The Same Question, Four Careers

For most of my twenties I believed I had a scattered career. Journalism, then advertising, then a consultancy advising boards, then building a company, then streaming. Five answers to “what do you do,” none of which explained the others. At parties I would pick whichever one the room seemed likeliest to find interesting and leave the rest out.

It took me an embarrassingly long time to notice they were all the same job.

The through-line is measurement. Not in the analytics sense — not dashboards — but the older, more uncomfortable version of the question. What actually drives this business, and which of the things we report every month are we only pretending to measure? Every industry I have worked in has a gap between those two lists, and every industry believes its own gap is smaller than it is.

Four versions of one gap

In a newsroom the gap was between what mattered and what was countable. I spent nearly a decade as a journalist, part of it on the five-person team that built out a national news channel, and the honest position was that nobody knew what was working. You had ratings that arrived late and described the wrong thing. Then the internet arrived with numbers attached to everything, and we discovered that the countable thing and the valuable thing were not merely different — they could be opposed. A story that mattered and a story that travelled were two different products, and only one of them showed up in the report.

At Publicis the gap was the product. I spent six years there, most of it working out what a marketing dollar actually bought in a market where the tooling changed faster than the accounting could follow. I grew the group’s digital practice in India from one office to four, and from ten people to more than a hundred, and the thing we were really selling — under the campaigns, under the media plans — was a defensible answer to a question the client’s finance director kept asking and nobody could answer.

At Xynteo the gap moved up a floor. As Chief Digital Officer I sat with executive teams at some of the largest companies in the world and asked whether their purpose-led growth strategies were actually working. Almost nobody had built the instrument that would tell them. Not because they were unserious — because building it was expensive, slow, and required a kind of attention that quarterly life does not protect. The strategy got measured by whether it survived contact with the board, which is a measurement of something, just not of the thing.

Then I built Laminar, and the gap became my own problem. We let media companies launch a full streaming service — backend through monetisation and analytics — in eight weeks instead of years. What I learned running it is that a founder’s real scarcity is not capital or engineering. It is knowing which of the forty things on the list actually moves the business, when all forty have advocates and only three matter.

The countable thing and the valuable thing are not merely different. They can be opposed.— the lesson, arriving late, four times

What changed this year

Here is the part I did not expect, and it is the reason I am writing this now.

For twenty-five years the reason organisations did not measure the thing that mattered was cost. Building the instrument was expensive. It meant an engineer, a data pipeline, a quarter of someone’s roadmap, and a political fight about whose number was right. So the instrument did not get built, the proxy stood in for the truth, and everyone agreed not to look too hard at the seam.

That cost has collapsed. Not fallen — collapsed. I have spent this summer building the kind of instrumentation that used to require a team, and the marginal cost of running it lands at fractions of a cent. A researched dossier on a company, a few cents. Extracting the fields from an invoice, about a penny. A harness that runs ten business tasks through three different model configurations and scores accuracy, latency, cost, and what left the building: a fixed set-up cost, then effectively nothing per run.

Which means the old excuse is gone. When the instrument cost a quarter of an engineering roadmap, “we don’t measure that” was a resource decision. Now it is a choice.

The scarcity moved

The obvious conclusion — that we are about to get much better at measuring things — is wrong, or at least premature. Cheap instruments do not produce good measurement any more than cheap cameras produced good photographs. They produce more measurement, most of it aimed at the wrong thing.

Because the hard part was never the building. The hard part is knowing which question is worth an instrument, which proxy is lying to you, and which number your organisation will actually act on when it arrives. That is judgment, and judgment has not got cheaper by a single cent. If anything it has become more valuable, because there is now nothing standing between a confident wrong idea and a working implementation of it.

I have watched this play out at small scale in my own work all summer. The failures were never the model. They were the moments I built something well before establishing it was worth building — a beautifully engineered answer to a question that did not need asking.

So the useful version of the question has changed shape. It used to be can we measure this. It is now should we, and will anyone do anything differently when we do. The first question has an engineering answer. The second one never did.

Four careers. One question. And the strange gift of this particular year is that for the first time, the asking is cheap and only the choosing is hard.

That is a much better problem than the one I started with.