Leaving Work Behind

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

Written by Tom Ewer on September 4, 2012. 52 Comments
Me With A Cake

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

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

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).

WPMUAs 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.

ManageWPWhat 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!

This Isn't Just Another "Make Money Online" Blog.

I'm sure you've had enough of hollow promises and get-rich-quick schemes.

I don't buy into that stuff; it's never worked for me. Instead, I create profitable online businesses through nothing other than hard work and persistence.

Here on Leaving Work Behind I share it all: both my successes and my failures.

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52 Responses to “Passive Income Dreams and Freelancing Success: My Story So Far [Part I]”

  1. Julie
    September 4, 2012 at 5:59 pm

    It is great reading your story! I too started on Ebay in 2000 but it didn’t amount to much. I did a little more between then and about 2005 but after that I haven’t really had much luck with Ebay. Blogging is a lot more fun 🙂

  2. CFA
    September 4, 2012 at 6:31 pm

    Very inspiring story Tom, you are a good example of what is possible when passion meets the Internet 🙂

    I await part II

  3. Ruth Zive
    September 4, 2012 at 7:00 pm

    You know I love your story, Tom. Your entrepreneurial spirit notwithstanding…you can really WRITE, and so it’s a story that is near and dear to my heart. I look forward to your continued success (and part 2 :-)).

  4. Michal
    September 4, 2012 at 7:01 pm


    I hope you will be able to achieve at least half of what Pat Flynn has achieved with his blog and his approach. I see many similarities between you with one huge diffrence – Pat was laid off and you have taken this decision by yourself. I’m keeping my fingers crossed for your success. I’m trying to take similar path with my Polish-language blog 🙂

    All the best Tom!

    • Tom Ewer
      September 4, 2012 at 11:43 pm

      Hey Michal,

      Let me see…$25,000 per month would be just fine by me 😉

      In seriousness though, Pat clearly is a big influence, and certainly a great person to be influenced by. Having said that, I’m hoping I can bring something a little different to the blogosphere and be a little unique in what I offer.

      Good luck with the blog! I had a look, then remembered I can’t read Polish 😉



  5. Joel
    September 4, 2012 at 9:55 pm

    I just found your blog and subscribed to your RSS yesterday. This article is super motivating to someone who is just starting out.

    I also didn’t realize there was a “from the beginning” passive income blog in existence (something I was just trying to start).

    • Tom Ewer
      September 4, 2012 at 11:44 pm

      Hey Joel,

      That’s exactly what I wanted it to be, so I’m glad I could help!

      There’s definitely more room for well-established “from the beginning” blogs. I’m sure they’re out there, but I haven’t seen any that have lasted for too long.



  6. Mike
    September 4, 2012 at 10:53 pm

    This post is great! I can’t wait for part two. Gives me some great perspective since I started five months ago with my own sites!

  7. Thomas @ Mobile App Tycoon
    September 4, 2012 at 11:07 pm

    Very interesting to hear the full story from start to finish. Looking forward to Part 2 🙂


  8. Tiago Simões
    September 5, 2012 at 12:02 am

    Hi Tom!
    Oh, my, i love to hear stories like yours.
    I can´t wait to read part II.
    Best wishes from Brazil!

  9. Henri
    September 5, 2012 at 10:15 am

    That cupcake sure looks juicy.

    “Once I decide that I want to do something, I tend to become very determined.”

    Sounds exactly like me, which is probably one of the reasons I was able to succeed online. I banged my head against the wall for a few years, but I refused to give up.

    Although I never actually had a real job. I did have a few summer jobs, and during those summer jobs, I realized that the 9-to-5 was not something I could do, unless I wanted to completely destroy my soul.

    It’s funny how you started Leaving Work Behind with almost the same idea as I did with Wake Up Cloud. The difference being that I was already making money online at that point, and I wanted to share what I knew with people.

    It has since then evolved into what it is today. It’s funny how things almost never turn out you expect them to.

    Nice cliffhanger at the end of the article.

    Great read though!

    • Tom Ewer
      September 5, 2012 at 4:49 pm

      Hi Henri,

      The cupcake was delicious. I only had a little bit though, shared it out amongst everyone else. There was a lot to go around!

