When Derek Hughes sat down to write his first online post at 51, he had no background in writing, marketing, or entrepreneurship. Just a little extra headspace after switching to a less demanding nonprofit job, and a hunch that maybe, just maybe, he had something to share.
Two years later, he’s running a thriving creator business.
From digital products and workshops to a multi-platform writing ecosystem, Derek now earns a growing income online, all while helping other writers get visible and build sustainable writing businesses. And he’s doing it in his 50s, proving that age is not a barrier but an asset.
This is the story of how he got here, and how you can too.
From Accidental Writer to Intentional Creator
Derek’s journey into the creator economy began the way many midlife pivots do, by accident.
In early 2023, with some mental bandwidth freed up, he started writing online. “It was just about getting thoughts out,” he says. “I thought you post something online and the whole world reads it. But the world doesn’t.”
After months of writing to no one, he nearly quit. But something inside him said: give it a few more weeks.
That’s when things started to click. “I doubled down on learning how to write for the internet. I picked up one skill each month, headlines, intros, formatting. It took time, but then things started to grow.”
Today, Derek has thousands of followers across platforms, a loyal audience, and a growing portfolio of income streams. But none of it came from chasing virality. It came from mastering fundamentals, one step at a time.
The Mindset Shift That Changed Everything
Derek’s secret? He stopped focusing on metrics and started treating writing as a craft.
In the early days, it was easy to get caught up in numbers, views, claps, followers. But he realized growth would come only if he got better. “I made peace with playing the long game. I learned one micro-skill at a time and applied it. That’s when real momentum built up.”
He adopted what he calls a “learning mindset” essential for any online writer, especially those starting later in life. “It’s not just about writing. You need to learn tech tools, marketing, sales and you need to do it in bite-sized chunks.”
The trick? Don’t try to master everything at once. Start with what you need now, and add as you go.
Tech Intimidation? Not an Issue.
For many 50+ creators, tech is the biggest hurdle.
Derek’s advice: don’t let the tech overwhelm you.
“You don’t need to code. Most tools today Kit, Substack and ThriveCart are built for non-techies. You only need to learn one thing at a time. Start with the feature you need. Emailing a newsletter. Creating a product page. And go from there.”
He now uses Kit for running his newsletter and ThriveCart to host and sell digital products. “I keep it simple. I don’t chase every new tool. I master the tools I already use.”
The result? A lean tech stack that supports his business without draining his energy.
Monetization: Multiple Streams, Not Just Subscriptions
Many writers think monetization equals paid subscriptions. Derek proves otherwise.
Here’s how he makes money from his writing:
Digital Products
Derek creates and sells digital guides, templates, and toolkits to help writers start and grow online. “My first product brought in thousands, and it still sells 18 months later.”Product Bundles and Upsells
Every product comes with an optional upsell, often a complementary guide at a discounted price. Most buyers go for both.Affiliate Sales
Other creators promote Derek’s products and earn a commission. “It builds trust and brings in new subscribers, all without extra work.”Live Workshops and Paid Memberships
He runs monthly workshops and recently launched My Writer’s Club, an all-access membership that includes every product, workshop, and tool he offers.Cohort-Based Courses
Derek also runs live courses like Digital Product Launchpad, teaching creators how to make and sell their first product, with AI prompts, email templates, and personal guidance.Substack Paid Tiers
While not his primary revenue stream, he also offers paid tools and AI resources through his Substack for those who prefer à la carte access.
Substack + Kit = Smart Funnel Strategy
Derek uses Substack to attract readers and Kit to sell.
Substack helps him grow his audience through Notes, Recommendations, and SEO-friendly posts.
Kit helps him segment his audience, send targeted offers, and run effective sales campaigns.
“Substack is great for reach. Kit is where the selling happens,” he explains. “I move people from Substack to Kit via freebies and nurture them there.”
It’s a smart two-platform strategy that balances visibility with conversion.
Why Age Is a Superpower, Not a Setback
Early on, Derek worried about being “too old” to compete in a space filled with 20-something growth hackers.
Until he wrote the line: “I’m 51 and I’ve been writing online for 6 months.”
That line exploded on Medium.
“I realized people want to see someone older succeeding. It gives them hope.”
Now he leans into his age as a strength. His readers, many also in their 40s, 50s, and 60s—relate to his story. They trust his experience. And they appreciate learning from someone who’s not faking expertise.
“The creator economy isn’t just for the young. It’s for anyone ready to share their journey, own their voice, and offer real value.”
Final Advice for 50+ Creators
If you’re over 50 and want to turn your knowledge into income, here’s Derek’s advice:
Start with curiosity. Don’t worry about being perfect. Be willing to learn.
Play the long game. Focus on building skill and offering value. The money will come.
Lean into your uniqueness. Your age, experience, and wisdom are your differentiators.
Build gradually. Pick one platform. Learn one tool. Create one product. Then stack the next.
Make a difference. The money is great, but nothing beats the joy of helping someone with what you know.
You can find Derek on Substack at The Irresistible Writer and subscribe to his free email course The Long Form Mastery: The 5 Step Writing System.
And if you’re over 50, here’s your permission slip:
It’s not too late.
You’re not too old.
You already have everything you need to build a writing business.
Just start. Like Derek did. One post at a time.
Enjoyed this podcast? Ready to turn your own knowledge into income, no matter your age?
That’s all from me today.
As always, thanks for reading.
