I spent three months applying for jobs. 450 applications. Five responses. Zero offers. I'm 57 years old. I have 30+ years of experience. A college degree. A portfolio. Skills most companies claim they need.
And nobody wants to hire me.
So I'm done. I'm not applying anymore. I'm not tailoring another resume. I'm not writing another cover letter explaining why someone with my experience would be happy with half the pay I used to make.
I'm doing something different. Something I should have done months ago.
I'm building my own thing.
The Moment I Realized This Was Over
I was sitting at my laptop in Tucson in October. It was 2 a.m. I'd been applying for jobs for 14 hours that day. Like I did every day for three months.
My eyes were bleeding from staring at job boards. Indeed. LinkedIn. Remote.co. FlexJobs. I'd applied to everything. Content strategist. Writer. Project manager. Marketing coordinator. Jobs I was overqualified for. Jobs I was perfectly qualified for. Jobs I had no business applying to but did anyway because I was desperate.
And I got nothing. Ghosted 99% of the time. The few responses I got were automated rejections.
That's when it hit me. I could keep doing this for another six months. Another year. And I'd still be in the same place. I'd still be in Tucson, away from my family, making zero dollars.
Because the problem isn't my resume. It's not my experience. It's not my skills.
The problem is I'm 57. And companies have decided that's a liability instead of an asset.
The Numbers Nobody Wants to Face
I'm not special. I'm not unique. I'm one of millions of people stuck in this exact nightmare.
The number of independent contractors surged by 50% between 2019 and 2024. You know why? Because people can't get hired. So they're creating their own work.
52% of people are considering starting a new business in 2025. Half of all workers are thinking about going out on their own. Not because they want to be entrepreneurs. Because they can't find jobs.
The hiring market is frozen. Companies aren't hiring. They're not firing either. They're just waiting. Waiting for the economy to stabilize. Waiting for certainty. Waiting for some magical moment that's never going to come.
Meanwhile, we're all stuck in limbo. Too young to retire. Too old to get hired. With bills piling up and savings running out.
What "Too Old" Actually Means
Here's what companies won't say out loud when they reject you for being too old:
They think you'll want too much money. You know what you're worth. You've been doing this for 20+ years. You're not going to accept entry-level pay for senior-level work. So they pass.
They think you won't take direction. Especially if your manager is 15 years younger than you. They assume you'll be resentful. Difficult. Unwilling to learn. So they pass.
They think you'll leave. As soon as something better comes along. As soon as you realize the job isn't what you thought. So they don't want to invest in training you. So they pass.
They think you can't learn new tools. That you're stuck in your ways. That you don't understand technology. Never mind that you've been using AI tools daily. That you've learned every new platform and system that's come along in 20 years. They see your age and assume you're outdated. So they pass.
None of this is about your actual abilities. It's about their assumptions. And you can't fight assumptions with facts.
The Lie About "Just Lower Your Standards"
Everyone told me the same thing. "You're too picky. Apply for jobs below your level. You'll find something."
So I did. I applied for jobs I was overqualified for. Content coordinator positions when I've been a content strategist. Writing roles that paid $40K when I used to make $100K. Junior positions when I have senior-level experience.
You know what happened? I started getting rejected for being overqualified.
Companies don't want to hire someone with too much experience for the role. They're worried you'll get bored. Leave quickly. Expect more than they're offering. Cause problems by knowing too much.
It's a catch-22. You're too experienced for lower-level jobs. You're too old for senior-level jobs. You're stuck in the middle with nowhere to go.
And that's when I realized: the system isn't broken. It's working exactly as designed. It's just not designed for people like us.
Why I'm Not Looking Anymore
I'm back in the Philippines now with my family. My son is autistic. My daughter's a teenager. My wife and I are figuring out how to make this work on whatever income I can scrape together.
And I'm done begging companies to see my value. Done pretending I'll be happy making half what I'm worth. Done tailoring my resume to hide my experience so I don't scare off 30-year-old hiring managers.
I have skills. I have experience. I have knowledge. And instead of trying to convince someone else to pay me for it, I'm going to use it myself.
I'm building what I already have.
What I'm Actually Doing
I've been writing on Medium for months. Some of my articles have gone viral. One got 1.2 million views. Hundreds of comments. People telling me "this is exactly what I needed to hear."
I've been posting on LinkedIn and Threads. Building an audience. Connecting with people who actually value what I have to say.
I've been ghostwriting for 20 years. I know how to tell stories. I know how to write in other people's voices. I know how to help companies and founders say what they mean.
I have all the pieces. I just need to put them together into something that pays the bills.
So that's what I'm doing. I'm building a Skool community for people over 40 who are going through career transitions. I'm packaging my ghostwriting services. I'm creating digital products based on what I already know.