      I like the look of your site – you’ve just got another RSS subscriber! 🙂



  10. Charley
    September 5, 2012 at 11:13 am

    Feels like I just finished watching a thrilling movie as I was visualising it all the way. This is very inspiring Tom. I’m still doing the “niche site” thing because I can’t seem to find something I’m really good at. I’ve also submitted several applications on job boards across several sites but I was declined on all but one. The client sent me a reply asking me to write a test article (without specifying my potential pay) along with a pdf containing very complicated, practically unintelligible, and seemingly unending writing regulations and instructions which he supposedly expects all his writers to abide by.

    It was way more daunting than I’d have ever anticipated and I ended up sending a rejection email to him, or rather, an abandonment email. I look back at my action today and I don’t regret it one bit. I’ve since refrained from any freelance application and confined myself to the seclusion of a content mill called Iwriter. But I don’t resent the clients who refused acceptance of my applications because it was expected.

    Blog owners are looking for writers who can add their opinions and personalise any articles they write and consequently create informative articles while sounding like an expert. You are good with WordPress, you got related jobs and you probably provided positive proof of your experience. I still don’t know what I’m really good at so I’m stuck at step 1 – I can’t confidently apply for a writing position; I can’t create a personal and authoritative blog like LWB, smartpassiveincome.com, etc.

    I guess everyone has different degrees of deterrents hindering their prosperity, lol!

    Can’t wait for pt. 2 🙂

    • Tom Ewer
      September 5, 2012 at 9:09 pm

      Hi Charley,

      First of all — it is clear that your writing is improving day by day. Your comment above was well written, and an improvement on what I have read before. You just need to keep doing what you’re doing.

      You were absolutely right to reject that job — or at least ask for clarification that the test article would be paid. No writer worth his salt needs to write free articles as a means of “interviewing” for a job — that’s what your samples are for.

      However, the sooner you get out of the content mill game, the better. And I think you’re doing yourself a massive disservice in saying that such places are your only option.

      I wouldn’t consider LWB an authoritative blog — it’s just an account of what I try to do to make money online. It’s grown with me, I guess. If you want to produce a similar blog, just start writing, and you’ll be on your way! And when I applied for my first writing job with WPMU, I had only been using WordPress for 5 months. I hadn’t even heard of WordPress before that time!

      If I had any comment to make about your writing, it is that it can be a little “formal”. I would relax a little, and let some of your true personality work into your words. That is perhaps the “je ne sais quoi” that you are looking for in order to take the next step.



  11. Sean O'Connell
    September 5, 2012 at 11:19 am

    First time commenter, following on RSS for awhile. Inspiring post – looking forward to Part II.

    Great read!

  12. Nick
    September 5, 2012 at 12:09 pm


    The most refreshing thing about your blog is that you’re completely honest about your initial inexperience in some areas, and on where you’ve gone wrong. This is in stark contrast to many other blogs, which are run by “gurus” who claim to have found a magical formula for success.

    Personally, I’m happier taking advice and guidance from someone like you, who carries the battle scars and isn’t afraid to share the learning from their mistakes.

    Speaking of which, this post was a real “slap in the face” wake up call for me. Having paid off my mortgage on Friday (I still can’t believe it really happened), I think I can shave 6 months off my escape plan. Your story triggered my reevaluation of the numbers – so thanks!


    • Tom Ewer
      September 5, 2012 at 4:51 pm

      Hi Nick,

      Thanks for your kind words! I’m glad you like my approach.

      Congratulations on paying off your mortgage – that’s a hell of an achievement!



  13. Tomoko
    September 5, 2012 at 4:41 pm

    Hi Tom,
    I too, love your story. It’s inspiring and motivating. I’m in a job right now that I really love. It pays great and allows me to use my research and writing skills. However, I’ve always wanted to be an entrepreneur. I’ve been building websites off and on since ’05. My current site generates a little income but nothing I can quit on yet.

    Thanks for the inspiration!

  14. Steve
    September 5, 2012 at 5:17 pm

    Great story Tom! It’s amazing to see a common trend in most successful journeys – Experience a number of failures/setbacks until you discover your true calling.

    I’m sure your freelance writing guide is going to be excellent. It’s awesome to hear that you’ve built a business out of an area where there’s an insane amount of competition.

  15. Diane Aksten
    September 5, 2012 at 11:01 pm

    Tom: Love your story and appreciate your willingness to be so transparent about your successes and failures.

    I, too, am planning to leave the 9 to 5 behind and I am looking forward to Part II from you.


    • Tom Ewer
      September 6, 2012 at 11:01 am

      Hey Diane,

      To be honest, I couldn’t imagine being anything other than transparent. It really helps me to write it down and get feedback from you guys!



