You've Got Mail: Hotel Routines, Fall Cocktails, and Brand Building

Answering your questions in 3,400 words.

Sep 04, 2025

∙ Paid

Each month on The Sunday Scaries Podcast, I’d do an episode that was completely dedicated to listener questions. While I had certain episodes I enjoyed recording, these were consistently my favorite episodes to put together. Answering questions that don’t naturally come to you is a great way of diving into uncharted waters, something I now do mainly through Wednesday “Ask Me Anything”-style stories on Instagram.

This week, however, I received a lot of questions that simply required more thought and time. I’ve always thought there needed to be a mailbag component to this newsletter, so what better time than now.

Here are all the questions answered in this week’s mailbag:

“What’s your routine when you walk into a new hotel room?”
“How do you choose which Sunday Confessions to choose?”
“What are the bougiest outdoor activities?”
“Earbuds or over-the-ear headphones?”
“Do you personally still get Sunday Scaries in 2025?”
“Which recipes would you include in a Sunday Scaries cookbook?”
“What’s going to be the Cocktail of the Fall?”
“What shoes are we wearing with our dad jeans this fall?”
“Do you have any tips for someone wanting to leave corporate America?”
“What did you do before Sunday Scaries? What was it like building the brand?”

Total Words This Week: 3,505

“What’s your routine when you walk into a new hotel room?”

The anticipation of walking into a hotel room is a rush that’s rarely matched. How many square feet is it? What’s the view like? Does it smell alright? Is there any marble in the bathroom? How nice are the robes?

I’ve loved hotels for as long as I can remember, and one of the most tangible “Sunday Scaries” occurrences in my life was leaving a Mexican hotel in 8th grade during spring break. As our airplane pulled away from the gate to head back to snowy Northern Michigan, I wondered to myself, “Why can’t life always be vacation?”

But for those times when life is vacation, here’s how I normally operate the second I enter the room:

Put my bag down, unzip it, and completely unpack. This is a new thing I’ve started doing in the past couple years and I’m so glad the change was implemented. Being unpacked makes it feel like less of a hotel room and more like a place you now live, if even for only a few nights.
Shower (and check if they have robes). While it’s nice to get the plane sludge off you, it’s also nice to be in a clean hotel room feeling spotless yourself. It’s a hard reset that normally washes away the annoyance of being in an airport for (likely) an extended period of time.
Establish the bed rules. This is normal a silent negotiation won by the person who puts their stuff on a certain bedside table first. Truthfully, I have no worries about which side of the bed I’m in when on vacation. Would I prefer a view? Sure. Do I mind being closer to the bathroom? Not at all.

From there, it’s all about getting your chargers and electronics plugged in before dashing to the hotel bar.

“How do you choose which Sunday Confessions to choose?”

Sunday Confessions has certainly emerged as a reader favorite on our Substack, and there are no complaints from me because I also find them to be highly entertaining. Most of the time.

Each week, I get about 300 total confessions that I go through first thing Monday morning. While I don’t always love starting my week with the dark, decrepit confessions of others, it is always a nice reminder that I have my life more together than I think.

When choosing them, I have some pretty loose parameters that I employ.

The first thing I ask myself is, “Is this actually a confession?” A lot of people use it as a sounding board to complain about someone or something in their life, so I always try to make sure it’s something you wouldn’t dare admit at a group dinner.

From there, I ask myself, “Is it entertaining?” This is a very broad requirement that essentially means something has to be funny, relatable, jarring, or empathetic. While some confessions may be considered more outrageous, I’m more likely to choose something funny and relatable than not.

The last step? “Is this true?” While most submissions feel true, it’s obviously impossible to vet them all given the anonymous nature of the column itself. While I hope people aren’t submitting falsities in hopes of getting posted, I’m also not naive enough to think they aren’t currently doing that.

Oh, and a final note on them: I won’t post any confessions that weren’t submitted on a Sunday. If people find the form mid-week or submit them at 9:30 on Monday morning, I simply gloss over them. To me, that authenticity is important. Even though it probably doesn’t matter.

“What are the bougiest outdoor activities?”

Here’s a list of random fall/winter-skewing activities off the top of my head, most of which are based solely on vibes:

Alpine Skiing — Bougie to do yourself, but amplified if you have (1) a baller après situation (2) a FIS race in the alps you’re watching or (3) you have a ski-in, ski-out situation on your hands.
Horse Races — As a 5-time Kentucky Derby attendee, trust me. And while I’ve never been to the Far Hills Race Meeting, it does appear to skew bougie as well. And incredibly messy.
Pheasant Hunting — But only if you’re at someone’s huge property drinking high-end scotch out of the back of a vintage Land Cruiser.
Sailing — And yes, this also includes going to America’s Cup races.
Golf — A sport that has become far too bougie in recent years, unfortunately.
Lying down hungover in a picturesque lawn near a body of water in a cable knit sweater — You get it.

