Turning Anxieties into Productivity

I’ve had a few people over the past few weeks make a special point of pointing out how (overly) productive I am. And because part of the way I do things is doing them in public, I figured I’d put together an overview of how I work for The Internets. Much of it is not healthy – I battle with temporal compulsiveness in a way I can only imagine is similar to the exerted control over diets those dealing with eating disorders display. So this is a less a “how to be productive if you find yourself uninspired” and more a “how to funnel your anxieties towards good use.”

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This is actively not a way to interact with people you’re Not Working With. This is a constant battle with me, as it’s easiest for me to interact with people around projects. But that’s not fair to people I care about AND work with. It might not even be a way to interact with people you are working with. I’ve tried to have that tension/disfunction show through in this post – the same things that make me really good at productivity are what also make me have unreasonable expectations of carbon-based life forms.

Some of the following advice also has to do with deceiving yourself or other people, primarily about timelines, in exchange for projects being delivered on time. Every person is different – it’s important to ascertain if someone can self-regulate on time and deliverables, or if they need to be managed and reminded. It’s ideal if you can have a frank conversation with someone about this – but I’ve had this go both splendidly (“I’ve got this” or “Yes, please pad my time”) or horribly (“you lied to me? How dare you” (while still delivering late)). YMMV. Informed consent is important.


Under Promise, Over Deliver

I consistently under promise and over deliver based on what can be achieved over the course of certain times based on ability, availability of time, other projects, etc. This also comes with long experience of knowing that while the work itself will take a short period of time, it is wedged in with other things, interrupted by emergencies and higher priorities, waiting on other people experiencing their own emergencies and reprioritization, etc. Computers crash, dads get sick, other people believe in taking different holidays and days off than I do, etc. If it’s a day worth of work, I request 2 weeks. I still strive to finish it quickly – and then take the extra time to do quality assurance, to add components, train up people, thoroughly document, and still get it in before the stated date.

Temporal Padding

Padding extends to the more granular as well, and helps maintain flow, productivity, and sanity. Each meeting should be padded by 15 minutes on either side beyond travel (more in the tools section for automation). This covers travel snafus, delivering on immediately actionable things from the previous meeting, and prepping for the upcoming event. It also prevents me from shooting myself in the face on days of back-to-back meetings – I can read a bit of a book, talk to a friend, grab a coffee, etc. When a few days of every week can be back-to-back meetings, those little pockets are what keep the whole thing running smoothly.
When I have any level of control over it, I end meetings 3 minutes early – people LOVE this, and it insists that time is respected. In a semi-related fashion, I tend to not pad the beginning of meetings for latecomers by any more than 5 minutes. The trick to this is good documentation in a known place – people arriving late can simply read through the notes and jump in (or at least I don’t feel responsible for catching them up). I also extend this to myself – that temporal compulsiveness means I freak the fuck out if I’m late to anything. By setting up meeting architecture that doesn’t require any one person to start it, and having a clear agenda in a known place, others can start without me if I happen to be late for one of my own meetings. This – along with working with incredible people who can pick up without a hitch – is helping me to relax a bit more.

An Hour to Anyone Who Asks

I work in a distributed way, highly reliant upon a breathtakingly diverse set of people to ask strange questions of at odd hours, request first readings of, and to say “this thing looks like…” The ability to do this is based upon something I adore doing, which could be seen as community service. I will give one hour to (nearly) anyone who asks for it. The link to request time is even in my Twitter profile (and we’ll talk about this in the Tools Section). This can be around an event they’re throwing, a thing they’ve been thinking about, or a question they specifically have. By being accessible, I have a high exposure rate to new ideas and beautiful brains, which I compulsively categorize and store in order to link with things that will make all components stronger.

Document and Reflect

I try to remember to document, and to do it in public. I tend to write blog posts about things I’ve learned, add components into project wikis or githubs, or schedule a podcast. This makes it easier to find things, and sometimes when returning to an idea a year or more later, people have built upon and improved it, which is just dreamy. Distributed communities and open culture for the win. Working this way also means I don’t use tools like Evernote, but rather things like The Brain – just like the NSA, the metadata is what is important to me, not the details. The few things that aren’t immediately actionable I store across .txt docs and keep running in VIM… and access to those documents are a part of my will.
Every project, meeting, day is a learning experience. I like to reflect on things.. what did I learn from this? What would i change? How could it be optimized? This helps alleviate the boring parts of administrivia and delivery, as well as ensuring I’m not going nuts nor going on autopilot. Instead of rotating on things that didn’t go well during the day, I have a chance to consider what could have changed to make things smoother. If it’s possible to automate some part of administrivia, I do it — and if not, I’m aware of how important it is.


