Leaving Work Behind

Passive Income Dreams and Freelancing Success: My Story So Far [Part I]

Amongst other things in the last 15 months, I won a giant cupcake. Big highlight.

This is Part I of a two part series. You can find Part II here.

The story of my journey from passive income dreamer to freelance success story is patchily documented on this blog and in various interviews around the Internet, but there is nothing in the way of a definitive account.

Given that I have always gotten a great deal out of reading other people’s stories of success (and failure), and that I am now rather “settled” in terms of my income, I thought that it would be a good time to publish a full account of my journey to date.

If you take one thing away from this, it should be that it was not easy. I put a lot of time and effort into different ventures with no clear prospect of success, before finally hitting upon a winning formula. Persistence won in the end, and I never forget that as I push forwards to achieve more.

May 2011

I remember the decision to quit my job as being a very epiphanic moment. There was no slow grinding down, no gradual burning hatred of my job that grew over time. I actually liked what I did, heading up the management and development of an eight figure property portfolio in my father’s business. I earned a good wage, I had great autonomy in my role, and the prospects were great.

Up until that point I had floated through my academic and professional life. I had managed to get that far without any real conscious decisions or ambitions. I had never had a plan. Although I was good at my job and worked very hard, the kernel of the position I eventually grew into had essentially fallen into my lap after leaving university. And in May 2011, I had finally realized that the path I was going down wasn’t for me.

I had entrepreneurial blood running through my veins – it had just taken 25 years for the effects to take hold. I always had this idea in my head that I would someday be a successful business owner, but had never actually taken the leap of establishing how that would happen. Now I was ready to take the leap.

And as people who know me will say, once I decide that I want to do something, I tend to become very determined. I essentially became unemployable overnight – working for someone was no longer an option I was willing to entertain. I wanted to be in control of my working life. I wanted my success to be down to my ability, and circumstance – nothing more.

My first port of call was to look into opportunities for making money online. I needed to establish a venture that I could run alongside my job – something that wouldn’t take too much time, and could eventually grow into something that would provide a full-time income.

To start with, I turned to eBay. I had previously dabbled in selling items on the popular auction site way back in 2000, when I was just 15 years old (a time when my entrepreneurial spirit was at its previous peak). I looked into the possibility of buying wholesale and selling retail. I soon found out that it was an intensely competitive environment with extremely tight margins. Not for me.

Pat Flynn

With my initial ideas discounted, I began searching for other methods of making money online that sounded appealing. I stumbled across a ProBlogger guest post by Onibalusi Bamidele, which referenced a certain Pat Flynn of Smart Passive Income.

To say I was inspired by Pat’s story would be an understatement. He was exactly what I was looking for – an honest voice in a niche ripe with snake oil salesmen.

In the space of an afternoon, I devoured a huge amount of content in Pat’s blog, and was especially captivated by his Niche Site Duel. The idea of creating a website that could generate a passive income was fascinating to me. I knew I had the writing skills to create quality content, so I felt that creating my own niche site was something to try at the very least.

And so on 23rd May 2011, and after extensive (and somewhat naive) keyword research, Modeling For Kids was born – my first website since my teenage years. I knew nothing about child modeling, but I felt that it was a potentially lucrative niche. With a clear objective now in site, I got my head down and started researching and writing content. Three articles per week, every week.

June 2011

Although I had barely even read a blog before, let alone created one, I had an idea that I wanted to run with. I was busy creating content and building links for Modeling For Kids, and it had started to climb the rankings in Google. But I felt that if I was going to succeed in my efforts to quit my job, I needed to find a way to hold myself accountable. That single thought developed into this blog.

I conceived Leaving Work Behind as an online accountability journal for my efforts to make money online and quit my job. Moreover, I felt that I had an opportunity to create a type of blog in the “Make Money Online” niche that hadn’t really been done before – one that told the story from the very beginning.