I don’t know. Just make sure if you are doing a bougie outdoor activity, you aren’t being an insufferable asshole about it. I struggle with that sometimes.

“Earbuds or over-the-ear headphones?”

I’ve been operating like a mad man lately.

While traveling, I’ve been bringing three different pairs of headphones for different situations. Not only is this unnecessary, but it’s also a nightmare to bring enough chargers to make sure everything is humming as needed. Here’s what I’ve been doing:

Apple AirPod Max — These are my normal go-to for pretty much everything. Flights to drown out literally everything, in bed to silently enjoy whatever I’m listening to, and at my desk while working.
AirPod Pros — I got these through a deal we did with Apple TV for Severance. This is important to note because I will never actually pay for AirPods as I know I’ll immediately lose one. I use these mostly for calls, listening to something in one ear before going to sleep, or if I don’t feel like having a massive noise-cancelling headset on my head.
Wire Apple Headphones — I operate the same with these as I do with the above, but I use them more often. You don’t have to charge them, the microphone is better, they’re impossible to lose, and untangling them takes all of 30 seconds. Yes, it also makes me feel like a Wired It Girl.

“Do you personally still get Sunday Scaries in 2025?”

This is one of the most-submitted questions during every Wednesday “Ask Me Anything” on Instagram. The short answer? Yes. The long answer? Well —

Like everyone, I still have my intensely anxious moments in life. I’ve worried about frivolous things my entire life and I really don’t see that changing as I grow older. “You’re a worrier, you worry, that’s what you do,” my therapist once told me. And yes, actually acknowledging that character trait put things into perspective for me a lot.

She also began asking me to characterize how I was feeling when I approached those anxieties: “Are you worried, or are you stressed?” Worrying is needless energy spent on things that haven’t happened yet. Stress is normally a fixation on something you know could go wrong. While they feel similar, making these in-the-moment designations has helped me keep things more under control than ever.

The big difference is that it’s usually situational and not repetitive. So while I may get what one would consider “Sunday Scaries,” these may just occur on other random afternoons or nights when something large is staring me in the face. They don’t occur like clockwork anymore — and for that, I’m thankful.

(I also think not going out every weekend night is the biggest driver of ridding myself of them.)

“Which recipes would you include in a Sunday Scaries cookbook?”

I was in a funk on Tuesday. It was one of those days where nothing I did felt like it was working. Where everything felt like it took 10% more effort than it needed. Where enough small things went wrong that it felt like massive things were going wrong.

The way I decided to cure that slog? Going to the store, buying only the ingredients I needed, and making dinner. As the person who does the lesser share of cooking in our household, it felt soothing to be back in the kitchen again with all the responsibility on my shoulders. I made The New York Times Grilled Steak with Tomato Tartare. While it turned out fine and forgettable, it did get my culinary gears turning again for the first time in a while.

Here are the first things that come to mind for a Sunday Scaries-themed cookbook:

Dishoom Chai — We drank this all through COVID after visiting London and became the recipe I talked about most on The Sunday Scaries Podcast. Simply put, the cookbook would be incomplete without it.
Sunday Roast — While this will likely be a straightforward recipe, it’s too on-brand to omit.
Sally’s Coffee Cake — I eat this mainly for the brown sugar crumble on top, but a piece of this coffee cake feels like eating a warm hug.
Carbonara — We don’t make carbonara as often as we should these days, but it’s a recipe I often crave specifically on Sundays.
Pot Roast — You know, maybe I just need an entire “roast” section of the book. But if the weather is brisk outside, there’s nothing like the feeling of walking into the house with a pot roast in the oven.
The Defined Dish’s Fish Florentine — You can already see the recipe here, but this is an easy recipe that makes you feel pretty fancy. And for those weekends where you ate every calorie in your general vicinity, this is a great way to feel healthy.

“What’s going to be the Cocktail of the Fall?”

Last year while at Blackberry Farm in Tennessee, I filmed some cocktail content that really never saw the light of day. We spent about 30 minutes with their team making a few different cocktails, all of which felt very Cold Weather to me. While I’m not sure any of these will end up as “The Cocktail of the Fall,” I do think making these at home could be a great late-autumn activity.

