How to be a Successful Optimist
Mark Stevenson

Introduction: It’s not always easy to keep optimistic. As the famous military maxim goes “no plan survives contact with the enemy”, which is why successful military leaders give those under them the freedom to improvise, but make sure they always know what the goal is. Americans call this ‘Commander’s Intent’. What I have learnt from working with some of the people who actually get stuff done is that they all have ‘Commander’s Intent’. But they don’t call it that. Instead they say, “these are my principles” or “these are my values”. When things change or difficult decisions need to be made they refer back to their principles, their ‘Commander’s Intent.’

Principle No. 1: In short, successful optimists don’t feel embarrassed to say that things could be better. They have no qualms about imagining an improved world and advocating for it, no matter how much derision they may receive at the hands of the cynical. In short they are not ashamed to dream good dreams. After all, Martin Luther King did not stand on the steps of the Lincoln memorial and say, “I have a five point plan.”

Articulating these goals brings the first test for the successful optimist. With cynicism being such an easy weapon for their opponents, successful optimists will soon have their ambition, and indeed their character, questioned. They will be accused of naivety, arrogance and stupidity, possibly all at once. And this character assassination won’t let up. In all walks of life, but especially in large organisations, successful optimists rarely triumph because of the prevailing culture, but in spite of it. [This reminds me of Admiral Hyman Rickover’s maxim: Good ideas are not adopted automatically. They must be driven into practice with courageous impatience.]

Principle No. 2: All successful optimists have a project that is bigger than they are. By contrast, people who have a project that is the same size as themselves are invariably miserable and tedious company. Once you’ve got a bigger car/ nicer house/ television bigger than God what’s left? As so many find out, eventually the answer is a nagging emptiness accompanied by the thought, “Surely there must be more to life than this?”

Principle No. 3: Successful optimists are therefore serendipity engineers. They find ways to smash themselves (and others) into new ideas – exposing themselves to different thoughts, philosophies and approaches. Somewhere in the ensuing mental car crash the right collision of ideas will provide them with another tool in their quest to make the world better. In fact, to the successful optimist this becomes second nature. “Creativity is just connecting things,” Steve Jobs told Wired in 1996. “When you ask creative people how they did something, they feel a little guilty because they didn’t really do it, they just saw something. It seemed obvious to them after a while.” So, if innovation is, as Matt Ridley puts it, “ideas having sex” then successful optimists are intellectual sluts, happily throwing themselves into forums where they aren’t experts, reading outside of their existing frames of reference, promoting debate and dialogue and finding joy in the accidents that might frustrate or annoy others. This is why that ideas-powerhouse the MIT media lab is full of glass walls, so that everybody can see into everybody else’s lab, and why the head of MIT’s Smart Cities group Bill Mitchell designs buildings to ensure people bump into each other.

Principle No. 4: We like to imagine we could change the world (or our corner of it at least) if circumstances were different. Inside our heads we are convinced that we are kind, forward-thinking, engaged members of society who, given half the chance, would be working to make the world a better place.

Pragmatic optimists take a different view, which is quite simply this: you are what you do. That miserable, grumpy, cynical, obstructive or unreasonable person you appear to be is who you actually are as far as the rest of world is concerned. Pragmatic optimists are not interested in what you might do if your circumstances or internal dialogue were different. They hold the opinion that you do what you can in the moment you’re in. It’s a view shared by pragmatic optimists across history from Ghandi (“You must be the change you want to see in the world”) to Richard Branson (“Screw it, let’s do it”).

For this reason you will notice that pragmatic optimists, the people who get good stuff done are busy. Very busy. In fact you’ll hear others often remark, “I don’t know how they do so much”. The reason is they fill the time most of us use to procrastinate with hours spent getting on with stuff.

Principle No. 5: Successful optimists deal with that fear by knowing they almost certainly will get something wrong, and that’s not only OK, it’s fundamental. They are not paralysed by the worry of making a cock-up. They know that the only way to see the right way to do things is with the benefit of hindsight, something you can never possess when you start the journey, so its pointless to expect such clarity at the outset. As author and entrepreneur Seth Godin says: “The way to get unstuck is to start down the wrong path, right now.”

Successful optimists therefore follow the principle that making mistakes is OK, it’s not trying that is irresponsible. [On my desk I have a card imprinted with Frank Herbert’s Bene Gesserit Litany against Fear: I must not fear. Fear is the mind killer. Fear is the little-death that brings total obliteration. I will face my fear. I will permit it to pass over me and through me. And when it is has gone past I will turn the inner eye to see its path. Where the fear has gone there will be nothing. Only I will remain.]

Principle No. 6: Successful optimists therefore know that a commitment to evidence is key, regardless of your beliefs, your favourite ideology or accepted wisdom. This principle is perhaps best summed up as: be more like an engineer and less like a politician.

Think about it. Engineers do not build bridges from a left-wing, right-wing perspective. They build them from an evidence-based perspective and, over time, bridge building gets better. Politicians often make their decisions from an ideological standpoint, and if the evidence fits well (or can be ‘made’ to fit) that’s nice, and over time – as I’m sure you’ve noticed – our political system has got worse.

Principle No. 7: Successful optimists understand that the beginning of many endeavours involves being told you’re mad, bad and dangerous to know. More practically they know that they will lose. A lot. At least to start with.

Successful optimists see their ‘Bigger than me’ projects as long games with many rounds. I tend to imagine 10 rounds per project.

As US trade unionist Nicholas Klein said, “First they ignore you. Then they ridicule you. And then they attack you and want to burn you. And then they build monuments to you.”

Principle No. 8: Cynicism, in fact, is a bit like smoking. You may think it looks cool but it’s really bad for you – and worse still, its really bad for everyone around you. For the cynic, a better world is a little too hard to imagine, and therefore not worth doing anything towards. What’s worse is that cynicism pretends to be your friend, by warning you against the harsh realities of going up against the world. It’s almost as if it’s saying, “but I don’t want you to get hurt”. But making the world better is a contact sport. We don’t tell rugby players not to go into a scrum because the other team want the ball, do we?

As this is the last blog in this series, can all eight principles (including this last one) be encapsulated in a single idea?


If it comes down to one thing it’s probably this: if you want to be a successful optimist judge your value not by what you own, but by what you create.


Leave a Reply

To prove you're a person (not a spam script), type the security word shown in the picture. Click on the picture to hear an audio file of the word.
Anti-spam image