Why I (finally) published an e-book of my writing

Over the week, I compiled some of my writing into an e-book that’s now for sale. The book Web Management For Regular People was an exercise in sharing what you know. I’ve been lamenting lately, the need to share with wider audiences than just the people who use Twitter or folks who have seen me speak.

It wasn’t about any of that, really. It’s about confidence. No matter how much I stand on stages, how many times I present, the idea of imposter syndrome is a very real one for me. I don’t care how many projects we ship, how many awards my teams win or whether people tell me I’m smart day after day. The fact is, I’m only as good as the last time anything good really happened.

So this was a long time coming, even though the actual execution wasn’t that difficult. I did some light editing (sorry in advance) of the older content, compiled the things that I felt made the most sense and organized them in GitBook and then exported them. I used Calibre to change the cover and make sure things didn’t look wildly insane.

Then I launched.

I could have been even more painstaking, but approaching products like this as a MVP rather than some kind of all-of-nothing proposition is the best thing for my sanity. It’s also akin to the ways that I’ve devolved my slide-making into a simple process with text and very few images. It’s had a positive impact on the ways that I present and it extends to the ways that I hope my writing is able to evolve.

Should I buy your book?

Not if you’ve read my posts in the past. You’ll probably not see a ton of things that are new. On the other hand, you can procure a copy for someone else. I realize a lot of more important people would want to read a paper book, but that’s not going to happen right now. I might consider doing a podcast version, if that would be more useful too.

I’m working on a few other projects this week. I’ve just had a few months where I wasn’t able to really produce much new content. Work kept me pretty much, so did things outside of work and getting more involved locally. I’m ready now to get back to doing the work that I love and sharing it widely.

The UX of online dating sites: Why You’re Meant To Fail

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Photo of teddy bear staring at another bear on a computer

I’ve been trying to explain to friends for a while why the design of today’s online dating apps don’t work to find them the love they seek. Depending on what you’re looking for, online dating can open a wealth of opportunities and possibilities that your neighborhood simply can’t compete with. One of the things we don’t ask ourselves anymore is whether this bounty of access is really good for us.

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Things Worth Reading (25 February 2017)

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Here’s the headlines:

Bees can train each other to use tools (ArsTechnica)
As an undergraduate, I took an insect biology class because I thought it’d be interesting. I didn’t retain much from those days, but bees and ants and their whole order fascinate me. This story tells what I mostly knew, bees are quite smart and apparently, can learn to use tools and teach other bees to do it too.

The Contestant Who Outsmarted ‘The Price Is Right’ (Esquire)
You probably don’t realize how much I love game shows. This is a story about someone who managed to get a perfect score in the showcase showdown, the first time (and only time to date) it’s ever happened, thanks to a Vegas card-counter. This is a podcast episode waiting to happen for some intrepid show.

Mars Needs Lawyers – (Five Thirty Eight)
Most people don’t realize that the majority of the treaties that govern space were drafted during the height of the space race in the 1960s. As companies continue to invade space, what will determine the rules of engagement as humans colonize space? Maggie Koerth-Baker talks about the need for more space lawyers.

The World’s Worst Skier Had Never Skiied On Snow (NYTimes)
I know a good half of my friends and followers are not regular sports fans, so I love introducing you all to these off-beat sports stories that I don’t think would otherwise end up on your radar. This is about a skiier Adrian Solano of Venezuela and his foray into the Skiing World Championships and his ‘unorthodox’ form. There are lots of warm-weather athletes who participate in cold weather sports despite no one in their country caring about that sport, the lack of training options and opportunities to get sponsorships. This one will be a useful dinner party story.

The Top 40 is anything but (Outline)
A glimpse into the outdated ways that music’s Top 40 charts get determined, radio programming gets dictated and as a result, why it fails to reflect the ways that real people listen to music in modern times.

How A Texas Teen-ager Became NYC’s premier truffle dealer (New Yorker)
Fascinating story of Ian Purkayastha and how he went from a Texas kid to one of the world’s foremost dealers in truffles? Life is a trip, man.

His book is my book rec of the week: Truffle Boy: My Unexpected Journey Through the Exotic Food Underground. 

I Lost My Olympic Dream By A Fraction of A Second (MEL Magazine)
I appreciated this story because I think there are few parallels to losing your dream when it’s not dictated by how hard you work, but by luck, timing and maybe someone being a fraction of a second faster than you were. I think there are not as many real life applications to this when your job is working in an office or something, but I still think it’s worth thinking about in the context of the work we do ever.

Listening: I’m always sharing old music with you all, here’s an oldies playlist I made years ago and it’s quite good.

