The Value of Conferences

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Was listening to this episode of the Working File podcast on the value (or not) of conferences. Specifically, the part where they were talking about reaching that point where speakers often do not attend events, but will speak at them. I have fallen into this loop where I just don’t have the time to also attend conferences that I don’t speak at.

I’m not sure when this switch happened. It probably has something to do with the fact that I went from speaking at conferences I’d attend anyway, to eventually pivoting from a “scene” to “different scenes” and eventually realizing that while there are events I’d love to participate in, there’s only so much time you can devote to such shenanigans. For me, the real truth is there’s a lot of anxiety with attending new events especially when you don’t know a lot of people. Being a speaker sometimes affords a status that sometimes makes it easier to talk to people without having to walk up to them and see what they’re into. It’s part of why I like speaking on the first day of an event, I find if people realize I’m a speaker and after they see me talk, they’re more inclined to chat with me and it saves me the awkwardness of figuring out who the ‘friendly people’ are.

As a speaker who is also an event organizer, I have spent a lot of time trying to curate the conference that’s welcoming, inclusive and warm. It’s not an easy feat, but it’s something I feel very strongly about and feel like we were able to accomplish with #GGRGT.

There are no easy answers, but there’s probably something of a conference bubble happening right now. The same 7 people get invited to speak at everything, depending on the industry. Smaller events do a much better job of providing speakers and attendees with a better experience. There’s impossibly difficult to cultivate new voices, because everybody wants to see people who have been vetted, but you can’t vet people without giving them a chance to flail (and possibly fail) on stage. I know there are events who do intensive pre-conference training that turn the speaking event into an almost full-time job, but that’s not tenable for most people.

It’s an issue that I think everyone is complicit in. Speakers, sponsors and organizers alike. More conferences need to be one-off events rather than sustaining communities that overlap. I like participating in conferences beyond just speaking, especially once my talk is done because it makes it easier to be involved. There’s a solidarity that often develops among conference speakers that add to the desire of participating to see your (often new) friends speak and shine. I really enjoy hearing people’s challenges, answering their questions and having my mind bent by someone’s unique perspective reinterpreting something I’d said with clarity I hadn’t considered myself.

On Cities & Building A Scene

The most interesting thing about living off-the-beaten path, is realizing that most people living in those places have some kind of tie to the smaller life. Whether it’s a family connection, a relationship or just a desire to “get away from it all,” I’ve encountered all types of folks with stories of their own on what motivates them away from “the big city.”

Yet, many of the narratives I hear from people building medium-sized cities like Bloomington (Indiana) where I live, revolves around startups, creating energy where it doesn’t currently exist and enticing 1) people who are here to stay and create jobs through some magic or 2) bringing capital (and people) from elsewhere to make our already good place a bit better.

Ignoring all of the challenges that comes with, I’ll just say that the most difficult part of building a scene is how much work goes into cleaning a particular corner of the sky. It can be vast, unnerving and frankly, a lot of patience. Most people seem able to invest in one or two pet causes and are happy with that. I find myself shocking close to the cauldrons of influence on one hand, yet often feel as distant from actual change as I’d feel in a larger place.

I like to say the biggest difference between say Brooklyn and a place like Bloomington, is the fact that in Indiana, there’s one of everything. In Brooklyn, I can find multitudes of organizations and overlap, but there’s enough space — somehow — to be involved in a niche or to craft your own lane if you have the right mix of money, time, relationships and whatever magic necessary to pull it off.

This isn’t a screed about why some places are better than others, it’s a reflection on the need for people making decisions about growing communities to be responsive and participating in the scene they’re trying to create. It doesn’t just rely on outsiders or insiders, it’s a mix of the two that combine to forge some kind of strategy that can propel a sleepy town into something better.

Every night, there’s a lot happening relative to a place of this size. Surely, having a Big Ten university helps tips the scales dramatically. The problem is, there are only so many people that you can engage. Students are a unique challenge due to their transient existence and other commitments that make them difficult to count in your total numbers for much of anything. That leaves the relatively small sliver of people who might be worth targeting.

I’ve been wondering aloud if I expended this same level of energy in a bigger place, what would the end result look like? There’s a lot to say for a critical mass. I wouldn’t be the first person to decide I needed something bigger, nor will I be the last. I have always been drawn to relatively small places, because the proximity and lack of pretense at times can give you an outsized ability to make an impact.

