The $1K Side Hustle Strategy for Freedom-Seeking Nomads

How to make your first $1,000 online (even if you’re starting from scratch)

Cyprus - Where I made my first $1000

There’s something magic about your first $1,000 online. (To be honest your first $100 online!)

It’s not life-changing money. But it is a life-changing moment.

Because when you earn that first bit of income from something you created and sold yourself, everything changes. It’s not a job or a wage. It’s your idea, turned into something useful, that someone else was willing to pay for.

Suddenly you start to see the possibilities ahead! You stop questioning yourself quite so much, and instead of waiting for the perfect plan, you start making progress.

Each small action you take starts to feels like a step forward, and before you know it, this whole idea of "working from anywhere" starts to feel less like a dream and more like like a decision you’ve already made.

I still remember to this day, making my first $28 from a PDF I put together from a video I'd seen about how to use Aweber optin forms!

It wasn’t fancy or polished and it was only $7 for goodness sake. I sold 4! I felt like Sara Blakely from Spanx. I'd made it!!!

That one $7 offer eventually became a $30k course, then a $117k launch, and eventually a business that’s funded my travels around the world for over a decade.

None of that would’ve happened without that first sale.

So if you’re stuck in research mode, jumping between ideas, or endlessly tweaking your website, let’s simplify things and help you get your first win: a real sale, from a real person, in the next couple of weeks.

But first;

Why Most People Never Make Their First $1,000

If you're struggling to get your ideas off the ground, it’s rarely about talent, potential or drive.

Most people don’t stall because they’re not capable. They stall because they’re trying to build the entire business before making a single sale.

• They spend weeks choosing a name.

• Redesign logos that no one will see yet.

• Trial half a dozen email platforms, hoping one of them holds the magic key.

Before long, they’ve used up all their energy and still haven’t sold a thing.

You don’t need a brand, a funnel, or the perfect niche.

You need one tiny, useful idea.

Something that helps someone, solves something, or gives them a quick win. Then you share it with real people and see what happens.

Here’s how to do it, one simple step at a time.

The $1K Strategy (Step-by-Step)

This is the same structure I’ve used in my own business over and over again.

It’s light, fast, flexible, requires no fancy tech, and helps you test the market before going all in on a brand, products, service or an offer.

Step 1: Pick a Problem

Start here. Not with a complete niche or a brand, just one simple problem you can solve.

Think small:

• Help someone plan their first house sit

• Create a 10-step process to simplify a morning routine

• Guide beginners through using Canva or ChatGPT

• Show artists how to prep digital files for Etsy

• Help fitness beginners build a travel workout plan

It doesn’t have to be deep or dramatic. It just has to be helpful.

Step 2: Package It

Now turn that solution into something someone can buy:

• A 1-hour Zoom session

• A printable PDF

• A recorded mini workshop

• A Notion template or checklist

Use what you’ve got. Canva. Loom. Google Docs, AI. Don’t worry about polish at this stage, focus on value.

Step 3: Price It Between $10–$50

We’re not building a high-ticket coaching program here. We’re building belief.

Start with something accessible:

• 40 people x $25 = $1,000

• 20 people x $50 = $1,000

• 10 people x $100 = $1,000

Pick a price that feels comfortable, (something you’d happily pay yourself), and build your offer around that.

Step 4: Share It

Here’s where most people freeze, but I promise, it’s easier than you think.

You don’t need a website or a funnel.

Just:

• Write a short blurb about what your offer is and who it helps

• Share it in 3–5 relevant places (Facebook groups, Instagram, newsletter, your network, here on Substack, Quora, Reddit)

• Use Gumroad, Payhip, or a free Stan Store page to accept payments

• Offer a discount or bonus for the first 5 buyers

Remember: you’re in the testing phase. You’re not launching to thousands. Just a handful of real people who need what you’re offering.

Step 5: Improve It

Once you’ve made a few sales:

• Ask for feedback

• Add a bonus

• Record a version 2.0

• Turn it into something more evergreen

Now you’ve got your own little system, that can grow.

Real Examples for Your First $1K

Need some inspiration?

Here are a few starter ideas that could easily become $1K side hustles:

Travel & Nomad:

• $27 “House Sitting Starter Kit”

• $17 digital nomad packing checklist for over-50s

• $47 Zoom session on “How to move to Portugal”

Creative & Artistic:

• $25 digital wall art bundle on Etsy

• $15 “Art Marketing 101” eBook for hobbyists

• $10 printable journaling prompts for self-discovery

Health & Lifestyle:

• $49 “Back to Basics” fitness plan for women 50+

• $30 healthy travel meal planner

• $19 anti-inflammatory recipe guide PDF

Tech & Productivity:

• $47 “Intro to Canva” recorded workshop

• $27 Notion template for trip planning

• $37 ChatGPT for beginners mini-course

If you’ve got a skill, passion, or obsession, there’s a version of it someone is willing to pay for.

What Happens After That First $1,000?

Everything.

Because now you’ve:

• Validated your idea

• Grown your confidence

• Proved you can sell

• Built a tiny list of customers

And from here, the next steps are simple:

• Raise your price

• Add a bundle or bonus

• Build an automated version

• Create a mini product shop or evergreen funnel

You can turn that $1,000 product into a $5k/month business if you want to. But only after you get that first sale, that first Stripe ping, and that first moment of:

“Wait… did I just do this?” 🎉🥳🍾

Your First Sale Is Closer Than You Think

If freedom’s been calling but the online business world feels overwhelming, this is where you begin.

Not with a brand, a funnel, or a long, complicated course.

Start with one small problem you can help solve. Create a simple offer. Price it at $27.

Then share it with real people and aim for 37 sales.

That’s your first $1,000, and the moment you realise your dreams are a possibility.

Let me know when you have your first product live, I'd be happy to share it! Go make it happen!

Jo 😊