supposed to ask ("How do I get a raise?") that she couldn't see the question she actually needed to answer ("Do I even want to stay?").

That's the power of coaching. It doesn't give you answers. It gives you clarity.

And clarity changes everything.

If you're ready to stop waiting for recognition and start advocating for yourself, let's talk.

Book a free discovery call at lifesnotsmall.com or reach out on socials with any questions!

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Brandon Small

Life's Not Small Coaching