How I Made $250k Online in 3 Years, ‘Lost’ it & What I’m Doing About It

DCF 1.0
DCF 1.0
Burmese money – this is actually around 20 quid!

Edit: When I use the word “poor” here, I am of course speaking in relative terms. It goes without saying that I’ve seen abject poverty of the most heartbreaking levels on my travels. It’s a total different ball game and I recognise that.

I wasn’t sure about writing this post and I’ve stalled on it for many months. I’ve always been very open and candid about my financial situation, but then again – I’ve always been broke as a joke and it’s weirdly a lot more socially acceptable to talk about a struggle as opposed to openly celebrating a bit of economic success.

For most of my life I’ve been an embarrassing financial failure. I was raised by my mother with help from my grandmother and we, as the old English saying goes; “didn’t have two pennies to rub together.” I’ll spare you the; “we may not have had money, but we were always happy,” rhetoric because that would be a massive lie and I don’t want to give credence to that.

There’s nothing glamorous or fun about being poor, even though that myth seems to strangely get perpetuated on a regular basis. There’s also a longstanding illusion that poor people are more morally sound than those who have wealth. Let me tell you that after thirty-one years of living – some of the most malevolent, psychotic pieces of vermin who I have had the misfortunes of meeting have been poor. Make of that what you will.

My village is a lot better than it was when I was younger and my city is absolutely gorgeous, but it wasn’t fun growing up due to financial constraints and the environment which it creates – It was horrible and when I left just over three years ago I said goodbye to more bad memories than good.

Screen Shot 2015-08-03 at 01.02.00

I’m not saying that money is the answer to everything – just that it’s an important ingredient in the recipe of life. To me it’s asinine to say; “there’s no point in having money if you don’t have health.” Since when do we have to choose only one? If we are lucky enough to not have any bad health in our lives – shouldn’t we try and look after all important areas of our lives? Health, friendships, career, love, money – I say let’s do our very best to tick all the boxes!

By the time my stepfather arrived on the scene I was well into my teens and growing into a (very immature) adult. The cycle continued into adulthood and I was always the broke one out of all of my mates. Pride would force me to lie about why I couldn’t come out for a few beers as I was so painfully ashamed to be like this. The funny thing is I used to always read personal growth ‘get rich’ type of books like they were going out of fashion.

I used to buy ‘The World’s Richest’ updated list with my paper round money as a teenager. I know now that back then I fell into a trap that many do nowadays – thinking that simply reading books and learning inspiring quotes was enough to deserve wealth and a better life. I see it every day and I want to shake people because I know how much they are wasting their time reading and not actually doing anything.

You reap what you sow and my mates deserved to be better off than me as they chose further education and I chose to be a bum – bouncing from job to job without any direction.

When I arrived in Chiang Mai, Thailand in 2011; things did not go according to plan. Bad health struck and a familiar tune was playing – I was down to my last $29 and I hadn’t made any money in weeks. Also I needed an operation which I didn’t have the money for – I was forced into a fight or flight situation and it was the making of me. I made $5K that month and it gave me the confidence that I needed to go onwards. You can read all about that here. However, it really wouldn’t be fair to not give a shout out to the legendary James Clark who helped me out with advice that would change my life forever – for the best.

Screen Shot 2015-08-03 at 01.06.07

From this moment I turned into a raging workaholic. If I wasn’t chasing people for advertising contacts, hitting up advertisers, or writing SEO articles – I was trying out new ways to expand and make more money.

I was a lunatic – sleeping 3-4 hours per day. I never turned down anything online which made me money. I must have personally written thousands of articles during this period. I have written for clients on a huge range of subjects; cities around the world, sex toys, interior design and I once wrote 5000 words on the female menstrual cycle (that’s a world I do NOT want to revisit).

Predictably – I burnt myself out. But I just couldn’t stop because if I did I was leaving money on the table. A friend invited me to take a trip with him to Malaysian Borneo. I love Malaysia so it was a no-brainer and so off we went – grabbing our PADI Scuba Diving certificates in the process.

However the trip turned out to be incredibly stressful as the more I rested – the more I left clients waiting and pissed off. When I got back I didn’t learn my lesson and I continued working myself down to the bone. Running on empty and constantly feeling like a zombie.

