Zero offers and I was spent.
Not one company wanted me. I’m 57 years old and the system decided I’m too old, too expensive, or too risky. Doesn’t matter that I have 20+ years of experience. The algorithm filters me out before a human ever sees my resume.
So I stopped begging for permission to make money. I stopped relying on a job market that was brutal and would betray you at every turn, especially those of us over 40.
I built my own income streams. Seven of them. Plus three more in development. Because when you can’t rely on one employer, you sure as hell can’t rely on one income source.
Here’s the exact playbook.
Let me be clear about something: I’m not rich. I’m broke most months. I’m still scrambling to pay bills. I’m still stressed about money every single day.
But I’m generating $1,650/month across multiple streams. Some months it’s $2,000. Some months it’s $1,200.
That’s not enough to thrive. But it’s enough to survive while I build.
And that’s the whole point. Multiple streams mean when one fails, the others keep you breathing.
Freelance ghostwriting dried up one month. Down from $800 to $100.
If that was my only income? I’d be destroyed. Evicted. Back in the Philippines with zero opportunity.
But I had six other streams keeping me afloat.
My course brought in $200. My ebook sold for another $100. Coaching sessions added $100. Content creation covered $1,100. Ko-fi donations brought in $50.
Not enough to thrive. But enough to survive.
That’s the point of multiple streams. When one crashes, the others keep you breathing.
What it is: Writing articles, blog posts, and content for clients under their name.
How I started: Posted on LinkedIn that I was available for hire. Built a portfolio from my published work. Cold-pitched companies in my niche.
What it pays: $100-$500 per article depending on length and research required. Some months I get 5 clients. Some months I get 1. Right now? One client paying $100/month.
Where clients come from: LinkedIn. Almost exclusively. I post daily about the job market, age discrimination, building alternative income. People see my work, reach out, hire me.
Cost to start: $0. You just need writing samples and the ability to pitch.
Time investment: 3–5 hours per client article including research, writing, revisions.
The catch: Clients ghost you. They don’t pay on time. They disappear after one project. The income is inconsistent and you’re constantly hunting for the next gig.
Some months I make $2,000. Some months I make $100. Right now I’m in a dry spell.
Lesson: Ghostwriting pays better per hour worked than most streams, but it’s unreliable. You need backups.
What it is: A paid community and course teaching writers how to make money through content creation.
How I started: People kept asking me how I built my income. I realized I could teach what I learned the hard way.
What it includes: Weekly group coaching calls, content reviews, engagement strategies, distribution systems across multiple platforms including Substack.
Pricing: $5/month forever for the first 300 members. After that, price goes up.
Where members come from: LinkedIn posts about my journey. My free “Over 40 and Unemployed” community. Articles I write that demonstrate results.
Cost to start: $99/year for Skool platform to host the community. That’s it.
Time investment: 2 hours per week for group coaching. 3–5 hours per week answering questions and reviewing member work.
Current revenue: $400/month with 40 paying members. Goal is 300 members at $5/month = $1,500/month recurring.
The catch: You need credibility first. Nobody pays you to teach them how to make money if you’re not making money yourself.
Lesson: Teaching what you know is a legitimate income stream if you have results to back it up.
What it is: “What to Do When the Job Market Fails You: A Survival Guide for Workers Over 40”
What’s in it: Everything I learned after 800 rejections. How to survive when nobody will hire you. Building alternative income. Mental health tactics. Pivoting when plans fail.
How I created it: Compiled my knowledge into a structured guide. Formatted it. Published on Gumroad.
Where sales come from: LinkedIn posts. Medium posts. Articles that end with a CTA. My free community. Email mentions.
Cost to start: $0 if you write and format yourself. Gumroad takes a small percentage of each sale.
Time investment: 20 hours to write, edit, format. Ongoing promotion through content and community mentions.
Current revenue: $100/month depending on how much I promote it. Some months $50. Some months $150.
The catch: Digital products don’t sell themselves. You need traffic. You need an audience. You need to promote constantly without being annoying.
Lesson: One ebook won’t make you rich, but it’s another stream that adds up.
What it is: Personalized coaching for writers and creators stuck at low income who know something’s wrong with their strategy.
How I started: People saw my LinkedIn posts about going from broke to building multiple streams. They asked for help. I said yes and charged for my time.
What I offer: Strategy calls analyzing their content, engagement, positioning. Real feedback on why they’re not getting results. Tailored action plans.
Pricing: $100-$300 per session depending on package.
Where clients come from: LinkedIn. People who follow my content, see the results, want personalized help.
