What High Maintenance Teaches Us About Storytelling

Kate Mills
RE: Write
Published in
5 min readNov 16, 2016

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The college student struggling with family expectations and tradition.

I have always been a little obsessed with the written word and the secret lives of people. As a kid, I was set on going into journalism for my adult career, like my grandparents did before me. When I got to college, however, I was a journalism major for one week before my first class on the media sent me to the advisor’s office looking to change to Film Studies. A couple years into college, I added on an English major because I was most of the way there anyway, having taken a multitude of literature and creative writing classes as electives (a trend continued from high school — totally cool, I know).

I will note here that I was an English Literature major, not a Creative Writing major. I never felt like I really had what it took to pull that off, and I may or may not have had a small issue with authority and taking constructive feedback when I was younger (I hope I have gotten better at that).

The blind daters — an episode that went from feeling boring to making me bust a gut laughing to warming my heart. ALL IN 6 MINUTES!

Regardless, I have always wanted to be a writer. Some of that finds an outlet through doing things like this — writing weekly on Medium. I will also periodically start a new blog, or get a story idea and write out a short story. Or that as-yet-unfinished YA novel that I started a few years ago and hope to one day complete. The characters still live in my head, and I am always taking notes on them and the world they live in.

And then there is the designery part of storytelling that I now find myself doing — and enjoying — for school: research, personas, and user journeys and scenarios. Digging into the lives of people and really getting to know who the user is that I am designing for. What makes them tick? What frustrates the hell out of them? What makes them do what they do or like what they like?

Cousin Matthew, except for a writer and stay-at-home dad.

I have taken the sage advice of my teachers and created personas that are based on research rather than my own assumptions about people. And there is another piece of sage advice that is always tickling at the back of my mind as I am writing out the story of my research-based personas, and that is this: personas feel the most real when they do something unexpected, something against their own self-interest. This is often where you will find the tension that you can design against.

Even if they are based on research of real, live people, the storytelling aspect of writing compelling personas is key. How do you bring them alive? How do you make them feel real to you or your team as you are in the design process? In the interest of writing compelling personas, I continue to seek out good examples of storytelling: sometimes in the form of the written word, and always depicting the secret lives of people.

The dogwalker.

Often that comes in the form of literature or the awesome storytelling of some of my favorite podcasts. Most recently, it has been High Maintenance, previously a web series and now an HBO series. It was created by husband and wife team Ben Sinclair (who plays The Guy) and Katja Blichfeld. To say I am obsessed is an understatement. I have watched the entire first season of full-length episodes on HBO and, as of this weekend, all of the short, 5–6 minute web episodes (webisodes?). I am a little heartbroken that I am now out of new material to watch. High Maintenance, why can’t your stories go on ad infinitum?

High Maintenance is one of the best anything in recent memory when it comes to storytelling. Within the same minute, an episode will go from being deeply touching to making me laugh so hard that I have to hold back tears. If the full length episodes are a joy, the web episodes are a wonder. They do in 5 minutes what many full-length movies fail to do in 2 hours.

The guy who loves Helen and is afraid of the world. My favorite.

For the uninitiated, High Maintenance tells the stories of New Yorkers who directly or indirectly are connected by one weed dealer, The Guy. But really, it’s not so much about weed as it is about the lives of people of all kind. The people of High Maintenance are eerily real; often when watching, I have thought, “I KNOW THAT PERSON! HOW DID THEY DO THAT?” What makes these characters so real? Let me throw it back to some of that sage advice: quite often, they do something unexpected or that is against their own self-interest. But here’s the thing: it’s never out of left field entirely. It always makes sense because of the people that they are.

And here’s another thing: sometimes the characters do exactly what you would expect them to do. And that always makes sense too because — you guessed it — of the people that they are.

The best friends.

These studies of people, who are sometimes funny, sometimes sad, sometimes touching, sometimes funny, sometimes annoying, sometimes spontaneous, sometimes awful, sometimes wise, will be a goal for me to aspire to. As I continue down my design journey, I will always work to know the story behind the person(a) that I am designing for. In this way, I hope to design for real people, and not for myself or the assumptions of others that I hold.

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Kate Mills
RE: Write

I do design things. Maker of stuff, grower of plants, eater of snacks. @lollerk8 // katemills.co