  16. Charley Chris
    September 5, 2012 at 11:09 pm

    However did my comment get trapped? 😉

    Thanks for the compliment and the advice concerning my writing style. I’m always looking for ways to enhance my writing skills. I don’t know if I’ll get out of this “content mill hole” soon because what ails me hasn’t been resolved yet. Frankly, unless I want to start a blog like charleychris.com and write about anything, it’ll be unfeasible to become a serious blogger. Thanks for sharing more details about your experience in the realm you applied within.
    I’m perhaps setting my standards too high (again) by underestimating my ability to write in unfamiliar niches. I’ll give it more consideration and put more effort in ascertaining the elusive niches I could excel within (I know they’re definitely there).

    BTW, this is the most fascinating post I’ve read in the past 3 weeks.

  17. Travis
    September 6, 2012 at 4:49 pm


    You’re posts continue to serve as a huge motivator for me. As someone looking to do basically the same thing as you, I’ve found it very helpful to follow your continued success. I love the open and honest style and the way that you engage constantly with your readers, whether it be through comments or emails. Keep up the good work, congrats on breaking the $4,000 barrier, and I look forward to reading the next part!


  18. Fred
    October 8, 2012 at 10:50 am

    Great inspiration i must confess. Headed over to part 2!

  19. Ruan | FreelanceWritingTactics
    November 16, 2012 at 12:34 am

    Hi Tom,

    I have been following Bamidele Onibalusi for quite some time now and even interviewed him a while ago. When I received his email just a few days ago and I saw the words “freelance blogger” in it; well that just got my smile going from ear to ear and I was on that interview he did with you within a flash!

    Tom, I strongly believe that everything happens for a reason and I believe that the reason I got to learn about you happened for a reason. Time will tell but I’m pretty convinced the words “freelance blogging”, “freelance writing”, and “documented journey” are all part of the mix.

    I currently write on a regular basis for sites like kikolani.com, WeBlogBetter.com (links to my author pages with posts written for them), Problogging Success and have just been accepted to Problogger as well as Famous Bloggers. I have no doubt in my mind that I have what it takes to succeed in terms of writing ability.

    I have never been paid for any of my blog posts. The closest I came to being paid for writing online was once when I did 6 articles of around 400-600 words and the person paid me $25 in total. I was HUGEly excited and thought to myself “Wow! I could do this for a living!” Never ever at that rate again though…

    To be honest, I haven’t even got a niche yet. All I know is I want to write, I want to get paid doing it and I want to document my journey from the start. I am not sure if I need to do this on a different blog than my authority site or niche site. I am quite skilled with WordPress, HTML and CSS so I guess I have the technical skills advantage over most.

    Why haven’t I done this yet? I. Have. Absolutely. No. Idea.

    I think my biggest obstacle is finding my niche and then to identify my target audience I need to write for. I tend to want to reach too many instead of finding my ONE person. I am not sure exactly how or where to find “them” and how many “they” have to be.

    Thanks a ton for the inspiration; you’ll definitely get a lot more to see and hear about me. Any suggestions you might have for me; I’d appreciate the help, Tom 🙂


  20. Raphael
    January 14, 2013 at 11:11 pm

    Your story is very inspirational, Im glad you didn’t gave up and you kept going and going,
    Im sure now you can tell it was worth it 🙂
    Lately I’ve opened my blog too, I think during the start the biggest issue is the question “What Im actually want to do?” In my case answer was “I want to give value to people, I want to help them”. I hope I will have enough persistence as you do 🙂

  21. Brooks Conkle
    April 22, 2013 at 3:20 am

    I just ran across your blog and have been reading this evening.
    This is great.
    You’re yet another success story of making money online.
    It’s great.
    Every time I think that I’m following all of the right blogs, I find new ones.

  22. Michelle
    June 2, 2013 at 5:06 pm

    Love your story! It sounds so similar to mine. I set a date for self employment and it’s January 1, 2014 🙂

  23. Julie
    April 26, 2014 at 2:28 am

    Hi Tom,

    I came across you site by accident, however strangely enough both myself and my husband were talking about making money online yesterday. We talked about blogs and I had no idea how or if anyone could actually make money in this manner.

    I have been growing my LInkedIn site with World Leading Professionals asking to be added as connections but all the jobs they have are international and as someone who has just migrated to Canada to be with my husband, I don’t want to move again.

    Your site it very informative and I hope to take this form of business further.

    Thank you!

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