Watching (Bonus): Speaking of game shows, did you ever hear about the Press Your Luck scandal of the 1980s? It’s about a man who figured out the algorithm and used it to win on the game for well over a month. Here’s the hour-long documentary that’ll be the highlight of your viewing.

Things Worth Reading (2/21/17)

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Here are this week’s articles:

How Albert Woodfox survived solitary (The New Yorker)

Why WNBA players go abroad during their offseason. (The Undefeated)

You’re about to see a big change to food sell-by dates (Washington Post)

How tech campuses hinder diversity (Wired)

How America counts its homeless & why so many are overlooked (The Guardian)

How To Navigate a Museum (NY Times)

Reading: The Happy Marriage (Tahar Ben Jelloun)
Listening: KCRW Eclectic 24 / Colorado Public Radio’s Open Air (via TuneIn Radio)
Watching: Jim Jarmusch’s “Paterson”

Things Worth Reading (2/16/17)

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Anyway, now let’s get to this week’s stories:

Sleep-Deprived Judges Dole Our Harsher Punishments (Harvard Business)
Turns out, justice is often dependent on a good night’s sleep from those exacting the punishments.

McDonalds reinvents the straw (FastCo Design)
Coming to a modern art museum near you, McDonalds new milkshake straw?

10 Stubborn Food Myths That Won’t Die (Lifehacker)
This is an older story that appeared on my radar, but still kinda interesting about the sort of myths that we harbor in the kitchen.

Science Fairs Aren’t So Fair (The Atlantic)
I think any kid that’s participated in a science fair, probably already knew this.

The Nerdy Artisanal Charm of Hand-Drawn Infographics (Wired)
If you’ve spent any time on Tumblr, you know this already. But nonetheless…

Video: In Istanbul, Cats are King (Wall Street Journal)
Soon to be the subject of a documentary, these Istanbul stray cats rule the roost.

Music: This Chance The Rapper cover of a Drake song “No Ways” is pretty great.

Reading: I’m half slogging through Mark Manson’s “The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life” via Audible, but I can already tell that I’m not going to be really able to get into it and it’ll be a return for me. I can’t recommend it.

You can send me a book recommendation, I would like to add it to my list.

If you want to subscribe to my podcast where I do this audio versions, you can do that via iTunes or Stitcher to whatever podcast app you use (or just search my name. It’ll come up.)

The Cost of Timestamps

Growing up, I loved getting mail. I recall waiting for the mailman on days when I was home. How much mail does a pre-teen get anyway? Not a lot. Some postcards, a note from my aunt stationed in Germany. Eventually, college packets and other junk would arrive as I got older. Instant messaging had at least a modicum of friction because it existed in a world where most people at home weren’t always online. I recall putting up an away message or letting people know when I’d be back, so there wasn’t an expectation they were being ignored.

These days, it’s almost impossible to keep up with everyone wanting a second of your time in one form or another.

In her book, Alone Together, Shirley Turkle explores this modern conundrum.

“Texting offers just the right amount of access, just the right amount of control. She is a modern Goldilocks: for her, texting puts people not too close, not too far, but at just the right distance. The world is now full of modern Goldilockses, people who take comfort in being in touch with a lot of people whom they also keep at bay.”
― Sherry Turkle, Alone Together: Why We Expect More from Technology and Less from Each Other

Nobody talks about the price of stamps as much as they used to, because we so rarely send personal letters. Postage matters when you care about Amazon sending you a flat rate package faster, but gone are the days of obsessing over the right amount of stamps for sending individual letters to your pen pal or friend across the pond who you haven’t called in weeks because it’s too expensive to do all of the time.

As marketers and product people, how often do we consider people’s time in our design? I’m not talking about page load times or the opaque “time on page” metric in Google Analytics. I once joked on Twitter that app designers should make their apps with the idea that people are driving 60 mph reading whatever it is on the screen. It’s a horrifying thought at first, but how much are we considering the stress cases that are a lot more unique than our ideal personas would have us believe. Eric Meyer and Sara Wachter-Boettcher explore this in “Design For Real Life”:

“As you write your personas and scenarios, don’t drain the life from them: be raw, bringing in snippets of users’ anecdotes, language, and emotion wherever you can. Whoever picks these personas up down the line should feel as compelled to help them as you do.”


Designers need to ask better questions about our complicity in a world that makes people more anxious through tools aimed at making our lives better. It’s not only an exercise in self-control, it’s recognizing the unwitting ways that our desires for connection leave us tethered when we should be more present. It might sell fewer widgets, perhaps fewer people will check into your app more. But what about thinking aloud about being human in the ways that we construct and design for real people? So much of our design is created for an aggregated populace; we traffick in habits and trends rather than real experiences. This construct makes it easier to detach ourselves from the impact and outcomes of design decisions made in an open-office somewhere far from where regular people are using what we make.

