The Need for Modes and Boundaries, Pt 2

We talked last time about the importance of boundaries and modes at work. But burnout doesn’t just exist as an epochal work event; it can apply to using new tools, or even “productivity” itself in getting life things done. Famed productivity expert internet comic artist Allie Brosh weighed in on this phenomenon: an initial burst of vigor, “finally getting my life together”, eventually wanes and withers into nonimpact. I am certain I am not the only person to have the same experience trying a new productivity tool: jump in, try really hard to work all my things into it, then eventually find I never use it and give up. Thankfully, the boundaries and divisions from workplace productivity are instructive, and apply just as well to personal productivity systems.

Draw a line between executing and not

It is exhausting to have the seemingly-infinite list of things to do constantly looming over you. Unless you differentiate between “trying to get things done now” and not, you are more likely to grow weary of even trying and abandon the entire project. Block off some time on a daily basis for knocking out your objectives, then honor that line and stop. You will not lose any weight on a diet you hate and abandon, and you will not get anything out of a productivity system you hate and abandon.

Block off right-sized time

If the tasks you need to do are simple, small, and uncreative, by all means schedule an arbitrary amount of time, perhaps in intervals across the day, and just fill it to capacity. But if the task is creative, like “do that drawing assignment” or “write that blog post”, block off a long, uninterrupted period of time that allows a period to get into and out of “the zone”. If you instead try to do that writing in short windows “whenever you have the time”, you will be less productive and less satisfied with your end-product.

Build healthy habits

There are better and worse ways to try to build systematic changes into your life. Setting reasonable sized goals, like only a few hours of execution rather than constant labor, is an obvious one. Other people have already done the experiments and written up their findings for what does and does not work in building habits; don’t reinvent the wheel! The short version: remove obstacles, add incentives, and use contextual cues to steer your actions without thinking about it. Instead of jumping head-first into a new productivity system and burning out, add a couple things to it, work it into part of your daily routine, and add more things as you are able. The “lost productivity” of not maximizing each of your initial days is dwarfed by the productivity gains from successfully working a good system into your life, so don’t endanger the latter to eke small gains out of the former.


Separate concerns for separate problems and frictionless systems are big themes in the research we have done for Bonsai, and are our motivation in developing it as we do. In work, in life, or in anything else, try to break the big things down and avoid straining yourself doing too much; ramping up your productivity in a sustainable way is the goal.


The Need for Modes and Boundaries

The research is pretty clear on what makes for a maximally-productive workforce. I want to talk about boundaries & modes that protect productivity from well-intentioned mangling, and especially the worst possible thing for productivity: burnout.

Burnout is the enemy of productivity, and has gotten all too common. Working longer and longer hours, answering email at all times of day and night; these are the signs of impending productivity collapse due to burnout, and they highlight two important concepts: boundaries (the lines that separate different things) and modes (the things being separated, ex work-mode vs relax-mode). In order to maximize productivity, you need to mind the lines between the three big mode dichotomies:

  • work vs not work
  • get-it-done vs unstructured work
  • manager work vs creative work

Work vs not

A common but oft-neglected bit of advice: you need to unplug. Even “Lean In” luminary Sheryl Sandberg observed a hard “out at 5:30” rule to separate work concerns from life concerns. Incremental minutes on work past 40hrs/week may individually seem like a good idea, but collectively compromise efficiency, work product, and personal health. According to the Centers for Disease Control and Prevention, studies show “a pattern of deteriorating performance on psychophysiological tests as well as injuries while working long hours.” Recovery from overwork saps efficiency from subsequent weeks.

Now-execution-mode vs freeform

Drawing sharp lines between “get it done” mode and less structured effort is healthy and can increase productivity. The Harvard Business Review notes that highly successful companies like 3M and Google share a best practice: specifically-budgeted 10-15% time for employees to work on their own projects. “Get it done” mode can be useful for short periods of focus, but that same focus impedes the creative thinking that produces novel, long-term products. AdSense was a product of 20% time, and produces ~25% of Google’s revenue. Sadly, the temptation to cut freeform time for more command-and-control time can be too real; that link and this one note the conflicted current state of 20% time at Google. Don’t kill the goose that lays the golden eggs; implement, respect, and enforce freeform-creative time.

Long-block vs short-block time

Paul Graham is the earliest source we know of on the difference between maker time and manager time. Basically, people who manage slice and dice their day into many short blocks; 1-on-1 with Jane, call Jim, sit in the Due Diligence meeting, etc for 30 minutes to an hour each, across an entire day. When you are a person with power and your time is scarce and expensive, this makes some sense for wringing as much value out of that time as possible.

