Month: September 2025

• 56-year-old Robert Poe has been job hunting for a year and a half after losing his six-figure role.
• Poe has worked as a real-estate agent, Amazon driver, author, and startup founder in the meantime.
• Despite struggling to find permanent work, Poe remains hopeful that he will land a role eventually.

This as-told-to essay is based on a conversation with Robert Poe, a 56-year-old former e-commerce director. His identity and former employment have been verified. This story has been edited for length and clarity.

I started my career at IBM in digital marketing. My brother used to say to me, “You’re always going to have a job.” I’ve been through layoffs and worked at companies that shut down, but I never really had to look for a job in my role.

My last position was as director of e-commerce at Badcock Home Furniture. I made $120,000 as my base salary. The company was eventually bought by a company that filed for bankruptcy. I lasted about six months in a new role that I landed.

I wasn’t worried about finding another job. But that was a year and a half ago. Since then, I’ve sent out over 1,000 résumés.

The experience has been a shock. My wife and I sold our house and moved into an apartment. We’ve had to claim bankruptcy. I sold my car. We’re partially living off of our sons’ Social Security and my wife’s job. Our daughter, who lives with us, helps pay rent.

I pretty much have given up on finding e-commerce director roles. I guess I’m too old. I hear a lot of people saying, “Go start your own business,” and “This is the time to reinvent yourself.”

So at 56, that’s what I’m trying to do.

I tried gig work

I got my real estate license and tried that for a little.

I was commuting about an hour each way to sit in an office with a bunch of 20-year-olds, doing exactly what I could have done at home. At some point, I realized that it’s not realistic to work off strict commissions and commute to an office when nothing is coming in.

So I tried out being an Amazon delivery worker for five months. I’m in shape and I work out. But at the end of the night, I couldn’t walk up the stairs. It’s a different world, especially when you’re not used to being spoken to that way. It’s a great side gig if you want some extra money, but it’s not enough to live on.

I’m giving entrepreneurship a shot

In addition to the gig work stuff, I’ve tried to be entrepreneurial.

I launched a digital marketing startup called JBP Media Group with a partner who used to work with me. It will be another six months before any income comes in and I’ve had money come out of my pocket just to get it going.

We’ve gotten a handful of clients, which is wonderful, and we have some employees offshore to help with some of the work. But when clients pay you $200 a month, you need a lot of those small clients.

I’ve also published a book. I have two 20-year-old twin sons with special needs, and the book is about the expenses that hit special needs families. There are probably around $60,000 a year in expenses per kid, including transportation and insurance.

Publishing the book has been a bucket list type of thing, and it’s one that keeps your mind going. Starting a company has also kept me busy. Even if I’m working technically for free, it keeps my skills sharp.

I keep trying everything on top of interviewing, thinking that something will hit. In the meantime, I have to keep going.

The system is broken

I have been putting out about two to five résumés a day. I’ve met with tons of recruiters and have relationships with some of them. But a recruiter will ask to schedule a call and then never get back to me. I’m hearing more and more of that happening, where you get through an interview round and they put the job on hold or find someone internally. It’s depressing.

Everybody’s saying, “LinkedIn’s not the place to be anymore” or “You have to make your résumé different.” It’s incredibly confusing. It’s like they flipped a switch overnight. The system’s broken.

For Gen X folks, it feels like if you’re out of a job, then it’s just too bad.

Right now, I feel like a failure. But my message to other people is that something will work out, even if you have to go from a six-figure job to making $50,000 a year. For me now, I want to work for the Special Olympics, where I volunteer and coach paddleboarding. Even if it’s a pay cut, I can start over, and we’ll figure it out.

Have you struggled to find a job? We want to hear from you. Reach out to the reporter via email at aaltchek@insider.com or through the secure messaging app Signal at aalt.19.

The Trump administration deprived the prestigious American university of $2.6 billion in funding, citing the fight against anti-Semitism. A federal judge ruled that the move was illegal.

• Executive coach Andrea Wasserman says timing is one of the most crucial parts of a promotion decision.
• Raises are business decisions, not gifts, and understanding the context around you is key to success.
• Build credibility and align with business needs to improve your chances of career advancement.

Over the course of my career at companies like Nordstrom, Verizon, and Yahoo, I’ve hired, developed, and evaluated hundreds of employees. Many of them were smart, capable, and ambitious. They wanted promotions, and they got them — but I’ve also turned down many requests.

If you think the group that got their requests granted was innately more talented or harder working than the group that didn’t, think again. The truth is that, most of the time, the request itself wasn’t the problem. The candidate wasn’t even the problem. It was the timing that made the difference.