As apps proliferate, we have to ask ourselves whether every intrusion is warranted. Instead of thinking of our product as the one solving problems others leave behind, we need to confront each interaction as an intrusion. Every time we ask someone to track what they did, when they did it and assume they meant it as a result, we’re creating an imprint that might trigger a domino effect that transforms their life — not always for the better.

Things Worth Reading (2/12/17)

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Living with a parent most common young adult living arrangement (Pew)
For the first time in modern history, more young adults in the U.S. are living with parents than any other living arrangement.

Capturing James Baldwin’s Legacy on Screen (The New Yorker)
The documentary, “I Am Not Your Negro” is filling up screens all over the country. It’s an interesting look into the legacy of Baldwin from his own words and juxtaposed against the modern landscape of race in this country.

Toronto man found after 5 years, living in Brazil. (CBC)
Part of his journey to Brazil included periods of walking barefoot, but his family found him after losing touch and worked on finding him help for some struggles.

Joyous African Take The Rails, With China’s Help (NY Times)
China is investing billions in African countries, aimed at precious natural resource deals and creating more jobs for their own citizens. These extends to creating rail access in widespread parts of African countries that were previous inaccessible.

Sisterhood of the Skateboard (NYTimes)
A story I read earlier last year, but wanted to share for the audio edition of this newsletter, about a group of young girls who skateboard through Upper Manhattan and The Bronx.

The Blazer Experiment (99% Invisible)
From a podcast, 99% Invisible, this is a story about the Menlo Park Police department who in 1968 decided to experiment with putting officers in blazers rather than uniforms as a method to improve relations with local populace which was strained at the time.

Book: A Square Meal: The Culinary History of the Great Depression
Music: Priests – Nothing Feels Natural (LP)

Reflecting on a digital footprint

For the past week, I’ve been doing this thing where I read old posts. Not old posts on work things, but personal blog posts. Across the web, like a virtual office strewn with coffee ringed papers, I have content I’ve been saving for myself off and on. A lot of these breadcrumbs were not written deliberately for me to revisit, I simply wrote them at the time because it’s how I felt. I don’t do much of this anymore, because it seems passé to write longform blog posts ranting your feelings.

What’s been interesting about going back and revisiting the past, is the assurance I take from understanding my journey at the time and what was ahead of me. It feels like a long time ago and at the same time, it feels very recent. Thinking about that context, makes me start to realize that the next 4-5 years will look and perhaps feel very different than what life right now feels like.

It’s easy in the midst of frustrations, to feel like things are permanent. Getting a sense of perspective is especially difficult when you move a lot, because the people in your world only have a sense of your immediate life and not the roads you took to get where you are now. Lately, I’ve been thinking a lot of about mindfulness and arranging my life in ways to stay present with what’s happening now.

Going back and reading my archives has helped immensely, because it allows me a chance to reflect on thins that no one else would know. I can conjure memories of complexities and thinking aloud how I would get from whatever space I was in, to the next stage of my life. I can recall often feeling marooned and plain-old stuck. Reminding myself to be grateful for the progress and the process has been instructive.

1. Curbing my social media usage

The post-Trump world of Twitter is surely a mental drain. I just haven’t been as engaged to participate. Not only about politics, just about anything really. I can recall feeling like for a long time, the only true friends I had were living in other places and I’d use the web as an excuse to communicate with them since it didn’t feel like at times the people in my everyday life really “got” me. I realized over time, the problem wasn’t the people, it was me.

Cutting back my usage has been helpful, though I backslide. Instead of feeling like I need to post a photo everytime something happens, I’ll sometimes take a picture and record it later. I’m also more judicious about what I share. For a long time, I didn’t really have much to post about, so I think there was a long period of time where I felt really good to have things to share and would share EVERYTHING. I’m over it, now.

2. Please Remember Rule #6

Don’t take yourself so seriously.

3. Defining discipline for yourself

Maybe it’s the fact that I spent four years in the Air Force that makes me view the idea of “discipline” as something hard-faced, stoic and downright painful. In reflecting on my challenges with the notion of discipline, I’ve had to interpret my own notions of what discipline means for me and how to configure a life where discipline dictates the parameters of things I’ll do and won’t do. For instance, I’ve never been drunk. It’s not because I want a medal for it, I just can’t bring myself to drink anything to excess. That’d discipline, but I never thought of it that way before.

4. Being a contribution

Instead of spending days wondering precisely what will happen, I approach days with a question, “How Will I Be A Contribution Today?” I’ve long been mindful of contributing, I’d just never put it into those terms before.

Reflecting has brought me full circle with my past. I think there’s still a strong element of figuring out where the future leads and how to trudge that road. But knowing how you got where you are, has a lot of value for orienteering your way to the next port.