Whilst I was a huge fan of the likes of Smart Passive Income and Niche Pursuits, those blogs were created at a point where the authors were already experiencing success in their efforts. In June 2011, I had achieved absolutely nothing, and I had barely got started. I felt that if I was successful in my efforts and was able to quit my job, the fact that my journey had been documented from the very beginning would be a great motivating factor for other people.

What Cricket Can Teach You About Blogging

And so on 27th June 2011, I launched Leaving Work Behind with five posts:

My focus was on complete honesty and transparency. When it came to my efforts to make money online and quit my job, I wasn’t going to hide anything. On the day of the launch, I attracted a grand total of 56 visitors – a number that wasn’t surpassed until 19th September.

July 2011

On the 1st July, I published a “mini-manifesto” of sorts on LWB – A Call to Arms.

In that post, I outlined my desire to help other people, and my hope that the blog would develop into a community of likeminded people who could work together to achieve a common goal. Looking back on it now, I feel that I have stuck close to my original aspirations, and hope that I have helped some people along the way.

July was a period of stagnancy for Modeling For Kids. I released two updates on LWB in that month, expressing some frustration at my inability to get on the first page of Google. That frustration was however tempered with some realism, as I still had every chance of hitting my goal (1st spot in Google within 90 days).

In that month, I also released two posts on LWB that defined my goals for quitting my job:

  1. What Do You Want?
  2. How to Succeed

At the time, my plan was to develop Modeling For Kids into a site that would generate enough money to support my existing quality of life. I set myself a deadline of quitting my job by 23rd May 2012 – exactly one year after I launched Modeling For Kids.

At the time I acknowledged that relying on one source of income is risky, and that I would likely pursue additional projects in time in order to achieve my goal. I didn’t know how right I was.

August 2011

August was a big month for Modeling For Kids, in which I published no less than three updates on LWB. But it was the final update of the month, published on the 24th, that delivered the news I had been hoping to publish – the site had made it to #1 in Google!

Although my achievement didn’t result in the flow of traffic that I was hoping for (as you can read in the update), I now felt that I had made an important breakthrough – I had demonstrated to myself that I could rank in Google. Regardless of how Modeling For Kids fared, I had set a precedent.

It was a pretty awesome time – I felt like I could see the light at the end of the tunnel in terms of being able to quit my job. I was blissfully unaware of the disaster that awaited me.

September 2011

I started September in a very positive frame of mind indeed – in fact, I hoped that it would be my first break-even month. With an average daily income of around $4.50 and growing from Modeling For Kids, I was feeling pretty bullish.

But that all ended on September 6th, when I discovered that Google had heavily penalized the site and dropped it way down the rankings. Not quite the birthday present I was hoping for.

At first I thought it might be to do with an issue I’d had with the site’s theme, but it soon became pretty apparent that overzealous backlinking was the root cause. Modeling For Kids was now dead in the water, with my source of traffic having disappeared literally overnight.

Not one to be discouraged for too long, I tried to look at the experience from a positive perspective and published What I Have Learnt From My First Niche Site.

In an effort to branch out into projects that might have a better chance of success, I started a JV with Joseph Archibald – someone who has dabbled in internet marketing for many years. We launched an authority site in the dieting niche – alldiets.org. We were targeting rather competitive keywords, but Jo felt that we could establish ourselves in the long term. I was to create the content, and Jo was to build links.

Furthermore, having been badly stung by my backlinking practices, I resolved to launch a new authority site that relied upon low competition long tail keywords. And so Deal With Anxiety was born. I revealed it on LWB as an experiment in white hat SEO – I would simply write content, and wait to see if Google would rank it of its own accord.

I don’t pretend that I wasn’t devastated by the almighty Google slap Modeling For Kids had received. After all, my immediate plans for developing my business had been destroyed overnight. In reality, I could see that I wasn’t making the kind of progress that I needed to in order to quit my job in May 2012. So on 20th September, on a whim, I submitted a bunch of applications for writing positions on the ProBlogger Job Board. At the time, I had no idea what I had just started.