Topic of the Day

I’m involved with a lot of various things. I assume everyone is. This involves a lot of gear-shifting, at a nonzero cost. Someone asking about the Tanzanian water mapping project while I’m livescribing a presentation at Berkman Center can be hugely disruptive. While all of these things absolutely relate to each other, and are part of the same world, the minutia and details merit focus. To limit these sorts of interruptions, I tend to have a Topic of the Day, and this is enforced by my scheduling tool. Geeks Without Bounds on Mondays, Berkman on Tuesdays, Wild Card Wednesdays, Civic on Thursdays, Friday for overflow and pro bono work. I try desperately to take Saturdays and Sundays off, as explored more in the Managing Stress section.

Money Hours and Pro Bono Hours

Just in case you’re not already well aware, I’m incredibly wary of Capitalism. I would prefer to live in a mixture of mutual aid, guaranteed basic income, small market structures for innovations, and transparency paired with accountability. This means I’ve also had a difficult time insisting on being paid in our current economic systems – leading to long-term financial instability, an ensuing lack of self-preservation, and resulting high stress. Which doesn’t help anyone I’m working with. So here’s what I do now: one day a week is for pro bono work, for projects I adore. These days book out pretty far. When someone asks me to come onto a project, after the initial hour’s check-in, I tell them how long it’ll be until I can take it on for free, or when it could be done as paid work, and at what rate. I’ve been amazed at both what this has done for bringing income, as well as keeping me sane with deliverables on ZOMGAMAZINGPROJECT.

Working Offline

I find working offline, especially with email, to be an absolute must. I cannot think long-term while connected to the internet. Preparing nodes for connection, then booting up the tubes for integration and cross-linking means the whole network is more complete, less fractured. The tiny minutes lost to Twitter and The Old Reader are eclipsed by the time it takes to shift gears back into working mode. If I’m going to futz around online, I’m going to do it in an intentional way, likely with a limit during working days, or without an concern for direction or time on days off.

Managing Stress

Temporal Padding for Self Care

Padding also applies to work/life balance. I aim for 3 days off nearly every week. Often as not, one is sacrificed for emergencies and pressing deadlines and one to overflow and pro bono / passion projects, leaving one actual day off. I usually spend that day entirely offline, with nothing booked, and try to “wing it.” I am exceptionally bad at this, and often feel adrift and incompetent on these days (“what do people do?!”) but I find I’m far more relaxed if I do this regularly. In the continuing trend of compartmentalization, this also means the days I’m sleep deprived or angsty I can tell myself “process on Sunday.”

Work/Not Work Dividers

Sometimes, I really miss serving tables. I miss that, at the end of the day, things were Done. Nothing to take home. Now life is not only a matter of long-term projects that Actually Impact People, but also managing cohorts’ timezones and the associated meeting times and submission deadlines. A meeting at the end of the working day in Dar es Salaam is my 7a. This means having dividers between work and Not Work is vital. From Jenbot, I picked up the “walk around the block before you start work, and when you’re done with work” when telecommuting from where I’m sleeping – hotel or home. It’s a lovely physical and mental divider between temporal functions.
When there’s space, I have a “no laptop where you’re sleeping” rule. This leaves anxieties at the door, forming a safe space for reading, snoozing, and cuddling. I could show you the difference in sleep patterns between when this rule is in action and when it’s not – I sleep more soundly, and feel better rested, when my sleeping space is also Not Working space. Because this isn’t always possible due to hostels, crazy travel schedules, and shared live/work spaces with other people, I’ve taken the habit of wearing my Pebble on my left wrist during work time (notifications of next meeting, incoming phone call, etc), on my right during focused self-care (sleep tracking, running/workout indicators), and not at all during unstructured time.
Regardless of how I’m delineating time, I try to always take the first three hours of every day away from email (not possible on those 7a days, but on most it’s manageable). This, again, has reduced my stress levels significantly. I can look at email subject lines from bed or in those three hours, but not open anything to read the contents. This is predicated on having triggers set up on email that if [URGENT] is in the subject line, I get a phone call via IFTTT.com. Anyone abusing this is sent a “fucking seriously?” email response. It’s amazing how much is urgent but unimportant, and setting these boundaries highlights this even more.

