I Entered Over 1,000 Competitions in One Month and This Is What I Won

It's Saturday morning and I'm 11. I walk downstairs to make myself an enormous combo bowl of Chocolate Snaps, Rice Krispies and Frosties – early onset diabetes in a dish – and turn on the telly to watch SM:TV Live. Some little bastard called Greg has just won a Hitachi stereo with a built-in MiniDisc player. Ant and Dec are both doing their thin smiles and Cat Deeley's going, "Exciting, isn't it, mum?" gesturing to Greg's mum, who's grimacing in the dark behind the young seated audience.

I think to myself: 'Why is it always kids called Greg from Welwyn Garden City who win Hitachi stereos and Dreamcasts? Why can't it be me?'

Over a decade later, I've realised the big main reason I never won any competitions is because I never entered any competitions. So, for the first time in my life, I thought I'd do just that. I googled "enter a competition" and a news story about a woman who calls herself Di Coke appeared. Di Coke is a 40-year-old "comper" – a serial competition enterer – who enters a staggering 400 competitions a week and claims to win £15,000 worth of prizes every year. Doing literally exactly what she does, I thought, I could definitely make at least £1,250 in a month.

As I'm a peon with a taste for masochism, I spend the majority of my week at work, so I can't comp full-time. But what I can do is wake up at oh-my-god-for-fuck's-sake-o'clock, cycle to a cafe near work and sign up for a bunch of stuff that's going to clog my inbox up with spam. On that note, I figured a comp-specific email account would make sense, and a believer in positive affirmations, I thought my e-mail address should be this:

"Sam is going to win" would be the mantra I would repeat with every competition I entered, increasing chances of winning by a percent each time.

PrizeBug is a site that collates competitions from across the internet to one site, then when you click on one link, takes you to the original site and opens about 400 pop-ups. I'm cheap and easy, so I was after anything and everything: iPhones, iPads, PS4s, a holiday to New York, a Fiat 500 (why not?) and even a Dyson car cleaning kit – not that I own a car, but I might one day, and anyway, owning as much stuff as humanly possible is always a good thing, right?

As I punched in my personal details and positive e-mail address, a page – sometimes more – of opt-in/out questions appeared. Some of these had weekly charges, so unlike with Apple's terms and conditions, I'd actually have to read these and stay vigilant.

After my first session, I'd entered 58 competitions, and it wasn't even 9AM. I went to work, sat down and began doing my repetitive task for the day, but I couldn't concentrate. Images were flashing through my mind: packages being delivered; "sorry, we missed you" cards from the postman; me listing unwanted prizes on eBay; me standing behind a sweaty, exasperated man in line at the Post Office, sending off those eBay parcels; me visiting places I'm likely to get heat rash; me driving to the home that Ant and Dec and their wives all share to wave my Dyson car hoover around, screaming, "Fuck you, Ant! Fuck you, Dec! I did it! I finally fucking did it!"

Checking my emails became a source of excitement. No more would I click refresh, full of hope, before finding two automated messages about unsuccessful job applications. Now, the only emails I'd receive would be ones telling me I'd won a car (or a load of spam emails telling me I need only take "one simple step" to enlarge my penis).

At the high tide of the week, I'd successfully entered 347 competitions, just under a pro's weekly output.

No wins yet. Just a series of emails saying stuff along the lines of: "Congratulations! You've been shortlisted to enter!" or "Well done, samisgoingtowin@gmail.com was exclusively selected!"

Was I just giving my personal details away for free to some shady advertising behemoth, allowing them to be sold on to companies that would then relentlessly pitch me products I have no absolutely interest in? I thought the world was better than that – that we all learnt a lesson about not being dicks to each other after Nasty Nick was vilified by the national press 15 years ago. Have we taken nothing from that?

Soon, I came across ThePrizeFinder, home to a staggering amount of competitions, which, again, linked you to other pages to enter, sending new pop-up pages flying around my screen like that bit at the end of Solitaire. This helped me re-focus. I barely took my eyes off my laptop, utilising the keyboard shortcuts expertly and positioning my cursor in the most efficient place possible for scrolling through pages.

Two weeks and 500 competitions later, my enthusiasm was justified – I hit my first jackpot: a free chocolate bar that some poor intern was going to have to package and post to my home address.

With a slightly melted chocolate bar the only thing I had to show for two solid weeks of competition entering, I went in search of more experienced compers, hoping they'd be able to help me out. Conveniently, MoneySavingExpert forums hosts a whole community of compers who regularly post new competitions and answers to competition questions.

One user, who wished to stay anonymous, was helpful and pragmatic when it came to comping. Suggesting to start by entering the comps that were ending soon, then the "instant wins", then the social media comps that only lasted for a day or so, and lastly entering comps that utilised skills I was good at – as fewer people enter them.

Another user, who'd only been comping since August of 2014 (I worried about seeking advice from a n00b, but I didn't have much choice at this point), put in around three hours a day during the week and over 10 hours over the weekend – and it had actually paid off. They had won a range of prizes, most notably an Accurist watch worth around £300, and a signed Motörhead drumhead, similarly priced.

Midweek, I was beginning to lose steam. During my break at work, enjoying a Bianca-banana (one with lots of freckles) I got a call. "Hi, is that Sam?" the lady asked. I confirmed, eagerly anticipating what she wanted with me. "We're just calling to let you know that you've won the opportunity to see The Darkness live at Absolute Radio!"

"Shit! That's sick!" I said, embarrassingly. She confirmed my email address and we laughed together. Oh, how we laughed – me at the fact "samisgoingtowin" had actually helped; her, presumably, in joy that someone out there was definitely leading a sadder existence than her.

After this moment of elation, e-mail addiction took hold of me; hope of a similar high had come to fill my bones every time I entered a competition.

I hadn't experienced live music in a long time; it had become a fond, distant memory, like Dwight Yorke, or running for 100 metres without feeling like I'm going to be violently sick. So, I have to say – and yes, I know this is a band defined by pinstripe catsuits and guitar solos – I was quite excited about going to a real life gig.

I arrived at the station's headquarters to find it filled with real The Darkness fans, who were genuinely excited and had pre-ordered their new album. "FRAUD! FRAUD! FRAUD!" was playing over in my head.

Hawkins, a mended man after going to rehab for alcohol and cocaine abuse a few years ago, was all self-deprecating humour, which is always kind of charming. And, by the end of the show, I too believed in a thing called love – even if it is highly unobtainable, embellished with Hollywood imagery and requires quite a lot of money to get it going.

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After nearly a month of slavishly entering every competition I could, I still wasn't satisfied. A chocolate bar and tickets to see The Darkness are fine, if you like chocolate and The Darkness, but I wanted an object I could hold in my arms that wouldn't melt – like a car. I wanted a fucking car.

The final days of my challenge approached and I was still going at it, hitting the thousand competitions mark. I couldn't give in. I wouldn't give in. Then, everything changed.

Two consecutive wins in the space of three minutes. Free copies of the novel The Forgotten Sisters and a book about an artist walking along the southwest coast of England, A Brush with the Coast, were mine. Determination, perseverance and positivity had finally culminated in something I could hold, that I could show to friends and take the below photograph of, before leaving it on a shelf and forgetting about it until I have to move house.

So what did I learn? A) That you really shouldn't put too much hope in making a living out of entering online competitions, and B) that cafes get really weird with you when you sit in there for hours at a time entering competitions and not buying any coffee.

@SamTahmassebi

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