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Task and Management Update

I haven’t written a blog article in about seven months. It has been about a year since I optimistically wrote “The Great Untasking“. Here’s an update of that graph. Big-picture, little has changed:

The “total queue” seems to be on average 280 items. “Days overdue” seems to be on average a month. Both series are structurally higher than prior to our first full-time hire in late 2016. This hire, which was the cause of so much optimism, gradually reduced their full-time hours until finally they went on full-time leave. This was for personal reasons, and we don’t begrudge them it. I was too cautious/optimistic in waiting for their bandwidth to return; MassLandlords should have re-hired much sooner.

We hired that one person full time before we should have. A single full-time hire leaves one vulnerable to changing bandwidth and personal circumstance. We have since hired four part-time people to replace the one on leave, and have been cross-training them in essential operations. We are now more immune to key personnel departures.

Despite the graph moving in the wrong direction, there are reasons to be optimistic. The new hiring process we used successfully identified new team members with the right skills, and took very little of our time. For the first time, I perceive my personal inbox to no longer be growing even with minimal attention. At time of writing, the inbox represents 188 items and 32 days’ worth of queue, no small percentage of the above backlog. So any day now, when I process that inbox down, we may realize what becomes a new structural low.

Types of Work

This graph shows the types of activities where I spend my time. There are three possibilities:

  • Individual contributor (IC; I am doing work that theoretically could be hired for)
  • Leveraged management (LM; I am working with or specifically to enable another team member)
  • Strategy and analysis (SA; I am stepping back to think about what is happening or should happen)

You can see when the MassLandlords employee went on leave in January, I realized I needed to change what I was doing. I spent much more time on the MassLandlords hiring process, and on our four part-time hires, and have prioritized keeping them busy. I don’t know how high I can drive the leveraged management bar, but the goal is that IC should go down to zero. If it can be hired for, we hope to hire for it.

Split Between Projects

This graph shows the split between my projects:

  • “MTL 7” includes running the house and shopping for a new property (it ought to be renamed from “MTL 7” to “real estate”)
  • “RH” is RentHelper
  • “ML” is MassLandlords
  • “Personal” is other unsorted work stuff like this blog

The real estate portion has been climbing because of the sudden vacancy, a renovation, and some open houses (maybe we’ll buy something). The real estate portion could fall back to long-term levels once the vacancy is filled if we don’t buy anything. Or we could buy a new property and it could climb.

RentHelper is not getting the attention it needs.

Overall, with the exception of the most recent week, I’m more engaged with my work than in the 2017 timeframe (more hours worked each week on average).


In the absence of any real “stepping back” to reevaluate what I’ve been doing, I’ve resorted to the trap of expediting. In the reminder system, some things are tagged as “must happen today.” For instance, each team member gets a “must happen today” reminder to address any remaining emails or overdue tasks at least once a week; 13 ticklers are related to team members. This effectively limits the time they’re waiting for my input on routine matters; they all get expedited answers by chatting or messaging me when they need it.

The rest of the priority ticklers are almost all related to cashflow management, taxes,and billpay. These are all tedious and you would think I could eliminate them, but the consequences of a possible mess-up have prevented me from delegating these.

The final ticklers are about reinforcing priorities. For instance, I purposefully work on the MassLandlords newsletter, MassLandlords events, and RentHelper lead nurturing ahead of older items in the queue.

The problem with expediting is that the queue keeps growing. So until I can work this list of priority ticklers down to zero, we shouldn’t expect to see the task queue decrease. I briefly experimented with eliminating the team-oriented ticklers, but as I wasn’t able to stay at inbox zero, I found our team became unreasonably delayed waiting for my input. So I added them back in.

If we’re thinking about structural issues, the major issues are certainly distractions from what will drive progress. A negative example: a MassLandlords contract partner felt threatened by our ascendancy and stated they would sue us; we offered to discuss and settle, they said no. A positive example: I was invited by the City of Worcester to participate in a task force for housing-first solutions to chronic homelessness; I said yes. None of the work I do on either of those will move the needle on these graphs, but the work needed to be done, both for our long-term well-being and for the public. So it goes.

