7 Lessons I Wish I'd Known Before Starting My First Online Business

From a balcony in Cyprus to a seven-figure Amazon brand, and every expensive mistake in between.

Welcome to ‘The Unretired Creator’. Every Wednesday I share ideas, stories and practical lessons for anyone who still feels called to create, contribute and build something meaningful, no matter their age. Because creativity never retires. 🎉

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I started my first online business in 2010.

Some friends of ours were living in Cyprus making a living from their lovely apartment through something called ‘internet marketing’.

Being the ‘nosy’ action takers we were, we quickly booked a holiday, picked their brains, devoured Tim Ferris’s 4 Hour Workweek book (on their recommendation) & volunteered to house sit for them when they went galavanting off around Europe!

(We don’t do things by halves! 😂)

Sea Caves - Paphos, Cyprus 🇨🇾

16 years on, I’ve built and exited multiple businesses, scaled an Amazon brand to seven figures (and trying to do the same again now), lived in multiple countries, raised a daughter in Phuket, Thailand, and watched the online business world transform from a few of us figuring it out in spare bedrooms (or balconies in Cyprus), to the industry it is today.

Along the way, I’ve made every mistake going and then some.

So I thought I’d share some of the biggest lessons I wish I’d known before I started, in the hope some of them save you a few of the years I lost learning them the hard way.

Unfortunately reading the list doesn’t replace doing the work, but it might shorten the curve a bit.

Let’s go.

1. There Is No Magic Button

I spent thousands in my first year on courses and programmes that promised quick results.

Webinars where someone told me that something worth $25,000 was mine for $97, today only, payment plan available. (Remember them?)

Magic-button systems where you just followed the formula and magically the money appeared. 💸

None of them worked. (Of course not!!!)

And it wasn’t because the people teaching them were inherently dishonest (though some were), but because there is no formula that bypasses rolling your sleeves up and doing the actual work.

What became my biggest money making secret was in fact a repeatable, boring system.

• Building my own audience.

• Showing up.

• Writing, recording, posting, replying, being visible.

It took time, focus, and repeatedly doing things outside my comfort zone.

There’s no shortcut around that, unless you have huge ad budgets. Even then you still have to put the work in to grow the trust.

Anyone selling you a shortcut, is usually teaching a course about shortcuts.

The work is the work and nothing replaces it.

(Incidently, it’s exactly the same today. Show up, write, publish, help people, grow your audience. That’s still the closest thing I’ve found to a magic formula.)

2. Let People Get To Know You

When I first got going, my main platform was Facebook. I did webinars, posted videos, chatted on forums, and was pretty much in people’s faces daily.

But I was also 16 years younger, had masses of energy & had no fear of jumping on camera.

These days I don’t want to be on social media 24/7, and I don’t have the same energy for video that I had 16 years ago.

But the good news is, nowadays you can record podcasts, or do faceless reels, or connect through writing.

The medium is less important than the message.

Tell stories, and let readers see who you are. Mention the dog, the husband, the bad day, your dodgy knees. People don’t subscribe to ideas, they subscribe to people.

Whatever format you choose, the principle is the same: trust builds when people feel like they actually know you.

Find the way that works for you, and lean into it.

3. Collaboration Compounds Faster Than Going It Alone

In my early Facebook days I ran an interview series called Money and Marketing, where I sat down with other creators and entrepreneurs and chatted all things online business.

The series itself did fine. But what it really did was open doors.

I started doing joint ventures. Other people promoted me to their audiences. I promoted them to mine. My list grew faster in the months I was actively collaborating than in any of the months I was working alone.

One day, a fellow business owner (love you Steve), mentioned me from the stage at an event I wasn’t at. The audience apparently gave a round of applause for me, even though I wasn’t in the room. The collaboration had carried me there in my absence.

It’s impossible for us to reach every opportunity on our own. But the people we've helped and connected with can open doors long before we arrive.

Here’s how to ‘build the well before you’re thirsty’ (as Jordan Harbinger says):

• Restack or share other people’s work.

• Reply thoughtfully to their notes.

• Send the email that says I loved this.

• Suggest joint posts, lives or interviews.

• Offer to be useful before you ask for anything.

• Build real relationships, not transactional ones.

To be honest, this is something I’ve just started to do more consciously myself. It’s so easy to slip into doing everything alone, but it’s lonely and you won’t grow as fast.

Plus collabs can lead to the best friendships!

4. You Don’t Have To Build It Yourself

About a year into my first business, I made an extremely expensive mistake.

I’d built a simple piece of software for Facebook fan pages which I’d paid about $100 to a developer to create.

I gave it away free, (anyone remember ‘Free Fan Page Templates - you know who you are oldie! 😂) and it helped me grow a huge email list. Brilliant first move.

Then I decided I should turn it into a paid product. I spent thousands working with developers across multiple time zones. The result was buggy, slow, and not as good as what bigger competitors were already making with bigger budgets.

Meanwhile, one clever bloke had taken someone else’s superior software (that did what I was trying to build), put his branding on it, and was outselling everyone without writing a line of code.

He’d worked out something I hadn’t.

You don’t have to build everything from scratch.

If someone else has already created something brilliant, you can often partner with them, license their software, recommend their work, or sell it as their affiliate and earn a commission.

