Being a UX Author and Poser in Hollywood

UX Strategy (2nd Edition): Behind The Scenes — Take 3

Jaime Levy
8 min readSep 20, 2019

I can and can’t believe it’s taken me another two months to post an update. So here’s where I am now.

Library at the California Institute of Technology (Pasadena, CA USA)

I had to come back to the same place I wrote the first edition and even sit in the same exact chair because I suffer from OCD writer’s syndrome. As previously mentioned, I’ve discovered the only way to knock out pages is to have a set routine. And my new one is different than in Berlin where I was taking a bus to the library and dealing with the heinous process of sorting my authorized possessions into a special clear plastic library bag, hiding any edible food in my jeans, and then walking around for 15-minutes to find an available desk. Now I’m back to driving the 13-minutes to the Caltech parking lot, parking there without a permit, walking the 8-minutes to my preferred campus library, and then hoping my special writing chair is available. Sometimes I sneak food in and other times I eat in their massive cafeteria which actually has some decent food options. I still miss and prefer Berlin… it’s just not a crazy romantic adventure writing in Pasadena.

But progress has been made…

When I returned to Los Angeles, I had already conducted an extensive online interview with Matt Stein, the VP of Product at Metromile.

https://www.linkedin.com/in/mattjstein/

Metromile is a San Francisco-based mid-sized startup that aims to disrupt the auto-insurance industry with their innovative business model and use of telematic technologies. I switched to them for my own car insurance after I learned that I could cut my monthly insurance bill in half. This is because their pricing model is based on miles driven, and I fit perfectly in their targeted customer segment: low-mileage drivers who don’t have long daily commutes and drive less than 12,000 miles per year. They also have a fantastic app with a bunch of cool features that I describe in the 2nd edition. But I didn’t realize how perfect an example of stellar UX Strategy they were until I got nailed by a mobile texter (a driver who texts while driving) on my way home from a meeting. I truly got to experience their aha moment when I used their platform for reporting the incident and then dealing with the repairs. Let’s just say their UX Strategy and Customer Experience is off the hook and Matt Stein is the man in charge of the whole shabang.

First part of long ass email to Matt

So I wrote him a long ass email to request an interview and permission to profile him in the 2nd edition. Shockingly, he quickly responded with a “Yes”! I set up the interview for a couple weeks off so I had time to prepare, which included reading all of Metromile’s press, researching their direct competitors, trying to piece together their origin story, and then preparing a set of questions.

Partial list of prepared questions

Link to the full list of questions here

My main challenge with profiling Metromile was getting the tidbits about how they started that weren’t mentioned in the press. Three of my four tenets were quite apparent: their Business Strategy, Value Innovation, and Killer UX. But whether they conducted Customer Discovery for gathering Validated User Research was an unknown. And as I learned, the Customer Discovery phase happened before Matt was hired. But with a little prodding of Matt, and Matt prodding their founders, I did find out how they got their initial start and were able to onboard new customers with the first online version of their service.

The next step was nailing the storytelling – I needed Metromile to be my lead story at the very beginning of the book. It’s actually pretty tough to grab readers and get them to read a book. And as you know, we often make a decision if we are going to buy or read a book based on skimming the first few pages. This is of course only after we have read enough positive book reviews or recommendation lists to warrant us wanting to read the book in the first place. But since I’ve obligated myself to doing a 40% rewrite, I need a lot of new content while maintaining the structure of the first book.

My first book is actually like a house of cards; so pulling out a structural bottom card like the Drug Treatment Center business case requires a steady hand because it is used to explain several techniques throughout the book. UX Strategy is a nonfiction tech book which means it’s not just a methodology or “How-To” book, but one that weaves together multiple narrative threads to keep readers conceptually engaged.

And for this reason, I have been really working on my storytelling skills since my first book came out… to improve both my writing and public speaking skills. I first took an improv class at Upright Citizens Brigade in Hollywood about two years ago. But because of my crazy UX conference touring, I missed too many classes and they failed me. So I took the same class again as a week-long intensive and passed it. Admittedly, I’m not a big fan of improv as a viewer or a performer, even though I have often enjoyed shows like Saturday Night Live. It’s just really hard to get improv right. But it truly helps to learn the techniques when it comes to teaching, bullshitting with clients/potential clients, and the Q&A portions after doing keynote talks. The common adage in improv is that you must always say “yes, and” after an idea is stated. You never shoot down someone else’s idea. Instead, you run with it and build on it to create something unexpected by the audience.

