Are you an optimist or a pessimist?

Are you more likely to succeed in business if you hope for the best, or prepare for the worst?

by Emma De Vita
Last Updated: 09 Oct 2013

Is your glass half-full or half-empty? We're said to be a nation of Eeyores whose gloomy outlook on life is summed up by philosopher Thomas Hobbes, the cheery soul who called human life 'solitary, poor, nasty, brutish and short'. Pessimist Jon Moulton, chairman of Better Capital, agrees: 'He was a miserable devil, but in some ways it's true. If you're born in sub-Saharan Africa, that's rather accurate.'

But most of us are luckier than that. 'Think of the way our lives have improved beyond measure since Hobbes' time,' counters optimist Luke Johnson, chairman of Risk Capital Parters. 'That tells you we have grounds for optimism and we should not give way to feelings of gloom.'

But wasn't it blind optimism that caused the bubble that led to the recession? What else explains the hordes who took on 125% mortgages, or the 'creativity' of investment bankers who were too buoyed up by their own over-inflated confidence to appreciate the folly of their deeds. If only we'd all been a bit more pessimistic, then perhaps we wouldn't have found ourselves in the mess we're in now ...

'There is a prevailing but not proven view that it is wiser to be pessimistic than optimistic,' says Miranda Kennett, founder of First Class Coach. 'The advantage of being an active pessimist is that you are likely to explore the worst-case scenario and to have taken steps to avoid it happening.' After all, who needs over-optimistic surgeons, structural engineers or FDs?

On the other hand, optimism is essential for the world of visions and ideas. 'Waking with hope in our hearts fuels the actions that make things happen,' says Kennett. But the right path is a balance between the two. 'Pessimism and optimism are on a continuum. At one end is Pollyanna and the other is a depressive cynic, who kills enthusiasm. Realistic optimism tends to characterise the most successful people: hope for the best, but prepare for the worst.'

Henry Engelhardt, CEO of Admiral Insurance Group, says his optimism is balanced by the pessimism of his business partner David Stevens. 'He's always looking for the risk and the possible downsides, and I'm the one playing up the possible good outcomes. That's an excellent balance to have.'

Here, MT speaks to two more optimists and a pessimist about their life philosophy and asks: which is it better to be? 'The world was built by risk-takers who didn't let the precautionary principle keep in bed because the ceiling might fall in,' says Johnson. 'No pessimist has ever sorted out the wide-reaching problems of a country or a socity.' Who will rescue us this time around - the glass-half-full types or their opposites?


'An optimist takes a fundamentally positive view of the world and has an in-built instinct that human ingenuity will always overcome whatever obstacle is thrown in its path, so my philosophy is one of confidence in the future.

Personal experience shows me that the optimists are always the winners, because if you believe in the worst then the best that can happen is you're proved right. If you believe in a better future and you bet on that, then if you're right, you win, and if you're wrong, you're no worse off than if you're a pessimist. Maybe I've lived a lucky life, so that's the grounds for my sense of optimism; but most of the research shows that your sense of optimism or pessimism is endogenous.

Humans are the only animals that realise they are mortal and this is a tough piece of intellectual information to grapple with. The idea that you will not endure means you have to make the most of the time you're here. That in turn means not burying yourself in fears but working in the belief that you will be able to create, invent and improve. There are always doomsayers and any number of apocalyptic visions, but for most of us, the worst never happens.

I think it probable that serious pessimists are actually depressives. Clearly it rains, people get ill, we all die - there are lots of grounds for pessimism; but the fact is that there are also lots of grounds for optimism. Unquestionably, having children is the single biggest basis on which people can be optimistic, because giving life and seeing children grow up and their sense of innocent optimism reminds you that age shouldn't be allowed to bear down on you.

Of course, there are disadvantages to being an optimist. You can overstretch yourself, get carried away with a sense of victory that never comes, and suffer worse disappointment. A lot of pessimists take the view, 'I'll fear the worst and then I'm never going to be disappointed'. Indeed! But I prefer the company of people who have ups and downs, those who go for it and enjoy life to the full. As long as they can cope with the moments when it's not quite so great, that's fine.

I can't explain some of the behaviour of some of the idiots who've led companies like Bear Stearns and Lehman Brothers to go bust, so, clearly, untrammelled optimism isn't a good idea. But I think you have to start from a sense of belief in a positive future and then try and put it into proportion, and test things. But, big picture, you have to be an optimist, especially if you're leading people and trying to boost their morale. I don't see how you can be an entrepreneur without being an optimist. A naive, ill-informed, brainless optimist is no use to anyone, but a pessimist is simply someone most people don't want to be around.'


