Founder Insight: Context Switching Might Be My New Olympic Sport

When you have spent most of your working life at one brand, you get used to living in one world.

You know the business, the audience, the politics, the language, the priorities, the things everyone says are priorities but definitely aren’t, and roughly where all the bodies are buried.

Even when the work itself changes, the context mostly stays the same, so your brain does not have to spend half its day packing up one entire reality and moving into another.

People who have worked in client services inside agencies will already understand this skill much better than I did. They are used to moving from one client to another, remembering that one brand is obsessed with penetration, another wants to be premium, another has a CEO who hates the word “innovative”, and another has somehow spent nine months debating whether a button should be blue.

Even then, you usually bring broadly the same discipline to each business. However, my experience in and out of agency was always managing one brand.

Becoming a founder with a portfolio business has taken that idea of context switching and turned it into an Olympic sport I appear to have entered without ever seeing the rules.

At any one time I can have four or more clients, all operating in completely different worlds, all with completely different commercial problems, and quite often wanting completely different things from me.

At any one time I can have four or more clients, all operating in completely different worlds, at completely different stages, with completely different problems to solve. One minute I’m thinking about positioning and proposition, the next I’m deep in a sales story, a website, a content plan or a founder narrative, before moving straight into another business where none of the assumptions I was working with five minutes earlier applies. It is less like changing hats and more like repeatedly changing jobs.

Then, somewhere in between all of that, I also must run and market StoryOne itself.

So, within a few hours, I can go from working on a client brief to remembering that I am also the finance department, and there is an invoice sitting somewhere that would quite like to be paid.

None of those things is particularly difficult in isolation. In fact, after years of looking after one brand at a time, I am finding the variety of work enthralling.

The switching is what gets you.

Your brain has to leave one business completely, load another one, remember its audience, proposition, commercial problem, tone, history, current priorities and approximately 47 tiny decisions you made three weeks ago, before somebody says, “Can we just quickly revisit that line from the deck?” and you realise you have absolutely no idea which deck they mean.

Just as I was getting slightly better at this, I recently became the co-founder of a brand-new business and, naturally, also the CMO.

Which meant I suddenly had another entire company requiring strategy, proposition, brand, content, systems, planning and all the other things that arrive when you build something from scratch, usually all at once and usually while you are doing something completely unrelated.

The challenge was not really whether I could do the work. It was working out how to stop this new business quietly expanding across my week like an overly confident houseplant and taking over StoryOne in the process.

Thankfully, I have also been training to build and use AI agents, which means that while I am teaching my own brain to switch between multiple StoryOne clients, I'm also training an entire marketing team of robots to help me make two businesses successful.

They have jobs, instructions, guardrails, brand information and very clear responsibilities, which is more than can be said for some teams I have worked in over the years.

It sounds slightly ridiculous when I write it down, but it has become one of the most practical ways I have found to deal with the reality of portfolio working.

For StoryOne clients, I can build separate brains containing their proposition, audience, tone, priorities, previous decisions and current projects, which means I can get myself back into their world much faster.

For the new business, I can go further and create agents around different parts of the marketing function so that every task does not have to begin, live and end inside my own head.

The thinking, judgement, experience and instinct are still mine, and I still have to know what good looks like, ask the right questions, make the calls and spot when something feels wrong.

What I am increasingly less interested in doing is using my brain as a storage unit for every project, process, decision, deadline and passing thought across several completely different businesses.

I used to think portfolio working was mainly about managing your time.

I am beginning to think it is just as much about managing context and being much more deliberate about what actually deserves space in your own head.

There is probably a sensible upper limit to how many businesses, clients and competing worlds one person can carry at once.

I haven't found mine yet, although if cloning becomes commercially available, I will be asking about pricing, lead times, and whether the clone can do school pick-up.