During this period I befriended Johnny Ward and he would constantly preach to me about working too much and how I should be treating myself for my hard work. I found it really annoying at first to be honest, but maybe because it was true and I didn’t want to admit it. Cognitive dissonance be a strong force!

Roughly a year later I moved in with him and other online guys in Bangkok and I started to feel terribly jaded with working so much; so I finally decided to do something about it. I went back to basics and read ‘The 4 Hour Work Week’ and implemented some of the advice from there. I then started employing and outsourcing my work – starting with my friend Caroline from Life is Limitless who was nothing short of a superstar, polishing up my terrible admin skills and generating money with her positively infectious personality.

This was undoubtedly one of my greatest decisions and from this moment my life became absurd – I was making fully passive income. Meaning I was getting paid handsomely even if I spent the week scratching my balls watching The Sopranos.

Swimming with whale sharks in Oslob, Philippines.
Swimming with whale sharks in Oslob, Philippines.
Holding a Cuscus in Papua New Guinea.
Holding a “Cuscus” in Papua New Guinea.

As fun as that sounds – I actually started travelling to destinations way beyond my wildest dreams. I flew to Samoa and we even paid for private charter planes to take us to untouched islands within the country.

Paradise lagoon in Samoa.
Paradise lagoon in Samoa.

I stayed with a tribe in the jungles of Papua New Guinea – holding animals I didn’t even know existed. I schmoozed in the swankiest of hotels in Hong Kong for my 30th birthday – celebrating it by doing the world’s biggest bungee jump, Macau Tower. I got to tick Okinawa off my life-long bucket list and fell in love with Japan. I swam with whale sharks in the Philippines. I went to the World Cup in Brazil with one of my best mates from back home. I even fixed my ugly British teeth!

Brazil Football World Cup.
Brazil Football World Cup.

These are only a few examples of the things I did and the most insane thing about it was that for the first year and a half – I would actually have more money in the bank at the end of the week after doing these things! I was experiencing the ultimate freedom – lots of money and time.

But even the once mighty Roman Empire fell, right?

The industry started to weaken and my income became progressively lower every month – but I didn’t hold back like I should have done. I kept on living, employing and spending as frivolously as it gets.

The crunch time came when I went to see about buying an apartment in Bangkok – in cash for $60k. I had just about that much in the bank and I was strongly considering buying it. I love Thailand, Bangkok not so much, but Chiang Mai – I have a lot of love for.

I agonised for a week about this purchase. I thought about how amazing it would be – to fully own a mortgage-free apartment in the capital of a country that I adore at the tender age of 30! But for some reason, I decided not to buy it. I was visiting home for the first time in three years very soon and I didn’t want to make a brash decision when I had so much to think about.

If you think that I’m going to be all ‘no regrets’ about this then you’re very much mistaken. It was idiotic of me to not tie in this money and have a place to call my own. It kills me that I didn’t do this!

I made a lot of rookie mistakes during this financially handsome period of my life; I gave away money to people in my life when I wasn’t even safe myself. I continued to employ people when I should have just went back to basics and work myself. I lost a lot on online business scams (ugh) and I never ever cared about the price of something that I paid for – I only cared about the value of the experience.

I stayed with these beautiful people in Tokyo free of charge after chatting on the plane to Okinawa. :)
I stayed with these beautiful people in Tokyo, free of charge after chatting on the plane to Okinawa. 🙂

I’m a gambler when it comes to business and the last time I gambled – it paid off tenfold. In the last half year I have spent around $25K on a project which is yet to bear any fruit. Maybe it will turn into another cash cow, or maybe it will die a painful death – that’s business. There are no certainties in this game.

Right now I’m back in 100% hustle mode. I’m living in Mexico City and although I’m working a lot – I remember my health this time around. I make an hour a day available for the gym and I am eating very healthy (when I was a workaholic in Thailand I would forget to eat quite often).

I’m juggling a lot of balls with regards to business right now and I’m very much focused on maintaining this life, which I love. I can’t say that I totally regret my lavish life for the last three years which enabled me to visit almost 50 countries (I don’t think there are many better things to blow your money on than travel), but I do wish that I reigned my spending back a bit – and I absolutely do wish that I had bought that apartment in Bangkok.

I joked to my housemate the other day that I am ‘transfinancial.’ Such as a transexual feels they were born with the wrong gender – I always felt like I was supposed to be born rich!

