How to Manage a Pessimist

Pessimists are people too and deserve the same respect as everyone else.

Okay, that isn’t as great a rallying cry as I thought it would be.  In life, there are people who will be pessimistic and people who will be optimistic.  You and I will end up working with some of these people.  Optimists, while annoying, are fairly easy to manage.  They willingly jump into situations believing they will be able to sort it out as they go.  Pessimists tend to be Cassandras… predicting doom and gloom at every turn.  These folk are a real bugger to manage because they aren’t motivated in the same ways as optimistic people are.  They don’t see new challenges as exciting, they see new challenges as new ways to fail.

I think I’m in a unique position to give advice on this subject since I’m a pessimist.  I like to think I’m a pragmatic pessimist but definitely not an optimist.  I’m the type of person who expects to be hit by a crazy driver running a red light when I cross the street.   Every new project is ripe for new ways to bring frustration, disappointment, and failure into my life.  As my boss once said to me sarcastically, “You are a joy to manage.”

So how do you manage people like me?  And ‘manage’ doesn’t necessarily have to be in a work environment.  I know my friends are often at a loss on how to deal with my negativity.

I first want to do a quick breakdown of what is going on in a pessimist’s mind verses an optimist’s mind as they experience the same type of events.


Something Good Happen –> Accepts that good things happen all the time, feels justified in postive expectations.

Something Bad Happens –> Realizes that life isn’t perfect, ignores the anomaly.


Something Good Happens –> Believes this was due to luck or extreme careful planning.

Something Bad Happens –> Bad things happen more often than good so negative expectations are validated.

Being an optimist or pessimist is like wearing colored lenses which alters the view of the world.  Optimists, at least from my perspective, do seem to enjoy life a lot more as they aren’t weighed down by the negative events that occur.  They are more likely to tell a story about finding the perfect parking spot then a story about the thirty minutes it took to find a parking spot.  A lot of time and energy can be spent trying to turn a pessimist into an optimist, but that is a job for an eternal incurable optimist to attempt.   It isn’t impossible, but that time and energy might be better spent doing something else.

Something to realize about pessimists is they don’t want the negative things to occur and in their view of the world, they are trying to stop bad things from happening.  Consider Cassandra in the ancient city of Troy.  She had visions of great destruction and wanted desperately to stop it from happening.  She was not working to see Troy destroyed.  That is the first thing we have to understand and accept about pessimists – they want to achieve success just as much as an optimist does.

How do you manage the pessimist?

Listen. Cassandra was under a curse by the god Apollo.  She had the gift of prophesy, the ability to see the future, but Apollo made it so no one would ever believe her.  Imagine that frustration.  To know that something bad is going to occur and no one will take you seriously.  The first thing to do with a pessimist is to listen and acknowledge what the pessimist is saying.  While listening, remember that the pessimist is viewing the world as if failure is the natural course and success comes through intense effort or luck.  This means every point of failure the pessimist mentions is something the pessimist thinks is a point relying on luck, which is fickle, and needs to be intensely managed.

React. Listening isn’t enough, you also have to take some form of action.  The action doesn’t mean buying into the pessimist’s vision but an attempt to demonstrate to the pessimist why these supposed points of failure are not a factor or are mitigated.  This may be hard for an optimist who believes ‘things will just work out for the best’ because they never really have given much thought to how that happens.

Engage. The final best management technique is to turn the pessimist’s energy to the project’s advantage.  Ask the pessimist to come up with ways to mitigate the risk or develop a plan ‘b’ if the project does go off the rails at a point the pessimist predicts.

I wish I had a great case study to present at this point but all I can present is how I manage myself.

When temperatures drop below freezing, I know that there are several points of failure that could prevent me from getting to work.  One, my car might not start.  It has been reliable most of the time but not 100% of the time so there is always a chance that it might not start, especially in the cold.  If that doesn’t happen, I have to catch a bus in order to catch a train.  If I miss that train, I will have to wait for the next train an hour later.  Sometimes the trains breakdown or are severely delayed.  These are just points of failure that relate to non tragic things, like getting in a wreck or getting hit by the bus.  Anyone who would come to me and say, “You don’t have to worry about getting to work” would be scoffed at.  There is plenty to worry about, obviously.   I can’t waste energy every morning worrying about this stuff though, I need to mitigate the risks.

On cold days I get up earlier so I can start my car.  If my car doesn’t start, I know I have time to catch the bus.  If the bus fails to show up in time, I can catch a cab to the train station.  If the train is delayed, there is nothing I can do about that.  I’ve reached a point where I cannot mitigate this risk, so I make sure that I set expectations on the other end.  I’d alert my boss and coworkers of the potential of my being late.

Instead of waking up every morning thinking that I won’t be able to get to work, I think that the worst possible thing, barring being hit by a bus or getting in a wreck, is I will be late.

Imagine I was your friend and I was fretting about not being able to get to work.  The wrong approach is to tell me that there is no need to worry about that.  Or even worse, “You’ll cross that bridge when you get to it.”  It is illogical.  I know that something bad will happen eventually and I need to know what to do.  The right approach is to listen to me, letting me know that my points of concern aren’t being dismissed out right.  You don’t have to agree with them, but accept that for some reason, I see them as something to be concerned about.  Next, react to what I’ve said.  Either present a counter-argument for the points of concern, or offer suggestions on how to mitigate these issues.  Finally, engage, turn the concern I have back onto the problems.  So instead of fretting about how I’m going to get to work on that one day this bad thing happens, I am thinking of ways to around these points of failure.

At the end of the day, the best thing anyone can do when managing or dealing with a pessimist is not to assume their expectation of negative things to happen is the same as wanting negative things to happen.  Pessimists want to see success as much as an optimist does.  They just are more sensitive to all the risks involved in the endeavor and need to know others recognize the risk as well.  If managed correctly, a pessimist is a great member of any team on any project.  If managed poorly, they can be dead weight.

3 thoughts on “How to Manage a Pessimist

  1. Good article. My personal ‘peeve’ with pessimists is how draining they are. Everyone has worries and issues. I try hard to keep myself positive. The time spent ‘dealing’ with the pessimist’s concerns puts me in the dumps too. Whenever I am able, I walk the other way. We’re not their counselors. Once in a while, ok. But pessimists have made this a way of life and will take hostage anyone who will listen.
    My addition to you article is ask them if they realize how negative they are and kindly let them know that as long as they seek problems instead of solutions, you and others will probably avoid them.

  2. hmmmm thanks truthfully I didn’t know the diference helpful I know just a person an have been very puzzeled by his ways an thoughts thanks for shining some light on this

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