Cost to start: $0. You just need expertise and a calendar.
Time investment: 1–2 hours per client including prep, call, follow-up.
Current revenue: $100/month average. Some months nobody books. Some months I have 3 clients for $300-$600.
The catch: Coaching doesn’t scale. You’re trading time for money. There’s a ceiling on how much you can make unless you charge premium rates.
Lesson: Coaching is good supplemental income but not a primary strategy at these rates.
What it is: Writing on platforms like Medium, Substack, and other publications that pay for content.
How I built it: Wrote consistently for years. Most of those years I made pennies. Then I figured out what actually worked, writing about real problems people face instead of writing for my ego.
Current state: Medium used to pay me $4,500/month. Now it pays $1,100/month. Same work. Different algorithm.
Cost to start: $0 to write. $5/month for platform memberships if you want to study what works.
Time investment: 2–3 hours per article. I write one article per day, sometimes two.
The catch: Platform dependency is brutal. You don’t control the algorithm. One change and your income disappears. That’s exactly what happened to me.
Lesson: Never rely on one platform. Use content creation as one piece, not the whole strategy. Cross-post to LinkedIn, Substack, your own blog. Diversify or die.
What it is: People can “buy me a coffee” (donate) to support my work. In return, they get access to more personal content and behind-the-scenes updates.
How I started: Set up a Ko-fi page, linked it in my content and LinkedIn profile.
Cost to start: $0. Ko-fi is free.
Time investment: 1 hour per month posting updates for supporters.
Current revenue: $50/month. Some months $20. Some months $100.
The catch: You need to actively promote it. People won’t donate unless you remind them it exists and give them value in return.
Lesson: Small but meaningful. Every $50 helps when you’re broke.
What it is: Free Skool community for people the job market rejected. Almost 700 members.
How I started: I was living the pain of 800 rejections. I knew other people were too. I built a space for us to help each other.
Current revenue: $0. It’s free. Future earnings based on sponsors and partnerships.
Future revenue: This is an asset. A list. When I launch products, services, or paid offerings, I have 600+ people who trust me and know my work. That’s worth more than any single month’s income.
Where members come from: LinkedIn posts that go viral. Articles that resonate. Word of mouth from members who found help.
Cost to start: $99/year for Skool platform.
Time investment: 5–10 hours per week moderating, posting topics, engaging with members, running weekly Coffee Hours.
The catch: Free communities don’t make money directly. But they build trust, authority, and an audience for future monetization.
Lesson: Give value for free first. Build trust. Then monetize later. The community is my most valuable asset even though it makes $0.
Here’s what this actually looks like in my current reality:
Ghostwriting: $100 (down from $2,000 — clients dried up)
Medium Mastery: $400
Ebook: $100
Coaching: $100
Content creation: $1,100 (down from $4,500 — algorithm crashed)
Ko-fi: $50
Free community: $0 (future asset)
Total: $1,850/month
That’s barely surviving. But I’m not dead yet.
What it is: My comprehensive 8-module framework helping workers build alternative income sources.
Current status: Successfully recruited 20 founding students within 48 hours. Validating demand.
Future monetization: Partnerships with organizations like AARP and workforce development centers. Grant applications. Corporate training programs. Speaking engagements.
Where leads come from: LinkedIn presence demonstrating results. The free community showing proof of concept. Media appearances as an expert on age discrimination and alternative income.
Goal: $500-$5,000/month through partnerships, licensing, and enterprise sales.
What it is: Video content about job market reality, building income streams, surviving rejection over 40.
Current status: Just restarted. Three videos posted. Building momentum.
Future monetization: Ad revenue once I hit 1,000 subscribers and 4,000 watch hours. Sponsorships. Affiliate partnerships for tools I actually use.
Where traffic comes from: LinkedIn driving people to YouTube. Cross-promotion from articles. Community sharing.
Time investment: 3–4 hours per video including filming, editing, uploading. Plan is 2 videos per week.
Goal: Start making money within 6–12 months. Even $300/month from ads would help.
What it is: Weekly podcast diving into topics I don’t cover in articles : success, fulfillment, work-life balance, self-improvement for people rebuilding after 40.
Current status: Very early stages. Planning format, lining up guests, building equipment setup.
Future monetization: Sponsorships from companies targeting my demographic. Affiliate partnerships. Premium content for paying subscribers.
Where audience comes from: LinkedIn promotion. Community cross-promotion. Guest appearances on other podcasts.
Time investment: 2 hours per episode for recording. 1 hour for editing and publishing. Weekly release schedule.
