The Justice Department did decide to back off, handing Zimmermann and his fellow pro-cryptography activists, or “cypherpunks,” what appeared to be an overwhelming political and legal victory. But it turned out to be somewhat hollow: the government had given up partly because it realized that encryption wasn’t going mainstream at all.

The main reason for this is as sad as it is simple: encrypting e-mail is just hard.

— The Daunting Challenge of Secure E-mail : The New Yorker

Cracking the problem of making it easy for ordinary people to encrypt their data and make their digital lives secure is one thing. Convincing ordinary people that encrypting their data and making their digital lives secure is something else entirely. Until someone accomplishes both of those, no progress will occur in this area, at all.

Patrick Rhone has a very simple productivity system. He writes three things he wants to get done on an index card, and he keeps a running journal in a notebook with a system he calls “Dash/Plus”. I’m not so good at remembering to write things down, but I’ve taken the idea of Patrick’s “Today Card” and incorporated it into OmniFocus, flagging three important things I want to get done today. I don’t always succeed at all three, but getting at least one done means I’m moving in the right direction.

But reducing the power of OmniFocus to something as simplistic as a single window with three things to click off has me reconsidering my stance on analog productivity. It hasn’t helped that I’ve spent a little more time in book stores, recently. The stacks of square-ruled Moleskine notebooks have been taunting me to pick them up and try using the Bullet Journal system during my day. I also notice my poor Hipster PDA, getting battered in my pants pockets, its bright white index cards tarnished and battered—but ink free. (And not because I don’t carry a pen.)

An overly complex OmniFocus task list I might not need

When I wrote about eschewing analog workflows back in March, the focus was on sustained writing, but some of the points extend to purely “getting things done,” too. [1] The default behavior when I have any new stimulus that needs capturing, is to whip out my phone and type it up as a note in Drafts. It’s my instant collection bucket, no more than two taps away from sending it where it needs to be. [2] It’s ingrained enough that it’s second nature, and why I make sure to keep Drafts in my iPhone and iPad docks.

A few of the notebooks I’ve yet to fill up over the past seven or eight years.

But the siren call of a low-tech solution to keeping track of things still appeals to me in some way. I look at the piles of stuff in OmniFocus, and wonder if I need such hyper-detailed lists of tasks for some of my projects, especially if I’m just doing three “things” per day. I wonder if I couldn’t just train myself to reach for a pocket notebook and pen when I need to take something down, instead of my phone. I wonder if I could actually improve my atrocious handwriting with the practice. I wonder what I’m missing out on by not having a hard copy record of my day, my ideas, and my life.

And I also realize that twice—more than twice—I’ve “burned my life’s work.” [3] I’ve turned piles of my writing from adolescence and (very) early adulthood into nothingness with a keystroke, but I have a small stack of half and quarter full notebooks that remain. They’re full of journal entries, snippets of fiction, doggerel verse, and random notes. The digital fragments of my old lives were much easier to destroy.

The sort of detailed OmniFocus task list I do need

In all honesty, I do need the hyper-detailed task lists I keep in OmniFocus—at least for some things. I do find it easier to write with a keyboard on my computer or iPad instead of on paper. I have a system that, more-or-less works. I also don’t have to completely give it up to try going analog for some things. Perhaps I’ll indulge my curious impulses, buy a new, empty square ruled notebook, and give the Bullet Journal system a go. A hybrid system may work, or it may not. It would be foolish of me to dismiss it without trying it first. I’ll report back on my findings.

The startup elevator pitch of “It’s like ___, but for ___!” has become such a cliché that it has its own generator site, capable of churning out stuff like “It’s like SkillShare, but for SAT tutors,” or “It’s like ShoeDazzle meets SeatGeek.” That doesn’t stop people. If you’re looney enough to look at AngelList, you’ll see that same basic formula repeated in any number of startup company descriptions. Why? Because it’s easy. Taking the business model of one successful startup company, and applying it to a similar, perhaps more niche space, and rolling out a functional beta is a safe and easy way for the VCs to pick up your scent.