But there are hidden consequences of this approach, with the biggest being disruption to the other paradigm of scheduling: creative work, which benefits from long, uninterrupted blocks. A manager usually has many smaller tasks with simple, clear context to work with, ex “Hey Steve, how’s it going, here is what I need from your TPS reports”. But creative work, which can include any sort of writing, art, programming, etc, is much harder to define and has more significant ramp-up and ramp-down costs. As Graham notes, adding just one meeting to the middle of a creative worker’s day can easily ruin productivity for the entire day, because it can take a long time to just get into the headspace needed to be effective.

A brief aside: creative work

Creative work is commonly the victim of misunderstanding the above boundaries, so let’s work an example to understand the important parts.

A key concept that can be unintuitive for some people, (especially managers, unfortunately): creative work is a lot like conducting an invisible orchestra. When I am working on a software problem, I have to be aware of:

1. what my relational database is up to,
2. what my web service is doing,
2. what my worker processes are doing,
3. what my message broker is doing,
4. what any client-side code is doing,
5. how all of this fits into my deployment pipeline.

Those are just the relevant actors. In order to change anything, let’s say in the web process, I have to think about:

1. what I want to be done, 
2. where I need to make changes, 
3. how these changes impact any other part of the system,
4. whether these changes push any other piece beyond what they can do, including at scale.

And then there is standard stuff like writing to match code style, test coverage, etc.

Everything is tangled together in an opaque snarl, and changing any piece can impact every other piece. Just like in conducting an orchestra, you usually cannot just double the volume or cadence of the timpani without causing a new problem: now no one can make out the flutes, or the musical phrases are out of sync, or something else. It requires substantial focus to build up the mental model in working memory, and most of your brainpower to make mental changes & reflect them in the world. Remember, all of this is invisible, without the benefit conductors get of asking the woodwinds what they think, so it is that much more difficult in addition. Obviously having a manager drop in “for just a few minutes” would blast away all of that built up mental model, and restart you from zero! Problematically, it is not just software that has so many concerns to juggle. Artists need to worry about visual hierarchy, inspiration sets, consistency of visual grammar etc; creative writers need to manage plots, themes, word choice, imagery, etc; lawyers and other technical writers need to recall interlocking precedents, argots, tropes, etc.


With these distinctions built up, we can construct more productive workflows from the start.

  • Creatives get boundaries of long, uninterrupted time blocks that are respected,
  • Managers get checkins/pull-ups etc at the sides of these blocks,
  • Approximately 80-90% of work time is dedicated to executional “get work done” mode, while the remaining 10-20% is used for worker-directed tasks plausibly believed by them to be important
  • At the end of the 8 hour day and the 40 hour week, everyone goes home and does not-work to stay energized and productive.

On Flow

Somehow, we have neglected to talk about one of the most important ideas in doing satisfying, productive work: flow. Let’s cover the basics of:

  1. what flow is,

  2. how to achieve it,

  3. how to sustain it.

What is flow

Flow is a state of active, energized engagement with an activity. Some people describe the same state as “being in the zone”; time slips by unnoticed as you keep surmounting obstacles and achieving your objectives. Sounds pretty great, right? Imagine cruising through your workday, or your to-do list, with exhilaration instead of trudging monotony. While some people seem to fall into this state habitually while others struggle, it is not just a hereditary superpower; predictable and controllable preconditions enable finding a flow state.

Getting into flow

Owen Schaffer proposed 7 key factors in a 2013 paper:

  1. Knowing what to do

  2. Knowing how to do it

  3. Knowing how well you are doing

  4. Knowing where to go (if navigation is involved)

  5. High perceived challenges

  6. High perceived skills

  7. Freedom from distractions

It is easy to be reductive about that list: “oh, all I have to do is totally understand my goal in every way and then just do what feels right? Thanks.” But really, it can be condensed into a shorter and more tractable version which gives more guidance:

  1. One must be involved in an activity with a clear set of goals and progress. This adds direction and structure to the task.

  2. The task at hand must have clear and immediate feedback. This helps the person negotiate any changing demands and allows them to adjust their performance to maintain the flow state.

  3. One must have a good balance between the perceived challenges of the task at hand and their own perceived skills. One must have confidence in one’s ability to complete the task at hand.

    (Source: Handbook of Competence and Motivation)

If you want to get into a flow state, you should arrange ahead of time to have well-understood:

  1. Goals (how do you know when you are done?)

  2. Feedback Mechanisms (“hotter or colder”, are you moving toward or away from the goal?)

  3. Skills to apply (what are my options here?)

Notably, this pre-planning problem is amenable to it’s own approach.

