I was never a pessimist for sport. It was a strategy. A rind. And like all armor, it got heavy — and started to rust.
Optimism has never worked in my favor. That has been the philosophical rain cloud that has loomed over me for years. For an overachiever with a protective streak, pessimism feels smart. It feels mature. Rational. Hope is for amateurs. Until I realized: so is joy. Pessimism feels like control. Like standing on a trapdoor but telling yourself you built the floor.
But it turns out the girl who is always ready, is rather miserable. And the one who dares to daydream — even delusionally — is the one living in hope. And hope, unlike dread, has better skin. Hope is happiness’s overlooked cousin — quieter, but just as crucial. And hotter. Good things are coming my way is a much better way to go through life than I’m about to be pelted with feces.
I wasn’t just a pessimist, I was valedictorian of Worst Case Scenario Prep School (WCSP). I graduated summa cum laude in Disappointment Management, with a minor in Anxiously Avoidant Optimism. In diametric opposition to the motto of my elementary school, San Francisco Day School, “everyone’s a winner at the Day School,” our school motto was “expect the bare minimum, you still won’t be pleasantly surprised.”
Our student body at WCSP was uniformly morose and our mascot was a snail to match — no pace, no spine, no hope. Fortunately for the state rankings of my aforementioned invented university, honors-track nihilists have been shown, clinically, to have outsized intelligence. We see more angles of things and dissect scenarios in a way that most people can’t. We’re more tuned in but also exponentially more glum as a result. We stick ourselves in more socially isolated situations, which in turn makes us more introverted, and even more fatalistic…and so the cycle tightens. The Snails may not win many basketball games, but we crush Model UN and demolish our SAT II’s.
I’ve had a topsy turvy spring. Although I think every season probably feels chaotic for everyone. I had moments during which everything at work was moving full steam ahead, hitting an unprecedented run of timed green lights up 6th Avenue — a rarity. Then an ambulance would cut off my taxi, and the climb of a lifetime got exponentially steeper. Good steep, good hard, but still extremely uphill. My personal life has been similarly wavy. Moments of feeling on top of the world, euphoric, bookended by dead air and worry that all of my choices were rooted in self-sabotage. My entire life has been a bit of an undulation. I just seem a bit more hardwired for the whiplash. I think it’s because I’m prone to waves of feeling down that I never understood were valid uncontrollable feelings, until rather late in my life.
The thing about the big scary word, depression, is that it sneaks up on you when you’re least ready for it. It’s like slicing down a perfect groomer on stiff racing skis and catching an edge right where the grooming ceased and the corduroy stopped. Sometimes you go flying, a yard sale Darwin awards are made of, and sometimes you pull it together with a lurch in your stomach as the sole token of appreciation.
When you’re a control freak, as I am, you naively believe you can control the down periods. Unfortunately, those periods are anything but receptive to my very strong will.
The thing people get wrong about depression is how it actually feels. It is not desperation, and it is not inconsolability, though there are certainly splashes of that during a downturn stretch. But depression really is numbness; it’s the feeling that you might never feel again.
I know I’m sloping downward when the nerves in my body have no tickle. Chuck a wine glass at my head? I don’t care. I probably won’t feel it anyway. Throw shit news at me? Rub it in? Who cares. The world has no meaning anyway. Depression is monotone; it is vibrating at such a low frequency you don’t even feel your cells wiggling anymore.
Happiness isn’t my default setting every single day. But I wake up every day and try with all my might. Most often it pans out; sometimes it doesn’t. Some days the wave washes over, suffocating my pilot light like you would smother a grease fire. Not today dopamine. Save your hits for another.
Nonetheless, I embarked on a quest to stave off slumps. And I did it by launching an optimism campaign — a rather toxic one. I always thought optimism was for people who hadn’t been through enough. I’ve been through enough. So many of us have been through enough. I know what splat feels like. I know what waking up day after day to tougher news does to mental health and, ineloquently, it sucks.
I thought cynicism was intellect in disguise. Turns out, it was just sadness in a lab coat pretending to be smart. Real power comes from letting yourself want something without armoring up for its loss.
I think there’s maybe a religious current in all of this. Jews (and 7th day Adventists) are inculcated with a doomsday prepping mentality. Sure, we believe we will overcome, persevere, but we also believe, know, that the absolute worst is probably headed our way and we should be ready. See: Matzah, the original unleavened anxiety snack.
