The Case for Positive Pessimism

Zach Clenaghan
April 23, 2020

Sounds like an oxymoron, right? Think again, they are not opposite ends of the same spectrum, and the combination of the two has served me well in building Edumadic. In entrepreneurship, both optimism and negativity can be deadly. It’s equally powerful when applied to our current situation with COVID-19.

Let me explain.


Optimistic vs. Pessimistic Outlooks


First, we’ll tackle pessimism, since this is probably the part that has you raising your eyebrow. Its counterpart is optimism. These both dictate your thoughts and expectations about the future.

An optimist always expects the best to happen.

“She’ll agree to marry me”

“It’ll take me 20 minutes to get to my meeting which is 30 minutes away (?!)”

“I’ll be able to pay off my credit card later”

“I’ll be hired for my dream job”


Unbridled optimism, in my opinion, is very dangerous. If you think that life is always going to go your way, you’ll never be prepared for it when it doesn’t, which (newsflash) will happen often! Optimists may be living on a cloud of happy thoughts most of the time, but when they hit a bump, they really hit it! They have no contingency plans in place; they’ve got to deal with the fallout from a standing start as well as overcome the emotional toll. 

Pessimists, on the other hand, expect the worst to happen.

“I’m not going to win the race”

“This business deal is going to fall through”

“He’s going to let me down”


Sounds pretty depressing, right? In isolation and unchecked, pessimism can be. But it’s what you do with these thoughts once you have them that gives power to pessimism, which is where positivity comes in!


Positive vs. Negative Mindset


Positive and negative mindsets dictate how you see the world as it is now and the control you have over it. I can’t think of many reasons why a negative mindset is ever useful, and yet it seems to me it’s the default mindset in our society. We hear a lot of negativity in the news, on social media, and from people around us. It manifests in people feeling unlucky, in blaming others for their hardships, and in believing we can’t do this or that.

By contrast, a positive person always sees the best. The best in circumstances, in people, even in themselves.

It’s important to make a distinction here. They don’t hope for the best to happen, they see the best in the now

So a positive person can be experiencing something that on the surface may be “bad” but have a positive outlook on it. They can always see the upside of any situation.

Combining positivity and pessimism then becomes an extremely powerful mindset. If you expect the worst to happen and play that out in your head, but with a positive attitude, you can ask the following:

  • What can I do now to decrease the likelihood of this outcome occurring?
  • How can I prepare for this worst-case scenario so that it doesn’t have a devastating effect on me/my business/other people etc?
  • What good can/has come out of this bad thing?
  • Is it even that bad?


An optimist never asks these questions, which means when this bad thing does happen, it’s way more devastating than it needed to be.

This philosophy of positive pessimism is especially useful in the situation we find ourselves in now with the COVID-19 pandemic. Considering the worst possible outcomes now, perhaps in relation to how long our lives are going to be restricted, opens the door for us to consider how we can use this as an opportunity for growth, rather than hoping it’s all going to be over tomorrow.

Try it on for size and see how it works for you :)