October 2011

With autumn rolling around, my niche/authority site prospects were looking ever bleaker. Modeling For Kids was still languishing in the Google sandbox, and my very short-lived experiment in white hat SEO ended in what I perceived as failure, as Deal With Anxiety had not achieved any rankings above 90 in its six week existence. So I decided to start building links to the site (using the lessons learnt from the Modeling For Kids fiasco).

As a result of my writing applications submitted in late September, I was given a paid trial run of five articles for WPMU. I wrote and submitted those articles, then sat back and waited.

I didn’t really know what to expect. I was struggling with the concept that I could be paid for something that comes so naturally to me. In some bizarre way, it didn’t seem right that it would be this easy, after I had spent so long failing in my efforts to make money.

On 6th October, I received an email from James Farmer at WPMU confirming that my trial period had been extended to an ongoing position. I had the job. Five articles per week, every week.

This threw everything out of whack in terms of my plans to quit my job. My dream had always been to establish passive income streams. Instead, a very practical business model had landed on my lap, ready to pursue. Whilst I still loved the idea of passive income, I knew that I would be foolish not to pursue freelance writing further. It represented a very real opportunity to quit my job.

And with that in mind, I decided that it was time. I explained to my father that I was planning to quit my job. Whilst the date had not been formally set, there was now no turning back.

Foolish? Possibly. Reckless? Perhaps. The right thing to do, in hindsight? Absolutely.

November 2011

November was to a month of excitement. Rather than being fearful of the fact that I would be quitting my job, I was galvanized into action. I had a little mantra at the time:

Sometimes you simply have to accept the risk inherent in things and move forwards, regardless of fear (tweet this).

The first key decision was deciding exactly when I would quit my job. I had discussions with my father about when it would be best in order to facilitate a smooth transition in the company. We decided that the end of the year would be as good a time as any, so my last date of employment was agreed – 31st December 2011.

With my eyes now firmly set on the horizon, I looked to freelance writing as a platform that I could build upon. My simple logic was that if I could find one client who was willing to pay me $x per hour, and that the hourly rate was enough to keep me solvent if I worked 7-8 hours per day, I was good to go.

The main issue, of course, was finding more clients. Having experienced quick success with the ProBlogger Job Board first time around, I figured I should submit a second round of applications. But this time around, I made it clear in my applications that I would not be able to start work until mid-January (as I was going to be on holiday until the 11th). My hope was that I could secure some clients in advance, which would give me a nice little boost to start with.

What I wasn’t expecting was a response to one of my applications from Vladimir Prelovac (the CEO of ManageWP), requesting that I submit a test article. Not one to ignore an opportunity (even though I barely had time for more writing), I quickly submitted an article.

By mid-November, I had the job – writing 1-2 articles per week for the ManageWP blog. I really couldn’t believe how easy it appeared to be to land freelance clients – all I had ever heard about freelance writing was how difficult it was to get paid anything more than pennies. I knew I was definitely onto something.

On the internet marketing front, I had made a fresh start with the Modeling For Kids content and was planning on publishing it on an entirely new domain. I’d also devised a backlinking plan for Deal With Anxiety, based upon the BuildMyRank private blog network. However, my JV with Joseph Archibald appeared to be stalling, and I wasn’t particularly bullish about its future prospects.

December 2011

Given that December was to be my last month of employment, it ended up being quite the anticlimax. That was mainly due to the fact that I was on holiday for most of it, which meant that I had little time to concentrate on developing my business.

There were no developments of any note regarding either Modeling For Kids or Deal With Anxiety – I simply continued to build links on a conservative basis. And after sputtering and stalling, my JV with Joseph Archibald ended (completely amicably, I must say).

There was no doubting my excitement for the future though. I had big plans, which I revealed in a post entitled Let’s Make 2012 A Game Changer (My Plans For The Coming Year).

The question was, would I be able to achieve my goals? Would I manage to establish income streams that could support my way of living? Find out in Part II!