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TDG #001: Starting something old

Updates, social media, emails, the future, and dive bars.

Skylar Renslow
Skylar Renslow
6 min read

Greetings from Florence, Italy! It's a little cold and a bit rainy, which is all the more reason to cozy up in a little wine bar with good company.

This is my second time in Tuscany in as many months, so I'm starting to feel confident about how to do it right. I have thoughts, many thoughts. But those wine-laden thoughts will have to be saved for later. This week is about starting something old.

If you're wondering who the heck is talking right now - it's an understandable question. I haven't sent an email to this crew in over a year. So let's back up.

My name is Skylar, and I run the newsletter The Daily Grog. At some point, you signed up for my newsletter - a sad newsletter that has been collecting cobwebs for too long. Far too long.

Warning: this will be a long email, but I'll try to make it worth it.

An Update

The last 6 months have been some of the most surreal in my life. I left my job in tech (for the second time), packed up my home in Seattle, WA, and set off to Buenos Aires, Argentina. Since then, it has been a whirlwind through 14 (and counting) different countries across Europe and South America.

I've attempted something like this before, which turned out pretty disastrous, and that is a story for another time. But this time around, the extended trip, though not without challenges, has felt right.

These last six months have also allowed for some reflection. Introspection in many ways, but most relevant to our conversation today, is reflection about the medium through which I like to tell stories.

A word on social media

My relationship with social media is complicated. I have never really been that involved on social media. Like any good millennial, I had social media accounts, but the novelty always wore off quickly.

But when I started The Daily Grog, it felt like something I should do. All the good travel-related content is on Instagram, right?

But when some initial success was had on Instagram, the success of The Daily Grog and myself became tied to the success of The Daily Grog on Instagram. That instant gratification and constant dopamine hits just felt too good to ignore.

And like all good social media platforms, it took my attention and didn't let go of it. All creativity and content was devoted to the tantalizing notion of "going viral." Optimizing for social media too much is where I lost the soul of what I was trying to make.

In a recent Ezra Klein Show podcast - which is a must listen if you're remotely interested in the topic of media or politics writ large -  there was a quote by Ezra Klein that has really stuck with me:

I spent most of my 20s and maybe even my early 30s building up a social media presence...slowly I've left both platforms and people always assume I did it because someone said something mean to me...the reason I left wasn't because someone said something mean, it's because I became more and more sure I would say something mean to somebody. There's a way in which my thinking would become more like the averaged out system...we were always told we acted upon the mediums - we can put whatever we want on Instagram, we can put whatever we want on Twitter, we can put whatever we want on Facebook. But in fact, Facebook, Twitter, Instagram, TikTok, are in those periods putting what they want on you - they are making you more like them.

Sadly, that became true for me as well - the longer I've spent on social media, the more I noticed how it started to change me, how I think, and how I respond.

To be clear, much of this has to do with my personality flaws - fear of missing out, lack of confidence, and insecurity, imposter syndrome...I'll stop there. But I've realized it's almost impossible for me to have a healthy relationship with social media. Honestly I'm not convinced it's possible for anyone to have a healthy relationship with social media. Still, I imagine it impacts some people more than others.

Outside of the mental health-related struggles - I also started to feel trapped in the same algorithmic purgatory many other creators have. And seemingly, the only way to escape is to make more content. And not just any old content, the performative type we're coalescing on.

Slower Content

One's relationship with email, on the other hand, is straightforward. It can be read, deleted, snoozed, or consumed at one's leisure. Email is impervious to the changing tides of platforms. It's simple. It's personal. It's slow.

It probably seems rudimentary and archaic, given the multitude of platforms available to showcase any artistic work nowadays. But the rudimentary and archaic qualities of email are precisely the point.

Email also allows for the type of storytelling that I find fascinating. I've been fortunate to have incredible conversations with chefs, restaurateur, bartenders, distillers, and fellow travelers - many with really incredible lives and stories.

But it's hard to convey the earnestness of the owners (a husband and wife team) of a small jazz bar, pouring me a glass of their friend's homemade rakia, into a 7-second video. Or any kind of video.

But those moments are special. They are human. They make traveling one of the most rewarding activities around.

And they should be told.

So what?

Alright so I've just been ranting for more than 500 words for what?

Well, The Daily Grog is reorienting to be a newsletter first and foremost. You'll still find me on some social platforms and tinkering with other medium, but this newsletter will be the primary channel for my work. Moreover, the switch to a newsletter represents a refocus on writing for me. At this point in my personal creative journey, I think it's necessary.

So every Sunday, you'll receive something from yours truly about some travel-related topics:

This is meant to be a little corner on the internet, devoid of algorithms but full of people. Think of it as weekly fireside chats where we can talk about the esoteric intricacies of traveling, swap stories, find cool gear, and just talk shop. It'll be weird, it'll be fun - I hope you're in for it.

Dive bars

Phew, that was...a lot, but I hope it was helpful context for where I've been, what's been on my mind, and where I think The Daily Grog will go.

Time for the more fun stuff.

A topic that some friends and I discuss often is - dive bars. Yeah, that's right, those rough-around-the-edges, no-frills, no-bullshit watering holes that you probably pass by with little thought.

But it should be noted that a good dive bar is a necessity.

You see, a dive bar represents an egalitarian community of like-minded imbibers simply seeking a reprieve from the day's frivolities. No waxed-canvas-clad bartender serving you $18 dollar cocktails with homemade tinctures. Just a beer, or perhaps a whiskey.

Another great thing about dive bars is they are ubiquitous. You can go to the farthest corners of the globe and you'll find one. It may look a little different, but it'll be there.

Sadly these establishments are becoming harder and harder to find nowadays - if you find a good one, don't let it go. So in honor of the beloved dive bar, I wrote a little poem ages. It's incredibly silly - but I hope you enjoy it.

A tribute to a dive bar

Oh the humblest of watering holes
How you do stand the test of time!
You always seem to hold a range of souls
And cold beer hardly more than a dime
The clinking, the clanking of glass
The friends, both old and new
A place where many nights do pass
And if we’re lucky, we’ll only remember a few
Amidst a sea of pretentious libations
You stay steady through changing tides
Saving bartenders from superfluous creations
Keeping a place where tradition abides
The ice, the taps, the eclectic decor
Oh glorious dive bar
I hope you do stand forever more
ChelaCabur, a dive bar in the San Pedro de Atacama, Chile

That's it for now folks. If you made it this far down, I applaud and thank you.

See you next week.


P.S. Comments and replies are always welcome. Let me know if you have a favorite dive bar where you're at - I love hearing about all the good spots!

The Daily Grog Newsletter

Skylar Renslow

I mostly walk around, take pictures, and write things.


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