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 of change.  (of course, it’s possible when the reward is super good — e.g., slack and git/github — bit those times are rare and more often than that an attempted re-workflow goes splat)

So I’ve been on the lookout for Anti-Workflow tools.  Solutions that solve a problem that you think requires a new workflow, but may actually be more effectively solved another, more clever way Today I want to talk about to-dos, because I seem to have found my own personal anti-workflow solution.

I’ve always struggled with to-dos — I’ve used every to-do management tool on earth, and have never been able to adopt a workable, effective system.  I’ve tried everything from complicated tracking systems like OmniFocus to simple to-do lists of every possible flavor.  Nothing has stuck.  For years and years, I kept trying, trying and trying again.

In the end, I just gave up and said, fuck it, I’m not using a to-do list anymore. Not going to even try.

What happened was that I ended up keeping track of my priorities in a totally different way — a way that was actually more in tune with my existing workflows.  One part of the solution was pretty obvious, and one was surprising.

On the obvious side: the calendar.  For things that I absolutely must do, and that require dedicated time, I just use my calendar.  I’m in my calendar all day long, so it’s the perfect place to block out time for important things.  So now I set calendar entries for myself, to make sure I set aside time for things that need focus.

The calendar is good for things I know I need to do, and that I know are important.  What it’s not good for is capturing notes, ideas, and small to dos, which often just need to be captured in the moment and prioritized & dealt with (or not) later.  This is the use case that has always drawn me back to to-do apps, to no avail.

In particular, the really bad thing about a to-do list for this use case is that all it does is make you feel guilty.  Items get added to the list, and whether you really need to do them or not, you feel drawn to.  And then when it doesn’t happen the to-do list just becomes a giant pile of guilt that you do your best to ignore (that’s what happens to me at least).

That brings us to the less obvious solution.  What I’ve found is that a great way to handle both the capture / prioritization issue and the guilt issue is to use a Sparkfile.  Long time readers will know that this blog is named after my favorite idea from Steven Johnson’s Where Good Ideas Come From: the “slow hunch” approach to developing ideas.  Another idea from that book — unearthed by studying epic thinkers of the past like Darwin and DaVinci — is the Sparkfile: a long, running list of thoughts & ideas.  Fragments that pile on one another over time. One way to cultivate the slow hunch is not only to keep a sparkfile (in addition to other kinds of journals), but to constantly pour back through it re-reading and reconsidering your previous thoughts, ideas and observations.

Turns out that this is also a pretty good way to filter inbound ideas of things to do.  Just add them to the spark file, continually review the list, and occasionally do things (immediately or via calendar), and then add new stuff to the top as you think of more things.  No pressure — and absolutely no expectation — to do everything on the list or turn it into a perfect set of priorities.  Just let the mind run, capturing as you go.

For me, this idea ties back into anti-workflow because I’ve been keeping a personal blog/journal for about 7 years now.  Which was in many ways a sparkfile, though it started out slightly more long form (starting with a private wordpress blog).  The big revolution happened last fall, when I switched over to using Diaro.  Diaro is a personal journal tool, with both a desktop web client as well as a mobile app.  The mobile app is the key, as it makes it possible to really quickly jot down a thought — as quickly as you’d do on a to-do app, or email, or notepad.

So in the end, the solution to my to-do workflow was not to add a new to-do workflow.  Rather, it was to extend the workflows I already had going, calendars and the sparkfile.  Boy it feels good.

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 »

This is what an Internet Candidate looks like

I just donated to Christina Gagnier‘s campaign for congress. I’ve gotten to know Christina recently, and I really hope she’s able to pull through this race and make it.  We need smart people in DC who understand technology, tech issues, and tech policy. She is without a doubt one of those people.  She’s an entrepreneur… Read more »


I got this in the mail: It’s an ad for an extended warranty, disguised as an urgent extension of existing coverage. This makes we want to throw up.  A business blatantly based on tricking people. “Immediate response to this notice required…. Our records indicate that you have not contacted us to have your vehicle service… Read more »