Sam Georgson
Pessimistic at Best
Welcome to Pessimistic at Best , a podcast for those with a penchant for frequent frustrations, personal gripes, unpopular opinions, honest observations, and the like. Hosted by Sam, your resident Pessimistic Patty, this weekly show operates on the belief that no complaint is too small. Each week, Sam sits down with a guest to explore t he good, the bad, and the ugly . A surprisingly good country album by your favorite pop artist, a bad bang trim you gave yourself during a manic episode, a military homecoming video on the internet that made you ugly cry. The list is endless, and therein lie...
Author
Sam Georgson
Category
Podcast website
Latest episode
May 12, 2026
Where to listen?
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Episodes
A Festivus for the Rest of Us 20.12.2022 32:00
Happy (almost) Festivus! Are you familiar with the holiday? Originally coined by Frank Costanza of Seinfeld, Festivus is a holiday based around the airing of grievances, a practice I’m quite comfortable with myself. Are you familiar with the TikTok trend, “the ick challenge?” Think of Festivus as the original ick challenge and join us as James and I air our grievances or share our icks with one an...
In His Flop Era 13.12.2022 37:42
Did you survive your work holiday party? We made it out alive, but not without taking a few Ls (literally) along the way. To sum it all up, I left my credit card at a bar after making the conscious decision to open a tab (classic) and James swapped jackets with one of my coworkers and lost his wallet in the process. So, naturally, the next morning was spent traipsing around Madison in search of cl...
That Wasn't on My 2022 Bingo Card 06.12.2022 32:15
We’ve been back and forth between Chicago and Madison quite a bit recently. We went home for Thanksgiving, brought the cats, Misho went down the laundry shoot, James shot a deer—it’s been eventful, to say the least! Anyway, we're heading back to Madtown this weekend for my work holiday party, wish us luck, xoxo. Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Fac...
The “R” Word 29.11.2022 1:06:59
Have you heard of the Camino de Santiago? It’s a popular pilgrimage through the north of Spain and my dad just finished his trek. He took the “French Way,” which is roughly the same length as the journey across the state of Wisconsin. Now that you have that perspective, does that make it more or less cool? For me, it’s tough to say, but I can confirm that I would not want to spend 45 days walking...
Susan’s Applehole 22.11.2022 1:04:35
Coworkers by day, Daycatcher groupies by night—we’re just a couple of girls slaying the social media game before pounding a respectable amount of Twisted Teas™ at a basement show and if that’s not your vibe, we don’t want it, sister. Ginny was my first hire at work and now she’s stuck with me forever! Join us for a conversation about surprises, long-distance moves, Ginny’s first snowfall as a Wisc...
Do You Think of Me Differently Now That I Have a Ring Light? 15.11.2022 38:36
The rumors are true—I bought a ring light. Which officially makes me the worst and most famous person that you know. What you decide to do with that information is frankly none of my business. In the meantime, follow me on TikTok, xoxo. What else have you missed? Let’s see—James had his first Chicago show, I lost my credit card, and I’ve officially started beef with our neighbor who somehow manage...
Fight or Flight 08.11.2022 33:31
Serving up my second public apology on a silver platter, honey! I’m genuinely so sorry for going completely MIA for a full three weeks. I had two back-to-back trips (because I’m rich) and am truly terrible at planning ahead but I’m back and ready to bitch about my least favorite airline, brag about my new iPad, totally rock your world, etc. Get silly with us on social: FOLLOW THE PODCAST Instagram...
A Crazy Amount of Squash 11.10.2022 34:20
James released an album (Playhead, out everywhere, xoxo!) and I asked him if he wanted to be on the podcast to promote it like a *real* guest and he laughed in my face! Anyway, join us for a conversation about tunes, tummy aches, and tons of squash if you’re into that sort of thing. Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest Website:...
Camp Girls Who Can’t Swim 04.10.2022 1:01:06
Were you a camp kid? Typically, most of us fall on one side of the fence, but then there are those of us who landed somewhere in between, went to camp, became obsessed with pop culture, and eventually started podcasts rooted in pessimism—just us? Oops! Anyway, meet my internet-friend-turned-real-life-bestie and learn more about life in Toronto, the reality of the dark web (AKA Reddit), how to play...
Living in Abundance 27.09.2022 1:14:08
We’re giving rich, we’re giving luxury, we’re giving opulence, honey! Jake, my former intern turned work bestie, also just moved to the Windy City™, and to say we’re thriving would be a massive understatement. Is our rent too high? Duh. Are our Ubers outrageously expensive? Obviously. But we’re rich in experiences, baby—and that's what counts. We’re just a couple of city gals living in absolu...
Chronically Online 20.09.2022 1:30:36
From the unanswered question surrounding Lea Michele’s ability to read to the Don’t Worry Darling red carpet drama to the Queen’s death (RIP in peace), it was quite the week—especially for those of us who simply can’t pry our eyeballs away from the internet. Sara and I are social media managers by day and pop-culture connoisseurs by night. We’re just a couple of gals with an incurable disease in w...
Running My Silly Little Errands 13.09.2022 47:19
Scheduling a dentist appointment to cement myself as a Chicago resident, wbu? Seriously though, there’s nothing quite like running undesirable errands to make you feel established in a new city. A trip to Milan Laser is next—time to fill that calendar, honey! P.S. Justice for Tasha, Love Island Season 8. xx Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pe...