Standing atop Mount Fuji, Japan at dawn.
Standing atop Mount Fuji, Japan at dawn.

For anyone who thinks that this post is meant to be conceited and ostentatious, or that I’m arrogant about the money that I made – I can assure you that this is not the case. There were often times when I travelled alone and almost broke down with happy tears because I was so grateful for what I was experiencing before my very eyes. It gave me time to appreciate the sacrifices that my mother and grandmother made in their lives for me so that I could have more opportunities in mine.

I also spent a lot of this time building beautiful friendships, maintaining those that I have already and I started to explore my connection and relationship with food – I’m healthier and happier now after going down this path. I have a greater respect for money now and if I find myself in the same situation as before; I’m pretty sure I’ll go about things differently.

I can’t believe that I’ve seen the things I’ve seen and done the things that I have done. I’m just a lad from Durham who had a dream and luckily that dream came true. I spent so much of my life feeling like a worthless piece of sh*t, and suddenly my life has meaning and purpose. My recent life has been a real-life dream and I don’t intend to stop any time soon. The party has only just begun!

One thing that I can’t bear is to see people not living up to their potential. It kills me! If you’re not happy where you are in life now, know that you are not powerless. Ditch those personal growth books, stop spending your time sharing positive memes and buying inspirational fridge magnets and get busy. You don’t have to be an expert – you always have to start somewhere. Get active and be relentless in your pursuit – just don’t kill yourself in the process please.

I’ll be talking more about making money online and lifestyle design on this blog in the near future. Next chapter beckons! 🙂

Song For The Moment: ‘Good Riddance,’ By Greenday

“So take the photographs, and still frames in your mind
Hang it on a shelf in good health and good time
Tattoos and memories and dead skin on trial
For what it’s worth – it was worth all the while

It’s something unpredictable, but in the end is right,
I hope you had the time of your life.”

Posted in

Anthony Middleton

Former loser who took a risk. Visited over 100 countries. Trying my best to not get skinny-fat during Covid.


  1. Laryssa on August 3, 2015 at 2:54 am

    Your outlook is awesome– it isn’t jaded, it’s wisdom. Looking forward to reading about your future success.

    And personally, I wouldn’t have minded making $250k passively and “losing it” all on travel 🙂

    • Anthony Middleton on August 5, 2015 at 7:27 am

      Thanks Laryssa – good luck too. Yes there are surely worse things to ‘lose’ money on. 🙂

  2. Patricia | Monthly Adventure on August 3, 2015 at 6:42 am

    Anthony – you rock. Your journey has been an inspiration to me. Big hugs from Vancouver!

    • Anthony Middleton on August 5, 2015 at 7:25 am

      Thanks Patricia, I’m a huge fan of your journey too! Hugs back 🙂

  3. Martha on August 3, 2015 at 8:06 am

    Very nice and inspirational story. Your life is so much richer than the people you left in the UK with only dreaming about your lifestyle! Keep om travelling and working!

  4. Shaz N Paul on August 3, 2015 at 7:37 am

    Great post, thanks for sharing the ups and downs, you'll always have the memories.. and nice teeth 🙂

  5. Gemma on August 3, 2015 at 12:34 pm

    Hi lovely,

    I haven’t seen or heard from you in a while as I decided to come off a lot of social media. I loved this article, so brutally honest. I’m glad things are looking up. Give me an email sometime to catch up.


    Gemma West

    • Anthony Middleton on August 5, 2015 at 7:24 am

      I was wondering where you got to 🙂 I would totally stay off social media if I didn’t have online sites! x

      • Gemma on August 5, 2015 at 11:04 am

        I’ve just activated Facebook again to get some contact details for people but it will be getting deactivated again I’ll send you an email soon as I have a new email address and we need to catch up. I’m still envious of your journey. Oh and I have left the lovely village we came from haha and it’s awesome being away from it and all the awesome people lol. Xxx

  6. Johnny on August 3, 2015 at 1:36 pm

    Brilliant article mate, loved it and it’s been a pleasure and an honour to share this part of your life with ya. Now on to the next one 🙂

    • Anthony Middleton on August 5, 2015 at 7:23 am

      Thanks mate, see you in Middle East! I’ve got something to work forward to. 🙂

  7. Cate Brubaker on August 3, 2015 at 2:12 pm

    Dude, you're like a goddamn unicorn, all mythical and very handsome. I'm sorry that our reunion has been delayed by a month, but San Cristobal is pretty special. You'd just better still be in DF when I get there. We'll be an unstoppable force.