Luckily, they were kind enough to allow me to take photos of the recipes. Here they are:

Blackberry Farm Penicillin (Rocks Glass)

2 oz Pig’s Nose Scotch
.75 oz Lemon
.75 oz Honey Sorghum Syrup
Atomizer of Lagavulin 8yr
Shake all ingredients except Lagavulin
Strain into a rocks glass with a big rock
Garnish with a Lemon Peel
Using atomizer spritz the top of the drink 5 times

Smoke off the Mountain (Rocks Glass)

2 oz Hi-Wire Smoked Bourbon
5 dashes Angostura Bitters
.5 oz Demerara Sugar Syrup
Mix ingredients in a mixing glass for 10 seconds
Strain into a rocks glass with ice cubes
Garnish with an orange peel and cherry

Back Country Flip (Coupe Glass)

1.5 oz Cynar
1 oz Sazerac Rye
.5 oz Clove Simple Syrup
1 Whole egg
Shake all ingredients and double strain into a coupe

And yes, you’ll probably see that unused content this December.

“What shoes are we wearing with our dad jeans this fall?”

Fall footwear is a gift and a curse for me. While I enjoy leaning into the season, I’m always a bit timid when it comes to purchasing. Next week on

Retail Therapy

, we’ll be recording our Fall Fashion Episode (normally one of our most popular episodes of the year) where we’ll do a deep dive. But overall, here’s what you’ll find on my feet this fall as it currently stands:

Tom Sachs x Nike General Purpose Shoe

I own two pairs of these and wear them pretty much everywhere. One pair is used for outdoor activities where they’ll get beat up, and the other is reserved for the office, flying, or times when I know they won’t get dirty. I wear these 90% of the time. They’re just a damn good shoe that I was lucky enough to snag at retail price.

Drake’s x New Balance Allerdale Trainer

Drake’s and New Balance Made in UK Allerdale Trainer

Are these shoes ugly? Yes, I think so. Is that kind of why I like them? Again, yes, I think so. The main reason I decided to purchase these is simply because I thought they’d be interesting to pair with a lot of the colors I already have in my wardrobe — dark green, plum, brown, and light green.

Crocs Quiet Clog

While I didn’t anticipate these becoming a staple in my rotation, I wear these for various purposes daily — playing fetch with the dog, watering the garden, running out for a quick errand. The ease of cleaning them has been the main factor for them replacing my Birkenstock Bostons, but I still miss the Boston life a lot.

Belgian Mr. Casuals in Lizard Calf

I originally purchased these shoes for my wedding in February of 2020. They’ve been my favorite dress shoes ever since.

After getting them resoled twice now, it’s truly like wearing a brand new pair of shoes each time I slide them on. Will I have the guts to wear them more casually this fall rather than just to nice dinners or dress-up events? Hopefully, but no guarantees.

“Do you have any tips for someone wanting to leave corporate America?”

Disclaimer: I’ve never worked in “corporate America” nor have I ever received a job interview to do so.

When I wanted to leave my previous job to pursue creative endeavors, it wasn’t as straightforward as it seemed. How can you justify leaving a job where you get regular paychecks to go in on something that currently pays me nothing? It was the main concern I had, but it was also the driving force.

When I first knew my time was up, I didn’t have many options for careers. But given that the career I chose wasn’t fulfilling me anymore, I knew I had to make a change. In making that change, I had to ask myself a lot of questions.

“What drives you?” For me, that answer was creativity. At the time, I didn’t care what I was doing but I knew I needed to be more creatively fulfilled.

“What are you good at that you can exploit?” For me, the answer was writing and graphic design. I knew that if I could deploy those two strengths somewhere, I could be reasonably successful.

“How can I monetize this?” The hardest question to answer. I wrote Sunday Scaries as a blog for two years before making any money from it. But deep down, I knew I enjoyed doing it so much that I was still willing to do it for free. Once I realized it had enough of a following to sell some t-shirts, well, things kind of spiraled from there.

While I don’t think I totally answered your question, that’s just a haphazard look at the three main things that drove me to go off on my own. But that path wasn’t a direct flight, as you’re about to see.

“What did you do before Sunday Scaries? What was it like building the brand?”

For seven years, I worked at a family-owned retail store named Huzza in Harbor Springs, Michigan. Self-described as an “independent family-run lifestyle store celebrating timeless design from past and present,” I found myself picking up a lot of responsibilities in my time there. Working the salesfloor, receiving and shipping orders, merchandising, inventory, cleaning, and anything else required at any given retail space.