  1. Its goal is to have an evaluable goal (knowing when you have completed it) and skills to apply against the goal that are exhaustable (you know when you have tried everything and need to find new skills or adjust your goal).

  2. Its feedback mechanism is specificity of predictions (“when X happens or at 5PM tomorrow, I will know this problem is achieveable or not”).

  3. Its relevant skills are time and work estimation.

Let’s work an example. Say you want to make an Android app that does something basic, like logs your progress in reading new books. (For a reason, all existing apps won’t do the job for you.) You need to do the preplanning to build a flow state during the actual work:

  1. Plan out the specifics of what features need to be in your app to be “done”. What does the interface look like? What are expected behaviors? (a goal)

  2. Identify what tools are at your disposal. Are you already familiar with Java and Android development? If so, plan out specific subtasks: getting the right development kit, what version control will you use, how will you distribute your app or measure “progress” reading. This is where you create specificity to enable flow in the work itself.

  3. Estimate: is this practical in the amount of time you have allotted? Is the road from your skills to the goal measurable, so you know when you are getting closer, moving farther away, or spinning your wheels? If the road is not clear, you may not have the skills you need (making flow in the work impossible) and you might be better served in acquiring those skills. (Note: that, too, is a flowable job!)

Objectives, feedback function, and skills in hand, you can dive into the actual app development itself by conquering subtasks: installing all the relevant software, mocking up interfaces, building the data storage, etc. If a particular subtask is too big to be tractable or underdefined, (for example you discover that learning Java is not a single-afternoon activity,) revert to the planning flow to make the task tractable or reevaluate the activity. In this model, there is an approach for everything, and the “next step” is always clear; no getting lost in the labyrinth and hoping to stumble on the path, which is stressful and agonizing.

How to stay in flow

So you’ve stabilized your plan/execute approach, and can work on achieving flow. Wonderful! There are a few known speedbumps that can knock you out of flow: boredom, apathy, and anxiety.

Apathy is linked to low challenge levels matched with low skill levels and a seemingly-unimportant goal; this might be mitigated by contextualizing the goal to demonstrate importance.

Boredom stems from high skill levels applied to a low skill task; even if the goal is desirable, no one likes doing something tedious. Investing in automation tends to be your friend here.

Anxiety is the trickiest: when you are in over your head, and your skills are insufficient for the task, anxiety naturally crops up. Taking a step back, and investing in the skills to get up to the task, is the best way forward.

After dodging these common traps, most of the job is biting off right-size pieces to work on, and maintaining a sense of progress. This is an iterative process; when things are not working well, step back and adjust! Your life will be much more pleasant as a result.


“Take twice daily”

Everyone has things that they need to do regularly, just not at particular times. Washing your sheets, cleaning out the refrigerator, hitting the gym, drinking two glasses of water; these tasks don’t have specific deadlines, and you can always push them back by several hours or days, but everyone still has their ideal rate. It might be twice a week, once a month, or three times a day, but these rates are hard to enforce: because they are infinitely deferrable, it is hard to ensure you are hitting the rates you want.

So what are we to do? I don’t have the definitive answer to this, but here are some different approaches.

Create external tools to keep you on track. One approach is to tweak the Jerry Seinfeld calendar technique. Seinfeld wanted to write new comedic material every day, and his trick was to get a whole-year calendar on one page. Every day that he wrote new material he put a big, red, satisfying X through the day. After only a few days, the impetus to “keep the streak going” helped reinforce good habits. With daily tasks, try keeping reminder stickynotes in your wallet and mark the calendar on each success day. Similarly, for each week mark success or failure in doing the x-times/week tasks. Don’t just continually look forward; block off segments of time and succeed or fail on those!

Make the reminders when you have the willpower, then do those things later. Tools like followupthen can be set to email you reminders on specific days (like March 31) or relative days (like tomorrow)to build a reinforcement system on top of the email we all already use. If it doesn’t matter when during the two weeks you wash your sheets, just pick a day and set the reminder for then. The freedom of “anytime” is exactly the thing that obstructs getting what you want done, so sacrificing that flexibility may actually make you more effective!

Account for how you spend your time, and fill in the gaps with anything on your “I ought to” list. Some things in life require intentionality and planning, for example putting in the time to become a sketch artist. But frequently, periodic tasks are easy and require no planning; you just throw your sheets in the wash when you have a moment. But unless you account for how you spend your time, it can feel like you are constantly overwhelmed when really you are wasting lots of time. Fight that phenomenon by taking measurements, so you can change things.

Your brain is good for many interesting things, but managing the dull and boring nature of periodic todos is not one of them. Why do the drudge work yourself when you can invent a system (a much more interesting task) and offload all the minutiae into that?