Firstly - a rebrand

You may have noticed the name change. This coincides with the rollout of my new website this week:

www.theuncommonfounder.com

I considered having them live under different names but honestly I value the coherence of having the different parts of my work fit together more neatly.

Why the 'uncommon founder'? 

For me this is not a change in direction but more about the right language for the existing one.

As I reflected deeply on those I've most loved coaching in recent years there were three key attributes I saw uncommon founders aspiring to:

1️⃣ Visionary builders determined to change the world

2️⃣ Thoughtful technologists focused on purposeful impact

3️⃣ Independent thinkers playing their own game, not everyone else’s

As someone whose spent much of my adult life sat at the intersection of technology and spirituality (or the things that make us deeply human) - these are the people I see the world calling for, and those that I'm most excited to continue to work with, whether that's 1-1, co-founder work, team coaching with Exec teams, leading offsites, or increasingly wrangling with what to do about AI.

It feels like a particularly important moment to be working with those willing to ask themselves the hard questions about how we build technology and organisations that help us as humans to flourish together.

To the many Uncommon Founders I've had the pleasure to work with so far - thank you. To those who might be curious to learn more then simply hit reply to this email.

Now on to this edition’s essay.

When productivity knows no bounds, what is enough?

As technology advances, the challenge of our times is not in doing more but in defining what’s enough.

Enough seems to exist like a mirage on the distant horizon, tantalising the endless thirsty souls desperate to be replenished - to arrive, to be quenched, to tell themselves that the work is done or just that what’s done is enough for now.

Technological gains in productivity were said to be the answer - this is what our economic prophets foretold - Keynes, in 1930, predicted that by 2030, technological innovation would allow us to work only 15 hours a week and be free for ‘the art of life.’

But the mirage has proved to be exactly that - an illusion of water that's never materialised. The technology and productivity gains have taken place, but Keynes’ prediction that we would work less as a result was wrong. Rather than quenching our thirst in the art of life, we seem instead to be lost in a desert of escalating work.

And now AI promises to lift the bounds of productivity altogether.

So how will we reinvest our new found productivity? Will we keep looking to the horizon for hope? Or is now the time to seek a less barren landscape? To revisit our definitions of success, what’s enough, and to seek out the art of life.

The shifting horizon of enough

In the 95 years since Keynes’ prediction, much of what he anticipated has come true: GDP has increased tenfold, technological innovation has enhanced productivity, material living standards have risen; and yet the average work hours for white collar jobs has escalated dramatically. (Hours have only marginally decreased for blue-collar jobs).

Our collective pattern, whether by choice or systemic, has been a default to more work - not just getting more done in the same number of hours, but working more hours altogether.

Perhaps no example is as stark as that of founders, who theoretically master their own time yet frequently report working 80+ hour weeks.

Most see long hours not as a choice but as part of the job description. To be a founder requires you to perpetually tread the thirsty path of our forebears. Never settling, nor resting. Just relying on your ability to endure, to do more, to outwork the competition, and to perpetually reinvest any gains in productivity straight back into the business of more work.

Bill Gates never took a day off in his twenties. Musk claims to work a 120 hour week. Jack Ma described the 996 culture in China as a blessing. The mythology of the successful desert-dwellers is endless, influential and understandably shapes the discourse.

But I fear that if this is the only mental model for success then no amount of work will ever be enough.

Even as AI promises to lift the bounds of productivity altogether, history tells us that enough will only move further into the distance. As each hour becomes increasingly dense with possibility, it tips the scales ever further towards work at the expense of all else. Rest, leisure and the art of life become more mentally expensive, so that even in those moments we tell ourselves we’re not working, the rising hum of anxiety is pulling us away from meaningful engagement in the present.

We can see this in the way we’ve turned leisure, self-development, and rest into frontiers for more work. I meet an ever-increasing number of people who only ever read non-fiction, who may meditate but solely based on the belief that it will optimise their performance, and who inevitably own a wearable to measure how they sleep. I’ve had clients regularly ask me for advice on how to relax ‘effectively’.

When our goals have no limits then possibility so easily tips into a sort of psychological pressure, to keep running through the desert even when presented with an opportunity to stop for water.

In defence of leisure

Let me be clear, I do not believe that work is bad, I just don’t believe that work is the only thing that’s good.

Even for a founder, whose knowingly thrown themselves into a harder and more encapsulating endeavour than most, I believe in the importance of leisure. Not just rest as a hack to work harder, but actual leisure.

Something which feels entirely undervalued by those adherents to the protestant work ethic that so predominates our modern western minds - advocating for work as our most noble state whilst stigmatising leisure. The devil makes work for idle hands.