Admittedly, coming up with a truly new product is a hard thing to do. A lot of real innovation comes in the space of the “adjacent possible”, that is combining disparate things in new and exciting ways. It doesn’t always work, but when it does, watch out. That doesn’t seem like what a lot of startup companies are doing, at least not the ones getting huge piles of money for bringing in lots of people. How many “temporary” image sharing services do teenagers need to share naked pictures on, or social networks that gamify content consumption? How many industries can be “disrupted” before the unemployed and redundant start rioting in the streets?

In my past job, I was inundated by talk about what flavor of the month company was raising so much from whomever—partially because I was working for a startup company in the “___, but for ___” vein that was soliciting funding, and partially because our second blank consisted of people who manage the money to invest in venture capital funds, and the venture capital funds themselves. It grew tiresome, especially with so many startups doing exceedingly boring stuff with the intention of just bringing in as many warm bodies and eyeballs as possible to increase their valuations. No wonder some people think we’re experiencing a second technology bubble.

All of this makes the “Silicon Valley can do no wrong” rhetoric sound even more arrogant. If the modus operandi of Silicon Valley were less about eyeballs, advertising, valuations and exits, and more about solving real problems that affect real people, claims like “it’s becoming excruciatingly, obviously clear to everyone else that where value is created is no longer in New York; it’s no longer in Washington; it’s no longer in L.A.; it’s in San Francisco and the Bay Area.” would come off far less obnoxious than they do. Only in the venture capital world would something as scummy as payday lending get $14 million dollars. That same money could go to helping people improve their lives and finances to save them from even needing usurious loans to make it through the week.

The problem is that approach takes a long time, and doesn’t have the same prestige for the founder and profit for the VC firm. There are very real problems facing people around the world that are simply beyond the ability of web and mobile apps to solve: global warming, income inequality, disease, famine, and war. Technology can be a part of those solutions—just look at the work Gates Foundation has done for improving the cold chain required for vaccines. Even worse, with philanthropy on the decline, nonprofits and other organizations that work to improve people’s lives are forced to find new revenue sources. These sources often end up being returns from their investments, which are increasingly including venture capital funds.

If the endgame of serial entrepreneurs was to make a few billion in the startup and/or VC game, and then turn around and use their largess to improve the world along the lines of Andrew Carnegie, it might not be so frustrating. However, the situation as it stands is not sustainable. The numbers don’t add up, and either people will figure that out, or the bubble will burst. The end result will, optimistically, result in new companies focusing on building sustainable businesses to last. More likely, it’ll just be like the intervening years between the first and dot-com bubble and now. I think we can expect history to repeat.

At the recent TechCrunch Disrupt conference, two teams of hackers introduced and presented sexist—to say the least—app ideas. TechCrunch was quick to deliver the typical non-apology apology that has become standard in the business. Their acceptance of blame only extended to admitting they didn’t scrutinize the apps properly before the conference. You can’t tell me that someone saw the name “TitStare” and didn’t think something was amiss. I doubt they assumed it was a birdwatching tool. “Circle Shake” had a more innocuous name, but its content was far from it.

Whenever sexist behavior pops up at a technology event, or whenever another woman in the technology world speaks up about the sexist bullshit she’s endured at conferences and elsewhere, the reaction is always the same. There’s a sheepish apology and promise to deal with the issue that never is fulfilled. Elsewhere, anonymous crusaders hiding behind screen names will take up arms and attack… the people who raised the troubling issue in the first place. Unlike cockroaches, who typically scatter when the light has been cast upon them, the particularly insidious breed of sexist that lives in the technology community only sees a sign to attack further.

And in the same breath, we often wonder why women are so underrepresented in technology.

Never mind that women are often shunted from birth into
“traditionally female” pursuits, and often discouraged from exploring technology. Even the lucky few women who are able to escape the societal conditioning that technology isn’t for them have to put up with institutionalized sexism from both the Old Boys Club and Young Boys Club that is the tech community at large. [1] When you have a luminary like Dave Winer claiming “[T]here’s something about programming that makes many women not want to do it. Programming is a very modal activity. To be any good at it you have to focus. And be very patient.” something is amiss.