'Pessimism is more often than not realism. You can illustrate it easily at the moment - the economy is coming out of a horrible recession. Some people see that in buoyant terms; I look at it and see an enormous load of debt and a lot of problems to come. Am I being realistic or pessimistic? I think I'm being realistic. I do a lot of private equity investing in small companies and lose a third of my money. I'm realistic about it.

I tend to plan for the worst and hope for the best, but I'm not very emotional about failure. I just see a problem, the next step, then move into it. It irritates my wife to death. Some major problem will occur at home and she lies awake half the night; I'm asleep in seconds. I don't worry.

There's less disappointment if you're a pessimist. Most people are hurt more by disappointment than anything else in this world. The person who rats on you, the bloke that doesn't deliver a deal - these are bad moments. In some ways, I think, pessimism might almost be a defence.

But we need a degree of optimism - if you think about the human condition, there are few things that are certain except death, so we keep going until then, but we don't have to get depressed about it. The real-world optimists are the ones who make megabucks backing a one-in-a-100 chance. And some of them work. The reality is that a lot of them fail a lot of the time, but without optimists we wouldn't have people who do such things.

I do wish I were more optimistic. The most expensive mistakes I've made have been always by not being optimistic enough. My best venture capital deal was Newbridge Networks - we sold out after two and a half years for something like six times the money and it was going up a lot, and I thought: that's far enough. In the event, I would have made another multiple of 12 if I'd held it for another year. That was far and away the most expensive mistake of my career. I lacked sufficient optimism, but riding bubbles is about optimism and I've never been good at riding bubbles.

I started to predict the collapse of the debt market in the autumn of 2005 and acted on it from the beginning of 2006, so I missed quite a lot of the opportunities to buy something for 100, flog it for 180 in six months and move on.

Should there be more pessimists in the world of business? The right answer must be that it would worry me if there were. I would be much happier if we had far more open pessimists in government, because this sort of PR desire that runs our politics is all about extreme short-termism on the most favourable possible view, and that can be our total ruin and catastrophic failure.'


'I would define optimism as being glass half-full - having a mixture of confidence, conviction and hope. It's not blind optimism, it's not Pollyanna, refusing to face facts or grasp the nettle.

I've always been an optimist. My parents were very can-do, upbeat people - those are the kinds of people I now hang out with. I can't think of any close friends who are pessimists. In a creative business, you thrive on energy, hope, conviction and momentum. I am surrounded by glass half-full types but I don't think we are skittish, irresponsible or superficial - there is rigour, analysis and introspection. Our attitude is a positive, energised one, not a draining, negative one.

I couldn't do this job as a pessimist - I wouldn't last five minutes. They'd say get rid of that misery-guts. I don't know that you'd find any pessimists in advertising: it tends to attract the enthusiasts, because it's a creative process. You have got to do your best, you've got to break new ground, to come up with original solutions to commercial problems. But we've always got a healthy paranoia - is it as good as it can be? Is it working as effectively as it needs to, whether it's a fish finger or a supermarket? I don't find it inconsistent that I've got healthy paranoia and massive optimism.

I think being an optimist provides a layer of resilience that is important. You can't win all the pitches and if you crumple every time you won't be able to get up the next day. You have to confront failure, learn from it and avoid repeating it. Some things are just definitively and exclusively vile, but I have seen so many silver linings that you have to believe in people first and foremost and that in the end some good will come from it.

We face economic turbulence the like of which we've never seen and there's plenty to be gloomy about, but even in adversity there's opportunity. I think optimists are better equipped to manage difficulty: they have a capacity to take on different tasks, extend their remit, and learn new things. But optimism must have realism and substance. You need some evidence behind the confidence to progress.

There's a great Churchillian quote: 'For I myself am an optimist. It does not seem to be much use being anything else.' It's the only way to be, isn't it? Your utility is to inspire and to lead.

I can't see that you would be much use as a pessimist, saying: 'Well, that won't work and that will never happen!' It would be impossible to be a pessimist and an enthusiast. There is a school of thought - to which I don't subscribe - that you get good work out of conflict and out of people having doubts, but I think the opposite. You get better results from collaboration, enthusiasm, optimism and conviction.'

Find this article useful?

Get more great articles like this in your inbox every lunchtime