Pessimism, cynicism and skepticism can help you get ahead AND become a better person!
You are irrational. But it’s okay, so am I. And that person over there is too. The robots will never understand us. We are squishy, emotional human beings and our motivations rarely stem from a place of rationality.
But we can all learn to understand just how people are irrational and unrealistic. Once we know and accept this we can all start to look a bit more critically at ourselves and our interactions with others.
But why?
Why does examining things critically matter? Is it just the sense of moral superiority it brings? Well partly, but it also allows you to begin to look at the world in a slightly different way. Is there a good reason for the status to be quo? Why are you doing that particular activity, going to that particular place, falling in line with the herd? Do you actually want to do that? Is that actually a good idea? Is that logically the best thing for everyone?
Each of the methods below has different pros and cons but I would say that a healthy dose of each leads to the most balanced and rounded view point.

Cynicism is an attitude or state of mind characterized by a general distrust of others’ motives.
Ah cynicism, the most maligned of the realistic arts. Cynicism is seen as somehow offensive, something that stops you being a “team player” and it is often discouraged. And this is harsh. To mistrust people and where they’re coming from seems to go directly against the idea of a healthy society. But it can also aid you. If you understand the motivation behind people’s actions, then you know what they actually want. If you look behind what people say, then you can find out what they really mean. This saves a lot of time and cuts to the chase a bit faster.
It isn’t a bad thing to be cynical, life teaches us that most people are not 100% honest and their motives are often not what they say they are (and sometimes they don’t even know that). By asking questions it stops them from sleep walking into decisions. Why do they actually want what they’re asking for? Just being questioned will uncover another level of thought. You can be the foil to their self realisation.

Pessimism is a state of mind in which one anticipates undesirable outcomes or believes that the evil or hardships in life outweigh the good or luxuries
Now this one is a bit more negative! However, there is definitely a positive side (not a very pessimistic attitude but still…) We should definitely prepare for the worst, but not dwell on the fact. It is okay to expect something to go horribly wrong because then you will naturally try to prevent it. Your behaviour will also rub off on others and they will feel a slight sense of doubt over positive thoughts. This will keep them on their toes and reduce the desire to be complacent.
Where pessimism can go wrong is dwelling on the fact that everything will probably go horribly wrong. It can then become an obsession, a single minded pursuit of fulfilling that prophecy, of being proved right. Balance is key here, just be pessimistic enough to know what will probably happen and prevent it. But don’t become the spectre at the feast, watching the world slide into the hell that you predicted all along. No one likes a nihilist.

Skepticism is generally any questioning attitude towards unempirical knowledge or opinions/beliefs stated as facts, or doubt regarding claims that are taken for granted elsewhere.
This is definitely the best tool to have. Skepticism is a muscle you should exercise regularly. You can practice anywhere; cast a critical eye over adverts, headlines, reviews. Work your way up to “thought pieces”, emails and then practice in real time during conversations.
You need to become almost evangelical about skepticism, infect others with it and make them question everything. Of course it can be tiring to question everything, but the more we as a society do this, the less there’ll be to question. Do the training and you’ll reap the rewards for a lifetime.
The only reason not to be skeptical is laziness. Sometimes you just want to believe, to not use your brain and just accept what someone is telling you. So take a rest day! Watch some TV, eat something with sugar and salt in and then get right back to it and keep fighting the good fight.
So what can you do?
Everyone will have different levels of skill at this already, so work out what this is. Are you doing enough? If you are… great! Keep up the good work, share the love. Make others appreciate the benefits.
If you’re not, start to train yourself. Look at things a bit more skeptically, question what you hear and see. Imagine that maybe things won’t work out okay, how could you prevent that? What is that person’s motivations? If you naturally try not to think like this, start with small steps. Ask yourself one of these questions about everything you see or hear. Learn what it feels like to think this way and you can start to bring it out when it makes most sense.
Don’t be afraid, the truth is out there.