This won’t come as a surprise to anyone who knows me – but I’m a bit obsessed with playlists and mixtapes. I like to make compilations of songs. There’s nothing particularly special about that, I guess. But it is something I think a good deal about. It’s kind of my thing.

Making mixtapes for other people has always been one of my favourite things to spend time on. I don’t do it nearly often enough these days, but I’ve never really stopped doing it. Since the age of about 13, my life has been spent in search of “the right next song”. And it’s something I’m still working on.

I always give it a lot of thought, and I’ll listen to and fine-tune a compilation a dozen times or more before I make a gift of it. It invariably means a whole bunch of different stuff to me than it means to the recipient, and that’s probably as it should be – but as a piece of communication, it comes in just above the long, handwritten letter on the genuine-ometer.

To be clear – mixtapes aren’t restricted to that nerdish romantic gesture they’re painted as in popular fiction – though to be fair, as far as I’m concerned, they do that job better than anything else I’ve come across. Mixtapes communicate something – about yourself as much as about the music or the other person. And they become souvenirs of a time, a place, a person and a feeling. It’s not the songs that take you back nearly as much as it’s those songs in that order.

To me, that’s kind of the most important bit: the narrative and meaning constructed through the selection and the arrangement of the tunes, even more than the songs themselves.

“Why this song?” is not as interesting a question to me as “why that song after this one?” or “why is that song track one?”. I’m intrigued by juxtapositions of artists in ways that work – or that mean something specific – and I love that moment of surprise and delight in a ‘gear change’ in the journey.

Actually, I find driving metaphors useful when talking about making compilations of songs. You can accelerate or take a detour, change gears from one song to another or signal an upcoming turn before you go off in a new direction. You want to set off with a purpose, and you want to arrive in style. At all costs, you want to avoid a complete car wreck.

Of course, not everyone’s a music fan and this might mean nothing to a lot of people. And even as music fans go, I’m kind of unusual. I’ve said before that I prefer recordings to live music. I’ve also said that if being a fan meant being willing to stand in the rain to see that artist play, then I can’t think of a single artist I’m a fan of.

Also, I don’t fit the mould of the walking music encyclopaedia. I’m embarrassingly ignorant about lots of music I’m completely passionate about. I collect records, but not facts, particularly.

What I’m in love with is what happens when you put music in an order. Which is to say – I know far less about Miles Davis than I do about what happens when I put ‘Blue in Green’ next to Radiohead’s ‘Airbag’.

But today, I’m thinking about the longer playlist. Not a 12- to 15-song mixtape, but something you can put on and leave on without having to mess with it. I’ve experimented with that idea a few times over the last couple of years. Even went so far as to set up a streaming radio station with exactly that ambition. Nothing more or less than “The Right Next Song” – great music, played in the right order, without having to skip or change anything.

Of course, even at home, I don’t seem to be able to do that terribly successfully. I either just put a whole album on from start to finish, or I’m forever fiddling with the track selection.

Worse – when I fill my iPhone with music, it’s always with exactly the sort of stuff I want to immerse myself in at that precise moment – but later, when I’m sitting on the bus with headphones on, I can look through a few thousand songs and not find anything at all to listen to. I just sit there going “What the hell was I thinking when I put all this Philip Glass in here?”.

Of course, one of the dumbest prevailing fallacies in the discourse of online music streaming services is the idea that you simply select music to match your mood – or worse, that you have a single, fixed ‘favourite music’ that doesn’t ever change with time of day, activity or social setting.

And here’s the problem with choosing and putting on “music I feel like listening to”: I don’t know about you, but for me it usually works the other way around. The music comes first, and that evokes a mood or an emotional response. And far more often than not, it’s not what I had anticipated would be the sort of thing that would work.

The best radio stations in the world manage to get me to turn up the volume time and again, because exactly the right song came on. And it’s always the sort of song that I had no idea I even wanted to listen to.

Quite often, we experience that as the “Oh my god – I haven’t heard this song in AGES!” effect – but it can just as easily be “Oh wow – what’s this?” or some other, less visceral reaction. It can just be something that maintains my interest until the next song comes along, or that I simply ‘quite like’ enough to keep me from wanting to get up and change the music right at that moment.

So, the trick is – I want to do that to myself at home, without continually having to mess with it. I need a musical algorithm for surprise, delight, familiarity, eclecticism and a journey with lots of light and shade. I want to be curious about what’s coming next – but I want to be into the song that’s playing now – and I want to do all that with detours and changes of gear, a whole different range of scenery, and no terrible incongruous ‘car crash’ selections along the way.

I do like the idea of curation, and while that’s what’s at the heart of great mixtape-making, when ported over to continuous music mixes, it has its drawbacks – and I don’t believe that simply putting a human being between you and a vast music library necessarily improves your experience of that music library.

That said, I want to be my own musical curator (after all, I have exceptional taste in music – which is to say, I enjoy music I consider to be good, and don’t like music I think is terrible). However, I don’t want to have to sit down and choose one song after another and put them in an order – because while the first hour or so of music would make for a fantastic mixtape – it’d be a case of diminishing returns quite quickly. Besides, I would end up spending the rest of my life selecting the tunes, and almost no time at all listening to the results.

The trouble is, there is currently no consumer playlist creator on the market that comes anywhere near doing what I want it to do. So it’s something I’m giving a lot of thought to.

Of course, with my background in radio, I have a model for approaching this stuff. I think in terms of rotates, dayparts, transitions, mood levels and artist separation. It’s these kind of rules and techniques that will give you a varied, interesting and reliable continuous set of music where you’re likely to hear a favourite song come up (or a forgotten gem), but without being too repetitive.

I certainly have a large enough music library. Most radio stations have around 300-500 songs in the active catalogue. I have around 100,000. These aren’t just songs – they’re MY songs. Songs I have actively chosen to put into my iTunes library. Of course, I don’t want to hear all of them randomly. That would make no sense at all. Nor do I want to sit down and put them in an order. iTunes Genius lets me pick one song and will grab a bunch of other stuff which is broadly related – but it will never put Airbag after Kind of Blue – let alone know what it means when you do that, or have any idea where you can go next with it.

I don’t have the answer. But I’m getting closer. Tonight, with the help of a series of algorithmically generated playlists-within-playlists, filters and a little manual editing, I’ve managed to go for six hours straight without problems. In fact, I’d go so far as to say that this is probably the best music mix I’ve heard all year.

I don’t know what’s coming up next, and while it might not be “The Right Next Song” – I’m reasonably certain it will be a solid choice. I’ve essentially built a DJ that I somewhat trust and I’ve let it loose in my record collection. So far so good – and there have been a number of moments while writing this post where I’ve thought “ooh – nice choice…” – but this will be a learning curve for both of us.

In the meantime, my virtual DJ gets top marks for playing Talk Talk’s ‘It’s My Life’ after Boards of Canada. Just exactly what I didn’t know I felt like.