A Pessimist's Guide to Positivitymaxxing
What would it look like to engage with anxious thoughts in an optimistic way?
Pessimism comes naturally to me. For most of my life, anxious has been my natural state of being, and anxiety and pessimism seem to go hand in hand. After all, it’s easy to think everything is going to go terribly when you’re hardwired to look for threats and nothing else.
I used to take some degree of pride in only seeing the bad side of things. “I’m just a realist,” I’d say, gesturing vaguely to the state of the world and all the terrible things going on. Working as a journalist only sunk me deeper into this mindset, as I gained incredible amounts of knowledge about all the ways the world was broken and caused people to suffer.
Back in the days when I was active on Twitter, I was one of those people who’d interact with posts like “OMG look at this thing that just happened in [insert place here]. You should be enraged!” or “Wow, look at this bill that passed in Congress. We’re sooooooo fucked.”
But you can only read and repeat the phrase “we’re so fucked” so many times before you start to wonder how and when exactly we’ll all “be fucked,” metaphorically speaking. (And if we are already “fucked,” then great, I guess? Now what?)
Living in constant anticipation of an apocalypse-level event — or at least, events that could actively threaten my daily life or my safety — is exhausting. And I’m not gonna say all my worries are overblown, because there are always terrible things happening in the world and sometimes threats do manifest at your doorstep. Like, early Covid was a scary time. What’s going on in the federal government right now is pretty damn scary, too.
No one’s safety is ever guaranteed in this world, and pessimists make a whole personality out of that fact.
That being said, pessimism has often caused me to neglect seeing the good things in my life. It also puts a lot on poor Ryan, who for years has listened patiently while I’ve fretted aloud about the possibility of getting in a plane crash or the government collapsing or being doxxed for something I wrote on the internet. So many things can go wrong, can’t they?
Now, you may have read the title of this newsletter and thought my solution to all this negativity is to become an unapologetic optimist. That’s not the case at all.
I actually think we’d all be better off if we learned to let pessimism and optimism coexist in everyday life. After all, life isn’t 100% good or bad — it’s a weird gray area, often devoid of moral meaning, which is why every individual can have such a radically different outlook on the state of things.
At some point in the journey of challenging my anxiety through therapy and peer support, I started to realize I had a choice in how I engage with my thoughts. If that sounds like a stupidly simple revelation, that’s because it is. But you really have to internalize that fact in order to act on it. Even though I may not be able to control my fears, I do have a choice in how I frame them — and it doesn’t have to be with pessimism.
Huh. So what would it look like to engage with my anxious thoughts in an optimistic (or neutral) way instead?
Ryan and I tried this out a few days ago in a pretty overt way after I’d been doomscrolling on Instagram for an hour. I started to freak out about a bunch of things, among them plane crashes, because I have to fly on a plane next month. My worries, which I voiced aloud, sounded something like this:
“Man, I don’t want to get on a plane in two weeks because there have been so many plane crashes. What if that happens to me? What if I die and leave you and Juno behind? I also looked at the forecast and there might be snow. If the plane doesn’t crash, what if I get stuck at the airport for like, hours, and I get super exhausted and grumpy and don’t have a place to sleep that night because the airline won’t pay for a hotel? Or what if I get stuck in Denver during my layover and the same thing happens? It’s gonna be a terrible day and I might not even live through it.”
Ryan and I call this type of thinking doommaxxing. You know, kind of like doomscrolling, but we’re just maximizing the thoughts of doom in our own minds. (I’ve definitely seen people online use this term, so I know it’s not original.)
Ryan kind of laughed at me after I went down this rabbit hole. Not in a mean way, but in a you’re-going-to-be-okay/why-are-you-so-worried type of way. Whenever he does that, it reminds me that my fears are probably blown out of proportion. It also helps neutralize my anxious thoughts, because I start to reconsider what’s actually likely to happen rather than what I fear might happen.
So after my panic moment, I had the thought: what if I put a suuuuper positive spin on the same scenario instead? “Let me try positivitymaxxing,” I joked. Here’s what that looked like in contrast:
“Wow, flying on the plane is going to be so amazing next month. I’m gonna wake up and it will be sunny out and a great day for flying! I’ll get assigned a window seat (my favorite) and we’ll leave on time and I’ll get to enjoy beautiful views on my way to Denver. I’ll even get some work done on the plane!! And best of all, the plane won’t crash or have ANY problems at all AND the beverage cart will still have ginger ale in stock when they reach my seat in the back. Then I’ll make my layover with time to spare and reach my final destination feeling so happy and relieved to see my friends!!”
It felt ridiculous trying to put a relentlessly positive spin on the event I felt anxious about. But in the process, I realized it was just as ridiculous to expect everything to go terribly wrong.

In reality, my flight next month will probably have some positive traits and some negative ones. I’ll likely get to my destination unharmed, but there is real potential for delays due to snow. And even then, I might not get delayed at all because the weather forecast could change on a dime.
Listening to myself play through two opposite scenarios made me realize how likely it is that they’re both partially false — and both partially true. Negative things have just as much of a chance of happening as positive ones do. When you worry about things going wrong, it can be helpful to stop and ask yourself: what if they went right?
Life is always going to be a mix of both good and bad outcomes. We’re not doing ourselves any favors by only fixating on what might go wrong. And it’s not great to only focus on positive outcomes either because that can mean getting our hopes up too much or ignoring the negative possibilities that still we have the power to change.
But envisioning two drastically different scenarios might help you see the full possibility of good and bad outcomes at the same time. Let yourself counter your overblown fears with overblown positivity, and then meet yourself in the middle where you’ll likely find reality.
This newsletter wouldn’t be possible without all of my readers, including YOU!
If this post brightened your day, taught you something new, or made you think, consider supporting my newsletter financially through a one-off or monthly donation. Any amount means the world!
Writing is my full-time job and your financial support helps me dedicate time every week to write new essays and develop writing classes. Help keep these things going by dropping a few bucks in my tip jar today.
And while you’re at it, give a round of applause for my 2025 supporters:
Dennis T.
Emma H.
KRW
Grandma Gin Gin
Maddie B.
Tara Y.
👏👏👏
I am trying a different approach today as I am in the midst of flying to a place I’ve not been with people I don’t know to do a job I am not totally up to speed on. I laugh as I wrote that. I am telling myself to feel my power. I totally have it within me to do this trip and be present and gracious and engaged. So I tell my anxious self to feel that power within me. No matter what happens it is nothing I can’t handle no matter how uncomfortable. I am strong enough. Remind yourself that you are a strong person. And you wouldn’t have to look far to see the evidence. And, of course, those people who love you and who are always with you are lifting you up in spirit.
This resonates with a video I just watched where they brought up “pessimistic optimism” as an ideal way to go about life. “Prepare for the worst, hope for the best, and expect something somewhere in between those two.”
I mostly jockey back and forth between the two extremes, but I hope one day I can find that sweet balance between optimism and pessimism that isn’t quite realism but a god mix of both.