A doctrine that counts amongst its most devoted disciples influential tech voices like Marc Andreesen, who outlines his many views on work in his techno-optimist manifesto:

We believe markets increase societal well being by generating work in which people can productively engage. We believe a Universal Basic Income would turn people into zoo animals to be farmed by the state. Man was not meant to be farmed; man was meant to be useful, to be productive, to be proud. We believe all good things come from growth.

[Confusingly, Andreesen goes on to list the British philosopher Bertrand Russell as a ‘patron saint’ of his philosophy; seemingly ignoring Russell’s famous collection of essays, in praise of idleness, in which he wrote, ‘I think that there is far too much work done in the world, that immense harm is caused by the belief that work is virtuous.’ Surely Russell’s turning in his grave at his newfound sainthood.]

So I feel compelled to defend leisure - not just because the core activities of being a founder - providing vision, clarity, fundraising, hiring, decision-making - get ever more difficult in a world of perpetual exhaustion, to which leisure is an important antidote. But also on a human level. Because I believe leisure is an important part of what it means to flourish.

Simone de Beauvoir saw work as vital for autonomy and freedom (particularly in the context of women’s emancipation). She emphasised its importance, not for the sake of productivity, but for the life it makes possible. And I can’t help but feel that this is getting lost somewhere in the discussion.

Admittedly, as I write this from the French Basque country, on a market day when local pensioners can be seen enjoying a glass of wine, then it feels particularly pertinent.

Perhaps more of the influential figures in the world of tech could do with getting off Twitter and spending more time in the great wide world to remind themselves what ‘living joy’ can actually look like?

A richer landscape

Let’s not pretend that success will magically decouple itself from hard work. Nor that a strategy of extreme work hours is necessarily bad for business - there are too many successful desert-dwellers to prove otherwise. But is this the only option for a founder? Is there another way? A richer landscape to be lived in? And what’s changing in the age of AI?

Measures of success

In tech there are many external measures of success for company and founder - funding, growth, valuation, ARR (annual recurring revenue), Forbes lists, personal wealth, and so on.

Each has its merits for a particular purpose, but as a north star for success they prove to be hollow and unbounded - a potent combination for dissatisfaction in which no amount proves to be enough, and even if it were it wouldn’t give you what you think it would.

So what would it look like to adopt a different set of measures? What are you truly optimising for? Power? Autonomy? Flexibility? Status? Connection? Love? What if you and the company could both win at the same time?

There is no right answer here. But in the uncertainty lies opportunity to build a new mental model of success that is uniquely your own.

There are more ways to play the game now

Whatever success looks like for you, the good news is that there are more ways to play the game emerging.

So much of the cycle of founding has been tied to funding and the VC model - a set of stage gates through which you have to pass, each requiring a given rate of growth in order to pass through, at which point the game resets and levels up.

Most of the money tied up in this game has been about putting bums in seats. Scaling the team to unlock further growth. But as it gets cheaper and cheaper to build, through leveraging AI, the options around how you build increase.

I’m sure some will still take the big VC money - there’s certainly no shortage of it flying into AI right now - but others may choose to run a different race, building a lot with a small team, taking on minimal external investment, and having more agency to define the rules as they see fit.

Leisure as a competitive advantage

But this is not just about team size and VC money. Regardless of the path founders go down, there are some fundamental questions to be asked about where you add most value as a founder; particularly in an AI-first ecosystem.

I’d argue that even in the absence of AI, leisure can be a competitive advantage. I’ve seen enough cases of founders who flourish energetically as they take up a new hobby, and then find they’re getting more done in fewer hours as a result.

And this accelerates in an age when delivery gets easier. The value creation continues to abstract to a higher level, calling on founders to think more clearly and creatively than ever.

Leisure might be the key here - not only for its restorative effects on energy, but also because leisure can be used to cultivate taste, and perhaps its taste above all else that might be the defining characteristic of future founders.

Spending the gains in productivity

And let’s not lose sight of the fact that the tools at our disposal are getting better at breakneck speed. The increase in productivity is palpable; it’s simply a question of how we choose to reinvest the gains.

In the last month I’ve used Gamma to build presentations in moments that might previously have taken hours; Granola as my ever present note-taker saving me at least an hour a day; deep research to cut several hours of podcast guest research down to the time it takes me to read a report - to name just a few.

Each gain presents a choice - whether to reinvest back into the business of more work or to invest in the art of life.

So we face some choices. As the bounds of productivity continue to lift, the truth is that what’s enough? proves to be a deep and provocative question that will never be answered for us.

If we follow the patterns of the past, then many of us will blindly tread further into the desert of escalating work, driven by a psychological pressure to keep up, destined to stare at the mirage on the horizon as we go.

But perhaps there’s a richer landscape to explore - one that’s always been within reach but is being made ever more accessible by the productivity wealth we’re accumulating - if only we choose to spend it that way.