In January of 2010, I moved to San Francisco for six months to build a website for the very same retail business. I handled the site design, wireframes for designers, UI/UX, and anything else that the project entailed. I had previously worked for a graphic design studio in college, so it was somewhat easy for me to naturally take on this job — a job that really wouldn’t exist in 2025 with sites like Squarespace and Shopify existing.

As I continued there, I began to reach the point where I knew I needed to move on. When I came back to Michigan from San Francisco, I moved back in with my parents and kept working in the store while also working on the site. While I enjoyed doing that creative work overall, I still wanted to do something that was creatively and personally fulfilling.

During the summer of 2012, I decided to start Sunday Scaries. What started as a blog on Tumblr then became a website hosted by Squarespace. While I had several different growth strategies, it’s growth was a slow burn that I enjoyed every second of. While working my job, I’d go home at night and dedicate hours upon hours to pouring myself into the blog. The way it all captured me was unlike anything I had ever experienced.

Knowing I needed to get the website out to larger audiences, I decided to begin freelancing for other websites. Most notably, Post Grad Problems in Austin, Texas. I saw the sites as being very similar at the time — PGP felt like the Monday through Friday version of Sunday Scaries, so it made sense to contribute weekly to them which I did from mid-2014 to mid-2015.

After some team changes at Post Grad Problems, it became evident they were looking for a full-time writer. I could tell that my writing had been doing well on the site, so it made sense for me to go all-in. In May of 2015, I quit my job in Michigan and decided to move to Austin, Texas to write for them full-time.

And for the next three years, that’s exactly what I did. The good news? The job itself gave me a lot of creative freedom that I had always wanted. Nothing was off limits, and they trusted me even when I decided to pitch things that no one really understood. The bad news? I had to put Sunday Scaries largely on hold for the three years I was there.

Once podcasting became more and more popular, I realized that there was a market for a show that releases on Sundays to help people with their anxiety. When I pitched doing The Sunday Scaries Podcast, they thought it was a good enough idea to pursue. Unfortunately, this all came at a time when the company was having several other issues. In January of 2019, I left to pursue Sunday Scaries in a more full-time way under the umbrella of Washed Media, something I’m still a partner in.

It wasn’t until early 2020 that Sunday Scaries really saw some monumental growth. The brand had existed in several different forms over the years — a blog, a merch vehicle, a podcast — but that was really it. In an effort to cure my COVID boredom, I began pouring that same graphic design experience I had into Instagram. Almost immediately, people enjoyed the style. And they shared, and they shared, and they shared.

Sunday Scaries went from about 20,000 followers in 2020 to over 100,000 by the end of the year. Today, there are almost 950,000 followers — truly an astounding number that I desperately try to not overthink.

While I was co-hosting Circling Back from 2019 until March of 2025, my responsibilities on the Sunday Scaries side of things became more and more significant. Knowing I had to choose one or the other, I ended up leaving Circling Back in an effort to accomplish things with Sunday Scaries that I’d always wanted to accomplish.

Today, I’m still in the midst of trying to accomplish a lot of those things. To everyone who’s been along for the ride, words can’t describe how much I appreciate you enabling to do what I love to do every single day.

If you have a question for a future iteration of You’ve Got Mail, please leave a comment below. Comments are limited to only paid subscribers, so I’ll make sure to prioritize any questions I receive here.

“What’s your routine when you walk into a new hotel room?”

But for those times when life is vacation, here’s how I normally operate the second I enter the room:

Put my bag down, unzip it, and completely unpack. This is a new thing I’ve started doing in the past couple years and I’m so glad the change was implemented. Being unpacked makes it feel like less of a hotel room and more like a place you now live, if even for only a few nights.
Shower (and check if they have robes). While it’s nice to get the plane sludge off you, it’s also nice to be in a clean hotel room feeling spotless yourself. It’s a hard reset that normally washes away the annoyance of being in an airport for (likely) an extended period of time.
Establish the bed rules. This is normal a silent negotiation won by the person who puts their stuff on a certain bedside table first. Truthfully, I have no worries about which side of the bed I’m in when on vacation. Would I prefer a view? Sure. Do I mind being closer to the bathroom? Not at all.

From there, it’s all about getting your chargers and electronics plugged in before dashing to the hotel bar.

“How do you choose which Sunday Confessions to choose?”

Sunday Confessions has certainly emerged as a reader favorite on our Substack, and there are no complaints from me because I also find them to be highly entertaining. Most of the time.

Keep reading with a 7-day free trial

Subscribe to Sunday Scaries to keep reading this post and get 7 days of free access to the full post archives.