‘The whole experience affected me profoundly.’ Photograph: John WIlson

I was 33, overdrawn and single. I hated the hovel of a home I lived in. “Home” is stretching it, really. It was a cold converted garage on the outskirts of well-to-do Winchester, five miles up the road from the safe Southampton suburb where I had grown up.

Everything I had taken for granted as a child was sadly lacking from my life: a garden, my own front door, security and the sense of belonging that family breeds. Mice – or were they rats? – clambered around in the loft and cavity wall, taunting me as I tried to sleep, alone, comforted by the sounds of The Smiths and the Stone Roses, songs that reminded me of happier student days in Manchester.

On waking, I would drive a few miles up the road to phone it in at the poorly paid university admin job I’d worked in for seven years. Many of those years had been spent trying to escape, unsuccessfully, to the kind of salary my successful friends commanded. A large and ultimately unhealthy part of my life after university had in fact been spent comparing myself with friends – those in my life and those from school, who I heard about on the real or Facebook grapevine.

It was 2014, and I was going nowhere.

Perhaps I had myself to blame. I had chosen cheap housing that enabled me to live alone, because I really didn’t want to share with strangers after a traumatising experience living with an alcoholic. Ironic, really, as beer had become my crutch, seeing me through the lonely nights. It was certainly my downfall too, when it came to meeting the woman of my dreams or, in fact, any woman. Any charm, wit and intelligence I had used to bag my one girlfriend in my mid-20s was lost every time I got drunk. Tinder and real life were equally doomed affairs.

As my one glimmer of hope – a journalism course – came to an end, I was searching for new ideas and recalled something I’d written in my teens: a letter to my future self. I’d written it for a school project (English, probably) in 1994, and the plan was for it to stay sealed until 2014. I remember wanting to open it in the years immediately after school, but Mum wouldn’t let me. For the last decade or so, the envelope had just been gathering dust at my parents’ house and I’d pretty much forgotten about it.

An idea was born. I would open the letter and track down those old school friends who were mentioned as “mates” at the time, and find out whether their lives had gone according to plan. Part of my motivation was to reconnect and understand why we’d lost touch, but I also wanted to know if they too had felt the kind of pain I had – the sadness, despair and loneliness.

I certainly hadn’t achieved the hopes I’d articulated back then. I wasn’t a millionaire or married to the girl at school who I’d fancied. I also wasn’t the “very respectable bank manager” my teacher had predicted I would become.

‘The letters lurched from fairly trivial matters, like the time I spent back then walking my dog Sadie.’ John Wilson in mid-1990s.

Opening the envelope on film for “Dear John” – as the project became known – was a surprise, as I genuinely couldn’t remember what I’d written. I thought it was just one letter to my future self but it turned out to be a series of letters which took me right back to growing up in Chandler’s Ford and all the people in my life back then.

The letters lurched from fairly trivial matters, like the time I spent back then walking my dog, Sadie, to a description of my “fantasy home”, full of everything I wanted in 1994: a Sony Mega Drive, jacuzzi, 30 jumpers and a fax. Then there were the heartfelt emotions I expressed when describing three people who had influenced me: my mum, my dad and one of my classmates.

The digital age helped massively with tracking down my long-lost friends. A Google here, a Facebook there often did the job. Contacting old friends via email, Facebook or LinkedIn, I tried to be clear about my intentions, explaining that I’d like to film our conversation, and to tactfully explore the hopes and dreams they’d had back then, to explore how they had changed with time, and why.

With a little gentle persuasion I lined up five interviews, and we slipped back into gear pretty easily. The conversations were long and sprawling as I had so many questions. My old friends spoke candidly about their lives and experiences: from divorces to cancer, they’d been dealt some cruel hands; but it was how they had approached life and coped with adversity that made me think.

In the early 1990s my father suffered kidney failure, which led to a life of dialysis and deteriorating health. Occasionally angry, often annoyed, I had struggled to understand and cope with this. Speaking to the classmate who had influenced me all those years before, discussing how he had handled his father passing away at a young age, really opened my eyes. I was keen to know what a life without a father was like and remember telling him, as we hugged at the end of our chat, that the conversation had been therapeutic.

When it came to success in life and love, for people like us who had been lucky enough to grow up in a relatively prosperous, stable environment, one quality shone through: confidence. These men had grown through their experiences and gone on to achieve great success. They had found a direction, a sense of satisfaction and self-worth in their jobs and growing families.

From the dating coach to the international businessman, confidence had helped them greatly on their paths. Comfortable in their own skin, they backed themselves and had what I wanted, what I needed: well-paid jobs, strong relationships, a place to call home.

The whole experience affected me profoundly. I knew I must back myself as I continued through life, and become comfortable with being uncomfortable. With the advantages I had, only I could change things. I consigned to the past my own self-pity, thinking the world owed me a favour, and letting rejections drag me down.

I took some action and applied for three jobs at one organisation. Undeterred by rejection one and two I rocked up to interview three and now find myself in a much better job than I had before, which challenges me and has enabled me to develop massively. The pay has helped too with sorting out my debts, and I’ve even managed a holiday or two. And through freelancing as a journalist I have found my missing purpose, direction and satisfaction.

I’m also about to celebrate a two-year anniversary with my partner. One we might just celebrate in our own home. Whether we’ll ever have that fax and Megadrive, only time will tell.