to the pessimist's
- Kimberlee Oliver
- Aug 22, 2021
- 6 min read
Updated: Aug 23, 2021
Hi, my name is Kimber and I am a world class pessimist.
I tend to mull over my circumstances with a worst case scenario mindset.
I initially expect the worst rather than the best and justify that as the “right” way to look at things.
Whether the world is literally on fire or someone gave me a dirty look in the grocery store, I use it as evidence to back up my claim that there is no hope in humanity.
If you resonate with any of that - the letter I’ve written below is for you. And honestly, for me too.
If you can’t relate, and might even be thinking “who looks at life like this?” - you are absolutely still welcome here!
Even though this piece is intended for people with a skeptical perspective, it can honestly be beneficial to anyone: whether it paints a clearer picture as to why a pessimist feels what they do or even provide some encouragement with some of the doubts, anger and fears you are grappling with at this moment.

To give a little background, much of what is written in this space is intended to encourage the reader and remind us of our “why”.
Though I feel this post is valuable, it wasn’t exactly “fun” to write - nor will you find it to be a relaxing read, I’m sure.
There will be call outs.
There will be affirmations.
And there will be some denial.
Okay, so then why did I choose to write for those of us who look at life through a dooms-day lens?
As it is with any tunnel-vision way of thinking, I am a firm believer that check-ins are critical in order for us to be better.
Whether you view life optimistically, with a bitter heart, or with only the highest levels of excitement - welcoming voices that differ from your own thoughts can provide more good than we may believe.
Pessimists, though deemed worrisome and hopeless, have the intrinsic ability to allow room for the raw feelings we often push down, and hold up the red flags to guard us of hidden dangers ahead.
Optimists, though seen as gullible and unrealistic, can create a space for hope with ease, and therefore giving those around them a push beyond the limits they thought to be set in stone.
We need both to discover how we can not only find a solution to get to the other side of things, but to learn how to maintain stillness in the moments that cause us to flee.
If we sit in our own way for too long, the result can be that like a weed in a flourishing garden. Inner turmoil can suffocate our relationships, it can damage our intentions, and it can alter how we grow.
I chose to dedicate this to the ones with a pessimistic view because from my understanding - and personal experience - we are more susceptible to falling into a downward spiral as a result of our repetitive thoughts.
That said, my hopes for us as we walk through this writing are as follows:
That we can walk humbly yet boldly, knowing our perspective matters.
That we affirm our experience as valid, without anyone having to validate it as if it’s a parking voucher.
That we accept the importance of community whether or not you believe you know what to do - even if the answer is to not do anything at all.
Without further explanation, here’s to you:
Dearest pessimist,
It's been ... well, hard to say the least.
In just the last two years, we've witnessed immeasurable pain, loss, injustice, separation, natural disasters, and other cruel factors in the world that back up our general anthem:
people inherently suck.
Bad things happen to good people, and good people are dealt the bad cards in life.
That’s just being real.
First of all: I see you.
I feel this on a deep level.
Especially on the days where it feels like everything is literally falling apart.
To make my first counter argument right away: that's not true, and I think you already knew that.
Or at least I hope you do.
The problem with this is the behind-the-scenes translation which includes how “everything” or “everyone” generally sucks.
My suggestion: add the word "few" to the beginning: few people inherently suck.
I’m not going to claim that nobody is a bad person, here, because there are some truly atrocious people that have, do, and will exist.
However, we're turning our vision toward something more steady, that there are not as many bad people out there in the world. Better than everyone, right?
A part of what makes you see the world as you do, including your gut instinct, is based on your personal previous experience and the way you've grown to see the world change. And this view of yours is necessary, and can even be right.
You call out what some often want to ignore.
You speak up when others want to remain silent.
You come off as rude when really, you are calling out the garbage in something or someone that should be known (even though we weren't really asking for it, frankly).
Here’s the turn around: your perspective and understanding of a given situation is not always right. Therefore your solution, often to an equation you weren’t even included in, is probably not correct either.
We don't know what tomorrow brings - the garbage, the stress, the wrongdoings - and we also don't know what tomorrow holds - the joy, the laughter, the support, community, the unexpected good we often lose sight of.
There will always be a reason to worry, to prepare, to have the desire to protect those around you with caution. Just as there will always be a reason to smile, laugh and shrug off the "small stuff".
The concern I want to bring to our attention is this: when the effort that goes into building the walls is ongoing, it can prevent us from seeking and holding onto the hope filled expectations we need in order to look over the other side of the situation we’re standing in.
We create a boundary.
We set a rule.
We build a rhythm.
How do we see it through?
What’s holding us accountable?
Surely not our negative assumptions on how everything is meant to just tear down before us. I mean, sure, that might work for a short period of time - but not for long.
Want to make something clear at this point: I don’t know your life.
I can’t begin to understand or contemplate the loads of heartache you’ve felt in the past, or are carrying now- collected over the years or in the last week.
Your experience and feelings are valid - what you’ve walked through led you here and that matters.
Your pain can carry a lot of reason and also not reflect what other people and other experiences are in full.
I don’t say these things to suggest you shift your way of thinking or how you process traumatic events or run-ins with crappy people.
Nor am I saying every little thing you say is crushing someone's dream or reality.
I just want it to be clear: there is more good in the world than we think.
And there will always be more. Maybe not as much as we want - but we are also a huge factor in how much the good can impact the world around us.
Now that I’ve essentially slapped you across the face with how you don't know it all, here are some things to remember (not to get you all filled with pride, but as a way to shut out the critical voices that might be a little loud in your head):
You can be a pessimist and still bring good to the table. You are not all doom and gloom. You are not defined by your perception alone.
What you bring to the table contributes to positive change.
You can do good while believing something should be drastically changed..
You can build amazing new starts while confronting people on their crap.
You can do good things because you took the worst case scenario seriously.
You care so deeply that you take the step to call people out and bring a solution that is “stand off-ish”.
We just need you to calm down with your approach, assumptions, and arrogant attitude.
When you find yourself on unstable ground, try not to automatically jump to the thought that you have to pull yourself up - there are others waiting with their hand outstretched to grab onto yours.
You simply need to open those judgmental eyes to see them.
We are capable of putting safeguards into place while also choosing to take risks.
It's hard to do both on our own - which is why community (big or small) and having people to call you out and hold you up is more impactful than trying to do it all on your own.
So here’s to embracing both the rain (pessimism) and the sun (optimism). Both have a seat at any table, and both can hold an abundance of grace.
P.S.
I created a playlist on Spotify for us called, Exhale, linked below. Includes slow and steady (okay, some are fast paced) tunes to reground us in this day.
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