In Conversation With Madison podcaster,
Sam Georgson
Tell us a bit about you and what you do.
Hey there, I’m Sam and I’m a writer, blogger, content creator, podcaster and self-proclaimed digital marketing maven. I love to laugh and explore to new cities, I hate spiders and loathe winter sports. I’m an only child, an extrovert, and a leo. You can check out my published work and/or my personal musings at samanthageorgson.com and you can listen to me bitch about just about anything at pessimisticatbest.com or on your favorite streaming service.
The First Episode
Welcome to Pessimistic at Best—a podcast for complainers, by complainers, hosted by me, Samantha Georgson. In this episode I introduce myself, share my motivations for starting this silly little podcast, and complain about the state of the world to anyone who will listen, including you. Enjoy!
On Creativity
What does creativity look like for you?
At its core, creativity is just about expressing yourself. There’s no right or wrong way to be creative and I think that’s what makes it so special. For me, creativity comes in all kinds of forms. One of my all time favorite creative outlets is writing. I love writing and I think it’s such a great way to clearly articulate, well, anything—thoughts, feelings, moods, emotions—you name it.
Another outlet I’ve really only recently started experimenting with is podcasting and I’ve totally fallen in love with it. It’s funny because writing is something you can sort of perfect, you can write and rewrite a single sentence one hundred times until you get it just right, and believe me, I do. Then there’s podcasting, which is way more off the cuff and in the moment and I really love that piece. Plus, I mean, I could literally talk all day, so podcasting is a great outlet for releasing some of that energy, especially after the year we’ve had.
I also really love fashion as a form of self expression. It’s so fun to experiment with different styles and I think changing up your appearance can be a super fun way to be creative.
When did Podcasting become more than a hobby?
I love this question, because for me it actually happened in the reverse—the first time I worked on a podcast was for work, my boss had a podcast dedicated to educating salon owners about best business practices and that was my first real introduction to podcasting. I’m a huge podcast listener, and when I realized how easy it was to actually create a podcast I started playing around with the idea in my head. Then 2020 rolled around, I was furloughed from my job, I had a bunch of newfound freetime on my hands and I was starting to go stir crazy from not spending any of my social battery that I got serious about starting my own podcast.
My podcast is called Pessimistic at Best. The idea for my podcast actually came to me pretty easily. For better or for worse, I love to complain. I think it’s funny, and frankly it’s my favorite way to deal with my problems—is it the healthiest way? Probably not, but it’s the most cathartic in my opinion. Anyway, my partner is always telling me I could stand to be a *bit* more positive, which is probably true… and he’s such a good sport, he always listens to me bitch, but I know he gets tired of it. So, long story short, I was like this is perfect, I’ll call my podcast ‘Pessimistic at Best’ and it’ll be the perfect outlet for my bad attitude.
I like to say that my podcast is a part of my journey toward becoming a more positive person, but of course, we do plenty of complaining along the way. I’m really enjoying it so far, and I love having friends, family, acquaintances and even perfect strangers on to chat about their smallest pet peeves, their favorite pastimes, their shitty jobs, their biggest fears—all of it!
And I also have to give credit to my partner, because I couldn’t do it without him. He makes music and knows his way around audio editing software like you wouldn’t believe. I do all of the talking, but he’s the man behind the operation, bless his soul.
How would you describe the vibe?
I like to think that my podcast is a silly-goose time. Sometimes when I try to put the premise of my podcast into words, I’m like ‘wow, I must sound like such a bummer’ but I promise it’s not just like some giant bitch-fest, it’s silly-goose and my hope is that it’s relatable, a little sour, and gives you a good laugh.
What’s something people might not know about podcasting?
Hm, this is a great question. Well, I don’t think many people realize how easy it to start a podcast. I mean you really don’t need much, you could record a podcast from your laptop with the mic on your headphones today and upload it tomorrow. I mean, of course, having high quality audio is great, but you can get started with some seriously rudimentary tools. So, if you’re thinking about starting a podcast, don’t wait until you have the perfect mic or sound-proof recording set-up, just go for it!
Where do you find inspiration for episodes?
Honestly, I draw most of the inspiration for my episodes from my little hum-drum life and I think that’s what makes it so relatable. I love telling stories, I love listening to the stories of others, and I think that’s what makes a great podcast. And I mean, I’m sure my bad attitude inspires quite a few of my episodes as well.
What advice would you give to your younger self?
I love this prompt. The biggest piece of advice I would give to my younger self would be to stop worrying about what other people think. It’s so much easier said than done, and honestly, I think a lot it just comes with growing older and growing more comfortable with yourself, but I wish I had just a little bit more of that when I was younger, especially when it comes to creating something. I mean creating something and sharing it with others is hard and big and scary and it’s really easy to tell yourself you’re not good enough. I know I felt some of that when I first started getting serious about creating my podcast. And my podcast won’t be for everyone, but that’s okay, the people that love it are the people I’m making it for, aside from myself, of course.
