I turned 55 right before my world shifted.
After five years in a remote role paying nearly $80,000, I faced a choice: wait to be laid off or accept a deferred resignation offer. I took the resignation. Then I did what millions of older workers have done before me—I started applying for jobs.
Six weeks later, I was sitting in a remote training program for my new employer.
What followed was a humbling, embarrassing, and ultimately hopeful journey that proved something I’d begun to doubt: there is still room for us in the workforce.
This is that story.
Remote Interview #1: Allstate
The first interview I landed was with Allstate for a remote role paying $54,000. The recruiter gave me a heads-up: be prepared to use the STAR method.
The recruiter gave me a heads-up: be prepared to use the STAR method (Situation, Task, Action, Result). I’d never used it before. So I spent the entire week doing nothing but learning that framework. I studied examples. I wrote out my own stories. I practiced until I could recite them in my sleep.
The interview went well. Really well. I walked away from that video call thinking, “I’ve got this.”
A few days later, the rejection email arrived.
I felt awful. Crushed. Like I’d wasted an entire week learning something for nothing.
Remote Interview #2: CCC Intelligent Solutions
Not long after, I got another invitation—this time from CCC Intelligent Solutions, an auto insurance technology company that uses AI to connect insurers, repair shops, and other stakeholders . This was a remote customer service role, starting at $18 per hour .
By now, I was still smarting from the Allstate rejection. I convinced myself there was no point in preparing. In my head, I’d already decided they wouldn’t want me anyway. I mean, $18 an hour? I have an MBA. Surely they’d take one look at my resume and know I had no intention of staying.
I bombed that interview so badly it still makes me cringe.
The interviewer, a man in his thirties, asked simple questions—the kind you can only mess up if you haven’t prepared at all. I couldn’t tell him about the company. I fumbled through describing my preferred management style. At one point, he looked at my resume, saw the MBA, and asked, “Do you want to be a manager?”
My response? “I could be a manager.”
Not “I’d love to.” Not “That’s my goal.” Just… “I could be.”
Deep down, I think he wanted to hire me. But I gave him nothing to work with. I walked out of that interview knowing I’d sabotaged myself.
Remote Interview #3: A Finance Company (and the One That Worked)
Then came the third invitation for another remote position. I’m not going to name the company—it’s in the finance industry, and they’ve been good to me. But this time, I did something different.
I prepared.
I learned about the company—not superficially, but really learned what they did. I pulled out those STAR responses I’d crafted for Allstate. I practiced. I showed up ready.
The first interview was with a recruiter, a man who sounded like he was also in his thirties. When he asked what I knew about the company, I recited bullet points I’d pulled from their website. Nothing fancy—just actual information.
He was impressed. Not because I’m brilliant, but because most applicants don’t bother. He told me as much: “Most people have no idea what we actually do.”
Within an hour, he’d sent me to the next round—a department head. He explained they had a training class starting in a month, but he was putting me on a fast track so I could join a class starting in one week.
That next interview was with a woman, also in her thirties, on video. I gave the same answers. She was equally impressed.
I got the job.
The Grey Hair Moment That Didn’t Matter
Here’s something I haven’t mentioned yet.
I showed up to that video interview with grey hair. Not hidden, not dyed—just there, visible, undeniable. The manager even acknowledged it in a small way, putting “Miss” in front of my first name during the interview.
My resume didn’t hide my age either. I’d left off some older jobs (casino experience I didn’t think was relevant), but anyone looking could tell I was at least 45. Probably older.
She didn’t care. Neither did the recruiter. What they cared about was that I’d done my homework, that I could answer their questions, that I seemed like someone who would show up and do the work.
From $20/hour to $1,000+ Monthly Bonuses
I got the job. I completed a six-week remote training program at $20/hour. At the end, I was promoted to another department and received a $2 per hour raise—now at $22/hour.
Six months later, I was promoted again to another department. This time, the hourly rate stayed the same, but I gained access to performance bonuses. Those bonuses now consistently exceed $1,000 per month on top of my base pay.
That $18/hour job I bombed? The $54,000 role that rejected me? They don’t matter anymore. What matters is that I kept going, kept preparing, and eventually landed somewhere I could grow.
5 Lessons from Rejection, Failure, and Finally Getting Hired
Looking back, I’ve realized a few things:
1. Preparation isn’t wasted, even when you lose.
Those STAR stories I crafted for Allstate? I used them in the finance interview. The time wasn’t wasted—it just paid off later.
2. Not preparing guarantees failure.
The CCIS disaster was entirely my fault. I assumed, I judged, I sabotaged. Never again.
3. Employers notice when you do the work.
Learning about the company, having real answers—it set me apart. Not because I’m special, but because so many people don’t bother.
4. Age isn’t the barrier we fear it is.
The grey hair was visible. The MBA was on my resume. They hired me anyway. What mattered was showing up prepared.
5. Entry-level doesn’t mean dead-end.
I started at $20/hour. Eight months later, I’m earning an extra $1,000 a month in bonuses. Growth is possible if you find the right place.
You Can Do This Too
If you’re an older worker staring down a job search, here’s my advice:
- Prepare for every interview like it matters. Because it does.
- Learn the STAR method. It works.
- Research the company. Know what they do. Say it out loud.
- Don’t assume they don’t want you. Let them decide.
- Keep going. Rejections and disasters happen. The next one could be the one.
I’m proof. Grey hair, MBA, and all.