The Great Untasking (aka Truck Number ~1)

This update gives a little insight into a GTD fail and recovery.

Last November MassLandlords hired a key full-time employee. Before then, we were already heading into task-trouble. The graph below shows the terrible climax. On March 6, 2017, I had 617 items overdue. The oldest was 84 days late.

Task Queue Total and Days overdue as of 2017-07-26

Most of these items were MassLandlords tasks, but the graph shows everything on my plate. The data points were taken when I felt I had time or energy to take data, which sometimes meant when I was feeling particularly bad or good about the situation. (If it were possible to create the graph automatically, I might have been more regular or scientific about sampling.)

When MassLandlords hired in October, I didn’t anticipate what I later came to realize: we weren’t ready to hire for that role. That key hire was great, but they exposed some weaknesses in our processes and resulted in a lot of extra work for me. We survived the last nine months with most of our customers. Most significantly, it’s now fair to approximate our truck number as slightly greater than one. We may be still be in a tenuous situation, but we are nevertheless in the best situation to date.

What’s Different?

Certainly the primary improvement was the addition of our second full time equivalent, despite the surge in tasks their new role created.

Another improvement made during this period was to start migrating all customer service responsibilities out of asana, which has no customer-service features, and into groove. Groove has put up almost no adoption hurdles for the team. It has streamlined and created a sense of perspective that was lacking before. Many tickets ran through my inbox before. I intend to remain accessible to MassLandlords members, but for their sake as much as mine, we are slowly going to start directing their communications to me through Groove. Many routine items (most common complaints: password issues, message board access) can be triaged by team members while we work to eliminate root cause. The items that need my attention can still be forwarded to me.

Another improvement was when I started prioritizing emails from team members. I do not use gmail’s priority inbox. Instead, I have a Monday priority reminder to search my inbox for messages from each team member and provide what they need. I believe that expediting is the sign of a broken process — my process is broken — but this expediting has produced managerial leverage, in the Andrew Grove sense: each hour I spend expediting frees up many hours of team member time. There are currently ten people on my leverage list, putting out 50 to 90 hours each week in total. With team members in the US, Philippines, India, Africa, and Europe, a response one hour late can result in a calendar day’s worth of delay. A sticky note on my monitor reads, “When you manage people, it’s all about them.” This is a great quote from Jack Welch, and a reminder to work towards team dynamics that don’t require me in the loop at all.

Speaking of monitor stickies, another sticky reads, “hire every day.” There are three or four essential roles still needed at MassLandlords before we can declare victory on the bootstrapping challenge. This may take another year yet. When we originally set out in late 2013, early 2014, I estimated it would be about five years to stability. We can’t yet prove me wrong.

Two more factors just in the last 30 days have resulted in a general freeing.

First, one of our most demanding and harassing customers (not a landlord but an organization) finally cut the tether holding them to reality and set sail for the great political void. I bid them adieu, and bid welcome to the newly freed timeslots on my calendar.

Second, I have had a total break from the demanding cycle of MassLandlords events. We are attempting to hire for a major event role before the 2017-2018 season begins. We also hope to reduce my attendance at some events with video. Events took up more time than I realized, and since there are no events in July or August, I have been able to close out a wide variety of tasks. There are currently 102 projects and focus areas in various states of need. Many of the projects will be closed out, and we will continue to offload focus areas as we hire.

So that’s the GTD fail and recovery. This fall, when events resume, we shall see whether I have made a lasting improvement.

Prioritization Grid

I drew this on a screenshare today while talking to a MassLandlords manager.

priority grid, hard high impact, easy low impact etc.

I don’t remember where I learned it*. The basic gist is that lots of people will suggest lots of things for you to do.


Some things are going to be hard and have a low impact on your goals. Write them down, but don’t do them.

  • These might become more relevant or less difficult in the future.
  • Writing them down, as opposed to outright rejecting them, lets you return to them in the future. It also is more politically palatable to a requester to hear that it’s in your system, albeit lower priority, than “I have deleted your request.”

Others are going to be easy, low impact. Most administration falls into this category. Hire for it if you can. If you’re not able to hire, do these items when you’re tired.