A final note on confidence: I also think that as women, we struggle with this a bit more. I can’t speak for all women of course, but in my experience, in so many facets of our lives we’re told we’re not good enough. And it really feels like we can’t win—we’re too loud, we’re not loud enough, we’re too much, we’re too little, whatever it is, someone will always have something to say, it’s rarely worth listening. I just want all women to feel comfortable and confident in who they are and in their place in this world, there’s quite literally nothing sexier.
Any tips for fellow creatives?
My best piece of advice for fellow creatives is to just do the damn thing.
Rituals + Routines
What do you do first thing in the morning?
My morning routine is nothing to brag about. I’m working toward becoming more of a morning person, both because I feel like I’m supposed to, but also because I really do love mornings and I feel like a better human when I get up earlier and actually make use of the start of day, but for the most part I get up, stumble over to the coffee pot and log into work—capitalism at its finest!
What’s a typical day look like for you?
For me, a typical day begins with a morning run, a cup of coffee, and a delicious egg scrambler if my partner is feeling up to it (he makes the best eggs). I work from home right now, so my current get-ready-routine really only consists of changing into an acceptable top for Zoom meetings, which makes it a breeze to get to my desk by 8:30am for my first meeting of the day. Then, in the afternoon my partner and I break for lunch together, if we’re able, and enjoy an hour away from our desks. After work we usually try to get out for a walk before we cook dinner or head out to meet friends for a bite. Depending on the time, we might squeeze in an episode or two of whatever series we’re watching at the time, otherwise it’s off to bed!
Perfect Date night?
This one’s easy—take me to a concert, a show, anything. I love going to see live music and we’re really lucky to have so many neat venues in Madison. I actually really love seeing shows at smaller venues, the experience is a bit more intimate, the drinks are cheaper and the vibes are top notch.
Where would you take someone visiting Madison?
Ooh, so many good places! I recommend visiting Madison in the summer, there’s so much to do. We’d obviously start our morning at the farmer’s market which wraps around the entire block of the Capitol Square. It’s the perfect place to grab coffee, pastries and you absolutely have to try the spicy cheese bread. Then we’d walk down State St., shop a little, grab another coffee or stop for lunch before heading to the Union for a beer.
The Union is right on Lake Mendota and it’s the perfect place to spend the afternoon, don’t forget your sunscreen!
Then we could head back up to the Square for dinner, there are so many good restaurants but one of my favorites is Graze. The menu is locally produced and the view of the Capitol is unparalleled, plus they make a mean cocktail. Finally we could patio hop around downtown, there are so many stops for drinks and everything is basically within walking distance, it’s the best.
tl;dr
— To Eat: Graze
— To Drink: Genna’s Lounge
— To Shop: Good Style Shop (Favorite thrift store!)
— To Do: The Union (Live music!)
What do you do to get out of a creative funk?
This one is hard for me because honestly, I suck at this. In my experience, it’s best to just give it time. I experience this a lot with writing, and I haven’t found any magic solution. I believe it’s best to set the project aside and direct that energy toward doing something else you love. For me, that usually means spending time with friends or family, bonus points for getting outside, it never hurts to spend a little time with Mother Nature, she can be v inspiring.
How about to unwind?
Actually, this one can be tricky for me too. I tend to be very go-go-go, but the pandemic has forced me to slow down a bit, and although I’m bored out of my mind and itching to get back out into the real world again, I can honestly say that I’m learning to appreciate my downtime a little bit more. One of my favorite ways to unwind is to curl up with a good book, or perhaps more often my kindle, and a glass of wine.
Fun Stuff
Rapid fire recommendations
— To Eat: Pork Buns
— To Read: The Goldfinch (One of my favs!)
— To Watch: Gilmore Girls (I’m a stan)
— To Buy: Vintage anything and everything
— To Consider: Astrology
What’s missing in…
— Your Closet: Shorts (I sort of hate shorts…)
— Your Pantry: Popcorn
— Your Bag: Chapstick
What is something most people would be surprised to find out about you?
I don’t know why, but people are always surprised to learn that I’m an only child. I think a lot of people have these weird stereotypes about only children, that we’re spoiled, self-centered (I *am* kind of obsessed with myself, but I feel like that’s a good thing, we should all be obsessed with ourselves!), and another I’ve heard is that we’re usually shy… I don’t know, I guess I give off that sibling-type energy, but it’s always just been little old me!
Gif that sums you up when you’re at your best:
And your worst:


3 centimeters by 2 centimeters, black