But contrary to historical timelines, this pessimistic conditioning doesn’t start with ancient history — it’s much more personal than that. I wasn’t born doubting myself, none of us were. Someone put the idea there. Maybe it was a passing critique that seemed harmless. A moment when someone told you not to get your hopes up, and you listened. A comment you overheard and extrapolated to mean you weren’t extraordinary. We internalize those things and bring them to life like Frankenstein’s more depressed wife. Often the worst things anyone ever said to us, to me, weren’t screamed. They were delivered casually, like advice. Like concern. Like realism. But they calcified. Those things get carried into rooms like prophecy.
When someone projects doubt onto you, it changes your trajectory. Not because they’re right, but because your body starts bracing against failure as if they are. And that’s where the compliment deflection spiral begins.
Pessimists can’t accept praise because we’re waiting for the “but.” Someone says “that was very good” and you immediately jump to, “they’re just being nice.” You deflect, minimize, or argue, which in turn makes people stop giving you compliments. The self-fulfilling prophecy strikes again.
I didn’t realize I was doing this until a smart friend pointed out that I always assume I’ve done something wrong. I walk into rooms apologizing for existing. Often, I haven’t done anything at all. Just existed. That’s when I started paying attention to how pessimism wasn’t protecting me, it was covertly booby-trapping everything I cared about.
If I brace for disappointment, someone I like doesn’t follow up, a deal falls through, at least I knew that scenario was a likely outcome. You don’t just prepare for failure — you pre-live it. Your words betray you, laced with low-grade dejection. You walk into rooms half-there, undercut yourself before anyone else can, your energy quietly whispering, don’t bet on me. That kind of energy isn’t invisible. People listen.
You go into a date with a mentality of “this probably won’t work out in my favor.” And then you know what happens? It doesn’t. You’re guarded, less present, maybe even a little cold. You assume he (or she) won’t call. So he never does.
You walk into a pitch expecting rejection, so you don’t bring your full conviction. The lack of confidence is palpable. The “no” feels inevitable because you telegraphed it.
It turns out that’s a horrible way to live your life because you’re making it all come true.
And so it goes: Failure becomes prophecy fulfilled, authored by your own doubt.
So I vowed to assume a new mindset: changing “if” to “when.” Not if this works out but when it does.
That strategy works very well. Every time I change if to when, I feel powerful for five seconds — and then I remember the IRS exists.
If I get audited sounds a whole lot better than when.
But by and large, optimism begins to loosen the grip of doom. You show up differently when you’re expecting a yes, in a similar way to how you arrive when you’re on an actual good path in life. When all the good things come my way is a much healthier way to go through life than if they ever happen to.
When I could sustain it, the change was remarkable. ‘When’ made me feel like I had a future worth planning for. ‘When’ made me research restaurants for a next date I felt certain was coming instead of already writing the post-mortem of why the last one was a dud. ‘When’ let me actually listen during conversations instead of scanning for nonexistent signs of disinterest.
Optimism rewires the reflex that assumes a phone call means someone’s dead, mad at you, breaking your heart — or all three. That maybe — just maybe — it’s someone calling to say yes. And maybe — just maybe — it took them so long to call because they wanted to make sure to say the exact right thing in the exact right words.
So I go to bed every night and begin with a plea to myself to not be so sure everything won’t work out. As I drift off to sleep I try to imagine the scenarios I most want in every facet of my life — many are amorphous, some are specific — and let my subconscious and the universe go to work. It’s out of my hands now but I can sleep steady knowing I’ve done my part to get it all in motion.
There’s a fine line, however, between optimism and delusion. They overlap, but diverge at the root.
Optimism is grounded hope — the belief that things could go well, even if they haven’t yet. Delusion is hope with blinders on. It’s not just believing things will get better, it’s refusing to accept that they might not.
Optimism says, “This could work out.”
Delusion says, “This will work out, because I manifested it with a crystal I bonded with at a witchcraft shop in Silverlake while having a nervous breakdown.” (And that certainly never happened to me.)
I thought I was being optimistic. But I was deep in fairy tale — the part right before the final act when everything magically comes together. I wasn’t optimistic. I was writing fan-fiction. Like a romantic comedy extra who thought she was the lead. Once you’ve mistaken fantasy for forecast, it’s a slick and slippery slide back into the abyss.