Promotions and pay raises are business decisions, not gifts. This means that even the strongest performers will hear “not now” if they ignore the situations that surround them.

Here are five of the most common timing missteps I’ve seen, and what I wish more rising leaders would do differently.

1. You just got promoted, and you’re already asking for more

This is surprisingly common. Someone gets promoted in January and, by April, they’re asking for another raise.

I once had a high performer who was promoted to senior manager after a solid year. Less than 90 days later, she sent me a proposal for another title change — accompanied by comp benchmarks and a list of expanded responsibilities.

She was doing more, but she hadn’t been in the role long enough to demonstrate success at that level, and she lacked the self-awareness that no one should ask for more every quarter.

What to do instead:

Keep a record of what’s changed. If your role evolves quickly, talk about that during check-ins with your manager. Understand your career path and the next opportunity for growth. Then, give the business time to see your impact before you ask to level up again.

2. You bring it up in your first few meetings with a new manager

It’s natural to want to impress a new boss. I’ve seen people use early 1:1s to talk about their career goals. This makes sense — to an extent. And it’s fine to let your new manager know if you had conversations with your old manager about your path to a promotion.

However, when it turns into “What would it take for me to get promoted this year?” before the manager even understands your role (and hers!), it can create the perception that you’re only thinking about yourself. It’s like walking into a room you’ve never been in before and immediately asking to rearrange the furniture.

What to do instead:

Start by understanding how your new manager defines success and taking an interest in her priorities and challenges. Ask smart questions, then deliver, and deliver consistently. You can talk about growth and next steps once you’ve built trust and credibility.

3. The team is off-track, or the business is under pressure

Some of the hardest “no” answers I’ve had to give were to employees who were deserving but seemed oblivious to what was going on around them. Even if you think you’ve done everything right, asking for more when the broader context is shaky can hurt your chances.

I’ve had employees come to me during expense freezes, department restructures, or right after we missed our numbers, sometimes with very strong cases for advancement. In those moments, the ask just wasn’t feasible for the business.

What to do instead:

Make yourself even more valuable by showing that you can lead patiently through uncertainty. Be the person who brings stability when others are scrambling. Once the business starts to recover — and you’ve played a visible role in that — you’ll be in a much stronger position to ask for more.

4. You missed a milestone or received feedback you haven’t yet incorporated

This happens when someone moves too quickly after a mistake or learning opportunity. Maybe a key project didn’t land, or they got feedback about how they lead meetings, and they haven’t yet corrected for it. Then, a few weeks later, they’re asking for a promotion.

Even if their overall track record is strong, the timing is off. Leaders want to see that you can take input, apply it, and grow from it. If you haven’t closed the loop on feedback, asking for more shows a lack of accountability and self-awareness.

I once had a direct report who delivered great work but struggled with cross-functional influence and managing senior leaders. We talked about it openly, and he was aware and committed to improving. Two weeks later, he asked if he was in line for a promotion that quarter.

It was too soon. He hadn’t had time to show progress yet, and asking so soon after our conversation made it seem like he didn’t understand the gravity of the feedback.

What to do instead:

Slow down, and shore up any doubts about your potential. When you hear feedback, don’t just acknowledge it — change something.

Then, when you make the ask, it will be even stronger because your coachability and growth will become part of the case for advancement.

5. You waited too long to bring it up

This mistake is almost as common and equally costly as the others. Every once in a while, someone has come to me unexpectedly and said, “I’m ready for the next level.” If we hadn’t been talking about growth, readiness, or performance over time, it could be challenging to make it happen quickly.

Big asks shouldn’t come out of nowhere. They require a track record with a narrative, relationships, and often a process. Depending on other career path timelines you’ve observed, your own performance, and the standard cycle of mid-year and year-end performance conversations, you might start talking about your career goals once you’ve been in your role for 6-12 months.

What to do instead:

Make career growth part of the regular conversation. Use 1:1s with your manager or HR to ask what overdelivering looks like. Get clarity on what’s expected at the next level. That way, when you’re ready to make a formal ask, your manager’s already on the same page.

It’s not just about how well you ask — it’s about when

There’s no perfect time to ask for a raise or a promotion. Yet, there are wrong times and there is a smart time. It’s usually after you’ve shown clear results, earned credibility, and positioned yourself inside the broader business picture.

If you’re preparing to make a case, put yourself in your manager’s shoes, evaluate what’s happening across the team or company, and ask yourself, “Will this timing make it easier or harder for me to get a ‘yes’?”