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A Lesson in Not Waiting for Perfection

Aug 20
6 min read

On Tuesday evening, Roxana and I hosted our first ever event together – a small, in-person facilitated conversation on how AI is reshaping the experience of work.


I got to The Fitzroy Tavern an hour before our first guest was due, and found our room with every chair stacked on the tables. A picture of the scene with a crying laughing emoji to my co-host and a joint improvised attempt at interior design later, people started walking in – all meeting us for the first time, and most likely never having heard of us until a week or so prior. Three hours in, we were still there, with the venue having to more or less usher us out.


Said picture of the scene
Said picture of the scene

Everything in between is roughly the story I want to talk about in today's article.


First, let’s rewind to how this all started

I first heard Roxana on a Generalist World podcast episode just over a year ago. Something in how she talked about her own career made me reach out – scrolling up in our LinkedIn DM thread, we are going all the way back to 11 August 2025.



Where it all began
Where it all began

Between us both building our respective businesses, it took months to actually meet in the flesh. When we finally did, it was May. I still remember London giving us its worst weather for the occasion – so bad we actually checked in with each other to make sure we were OK with the prospect of being caught in torrential rain on the way to the coffee shop.


It was one of those conversations you lose track of time in: Roxana is the founder of Neuryz, an interdisciplinary research platform at the intersection of AI and cognition, drawing on a background in neuroscience and organisational behaviour; and as for me (hopefully you'll know full well if you are here with me now), I brought my experience of coaching people who are experiencing what it's like to be a leader in organisations, and a world, that are changing faster than they used to. Underneath these different lenses was the same question: what is AI actually doing to the experience of work?


We also reflected on something else: London has no scarcity of events on a whole host of topics – you'd hardly get bored. In fact, you'll most likely have a hard time choosing between a handful happening on the same night. This was even more true for AI-related events, where panels, fireside chats and talks from expert speakers have the lion's share. Often, audiences are so large that people rarely get the chance to contribute to the conversation, let alone get to know other attendees beyond a surface-level introduction. Whilst we both agreed there is real value in that format, we also identified a clear gap for something smaller, where everyone in the room could actively contribute and learn from each other's lived experience.


Fast-forward to July

By the time we had an actual plan, it was well into July. Getting there took two half-day, Mural-supercharged, brainstorming sessions. It was now time for us to firm up a date in the calendar.


By this point, I'd be lying if I said we weren't starting to feel a bit nervous about it. What if no one comes, what if people don't enjoy a format built entirely on interactive contribution, what if the room stays quiet and nobody actually participates. Then, we found ourselves thinking: August is quiet, people are away... Wouldn't September make more sense, when attendance would most likely be higher and we could spend more time nailing down all the tiniest details to make the best, most perfect, experience on earth?


OK, I am clearly exaggerating here, but you get the gist. We sat with that for a bit – 'slept on it', as I often do when I want to let something simmer in my brain for a little longer. In the end, we went with August anyway, with the awareness that we were risking falling into dressing up caution as consideration, telling ourselves we were being sensible when really we were finding a reason to wait until everything aligned.


We all know that world doesn't exist, even if at times we might forget about it – whether we're deciding on an event date, a next role, or a difficult conversation we've been putting off.


Here’s how things went in the end, and what we learnt

Roxana kicked us off by sharing the findings of her research on how AI is affecting human agency. Based on a survey of 299 UK employees she ran earlier this year, it looked at the human experience of AI adoption (cognition, identity and working relationships) – an area which is relatively less developed in AI research compared to topics such as productivity and efficiency.


With her data setting the scene, I then shared a few themes I've been sitting with, both from my own client work and from what I've been reading. First, the recent findings from PwC, which offer a more nuanced perspective on a concern I hear raised a lot – whether AI is going to make us less valuable workers, or replace us entirely. The data tells a more specific story: where AI augments what humans do rather than substitutes it, the number of roles has grown twice as fast, with 42% higher wage growth.


I also talked about the worsening stats on stress and employee engagement levels reported by Brunswick and Gallup – alongside my own theory of what might be going on: leaders are being asked to set direction, develop others, and now also constantly learn to keep pace with a tool that often takes several iterations to get right. This is even before we consider how many organisations are still pushing their employees to use AI as much as possible to justify their significant spend – with significantly less effort spent communicating the strategy around AI adoption, or providing tailored training to use the tool effectively.


Ultimately, there were no polished lines (let alone snazzy slide decks) from either of us – just sharing what we'd been doing and seeing, before we spent the rest of the time having an open and honest conversation about big questions:

  • How is AI shaping your experience of work?

  • What makes work meaningful in the age of AI?

  • What skills become more valuable as AI improves?


What I witnessed was exactly the vision Roxana and I had when we decided to create this space: I watched people who'd introduced themselves less than an hour earlier share their lived experience, admit what they didn't know, constructively challenge each other's thinking, and stay curious rather than defensive.


Remember what I said about taking action? This is exactly why validating an idea with a real-life audience is worth so much more than spending hours strategising and refining it alone in your own head.



Amongst the things we learnt was how not to position the camera next time
Amongst the things we learnt was how not to position the camera next time

Our intention was for the space to be intimate – but when I say this, it is compared with the 100+ people events we had both been attending recently. Even with capping numbers at 20, and early sign-ups closing at just under that, about a third of the people who'd originally registered actually showed (this attendance rate is apparently completely normal, we later found out). In the end, smaller turned out to be exactly right. We even went over time with the discussion, and as one of the attendees rightly pointed out, a larger audience would most likely have worked against our original goal by limiting the depth of the conversation.


What lesson all of this has taught me

Yes, we could have waited for September, with a longer runway to prepare and confidence around there being more people back in London. Instead, we decided to go ahead anyway, aware that our reach would be smaller in the first place.


It went further than either of us expected: we spent more time in conversation exactly because we had made choices which gave us the right space and amount of time to allow everyone to contribute, and people asked before they'd even left when the next one would be. We'll never know what a September version would have looked like – but we know what this one did, because we ran it instead of imagining it.


I often talk about how done is better than perfect, and this experience showed me, once again, how true that is.




References

PricewaterhouseCoopers (2026) Two futures for jobs in an AI era: 2026 Global AI Jobs Barometer. Available from: https://www.pwc.com/gx/en/1/services/ai/ai-jobs-barometer.html


Brunswick Group (2026) The Brunswick Leadership Stress Index. Available from: https://review.brunswickgroup.com/article/brunswick-leadership-stress-index/


Gallup (2026) State of the Global Workforce 2026. Available from: https://www.gallup.com/workplace/349484/state-of-the-global-workplace.aspx

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