When you’re not in it, depression is kind of hilarious. I see it for what it is. Overblown and hysterical. When I’m in it, I’m underwater in my own apartment, stuck in something bottomless. Can’t leave my apartment out of fear of being seen or burdening someone with my state. Can’t get out of bed because the world feels so unlivable and my legs physically won’t take me further than to fetch the remote. Outside moms are pushing strollers carrying giggling kids. On an 80 degree day everyone is seemingly playing hooky and day drinking outside Bar Pisellino. I, however, am catastrophizing and performing a one woman play of the end of the world. The reviews are abysmal but the run gets extended longer than The Fantasticks. And I am the only audience member who never gives her own performance a standing ovation.
Everything will be fine in a few days; everything, most likely, is already fine. From 30,000 feet, or even just the 20/20 hindsight of a few days, I will see this. But there’s no way to rationalize with myself because my feelings have gone from sad to devoid of all nerve endings like a tortured artist who has nothing to be tortured over. I am Picasso’s Lady in Blue. I am the embodiment of Edvard Munch’s Melancholy. I am a Tumblr account in 2013. I’m so dramatic and all I want is to tell myself to shut up and get over it.
Eventually, I come out for literal air. I leave the apartment for the first time in three days, blinded by the sunlight like a vampire emerging from a bender of self-pity and existential doom. Reborn like Jesus, I shake off my depressive crust like a dog. And where do I go? The same place everyone in this city goes to be alone together: a bar. Not because I need to drink, but for the company. Baby steps.
New York is a city just waiting to kill our optimism but in a way that almost nullifies our very rock bottom sadness. Get a fresh blowout? An air conditioner will drip on your head every three blocks. Feeling sexy in a sun dress? Bus rips by and blows exhaust up your crotch. Snagged a reservation at a trendy new restaurant? The waitress politely informs you, “we have someone else sitting here in 45 minutes so you can’t order anything cooked.” And this last one actually happened to me recently. We live in the greatest city on earth, never let anyone tell you otherwise.
So even when New York does its very best to smush your existential dread deeper into your soul, so that you and the invisible monster become one and the same, you sort of can’t help but giggle. Sure, it has rained 16 Saturdays in a row and a taxi cab baptized my suede cowboy boots barreling through one of the larger puddles on Hudson. I start to curse the day the driver was born and then take the moment for what it is: levity.
I begin to write about it as I’m lifting myself out of my mental manhole and know it’s not a distress signal. It’s proof that I came out the other side and always will.
I continued on my walk toward a wine bar. I sat down at Moonflower during one of the rare breaks in rain and fog we’ve had in the past month. The sun was trying its hardest to poke through the clouds. I chose a stool in the window. Good people watching and more exposure to the light — literal and philosophical. The waitress came over to take my order. I looked down at the menu and saw that the wine list was broken down by horoscope. The Aquarius wine looked interesting — funky and natural. I chose to believe the universe was telling this moody Aquarian that everything would be all right through a wine list. If God speaks through burning bushes, surely he can speak through vineyards too.
As she walked away to get my glass, I realized this was exactly what I needed — not just the wine, but this kind of gentle human interaction that didn’t require me to perform or explain myself. She brought the glass and I settled in, watching people hurry past the window while I nursed my cosmic recommendation and maybe the cosmos too. I barely took a sip, but holding it I finally felt a little closer to myself again. Small moves, soft landings.
No one understands melancholy quite like a bartender. They’ve seen it all. The grinning drunken make-outs, the drowning tears in a pint of Guinness, and the lonely just looking for a glass of wine and a momentary friend. I once told a bartender I was fine, just tired, and he replied, “No one drinks Sancerre alone on a Tuesday unless something’s wrong.” I tipped him 40% for the diagnosis.
Next I sat down at the bar at Gene’s (the marvelous Italian spot in the village with a G, not the place for underage girls who look like they just walked out of a Jacksonville tanning salon on Lafayette with a J), and ordered a glass of Chenin Blanc. The red rings around my eyes told a story of a week lived a little too hard, as I typed my heart out onto the keyboard in front of me. I was just starting to reemerge into the world, and my skin was raw. I told the bartender I was going through it. He nodded, poured himself a quarter glass, air toasted me, and said, “Same.”
We didn’t talk again for the rest of the evening. It was one of the better connections I’ve had this year.
And just so we’re clear, I’m very much upright.
Hope has better skin 🤍
https://open.spotify.com/track/5rAff9XfcWx7rguN3t0fkW?si=qAWcN-VbRUygLlRp7XBK0w