Every (Work) Email Should Be the Last

It’s super easy to get caught in an endless back-and-forth of logistics over email. Piles of these sorts of messages add to stress, the length of a project, and non-useful documentation (i.e., shit to go through to find a bit of information needed). I’ve recently taken to the practice of considering, at length, what it would take for any email I send to be the last in the thread. What questions need to be asked? What can I preemptively answer? How can I say these things concisely?
Note: this is not the way to respond to friendly correspondence. Another reason why compartmentalizing time is important – I’ve felt unnecessarily annoyed with “idle chitchat” in email threads with friends while in this cognitive space. By tagging emails correctly, using multiple inboxes, and answering the associated email in appropriate time blocks, I’m excited to hear about friends’ lives and happenings rather than thinking “what do I need to say to be sure I don’t get an email back?” I know this sounds harsh, but remember what the opening to this said – this is a guide for channeling anxieties in a healthy and useful way, not for people who need help bootstrapping into productivity.


Scheduling: meetme.so

I used to spend about 4 hours every week (more if I were to include gear-shifting time) on “how about DATE at TIME?” I also had to self-manage Daily Topics, padding for meetings, etc. Automating that has been amazing. Tungle was sunsetted a couple years ago, to my never ending heartbreak, and doodle doesn’t do it for me for personal scheduling, but meetme.so has done a fairly good job of stepping into the space I needed. I have three calendars – one for Geeks Without Bounds, one for academia, and one for personal and pro-bono work. In the tool, I set what days and hours are available for each of those calendars, how much to pad between bookings, how much advance I need to book something, etc. It’s pretty amazing, and well worth the nominal cost.


Because I operate on inbox0 (hahahaha *weeps quietly into inbox137 and inbox113 (speaking of compulsivity, I snooze to prime minutes and keep my inbox unread and total counts at primes…)), Boomerang is great. When I send one of those “I hope this is my last email,” but which requires follow-up, I can have it return to my inbox at a later date. It makes it seem like I am SO ON TOP of everything. “Hey, it’s been a week and I haven’t yet heard back. Do you have all the information you need?”
The same tool separates scheduling from sending, with a “send later” function. This is great for 1) being manic at 3 in the morning and wanting to send an email but not seem crazy – just schedule it for 9a the next day instead! 2) Having a bunch of staggered questions or milestone reminders that you’re thinking about right now – you type and schedule now, but send on schedule 3) Responding to business cards from conferences – I hate the deluge of mail I get post-conference, so I tend to schedule a “hey we talked about this, and we should schedule a time to continue collaborating” to send a week after the conference… by scheduling it at the event, I haven’t yet lost that tiny piece of paper people insist upon indicating their details via.

Task Management / Tracking

After trying Omnifocus, Basecamp, Open Atrium, and any number of other project management platforms, I really like RedBooth (formerly TeamBox). It embeds information, does time tracking and Gantt charts, is useful as a single-player experience, and also hyper useful for teams. For anything odds-and-ends / not-project associated, I use any.do as an app on my phone.


Because I like to be so focused on what it is I’m doing, and because my phone has a long password on it, the Pebble is pretty great. So long as I set my calendar alarms based on travel time and padding, I get a tiny buzz to wrap up what I’m doing, and another to head out. I can keep the rest of the tech away during a meeting, lunch, whatever — without being freaked out I might be making myself late for something else. It’s been surprisingly useful.

Looking for Travel Tools and Practices?

I wrote an entry and gave a talk on that specificity a bit ago.

Sum Up

Being clear about time boundaries sure can be useful. It can also bring a lot of stress, or be an indulgence in compulsions. It’s important to have tricks to optimize self-care as well as work. And focused, solid units mean a more robust, congruent network of nodes.

3 thoughts on “Turning Anxieties into Productivity

  1. This is great! I’ve always tried to follow the “under-promise and over-deliver” advice, but I’ve found it particularly hard in software where scope-creep is common. Do you ever run into that?

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