    • Anthony Middleton on August 5, 2015 at 7:23 am

      Haha that’s if I don’t move south towards the sun and cheaper accommodation! Can’t wait to see you 🙂

  8. Jo on August 3, 2015 at 3:20 pm

    Work load must have been crazy if you forgot to eat !!

    Highs and lows but you’ve made some amazing journeys, memories and friendships along the way.

    As you said… The next chapter beckons. xx

  9. AJ Bevis on August 3, 2015 at 5:52 pm

    honest and beautiful. a good reminder in several aspects. 🙂

  10. AJ Bevis on August 3, 2015 at 5:52 pm

    honest and beautiful. a good reminder in several aspects. 🙂

  11. Janet Newenham on August 7, 2015 at 8:07 am

    Amazing to read this, especially as someone considering quitting her job and working fulltime as a freelance writer. Thanks for sharing.

  12. Man Vs Clock on August 7, 2015 at 8:30 am


  13. Man Vs Clock on August 7, 2015 at 8:31 am

    All the best, Janet. Just stay focused on what's important to you – it's vital to have a fast and strong answer to "why am I doing this" when it gets too tough.

  14. crazy sexy fun traveler on August 7, 2015 at 9:57 am

    I could just say ”Been there, done that” 😀 Gotcha, my friend!

  15. Nelson Anthony Cuesta on August 7, 2015 at 11:13 am

    Great read bud. Get that hustle on.

  16. Pranav Sukumaran on August 19, 2015 at 3:21 pm

    That was really an amazing read!!

    Now, i would really need your advice in making money online.

    I had finished my aeronautical from the southern part of India in 2014. Unfortunately there is no opportunities for the aerospace sector here in India and further studies are too costly that my family cant afford.

    I myself have no idea how i ended up taking aeronautical, so please dont ask about that.
    So, my dream? A food safari!!
    But i need to make cash…..give some to my parents too…make them feel comfortable and secured.

    Now brother, you gotta share your divine insight and suggest me a way to get thru this financial crisis.
    How to make cash online?

  17. Sandy Thom on April 12, 2016 at 12:55 am

    Wow nice text! I feel much more inspired after reading it, thanks for sharing!

  18. Wicked Walkabout on July 1, 2016 at 8:10 am

    Well, too many 'new tabs' opened from links to read from your site! What a roller coaster of emotions and highs and lows! Well done, keep it up!

  19. Frank on July 1, 2016 at 5:40 pm

    Enjoyed the post, quite the story! Whether rich or poor, it’s inspirational that you could turn it on and make money as you did. I know too many people with no drive who would/could never get started.

    I was in Mexico City a week ago, not the usual blogger hangout. I like the place though, very underrated.

    Frank (bbqboy)

  20. Stephen on July 4, 2016 at 7:36 am

    I had an inspirational coffee chat with James Clark one time…

  21. Hugo - Bons Plans Voyage on August 24, 2016 at 5:58 pm

    Impressive. Thanks for the tips!

  22. Jo on September 3, 2016 at 10:05 am

    Great read, you’ll always be ‘transfinancial’ to me. x

  23. Radu on June 20, 2018 at 12:31 pm

    Inspiring read! I identify myself as a “transfinanical” also, so I can definitely relate to you. I’m also on a journey of growth both personally and financially articles such as your help keep the fire burning. Would like to get in touch with you sometime and share experiences.

  24. Blogger Zune on May 7, 2020 at 7:52 pm

    Great Tips! Really helpful and contains lots of detailed info about starting a blog. Actually these are some common very very important steps to start a blog or a website, First few steps are very important, without these steps no one could be able to start a proper blog. Thank you for sharing this great post. All the information is totally amazing. Keep Posting.

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Man walking through Sahara Desert at Marathon des Sables

Hi, I'm Anthony!

In November of 2010, I took on a mammoth challenge against the clock in a quest to upgrade my miserable life. I went out of my comfort zone and turned it all around. Ten years later, I’m completely location independent…

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