Truth be told, the primary reason I took the improv class was because it was a requirement to get into their storytelling elective. This class was particularly popular for posers like myself who aspired to get up on the stage at a Moth storytelling event. I was able to make it through the class the first time through, and I learned a lot about structure, editing, and performance skills. One of the seven students in my class made it all the way up to the final slam in Downtown Los Angeles. But I just could not summon the courage to get up in front of a Hollywood “writers” crowd, often peppered with hipster celebrities, and I still have yet to put my name in the hat.

The first day of class, I was a total joke trying to sneak up my laptop like it was a UX talk. Nope, both with storytelling and stand-up comedy, you have no props when you are up at the mic. I felt naked without my clicker, and I soon realized that I needed to learn rote memory techniques in order to talk for five minutes without one of my blingy slides to remind me what I was going to say next. What worked for me was first reading the story numerous times to get the flow right. Then I would record it using the Voice Memo app on my iPhone. And then I would play it back in larger and larger chunks, each time repeating it back until it was committed to memory. Additionally, when I do keynote talks I memorize the first two sentences of my talk. This helps me kickstart my talk with great emphasis and get past the initial stage fright.

So then I moved on to something even more intimidating, a stand-up comedy class at Second City in Hollywood. I took it with my dear friend Marjorie Kaye, another UX Strategist who happens to be quite funny. I have to say, if you are nervous about taking classes, take them with a friend. It just makes it a lot easier, especially if you want someone to work on material with who knows you really well. This class was the most useful of all of the classes I took in terms of both writing and performing. Each week we worked on something different, including microphone technique, one-liners, storytelling, impressions, and crowdwork. Like the other classes, it culminated with a group show where we could invite family and friends to attend. And yes, I did invite my then 13-year-old son to see me perform a bit about getting my first Brazilian wax.

Since then, Marjorie and I have been to at least five open mics in Hollywood where we did get up on stage and learned to be totally okay with bombing. Bombing is to stand-up what failing is to an MVP experiment when doing product strategy. The more you fail (so long as you learn from it), the less scared you become of failing and the closer you can get to succeeding. Practice, practice, practice. The biggest reward from taking all of the aforementioned classes, along with the bombing experience I had in Hollywood, is that it has given me greater insights into deconstructing the art of storytelling so that I can more confidently apply it to the 2nd edition of the book.

And here’s me using my improv, storytelling, and stand-up skills in a keynote in Rio last year in a talk called “From UX Strategy to Digital Transformation”.

2018 Interaction Latin America — Rio De Janeiro, Brazil

On August 30th, I hit my deadline and turned in the first two chapters!

And you can bet that I worked all the way up to less than five hours before they were due. They needed to be pretty close to complete so I could get them approved, which meant I needed to turn them over to my magical UX Strategy first edition book editor, Sarah Dzida. Sarah does not work for O’Reilly Media, but she has worked for and with me for numerous years as a UX designer, strategist, and editor/writing mentor. She’s also an amazing author, writer, UX writer, etc., so of course I engaged her again to be the editor of the 2nd edition. Sarah reviewed the chapters and gave me feedback in Google docs.

https://www.linkedin.com/in/sarahdzida/

And even though I turned the chapters in, there are still several areas that will need hashing out over the next eleven months. Perhaps some of you saw me asking questions on LinkedIn, such as whether to go with Slack vs. Spotify for explaining the connection between Killer UX and Value Innovation. Some of the comments made me realize that crowdsourcing feedback is an incredible way for making editorial decisions. It has also helped me identify subject matter experts to interview. And most importantly, it has made me realize that this time I’m not all alone, trying to figure something hard out in a library.

Please CLAP 50 times if you dig!!! Thanks for all your support!

Link to the last post, Take 2 –“Writing UX Strategy II in Berlin”

UX Strategy & Design Services | Author of “UX Strategy” |​​ University Professor

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Jaime Levy

Me = UX Strategist, author, university professor, mom, experimental music lover.