Crying in Public 06.09.2022 38:57
We’re BACK! Did you miss us? Because we sure missed you! It’s been eight long weeks, but to recap everything you may have missed—we made the big move to Chicago, one of us has picked up a new habit of crying in public, and the other’s been dabbling in AMAs on Instagram. Anyway, it’s great to be back! Season four, here we come. ;* Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimis...
Being More Intentional or Whatever 28.06.2022 41:05
And that’s a wrap on season 3! Join us for a mid-year intentions check-in where we discuss how little I’ve worked on being better at spending time alone and how much more “intentional” James has been since setting his new year's intention as being more intentional. Confused? Same! Hope to figure it all out once I turn 26—see you in August, xx. Get silly with us on social: FOLLOW THE PODCAST I...
Hot People with Tummy Aches 21.06.2022 47:22
James and I just got back from the PNW, are you jealous? We thought so! We took a trip up to Seattle and Vancouver to visit friends and family and had a blast, but unfortunately, we also had tummy aches the entire time—you win some, you lose some! Enjoy this little trip recap and see if you can guess what made our tummies hurt! xx Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimi...
Computer Games Raised Us 07.06.2022 2:03:09
Did you grow up playing computer games? Did you base your friendships on whoever had the best internet connection? Did your parents take money out of your allowance so that you could be a member of both Club Penguin and RuneScape? Well, you're in luck, because Annie and I can very much relate! Tune in to this week's pod to listen to us reminisce on our early friendship, divulge our elem...
The Crushing Weight of Existing Online 31.05.2022 31:26
For someone who works in social media, I admittedly have absolutely no idea how to be online. I can’t remember how to Instagram, I still don’t know how to Tiktok, I’m on BeReal for some reason, and I’ve recently developed social media anxiety? Cute and hot! James and I take to the pod to discuss the crushing reality of existing online whilst trying to promote our various projects, the irony of onl...
Sitting Next to Someone at the Airport is Brave 24.05.2022 44:56
Something that nobody’s talking about is that it’s actually really brave to sit next to someone at the airport. Personally, I would never be caught dead doing something like that, but to each their own! Desperate for more airport etiquette by yours truly? You’re in luck! I just got back from a work trip and I saved all of the juicy details just for you, tune in! Get silly with us on social: FOLLOW...
You Literally Can’t Go Home If It’s the Weekend 17.05.2022 46:37
Did you know that during the weekend you’re supposed to spend as little time at home as humanly possible? That’s right, Saturday and Sunday are for leaving the house and never returning. You literally can’t go home until Monday, if you do you’ll probably light on fire! Anyway, here’s what’s been keeping us busy on the weekends when we leave the house. Get silly with us on social: FOLLOW THE PODCA...
Life? She’s Messy! 10.05.2022 38:27
Most of the time you plan your little events and your trips and your dinners with friends and life is good, other times you have a quick menty-b and dissociate at work while looking at memes about having your rights stripped away, it’s called BALANCE. Ironically, the week that I return from my unplanned podcasting hiatus just so happens to be National Mental Health Awareness Week, perhaps a sick j...
Water Is Not a Beverage 12.04.2022 34:26
The #1 rule that I live by is this: If you consume three or more specialty beverages within a short period of time, that automatically means you’re having a good day. And just so we’re crystal clear, water is not a beverage. We’re not here for hydration, we’re just here to sip our little drinks and be merry. It’s simple really. What else are we drinking? We’re drinking the Shonda Rhimes Koolaid, h...
Just a Couple of Gals Doing Local Things 05.04.2022 53:26
Hobbies are exhausting. I know because I have one, it’s this podcast, and I’m literally tired all the time. Now just imagine having enough hobbies to own and operate 17 [seventeen] different Instagram accounts. This week on the pod, I’m joined by my internet acquaintance turned real-life friend Sigra to chat about all of her various avocations which range from bands to bugs. She’s 10x more interes...
Meet Me at the Impound Lot 29.03.2022 40:55
We’re back after an unexpected hiatus, so it’s time to ask the question—did you miss me? Because boy, did I miss you! Let me start by apologizing for my unplanned absence, last week was truly a week from ~hell~ and I simply needed to take a beat. The good news being that my streak of terrible luck left me with plenty of fuel for the pod. Ready to catch up on everything you missed? Well, buckle on...
She’s Not a Regular Art Teacher, She’s a Cool Art Teacher 15.03.2022 1:07:54
Girls who had their friend's parents blocked on Twitter in high school (*cough, cough*) now have severe social media anxiety. Can you imagine growing up with social media today? It was one thing to stress over which song you were going to select for your Myspace profile, but being 16 and feeling the pressure to be hot on main ? Pass! This week on the pod I’m joined by none other than my best...
A Bout of Seasonal Depression or Whatever 08.03.2022 34:55
Gorgeous, gorgeous girls suffer from seasonal depression! I don’t know about you, but this gal is desperate for some vitamin D. Winter sucks for a myriad of reasons, but first and foremost the fashion is absolutely atrocious. Practical footwear? Parkas? If I have to even so much as look at my winter coat again, I’ll scream. Then there’s the snow, the cold temps, the dry skin—anyway, we’ll just be...
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