  • Anna Dietrich described these items as “zombie tasks” or “shooting zombies” because they are repetitive and won’t ever die. I like that analogy.
  • When possible, try to eliminate the source of the zombies. Automation or process changes can eliminate a lot of the low impact work we take as given.

Some things are easy and will have a high impact on your goals. Do these asap.

  • This is the most difficult thing for someone detail-oriented like me to do. I like to have a clean desk and inbox zero. Much of my best work happens because I ignore the other pressures.

The final set are things that will have a high impact but are hard. These require project plans and a longer-term commitment.

  • It’s extremely important not to let a “high impact” item linger because you haven’t created the project plan. Oftentimes the first “action” is a brainstorm or research. Get these items into your task list. David Allen’s advice is invaluable on this front. Define the next action. The journey of a thousand miles begins with a single step.

I don’t like spending lots of time bucketing items into different categories. I don’t like systems that have nine or 16 squares. This four-square framework can be useful for communicating when you will or will not work on something. Otherwise, just get back to work.

*Covey’s Original Prioritization Framework

It turns out Stephen Covey popularized this, but he didn’t have “difficulty,” he had “urgency.” This switch hides any recognition that management or project planning might be needed. I might have learned to replace “urgency” with “difficulty” at Pratt & Whitney, I don’t know. Suffice it to say I think of the grid above when I think of priority frameworks.

Thinking of “urgency” works better in the “personal productivity” space, but less well in organizations. Everything is urgent to the requester.

The Worst GTD Backlog Since Tracking Began

This afternoon I’m at the worst backlog of “things to do” since GTD tracking began in late 2014. I have 333 items in my inbox, on my desk, and in my task list that all demand attention yesterday. What’s astonishing is that “days overdue” is only 8, which means none of these things really originated before the last week. That’s 300 things to do since last week.

graph of task queue and average overdue

I can take a lot of pressure, this is getting near the limit.

A big part of it is the MassLandlords meeting cycle, which holds back a lot of ideas and issues over the summer and then many of our 1,200 members start sending them in. That’s wonderful, but also difficult to manage. I’m lucky we have new part time staff in Springfield to help with some of these requests. But then again, the Springfield group’s dissolving and folding in has taken a lot of my capacity the last two weeks, contributing to the backlog.

The other thing that’s happening is I’ve implemented a really great expediting system, which is a sure sign of flow failure if ever there was one. Expediting certain tasks ahead of older ones in the queue signals my lack of bandwidth. It keeps the fires from raging but it builds up pressure on the overdue items and creates stress. The right way to schedule is to create excess capacity or flex capacity so that things like phone calls don’t send us off on a tangent that we didn’t have time for.

Clearly we need more staff at MassLandlords. I’m working on it. But as I’ve learned over the summer, it can be worse to put the wrong person in the job than to have no one at all. The wrong person can cause more harm than good.

My average pace has been 57 hrs/wk. I had a nice relaxing summer, where the average went down to only 37 hrs/wk. In the big scheme of things, I still exercise, and eat right, and sleep adequately. And I’ve put in harder hours in the past. But boy, I really could use another Friday right about now.

How to Stay Productive and Get Things Done When Tired

It’s nice to look back on a day and think how productive we’ve been.  But all too often our natural ups and downs take us to a point where we’re too tired to get things done.  The best advice I was ever given wasn’t about “taking a break,” or “getting some coffee.”  But those do help sometimes.  Really, the advice boils down to “prepare to be tired.”

What does it matter if I’m not productive?

Think about your bathroom at home.  If you’re like me, you don’t have a maid to come in and clean it.  You have to clean it yourself.  You really have one choice about it:  clean it yourself or don’t.  No amount of preventative care is going to keep grime from coating every surface.  If you’re productive enough to keep it clean, you’ll enjoy a higher standard of living than someone who isn’t and who doesn’t.

The same applies to your work.  The same applies to everyone’s work.  The Bureau of Labor Statistics provides the data to make this graph, which shows relative non-farm productivity per hour since 1947.


This gives some value to how much higher our standard of living is now than in 1947.  We enjoy at least four times the standard of living.  Three examples:  quick healthy food options, Internet data sources, and cars that start reliably in zero degree weather.  I’d say those three are at least 10x improvements.

