Wanted: email apology bot

Maybe we all live in the email anti-Lake Wobegon, where we’re all “worse than average” at email, in our own minds.

One problem with email is the giant guilt pile it creates — the psychological consisting of the number of emails you know are in there that you have forgotten about, ignored, or missed. My guess is that there’s actually a disconnect with the *actual* problem in your inbox and the size of the guilt pile, as much of what’s in there is probably out of date or irrelevant anyway. But nevertheless the guilt pile persists, and only grows.

I do my best to tackle this. I try and respond to short emails in-the-moment as much as possible, and I star things that require a more thoughtful response, and work through my starred box regularly. Recently, I started using Zirtual, and my new virtual assistant Michelle is handling all of my scheduling emails — that helps a LOT. But still, the guilt.

And, on the flip side: it sucks when people don’t respond to your emails. Especially when it’s someone or something you care about, and that message can leave you wondering: “did they miss this or am I a loser?”

So, here’s one idea for a solution, inspired by Joel’s text-me footer: an auto-apology email bot that periodically scans through my inbox and sends an apology to everyone who has a lingering message with me. The apology would say something like:

“hey — I’m really sorry but it looks like I’ve gone and ignored/missed/forgotten your email. I suck at email and it kills me. Here are the messages in my inbox that I haven’t responded to in the last [7|14|30] days: {list of email subjects} If anything in there is really important, please respond here and I promise I’ll get back to you.”

Perhaps this is impersonal and robotic, and it’s clearly not as good as me actually responding to your email the first time around, but wouldn’t it be an improvement?

Venture capital vs. community capital

Photo: Rudy (Loïs) Pignot I am in Paris this week for OuiShareFest, and spoke yesterday morning during the opening session.  OuiShareFest is in its third year as a large international gathering of folks interested in the peer/collaborative/sharing/networked society, put on by the community organization OuiShare. The topic of this year’s fest is “lost in transition”, and… Read more »

Anti-workflow: to-dos

A while back, I wrote about Anti-Workflow Apps — apps that solve problems for you without forcing you to adopt a workflow that you may never fully be able to adopt.  Workflow apps (CRMs, to-do lists, project management tools) are super hard to drive adoption towards, as everyone works differently and really resists this kind… Read more »

Dick Pics and Cable Company Fuckery

John Oliver has become the most important voice in tech policy (and maybe policy in general). His gift, his talent, his skill: turning wonky policy language that makes people glaze over into messages that people connect to and care about it. Last fall, he did took what may be the most boring, confusing term ever,… Read more »

Failure is the tuition you pay for success

I couldn’t sleep last night, and was up around 4am lurking on Twitter.  I came across an old friend, Elizabeth Green, who is an accomplished and awesome education writer — you’ve probably read some of her recent NYT mag cover stories, and it turns out she has a new book out, Building a Better Teacher…. Read more »

Financial Planning for the 90%

A few weeks ago as I was walking down Beacon Street in Brookline, I happened upon something amazing: The Society of Grownups. The Society of Grownups is a self-proclaimed “grad school for adulthood”, the idea is to give people the tools they need to manage their grown up lives.  The primary focus is on financial… Read more »

The Light Inside, The Fire Inside

Last week, a friend passed away after a relatively brief but intense battle with lung cancer.  I didn’t know Paul well, but he was very close with a few of my very close friends, and I had spent enough time with him to understand that he was special: he had a light inside of him.   A… Read more »

Regulation and the peer economy: a 2.0 framework

As part of my series on Regulation 2.0, which I’m putting together for the Project on Municipal Innovation at the Harvard Kennedy School, today I am going to employ a bit of a cop-out tactic and rather than publish my next section (which I haven’t finished yet, largely because my whole family has the flu… Read more »

Web platforms as regulatory systems

This is part 3 in a series of posts I’m developing into a white paper on “Regulation 2.0″ for the Program on Municipal Innovation Harvard Kennedy School of Government.  For many tech industry readers of this blog, these ideas may seem obvious, but they are not intended for you!  They are meant to help bring… Read more »

Technological revolutions and the search for trust

For the past several years, I have been an advisor to the Data-Smart City Solutions initiative at the Harvard Kennedy School of Government.  This is a group tasked with helping cities consider how to govern in new ways using the volumes of new data that are now available.  An adjacent group at HKS is the… Read more »

The magic of making hard things easy

I wrote earlier this week about how life is, generally, hard.  There’s no question about that. One of my favorite things about the Internet, and probably the most exciting thing about working in venture capital, is being around people who are working to re-architect the world to make hard things easier.  And by easier, I… Read more »

Everyone is broken and life is hard

That’s a pretty depressing and fatalistic post title, but I actually mean it in a positive and encouraging way.  Let me explain. It’s easy to go about your life, every day, feeling like everyone else has their shit together and that the things you struggle with are unique to you. But then, when you get… Read more »

Anti-workflow apps

“Workflow” apps hold so much promise.  Whether it’s a CRM, project management tool, to-do list, or some other tool, the promise in each case is to clean up our messy lives and help us be more organized and effective. The problem, though, is that getting people to adopt a workflow is really really hard.  That’s… Read more »

Finding Flow: writing vs. coding

When I first started to learn programming, about 15 years ago, I remember being surprised at how easy it was for me to get focused and stay focused.  I loved (and still love) the feeling of getting lost in a project, and could easily spend hours upon hours “in the zone”. No procrastination, no resistance, only focus… Read more »

Crowdsourcing patent examinations

Yesterday I spent part of the afternoon at a US Patent & Trademark Office roundtable discussion on using crowdsourcing to improve the patent examination process.  Thanks to Chris Wong for looping me in and helping to organize the event.  If you’re interested, you can watch the whole video here. I was there not as an… Read more »

Support services for the Indie Economy

Over the course of the past year, I’ve been interviewed a bunch of times about the “peer economy” or the “sharing economy” (Fastco, Wired, NY Times, PBS Newshour), with most of the focus on the public policy considerations of all this, specifically public safety regulations and the impact on labor. A question that comes up every… Read more »

The Professional Amateur

One way I have described myself is as a “professional amateur”.  I am both deeply proud and deeply ashamed of that.  Let me explain. For basically my whole career, I’ve been learning new fields and professions from the outside-in.  While I have an undergrad degree in Urban Studies, which ostensibly prepared me for interdisciplinary work regarding… Read more »

Half, not half-assed

My favorite book on product development and startups is Getting Real, published in 2006 by the folks at 37signals (now Basecamp).  If you haven’t read it (it’s freely available online), it’s essentially a precursor to The Lean Startup (2011). Back when I was leading a team and running product and OpenPlans, it was like my bible…. Read more »