At 65, I Finally Have My Dream Job. I Wish I Hadn't Waited 20 Years to Demand It.
Welcome Storytellers:
Today's story comes from a 65-year-old woman who finally has everything she always wanted: VP of Sales at a $7 billion company, leading teams across North America, a voice at the table. But here's what keeps her up at night—she could have had this in her 40s if she'd just believed she deserved it. This is the story of what fear costs us, why demanding what you're worth feels impossible when you're scared, and the one thing she wishes she could tell her younger self.
*To protect this woman's privacy, we have omitted names and company references.
In the late 90s, I was one of the top salespeople at my company. Year after year, I consistently crushed my numbers. Closed major deals. Outperformed most of my peers.
I'd been quietly hoping for the sales leadership role that everyone knew was opening up.
Then I went on vacation.
When I came back two weeks later, they'd promoted someone else. A man with equivalent experience who'd asked for it.
No one had even asked if I was interested.
Months later, when I finally resigned, they said: "We never thought to ask you because you were making so much money. We didn't think you'd want it."
But they didn't ask.
And I didn't demand.
Here's what nobody tells you about being afraid: It doesn't just cost you one opportunity. It costs you decades. Every time I was passed over, I told myself the same story:
- I'm a single mom. I can't risk this job.
- I need stability. The benefits. The paycheck.
- What if I speak up and they fire me?
- What if I'm not actually good enough?
So I stayed quiet. I moved companies when things got bad enough. I let fear make every decision for me.
And the pattern repeated. Different companies. Same story.
There was the time I uncovered a major opportunity after a colleague abandoned me mid-meeting in Paris. When I reported his behavior to HR, they told me I'd "misunderstood." Then they prohibited me from working international accounts.
I had documentation. I could have fought. My daughter asked why I didn't.
The truth? I was exhausted. And terrified.
I've thought a lot about why I waited so long to demand what I deserved.
Here's what I know now:
We're taught that needing the job means accepting less. Single moms. Women with kids. Women who can't afford to lose health insurance. We're told our desperation makes us powerless.
We're conditioned to be grateful, not demanding. "Be thankful you have a job." "Don't rock the boat." "Maybe next time."
We internalize every rejection as proof we're not ready. Every time someone says you're "not experienced enough" or "not tough enough," it becomes evidence that they're right.
We mistake fear for intuition. That voice saying "don't ask" isn't protecting you. It's limiting you.
I learned too late that the moment you stop needing any single job, everything changes.
In my last two roles? I negotiated hard. I had leverage. I demanded what I deserved.
And suddenly, I wasn't just accepting whatever was offered.
Today, I'm VP of Sales for North America at a $7 billion technology company. I lead teams. I travel internationally. I have a seat at the table.
I made it.
But here's what haunts me: I could have demanded this 20 years ago.
I spent decades being passed over because I was too afraid to demand what I deserved.
Now I have my dream job, and all I can think is: I wish I hadn't waited.
If I could go back to that scared single mom who stayed quiet because she needed the paycheck, here's what I'd tell her:
- Your fear is valid.
- Your bills are real.
- But your worth isn't negotiable.
- Demand the role. Ask for the promotion. Name your salary. The worst they can say is no—and you'll survive that. You've survived worse.
- You don't have to wait until you're financially secure to act like you're worth it.
The women who get ahead aren't less scared. They're not less worried about their kids or their mortgages. They just refused to let fear make the decision.
Every year you wait is a year of income you'll never get back.
Not just money—opportunity, advancement, the career trajectory that builds on itself. You can't make up for lost time.
Don't do what I did. Don't let fear cost you 20 years.
Your kids need to see you demand what you're worth more than they need you to play it safe.
You deserve the role now. Not eventually. Now.
Have you ever stayed silent when you should have demanded more? What held you back? Share your story in the comments, I want to hear what fear has cost you, and how you're done letting it win.
This is I'm Her Story, where we tell the truth about what it really takes to build the career and life you deserve.
- If this resonates with you, you're not alone.
- This is exactly why we need spaces where women can share these experiences without judgment. Your story matters, and there are thousands of women who need to hear it.
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