TL;DR: I have a dream that feels pregnant with meaning. As I jump down its rabbit hole of free association, I find important messages.

The Dream

A priest calls to ask if I can step in for him. I accept, but as I hang up I’m overcome with dread. Next thing I know, the service is about to begin and a crowd come pouring into the church. I’ve no clue what to say to them.

But then I realise I don’t have to preach, that it’ll be so much better if we all just talk to each other.

We do, and it works; everyone is having a great time.

The Interpretation

My dear old English teacher once explained how the word broadcast originates from the motion a farmer goes through when “sowing by scattering”. That is to say: the act of broadly casting seeds around to fall where they may.

Centuries later, the term was adapted to signify a certain type of mass media.

That wasn’t just linguistically creative, but also philosophically accurate; broadcasting is indeed an efficient way to reach the masses, but at the same time crude and unlikely to bring about real change in people’s hearts. It’s like randomly scattering those seeds, many of which will never germinate.

It always seemed to me that preaching has a lot in common with broadcasting. But I wouldn’t really know, I’m not a religious person. So why then is my subconscious placing me in the shoes of a priest?

Perhaps because preaching to the congregation is a fitting analogy to some aspects of what I do for a living.

In my day job, I help churn out startups. In this business, there’s always a strong temptation to find formulas and frameworks, recipes for success than can be copied and pasted. This constant strive towards standardised truths is probably why the whole entrepreneurship circus can sometimes seem a bit church-like.

In fact Bob Sutton and Huggy Rao gets very explicit about this analogy in their book Scaling Up Excellence, where they describe how the growth of a successful company can happen either the Catholic way – where “the aim is to replicate preordained beliefs and practices” or, more rarely, the Buddhist way, where it’s “the underlying mindset that guides why people do certain things, but the specifics of what they do can vary.”

I find it interesting that when I dream I abdicate from my preaching and let people talk to each other, it feels forbidden; almost literally like swearing in the church.

Why would that be?

The question can be flipped: Why does the pattern of communication in a church; a mosque; a synagogue, always follow the pattern of a central node broadcasting a message to the masses?

And what would happen with a religion where that wasn’t the case? Where stories – because religion is all about stories – are passed from person to person and nobody’s interpretation is sanctified?

Perhaps even where scripture is replaced by psychoactive substances, opening up unpredictable new vistas?

I guess that’s a fair description of how many indigenous people worship (and the fact that they’ve often been persecuted and harassed goes to show what a threat that has posed to preserving the status quo.)

There’s another interesting detail about that dream: the person who is cast as a priest, very much resembles a friend of mine who is a successful writer in waking life.

I like to think of good writing as narrow-casting. It has the reach of mass media, but the tone of a personal conversation. Submerging oneself in a novel feels a lot like being invited into an intimate space where anything is possible.

In its elegant compression I think the dream is trying to remind me of something I’ve always known to be true but that’s all too easy to forget in the hubbub of everyday life.

It’s telling me that preaching doesn’t work. To not fool myself into thinking that I have it all figured out, to be humbled by the fact that everyone needs to find their own truths. That knowledge of the most fundamental kind, simply isn’t transferable.

Now of course that doesn’t mean you can’t teach calculus or the conjugation of French verbs. The kind of knowledge I have in mind is more boundless in nature. Like, can you really teach chess, for example? Or creative writing?

Only to a degree I imagine, beyond which the student must tread alone.

I guess entrepreneurship falls somewhere close to chess or writing on that spectrum.

So how do you teach entrepreneurship?

I seriously doubt that it’s possible, at least in a traditional one-to-many model. The patterns are too irregular to be codified and neatly packaged.

Yet at the same time…

…we all know it’s somehow contagious…

…that it can run in the family…

…as it did for me…

…as if some kind of cultural osmosis starts to happen if you spend enough time with people who are in the thick of it.

Any attempt to translate the dream into plain English will probably fall short of capturing its wisdom but if I’d try, it’d go something like this:

If the goal is to support people in sharing and making sense of confusing and often transformative experiences – such as anyone who takes a stab at entrepreneurship is bound to live through – then the best we can do is to establish the kind of safe space that can be symbolised as a house of worship, and then simply let them talk openly to each other. Not listen to some guru on a stage, just have actual unfiltered conversations with each other. That’s when real learning can happen.

Post Scriptum

Like poems or songs, dreams resist interpretation. They’re already the perfect manifestation of what they “want to say”, so any any attempt at picking them apart runs the risk of being counter-productive, introducing noise instead of clarity.

In a way, dreams are the perfect manifestation of Shannon’s information theory, which holds that compression needs to remove as much redundancy as possible from a data-set, yet has to keep just enough in order to make it possible to distinguish the compressed message from its surrounding noice.

That’s why dreams make for notoriously bad dinner conversation: in and of themselves they’re typically only interesting to the dreamer, and any kind of interpretation risks being too revealing; completely confusing, or both of the above.

Knowing this, I really wasn’t sure about trying to base a blog post around one. Still I decided to give it a try, treat it as an experiment. Perhaps in a sense it failed, at least if the assumption I wanted to test was that I’d be able to distill a clear message and connect it to a generalised point of view, much like you’re supposed to do in a blog post. It’s *hard* to achieve clarity while jumping down rabbit holes.

As any scientist will tell you however, failed experiments are just as interesting as successful ones, since they give momentum and feed into the next assumption. The one that is currently forming in my mind is this: Perhaps a different kind of post is possible to write. One where – based on dreams or not – there isn’t a clear punch line. Where instead, broad themes are examined and loosely interconnected. I assume such posts can indeed be written, but I also have a feeling that it would require skills that are presently beyond me.

There’s more where this came from