Bulletin 13 September. On the depth of learning and embracing frequent failure

New wine in snake skins

One of my favourite books was, and remains, The Voyage of the Dawn Treader by C. S. Lewis (yes, I cried when Reepicheep went over the sea). And one of my favourite passages is when Eustace is turn into a dragon. From a note (I think) he learned that, to become human again, he needed to shed a dragon skin (like a snake skin) and bathe in a certain pool.

So, he tried. He shed a skin, but it wasn’t enough. So he shed another, then another, bathing each time, but each time he emerged a dragon. Somewhat unexpectedly, Aslan the lion happened upon him: it’s not working, said Eustace. That’s because you are doing it wrong, said Aslan, who took out a huge claw and cut through Eustace’s many skins like an onion. That time, he emerged from the pool a boy again.

A couple of times in my career, I have been quite convinced I know it all… working back from the punchline, only to discover, quite uncategorically and without mercy, that I seriously do not. The first came just after I had been over-promoted to the point of deep stress, when working as an IT manager for a subsidiary of Alcatel.

Alongside the coping strategies and very real learning I was picking up on the job (I have, essentially, dined out on that experience ever since), I came to the conclusion that I had this management thing nailed: I doubted was anything else to learn about keeping saucers on sticks, running meetings, facilitating, time management or anything else administrative.

I then joined Admiral Management Services, a company whose ethos gave short shrift to any such idea of grandeur. Yeah, whatever, was the attitude: take some minutes and be a good boy, would you? Learning the hard way (failing fast and frequently), I unpicked everything I thought I knew and re-knitted it into some semblance of genuine best practice. Which I have also dined out on ever since.

The next big moment of big-headedness came a couple of years into my analyst career, when (at the heights of the dot-com) I thought it a really good moment to set up on my own. The lows of the dot-bomb followed almost immediately, mirroring both my feelings of utter incompetence and my bank balance. So many lessons learned, not least, cooking on a shoestring.

I didn’t mean to say all that: I was only going to talk about my memories of being in (what felt like) financial difficulty: any money we had was always in the wrong place, cheques bounced and bills went unpaid, with banks gleefully adding their fees to any debts incurred. I wasn’t going to say that either: I was only going to make the point that getting back on track didn’t just take extra effort: it took extra effort beyond what I thought extra effort meant at the time.

Like Eustace, sometimes the problem goes far deeper than we have the ability to understand. Not least in questions of learning, particularly when we come to it from a position of knowledge. Surely, people understand what is being discussed, we say, or can understand it as long as we explain it correctly. Even if they are a bit behind. And so, in areas of so-called ‘new thinking’, we can have whole conversations without realising that what we are saying is of very little relevance.

I’m coming to think this is the case for my own current area of specialism, DevOps. Even as I discuss how to make it work better (a.k.a. ‘to scale’), I have my good friend (and practitioner) Andy’s words ringing in my head: that nobody is really doing it, they just say that they are. Perhaps to get the analysts off their backs. It’s not just DevOps: the reason we can keep saying the same things about best practice, webinar after webinar, year after year, is that people still don’t get it.

To whit. I’m not sure what the answer is but based on my own experience, perhaps part of it is to recognise the fact that we are a lot less mature than we would like, as organisations and as people. And we need to deal with this as Eustace, not superficially but digging really deep, getting right down to the base, beneath layers and layers of traditional practice.

Not to do so will cause us to reinvent whatever we are talking about, for a number of reasons. First to avoid boredom — you can only hear people bang on about the same thing so many times, before cognitive filters push it into the background. Second because it loses its effectiveness as the world moves on. And third, because lovely marketing and PR people want something new to talk about, in the name of differentiation or thought leadership.

These days I have come to realise that ‘knowing it all’ is a false summit, a thinking person’s Tower of Babel. Rather than embracing my own inadequacy and giving up, I’ve found a joy and freshness in learning: in essence, I’ve come to terms with my own, valid feelings of imposter syndrome. Perhaps we could all do with recognising that we don’t all get it, neither at a superficial nor deep level.

There is no shame in this, as such an admittance is the first step in actually working out what the heck is being discussed. Like Eustace, we can all benefit from digging particularly deep in terms of what we don’t know, understanding the problem we are trying to solve before applying the latest iteration of solutions.

Thanks for reading, Jon

P.S. I said these bulletins would be more factual from now. This one isn’t but I’m on holiday, so sue me.

Bulletin 13 September. On the depth of learning and embracing frequent failure