Recent Things

Hustling, Grinding, and Building

Here’s a tweet I saw the other day that made me — as the kids say — “LOL”. Touche. This is a really, really annoying part of today’s cult-of-entrepreneurship. You can blame it on internet culture, or venture capitalists, or the way the media covers and informs the public about these things, but either way the end result is often a incredibly clumsy grouping of unrelated challenges into a single, stupid bucket. You don’t have to be an especially cynical person to roll your eyes at the idea of how “tech companies”, “startups”, “SaaS businesses”, or any number of vaguely defined

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Why is it So Hard for Workplace Tech to Make a Difference?

The cyborg generation that never was When I was in high school, the world was all abuzz about the fact that many people my age had “grown up with technology”, which really meant “grown up with personal computers and, for a while, dial-up internet”. The idea was that while our parents’ generation struggled to deal with trash can metaphors and concepts like double-clicking, to us bleeding-edge early millennials, digital technology would be second nature, and thus we’d all be really good at it. At the time, this made a lot of sense to me, and I eagerly awaited a world

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Confidence : Organic vs. Constructed

One of the truisms I’ve run into in life is that “confidence is king”. This is one of my least favorite truisms, because I’m a naturally skeptical person who very intentionally applies that skepticism to his own ideas. But that personal inconvenience doesn’t change the fact that everywhere I go, confident people are winning arguments, making decisions, and driving the institutions I care about — whether that’s off to fame and glory or an obvious, avoidable cliff. People worry about whether leadership is “confident” all the time, but so far in my professional experience, I’ve never worked for a management

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Parents with Great Jobs

“This is my daughter.” I keep saying that as often as I can because it doesn’t seem possible. But since Sunday morning, it’s been undeniably true — this little freaking person lives in my house and loves me and my wife more than anyone in the entire world. There’s a playbook for having a kid when you’re someone like me; a.k.a., a college educated white guy professional in his early-mid thirties. Not everyone follows it, but a lot of people do — having a child changes the way you see everything, puts your high powered career into perspective, and makes

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The Proper Work Metaphor

junior varsity disclaimer Since I’m about to extol the benefits of sports (or at least some of the thinking behind them), I should probably clear up a few things. While I’ve always loved sports, I am not an especially good athlete, and never have been. I was an abjectly terrible baseball player who quit Little League once it started becoming clear that how well you played baseball had very little to do with how much you loved baseball (so about 11 or 12). From there I floated around, playing pickup basketball and football with normal kids, until at 16, I

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Let’s Talk About $$$

I’ve been meaning to write about how people in my kind of work get paid for a while, but it’s a tricky thing to talk about in any kind of publicly consumable form. That’s because people — even myself, regrettably — can get incredibly sensitive about how they and their co-workers are compensated. So let’s get a few things out of the way, for the sake of everyone’s emotional health. 1) I really like my current job, and I think I get paid a fair amount, based on my admittedly limited knowledge of the job market. I also like the

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It Sucks to Grow Up (but Everybody Does)

Truly entrepreneurial people are usually pretty action-oriented. Sometimes I meet rich people who describe themselves as entrepreneurs, and it’s immediately apparent that they’re pretty averse to doing any actual work. I know this because (except for the being rich part) I’m kind of like that. I’ve actually had to build up an alternative work personality that’s extremely production oriented to combat my own navel-gazing strategic dithering, so I totally understand where these people came from. (Side note — about five or six years ago, my productivity-oriented work personality then doubled back on me and started taking over my hobbies and personal

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Why OKRs Kind of Suck

The last two companies I’ve worked for have used OKRs, a system for company, team, and employee goal setting popularized (and possibly invented, for all I know) by Google. Personally, I’ve been very frustrated by OKRs, and if anything, they’ve made me less productive. I don’t think I was alone, and that’s one of several reasons Contactually scrapped them last spring. It’s not a bad system, but like a lot of a business theories coming out of the startup world these days, it suffers from a desire to constantly evaluate everything quantitatively that isn’t matched by an ability to effectively

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Well, That Escalated Quickly

Once upon a time, in Washington… One night, in the fall of 2002, three twenty year old kids from Rhode Island were, once again, driving to band practice somewhere out in the less-tourist-friendly inner suburbs of Maryland. They were early in their junior years of college, and two of them — the annoying bass player and the goofy drummer— were visiting from far away schools. The world’s worst rhythm section had convinced each other that a semester somewhere else would be a great way to meet girls, which probably says a lot about how well that had been going for

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We Should Care About Why We Get Paid

The amoral dumpster fire that is online advertising I very briefly touched on this a few weeks ago, but to state the obvious once again — online advertising is a mess. The landscape is a rapidly changing free-for-all with multiple business interests (wireless providers, hardware makers, publishers, social media platforms) all trying to shake money out of consumers. For instance, wireless carriers want to charge you for data as if you had any idea how much data you need, and publishers want to load up 100kb web pages with 15 megabytes of animated ads and javascript trackers as if data

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