Thinking in Bets

It seems that so many aspects of day to day personal and business life are changing so quickly, and so randomly, that it is easy to dismiss it as a period of chaos.

I don’t think it is. 

I think that, as Annie Duke would advise, we learn to think in bets

There’s a pattern to it. It’s complex, very challenging to the habits we have formed in dealing with our world for the last several decades, and is complicated by the fact that the change is moving faster than our understanding of it. Even when we’re putting in long hours of hard work at what we do today, it’s still leaving us behind. 

It doesn’t have to be that way, but to change it requires that we accept we have to make some fundamental changes to the way we live and work.

If we scratch beneath the surface, even a little, things begin to clear.

“Life as Usual”

Most of us, whether a “boomer” like me, or a new school leaver, have been brought up and educated within a system that assumes tomorrow will be much like today. That if we work hard, get good qualifications, and find a good employer, our lives will work out.

That no longer holds true, regardless of our age. 

The changes have been happening, in plain sight, but quietly. The financial crisis of 2008 has catalysed them, and we now have work environments that are fundamentally different to ten years ago.

Many approximations equate only marginally to what is needed to thrive in a much looser “gig” environment – whether you are a graduate delivering Pizza, working as an Intern, or long hours for little pay as a professional. Right now even architects are looking to unionise

Elsewhere, we know workplace engagement is low. Surveys seem to agree that around 70% are disengaged, some so fundamentally that they commit the equivalent of organisational self harm. This may be related to the types of job we are creating, many of which meet David Graeber’s conditions of “Bullshit Jobs”.

The changes have been happening gradually, but now suddenly, and we find ourselves on the edge of a situation where the nature of work is not compelling enough to hold society together. Populism, of one form or another, flourishes.


It’s over fifty years since Rachel Carson published “Silent Spring”, and we’re only now beginning to get it. Along the way, we’ve ridiculed those like James Lovelock and Gaia theory, and others, as marginal cranks.

Even now, despite overwhelming evidence that they are far more right than wrong, we still have those who find it convenient to deny it, as it messes up their business models. Right now, we’re looking at the biggest IPO ever from arguably the biggest single polluter ever.

Elsewhere, here in the UK we have business and councils declaring “Climate Emergencies” in response to the energy created by a variety of initiatives, not least Greta Thunberg’s climate strikes. 

And yet, if we look at the action plans for these “emergencies” they are more akin to finding out our house is on fire, and relaxing because we’ve order some fire extinguishers.


We’re moving very quickly now from what I think of as “Passive Technology” – the web, internet, the cloud, apps; to quasi sentient technology – Machine Learning, Artificial Intelligence.

We seem to have an odd relationship with this change – on the one hand, alarmist but authoritative articles, and on the other, a more relaxed, almost anthropomorphic view of being assisted by friendly robots.

Generally, I find, many of those most likely to be affected have not engaged with what’s really happening – which is as exciting as it is threatening – or understood what it might mean. 

For generations, we have been educated and employed to process.

In the future, we need to think and create. That’s a big cultural and personal transition.


For me, this is possible the biggest, as it seems likely to act as a catalyst for all the others. The combination of capitalism, globalisation and technology has concentrated economic wealth in the hands of a tiny minority. It’s not that those who have accumulated are “bad” (although, I can think of exceptions) so much as they’ve been in the right place in the system to benefit.

If this systems remains, without question or adjustment, the benefits from the next phase of concentration will concentrate wealth even further – to those who provide the capital, rather than the knowledge, to enable machine learning and AI. 

David Graeber makes a powerful point. In 1930 Keynes argued that by 2000, we would only need to work 10-15 hours a week, as efficiency and technology would do the mundane work. Those who should benefit from the gains – those whose mundane work can be taken away to free them to do more worthwhile things – end up losing out. 

The level of equality we have is unsustainable, let alone that which might emerge unchecked. Those that have meanwhile, are likely to be willing to reduce their share – but unless we find a discourse that examines that, in a way that seems fair to all, we face the likelihood of a much more abrupt, and unpleasant adjustment.


These trends – a sort of technological “four horsemen of the apocalypse” – require us to own the challenge – not deny it, or delegate it to someone else.

Individually, and collectively, we can question the work we do, and how we it benefits our collective good. 

We can address our individual carbon emissions of around 10 tonnes of CO2. Walk more, fly less, address diet. An aggregation of a lot of little actions won’t cure the problem, but might buy us time to work out how we do.

We can learn to be powerfully human, rather than efficient servants of a process. To create more than just redistribute. 

And we can learn to be humble. As countless studies have shown, our lace in the system, rich, poor or destitute, is largely a matter of luck, not effort or virtue.

We can all do something more than observe or comment. It’s time we did.

It will mean doing things we’re maybe uncomfortable with, or uncertain about, or even afraid of.

However, we’re all making a bet, one way ot the other. Whether we like it, or not.


Stories are the way we make sense of things, as well as commit them to memory. They are at the heart of our histories. Stories are fractal – every story has smaller stories within it, and is itself part of an ever developing larger story.

I’ve come to understand that stories are a good way to understand our relationship with our work. At any one point, both the organisation we work for and ourselves are at different points along our story line. We are founded, or born, and spend the rest our our time time working out who we are and want we want. It changes.

As we develop, sometimes the story of the organisation and the story of us align. We are good together, companions on a path that suits us both. We learn from each other, support each other, and enjoy the journey.

At other times, our stories diverge. Our needs become different. The organisation wants to settle down, but the individual wants to explore – or maybe the other way round. Either way, there comes a point where paths separate if each is to achieve what it wants from life.

The complication arises when separation needs to occur, but doesn’t. One becomes dependent on the other, or perhaps just takes it for granted. The pain comes when something unexpected happens, and a separation is forced upon the relationship. Business Failure, Headhunters, Circumstance.

When that happens, one or the other, or maybe neither is prepared. They’ve forgotten their story, and have to try and remember it; to pick it up where it trailed off.

It’s a salutary lesson. If we are not actively living our story, developing it, exploring it, the story goes into hibernation.

If we’re not aware, right now, of where we are in our story, either as individuals or organisations, and are making sure they are developing, we have a problem.

Getting Unstuck

We all get stuck, particularly those of us who try to help others get unstuck.

I know when I’m getting stuck when I find myself repeating the same message in creative new ways. It means I’m not moving on, I’m making camp.

Amongst those I know are those who notice, who can’t be fooled, will call me out and move me on. I value them enormously.

Some of them I don’t know personally, but they have a talent for communicating that I get the same kick as if I did.

I was reminded of this listening to Margaret Heffernan on Radio 4 “Thought for the day” on Sunday. A good way to spend ten minutes listening to here challenge the ease with which we accept what we’re told.

Charles Handy has been a mostly unwitting mentor all my working life. A gentle but incisive philosopher of business, I find his work has a way a centring me when I’m stuck.

Rumi, Marcus Aurelius, Antoine de St Exupery. These are just a few amongst many. What I value is their honesty, their lack of lecturing or trying to be right. They question themselves as much as me, and in doing so create a way forward.

In the times we find ourselves in, a search for answers is much less productive than finding those asking great questions.

You don’t have to know them, just make space to spend time with them.