You can run a course around someone else’s tool, teach a method built around an existing product, and be the person who explains, recommends, or pairs with what already exists.

I was so focused on making my own thing that I missed the option to collaborate on something that already worked. That mistake cost me a lot of time and a lot of money I didn’t need to spend.

5. Don’t Keep Restarting

This has cost me more years, more money & more stress than I care to admit.

For 16 years, my underlying message has been roughly the same: build a business you can run from anywhere in the world.

Travel & Business. Pretty clear.

That’s what I was teaching in 2010 from a balcony in Cyprus, and it’s what I’m writing about now from a cafe in Vancouver.

The thread hasn’t changed. What I kept changing was the wrapper.

I started with Free Fan Page Templates. Then I became the Social Networking Academy. Then Sell With A Smile, Online Marketing Addicts, Your Lifestyle Business, The Working Traveller & then I looked up recently and realised I was doing exactly the same thing with The 50+ Nomad.

My newsletter is The 50+ Nomad, so surely my socials, my branding, everything must be The 50+ Nomad too?

And that’s when it dawned on me that for years I’ve been making the model I’ve been running at the time, my whole brand.

I was building an app, so I called it Free Fan Page Templates. I built a membership site, so I became the Social Networking Academy. I started blogs, so I was Your Lifestyle Business, then The Working Traveller. I launched a Substack, so I became The 50+ Nomad. Every time the model changed, the brand had to change with it.

No wonder I felt like each one boxed me into a corner.

If I could go back, I’d call myself Jo Barnes from day one, build everything under that name, and let the projects come and go underneath the same umbrella.

The lesson: if you’re building a personal brand, brand the products and keep the umbrella as you.

Your name is broad enough to carry every model you’ll ever run and everything you’ll still be doing in 20 years.

If you’re building a company around a product, that’s a different discussion. Virgin Atlantic was never going to be called Richard Branson.

But if the plan is you at the top, with digital products, a newsletter, books and whatever else underneath, then the umbrella is better off being broad, and there’s nothing more flexible than just naming it you!

6. Your Audience Is Your Greatest Asset

Luckily, this is one lesson I learned early.

When I started online in 2010 I joined a forum of people all on a similar journey of building a business online.

As I was deep in learning mode I naturally showed up, asked questions, learned new things, shared what I was learning, built a lead magnet and started growing my audience.

I was posting on Facebook every day, running webinars, interviewing other entrepreneurs and helping anyone who came my way.

That audience became the foundation of my first six-figure launch and the businesses that followed.

Here’s why that model still works today:

• Platforms come and go.

• Business models evolve.

• Markets change.

But an audience of people who know, like and trust you is an asset you can build on for years.

As a creator you need to spend less time worrying about logos, websites and finding the perfect niche, and more time consistently creating content that helps people.

Whether you eventually sell books, guides, courses, coaching, physical products or something you haven’t even thought of yet, your audience is what gives every new idea its best chance of succeeding.

If there’s one thread running through almost everything I’ve written in this article, it’s this:

Build your audience.

Everything else becomes easier when you’ve got people waiting to hear what you create next.

7. Outsource Where You’re The Bottleneck (But Only When You Can Afford To)

Don’t mistake the word solopreneur for having to do everything solo.

The beauty of building a business today is that you don’t need employees to get help. No payroll, no holiday pay, no pension contributions, no long-term commitment.

You can hire contractors from Upwork, Fiverr or OnlineJobs for a single project, a few hours a week, or a short stint while you get something over the line.

So when should you? When you’re the bottleneck.

Where you personally are holding up the work: because the task takes you longer, drains your energy, you don’t know how to do the thing, or stops you focusing on what you should be doing.

Maybe you’ve spent three weeks trying to design your own book cover, format your guide in Canva, build your website, edit your YouTube videos, or figure out why your email signup isn’t working.

If your business has stalled and you know exactly which job is causing it, do yourself a favour and hire someone to do that job.

For me in the early years, it was tech. Right now, with my ecom brand - This Big World - it’s creator outreach & Amazon PPC. It’s such a new business I can’t really afford to outsource, but I also realised I couldn’t afford not to, I was the bottleneck and the business was growing too slowly.

And yes, when you’re bootstrapping, money is tight. But do the maths: what could you achieve if someone came in and finished the project you’ve been stalling on for three months, versus the cost of it staying stalled?

Every month a project sits unfinished is another month it isn't earning you money. That has a cost too.

Just Start

Looking back over these lessons, there are dozens more I could have added.

Some I’ve forgotten. Some I’m probably still learning. And there are lessons waiting for me around corners I haven’t reached yet.

That’s the funny thing about building a business. You never really finish learning.

You can read posts like this one, listen to podcasts, watch YouTube videos and take courses, and I genuinely hope you do because they can save you years of frustration. But they can never replace experience.

At some point you have to press publish, launch the product, make the offer, spend the money, get it wrong, adjust, and do it again.

That’s how every business is built.

So don’t wait until you think you know enough, because you never will. (I still don’t after 16 years!)

Start before you feel ready, learn the lessons as they arrive, and keep moving forward.

If this article helps you avoid one or two of the mistakes that cost me years and thousands of pounds, then it’s done its job.

The rest of the lessons are waiting for you to discover for yourself.

Have fun!

Jo 😎