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THINKING

How Reflection Journal started

Lockdown, mentoring, and the limits of being the system.

I set up my consultancy business in 2019. It wasn't a mentoring business and it had nothing to do with reflection as a product or building technology.

Then lockdown happened, and the work changed shape. People didn't come looking for solutions. They came needing space to make sense of what mattered, not so someone else could fix things, but so they could see their own situation more clearly. Mentoring crept in. Then more of it. Then a lot more.

During lockdown, a colleague and I built a very lightweight, digital-but-manual reflection process. Around fifty people used it. Weekly prompts, virtual check-ins, shared insights. The purpose wasn't to solve problems. It was to help people name what mattered most so they could start making sense of it for themselves.

It worked and it also showed the limits. Everything was manual. We couldn't connect insights over time or see patterns forming across weeks and months without a lot of manual labour. Each session became its own event. What people were feeling right now kept replacing what they'd already said was important. The work moved forward, but it didn't accumulate.

As demand grew, that limitation became hard to ignore. If I was going to be genuinely useful, I couldn't keep being the system. I needed a way to understand what actually mattered over time. Patterns, drift, and early signals, not just what was loudest in the moment. Without that, mentoring wasn't evolving, it was circulating.

Running alongside all of this was a long-standing set of conversations with Tim. Tim is my wife's cousin's husband (a bit of a mouthful, I know), so we'd see each other a few times a year at family gatherings. Breakfast conversations. Long evenings with a beer. We nearly always ended up talking about work.

Tim had been building with large language models, sentiment and thematic analysis long before those things were widely accessible or affordable. I'd worked around digital start-ups and could see what AI could and couldn't do (and where it was heading).

When I explained what I was seeing in the mentoring work, something clicked. Not a dramatic "startup moment", a practical one. The constraint I was living finally matched capability Tim had been developing for years.

At that point, the question wasn't whether to build. It was whether to keep pretending the existing way of working was enough. Once it became clear this was both solvable and necessary, we built something small, tested quickly, and let reality push back.

That's where this journey actually starts. Not with a product or a pitch, but with constraints that refused to go away.

What we have now is real and in use doing the job it was built to do. It's taken far longer than we expected. Like most things worth creating, it's iterative rather than finished.


If this is the kind of thinking you're looking for, we can work together.