Is it scary? Yes. Will it work? I don't know. But it's better than sending out another 450 applications and getting ghosted again.
Why This Might Be the Right Time
Here's the thing nobody talks about: this might actually be the worst time to look for a traditional job. And the best time to start something on your own.
Companies are paralyzed. They're not making decisions. They're sitting on their hands waiting for economic certainty that isn't coming. The hiring freeze could last another year. Maybe longer.
But 72% of business owners plan to invest in growing their business in 2025. People who own their own thing are still moving forward. Still building. Still growing.
And 82% of freelancers report more job opportunities in 2025 than the year before. More opportunities than traditional employees. Because companies that won't hire full-time workers will still pay contractors.
The door to traditional employment might be closed. But other doors are opening. You just have to be willing to walk through them.
What Other People Are Doing
I'm not alone in this. Millions of people are making the same pivot.
33% of people starting businesses in 2025 are keeping their day jobs and running side hustles. They're not burning bridges. They're building safety nets. Creating their own opportunities while keeping whatever stability they have.
Some are freelancing. Some are consulting. Some are selling digital products or running e-commerce stores or creating content.
They're not all succeeding. But they're all trying. Because sitting around waiting for a company to hire you feels like waiting to die.
The Reality Nobody Warns You About
This isn't some inspirational pivot story. I'm not here to tell you I quit my job and now I make six figures working 10 hours a week.
I'm broke. The money ran out in November. I'm using credit cards to buy groceries. I don't know where next month's rent is coming from.
The only thing that might save me in December is my surprise earnings from Medium. I went from making $10 in October to over $2000 in November.
But I do know this: I'd rather bet on myself than keep betting on a system that's already shown me it doesn't want me.
At least when I fail at my own thing, I'll know I tried. When companies reject me, I'll never know if it was because I wasn't good enough or because I was born in 1968 instead of 1988.
What You Need to Start
You don't need a business plan. You don't need startup capital. You don't need to quit your job and go all-in. You just need to use what you already have.
- Can you write? Offer freelance writing or ghostwriting services.
- Can you design? Start taking on design projects.
- Can you teach? Create online courses or coaching programs.
- Can you manage projects? Become a freelance project manager.
Whatever you've been doing for the last 10 or 20 years, someone will pay you for it. Not as an employee. As a contractor. As a consultant. As someone who solves their problems without the commitment of a full-time hire.
Start small. One client. One project. One sale. Build from there.
Will it replace your salary immediately? Probably not. But it's income. It's progress. It's better than refreshing your inbox waiting for responses that aren't coming.
The Hardest Part
The hardest part isn't the work. It's the mindset shift.
For years, someone else gave me work. Someone else paid me. Someone else told me what to do and when to do it. I showed up. I did the job. I got paid.
Now I have to create the work. Find the clients. Set my own schedule. Figure out what to charge. Decide what's worth my time and what isn't.
It's terrifying. Some days I wake up and think "what the hell am I doing?" Other days I feel like I should just keep applying for jobs because at least that's familiar.
But I can't go back. Not after three months of getting rejected. Not after realizing the game is rigged. Not after understanding that age discrimination is real and I can't fix it by being better or trying harder.
The only way forward is to build something they can't reject me from. Because it's mine.
If You're in the Same Boat
If you're reading this and you're over 50 and you can't get hired, I see you. I know exactly what you're going through.
You've sent out hundreds of applications. You've gotten maybe a handful of responses. You've had interviews that went great until they saw how old you were.
You've lowered your salary expectations. You've applied for jobs you're overqualified for. You've done everything everyone told you to do.
And it's not working. So maybe it's time to stop trying to fit into a system that doesn't want you. And start building something that does. I'm not saying it's easy. I'm not promising you'll succeed. I'm not even sure I'll succeed.
But I know I'm done waiting for permission. Done hoping some hiring manager will see past my age. Done pretending that if I just try a little harder, send out a few more applications, this time will be different.
It won't. The system is what it is. And it's not changing anytime soon.
So I'm changing instead. Building something with what I already have. Taking whatever skills and experience I've accumulated over 20 years and turning them into something I control.
You can too. Start small. Use what you know. Build something that's yours.
Because we're too young to give up. And too old to keep waiting for someone else to give us a chance.
What are you building? Drop a comment if you're making the same pivot. Or if you're thinking about it. Let's figure this out together.
I sent out 450 applications at 57. Got nowhere. Now I'm freelancing and helping others do the same. Join my Skool group if you're 40+ and ready to build something that doesn't depend on age-blind hiring. It's free.
Also, if you are on LinkedIn or Threads and want to connect, let's do!
One more thing…
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