But across the board, I find that it’s a lot more difficult to penetrate whatever smallness pervades everything from the local politics to the ways people become close friends. I’m sure a lot of this has to do with dynamics of American life, and are present in other places. I’m quickly getting to a point personally and professionally, where I want to be intentional about what I work on, how I work on it and why. Especially extracurricular/passion projects, because I’m one of those people with lots of ideas and often feel like I’m “running out of time” to clear my own docket.


March 18, 2017 edition of my newsletter

Here’s the latest edition of things worth reading. You can subscribe at Tinyletter. No podcast edition this week.

Monopoly replaces boot, thimble and wheelbarrow with a T-Rex, penguin and a rubber ducky (Telegraph)
So rarely do I play Monopoly anymore that I had no idea they were retiring pieces in favor of new ones, but alas. Are you outraged? Or is this a sign of progress? Ha.

The Problem With Interactive Graphics (FastCo)
Turns out, nobody actually looks at interactive graphics? Shocked? Not in a world where millennials confess to only reading headlines and people have less time to engage with things.

The decline of first-generation college athletes (ESPN/The Undefeated)
One of the great myths of college athletes not being paid is how it’s providing opportunities to kids who’d otherwise not be able to go to college. That might be true, but it’s a lot less true now — across all sports — than it used to be, as fewer first-gen kids are getting scholarships.

The Roots of Cowboy Music: The Search for the Black Self in The American West (MTV News)
I thought this was just a good piece of writing about self-discovery, so I shared it.

The disturbing trend of homeless community college students (Washington Post)

Craigslist Is Old, Janky and Unbeatable (Backchannel)
In 2003 when I was interned at the Boston Globe, Craigslist was responsible for me finding my apartment, my computer and pretty much all of my non-work friends.

What I’m Reading: Memoirs of a Polar Bear (Yoko Tawada)
Why We Can’t Look Away From Our Screens – A review of Adam Alter’s book “Irresistible” which is also what I’m reading this week.

What I’m Listening To: Quilt – Plaza (LP)

On being known for a particular craft


How do you get to a place where people recognize you for a particular thing or discipline? Doing it a lot or doing it successfully. Perhaps the two go together?

I’m always fascinated when I meet people in real life and find out what they know. It’s the distinctive things that stick out. Maybe they’ll watch a video of one of my talks at a conference somewhere. Mostly people don’t ever meet at a conference at all, so it’s harder to translate what I do on the road with folks I meet in everyday life because it just seems so distant to them.

For these folks, they’ll remember invented Tennis Polo years ago, the shoe brand I started once or more recently, that I launched a conference or my obsession with Finnish Baseball.

As I think about ‘branding’ myself or plot my course professionally, I am always struck by what things to accentuate and what thing to put down into the background. What people remember and what I tend to accentuate don’t often match, making me think there needs to be a repositioning. That said, most of the fun stuff I do isn’t especially lucrative. I have a lot of tangible skills that I think I’d do well to share. It’s just a question of choosing what things matter and then moving the ball forward.

The real issue here is being known as a jack-of-all-trades in a world that rewards specialization.  I try to specialize, but it becomes very difficult to slough off the other skills I’ve honed over the years. So. I’ve come to the conclusion that I need to stop trying to fit myself into a paradigm that’s perhaps better suited for people with more conventional, linear professional paths. That means (somehow) melding the memorable with the marketable. It also means consolidating my myriad web presence into something a bit less confusing, so a new person discovering me for the first time doesn’t have to chase down what it is I’m actually good at.

Things Worth Reading (4 March 2017)


Here’s some things worth reading this week:

Are the 2010s like the 1930s? (The Guardian)
I’m intrigued reading about the Depression, because most first-world living people don’t have a real concept for a world with that kind of scarcity.

The world’s worst flavor was designed in a lab by accident (Tedium)
Apparently Bitrex is everywhere and we don’t even realize it.

Earth In A Suitcase (538)
What would space colonists need to take with them on a trip away from Earth?

Sex, Husbandry and the Infinite Scroll (Design Week Portland)
A piece about real life and navigating spaces in a social media dominant world.

Why do we work so hard? (1843)
Contemplating work.

Reading: The Art of the Restaurateur (Nicholas Lander)
Listening: Quilt – Plaza (LP, 2016)
Luminous, unfiltered, haunting psych-folk that teeters among three dangerously creative mind

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


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.

Continue reading

Things Worth Reading (25 February 2017)


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.