Goal: Launch within 2–3 months. Start monetizing within 6 months.
Here’s what nobody tells you about building multiple income streams: you need one place where people find you.
For me, that’s LinkedIn.
I post daily. Sometimes twice. Job market reality. Age discrimination. My income numbers. My struggles. My wins.
Those posts:
Bring ghostwriting clients
Drive people to my free community
Sell my ebook
Fill Medium Mastery spots
Book coaching sessions
Build my email list
Attract future podcast guests
Create partnership opportunities
LinkedIn isn’t an income stream. It’s the distribution engine that feeds all the income streams. I went from 1200 followers to almost 3,000 in six months by posting brutal honesty about what it’s like to be 57 and unemployable.
Every single income source I have traces back to LinkedIn visibility.
Lesson: You need one platform where you show up consistently and build an audience. Everything else flows from there.
Building multiple income streams sounds great until you realize:
Time: I work 12–14 hours a day managing all of this. Writing content. Pitching clients. Coaching. Running communities. Creating products. Promoting everything.
Mental load: Juggling ten streams (seven active, three building) means ten different systems, ten different promotion strategies, ten different ways to fail.
Inconsistency: Every stream fluctuates. Some months ghostwriting dries up. Some months content platforms crash. Some months nobody buys the ebook. You’re constantly hustling to keep them all alive.
No vacation: If I stop working, the income stops. There’s no paid time off. No sick days. No safety net.
Burnout risk: I had a heart attack in 2022. The stress of building all this while broke is literally life-threatening. I have to watch myself or I’ll kill myself trying to survive.
But here’s the thing: I’d rather be exhausted building my own income than exhausted applying to jobs that reject me.
You don’t need money. You don’t need connections. You don’t need permission.
You need:
1. One skill you can monetize Writing, design, coaching, consulting, teaching. Whatever you’re good at.
2. The willingness to work for pennies at first I made $10/month for years. You will struggle. Accept it.
3. One primary distribution platform LinkedIn, YouTube, a blog, a podcast. Pick one where you’ll show up every single day and build an audience. Everything else feeds from there.
4. Multiple ways to monetize that audience Freelancing, courses, ebooks, coaching, content creation, future products. Don’t rely on one.
5. The ability to pivot when something fails Ghostwriting dried up? Push the ebook. Content platform crashed? Activate coaching. Stay flexible or die.
6. Brutal honesty about your situation Nobody wants fake success stories. They want real struggle and real solutions. That’s what builds trust.
For years, I tried to build one big thing. One successful blog. One viral YouTube channel. One perfect business.
I failed every time. Then I got desperate. 800 job rejections desperate. Can’t-pay-bills desperate. I stopped trying to build one perfect income source and started building ten imperfect ones.
And it’s working.
Not because any single stream is amazing. But because ten mediocre streams together create survival.
When ghostwriting crashes, the course keeps me alive. When content platforms tank, coaching fills gaps. When everything slows down, the free community keeps building an asset for future monetization.
It’s not elegant. It’s not scalable. But it’s working.
Here’s what the next six months look like:
Months 1–2: Launch podcast. Get first 10 episodes out. Start building YouTube momentum with 2 videos per week.
Months 3–4: Reach 100 YouTube subscribers. Start pitching partnerships for “The Great Pivot” framework to workforce development organizations.
Months 5–6: Hit monetization threshold on YouTube. Land first partnership deal. Launch premium podcast tier.
Goal: Add $1000-$2,000/month across the three new streams by month 6.
Combined with existing streams recovering (ghostwriting clients returning, content platforms stabilizing), that gets me to $2,500-$3,000/month.
Not thriving. But breathing easier.
Building multiple income streams won’t make you rich. It will make you tired. Stressed. Stretched thin.
But if you’re over 40 and the job market rejected you 100 times, 500 times, 800 times, you don’t have the luxury of waiting for the perfect opportunity.
You build what you can with what you have.
You diversify because you can’t afford not to.
You hustle because sitting still means going broke.
I’m not telling you this is easy. I’m telling you it’s possible.
I’m 57 years old. Broke. Stressed. Scrambling every month.
But I’m surviving. And I built it all after the system said I was done.
Seven active income streams. Three more in development. All built from zero after 800 rejections.
If I can do it, you can too.
What about you? How many income streams are you building?
Jason Weiland is the founder of The Great Pivot and the Over 40 and Unemployed community on Skool. He writes about building income outside traditional employment, surviving a broken job market, and what it actually takes to start over when everything falls apart.
The second cohort of The Great Pivot launches in April.
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