There’s certain aspects of the type of people the tech world attracts that help make sexism so pervasive. First, there’s the societal bubble of technology as a primarily male pursuit. With few female voices, technology becomes an echo chamber of men. This becomes deadly when combined with the geek tendency to overgeneralize. [2] Geeky people think in terms of systems and tend to become dogmatic, fining variation difficult to handle to various degrees. (This is a problem I’ve struggled with, too.) So, when a geeky guy who has surrounded himself with fellow geeky guys suddenly sees someone who isn’t like him penetrate his bubble of geekery and masculinity, how does he react? All too often, with fear and hatred.

Even in their bubble, geeky males can still take on the victim mentality, even when there are real victims who are being victimized by the same community and tools that can be used for constructive purposes. This victimization manifests itself in awful places like the Men’s Rights Movement, which leads a lot of the harassment of women who dare speak up about sexism online.

I wish I had an answer on how to fix this. Whenever an event like the TechCrunch debacle happens, or when someone like Melody Hensley dares to just be female in a male dominated space, plenty of decent people step up to make noise and shout down the assholes from their public perch. It’s the private attacks and harassment that make things troublesome, and that the allies of the harassed get more people listening to them than the people they support makes it even worse. These are symptoms, not causes, however. Though there’s more vocal defenders and allies then there were in the past, their support seems to only embolden the forces of sexism. All I think we can do is hope for a tipping point, and to continue to force the discussion about sexism in technology—and elsewhere. Expect a long, drawn out battle.

Twitter founder Ev Williams gave a speech at the 2013 XOXO Conference where he described the Internet as “a giant machine designed to give people what they want.” He then went on to describe a formula to build an online business that is almost guaranteed to succeed: “Take a human desire, preferably one that has been around for a really long time… Identify that desire and use modern technology to take out steps.”

Recasting the Internet as little more than an engine of convenience seems painfully reductionist. This is the same technology that’s democratized media, and put the world’s collective knowledge at our fingertips, right? Ev seems to be reducing the whole thing to something more akin to plumbing, a series of tubes [1] that gets stuff we want to us faster, or at least easier. I’m guilty of ordering things off Amazon I could find at a local store, because I didn’t feel like tracking it down and the need wasn’t urgent.

We’re a long way from the cyberpunk ethos of the early late 80s and early 90s and the sense that the Internet would remake civilization once everyone was hooked up. Now, we look at attempts to wire the rest of the world [2] with the cynical understanding that it really just means more eyeballs for Facebook and Google to serve ads to. Who cares of those eyeballs aren’t going to be able to afford any of the products the ads are trying to sell, or may go blind from disease. There’s no money in improving poor people’s lives. You can leave that to Bill Gates.

There’s a crassness to Ev’s interpretation of what the Internet is for. I don’t know if it’s deliberate crassness, but I can’t ignore it. It’s a crassness reflected in how Venture Capital firms select startup companies to fund. Profit, sustainability, and actual world-changing are second to sheer numbers of users. The VC firms can then make back their investment when the startup gets bought out by a larger company, or when they have a huge IPO. After that, they can wash their hands of the whole affair, and use the profit to start the process again. [3]

The system’s worked well for Ev. He’s made a fair amount of money by building stuff and selling it at the right time, and some what he’s made is immeasurably valuable to a lot of people. It’s why I’m not sure he’s deliberately crass when he describes his formula. The guy from a small town in Nebraska, who made two services that help people communicate and connect certainly doesn’t come off as crass in his talk. He comes off as earnest. I certainly don’t begrudge him his success, either.

What worries me is that this idea of convenience above all will convince more shallow, crass, wealth-obsessed people that they can get rich quick. It means creating more gimmick apps and services that get popular fast then get acquired, instead of creating something of real value for the long-term. Even if Ev is absolutely right, and the Internet is nothing more than a convenience engine, it doesn’t mean we can’t use it to help everyone improve their lives in measurable ways instead of just lining the pockets of a few. These aren’t even mutually exclusive ways of operating. You can make lots of money running a successful business that employs a lot of well-paid, hard-working people. It just takes longer, and don’t count on venture capital to help.