So you can sit back and relax, or you can do something to work towards that car you’ve always wanted.  (It’s not a mid-life crisis, it’s about standard of living!)

So how do you get things done when tired?

Don’t do easy stuff when you’re full of beans.

Let me reiterate that:  being productive when you’re tired is more about not doing than doing.

Here’s the example that drove it home for me.  I used to grade papers and write problem set solutions for a technical class.  The professor running the class looked at the dark circles under my eyes and said, in effect, “I can see you’re not coping.”  (He likes to cut to the chase, and I appreciate that.)

“Grading is easy, right?” he asked.

“Yeah,” I said.

“These problem set solutions are not very good, are they.”


“Do your problem set solutions when you’re fresh.  Knowing you, I’d say that’s in the morning.  Grade papers late at night.  All you’re doing is pattern-matching against the solution anyway.  You can do that in your sleep.”

And he was right.  Very, very right.  It’s been a while, but maybe I can still grade thermodynamics in my sleep.

You can stay productive and get things done when tired

The Getting Things Done Implementation

To prepare for being tired, you need to resist the temptation to do easy things when you’re fully alert.  But you don’t want to forget the easy things that still need to get done.  Enter David Allen’s seminal book, “Getting Things Done: the Art of Stress-Free Productivity.”

Allen advises a “collection habit.”  That means when you think of something that needs doing, you write it someplace you’ll check later.

For me, that’s an Excel spreadsheet.

Whatever format you use for your task list, it should indicate the context in which you’ll do the task.  Some tasks require a phone.  Others require a specific person.  Any task can be put in the context of your energy state.  Here’s a screenshot of my actual task list:

Sample "to do" list allowing for being productive when tired

The column headers are

  • Which project does this task support?
  • In what context can the task be done?
  • What is the task?  (Really specific, so I don’t have to think too hard about it)
  • Status. (blank = not done, “waiting for” means we’ll filter it out until the tickler comes up. “maybe someday” is a parking lot)
  • When do I want to be reminded about this task?

You can see down the “context” column that all these tasks require a network connection (most do nowadays), and

  • The “high energy” tasks are things I do when I’m energized.  They’re often long tasks.
  • The “scattered” tasks are the things I do when I’m over-caffeinated, likely to be interrupted soon, or tired.  They’re all short little things or things that don’t need much concentration or willpower to do.
  • The “leisure” tasks are things I do when I have some fun time.

The natural implementation

If you’re too tired to filter a spreadsheet down to “tired” tasks, just look around your desk.  Something can be filed.  Something else can be shredded.  That collection of receipts can be entered into QuickBooks.  That coffee mug can be washed out.

That is, as long as you didn’t do those this morning when you were operating at 100%.  If you did, you’ll be staring at a clean desk with an egregiously difficult cover sheet to write for that TPS report.  Not good.

Saving these light-weight tasks amounts to planning a productive little break.  While your tired brain is resting, you’ll still be doing productive things that need to get done.

Try it and see for yourself.

Time Management and GTD During My “Search”

I’d like to share some interesting time management data I’ve collected over the last nine months.  When I first left Terrafugia, in October 2012, I started what my McKinsey friend called “search.”  That’s when your full time job becomes finding your next full time job.  I was busy with “search” the very first day off of work, finding entrepreneurial networking groups, looking into various business ideas, and meeting with all kinds of people about all kinds of topics.

After a time, it became clear that certain projects would earn my regular and ongoing attention.  The graph below shows one series for each such project.  The data begin on January 24, 2013, but they’re smoothed out as 40 day moving averages.  The vertical axis shows “level of effort,” or what percent of my working hours went to a given project.


A short legend:

  • mtl 7” is my rental property.  It’s a steady 10% effort except during vacancies, like in March and April.
  • ArtistBomb” is a bona fide tech startup with real potential; it’s where I put most of my effort now.
  • ghost bear” was the code name given to a project to develop a luxury consumer product.  This was canceled due to what we forecast as shrinking margins and rising development costs.
  • stocks, finances, and accounting” is the time I spend keeping my financial house in order.
  • wpoa” is the Worcester Property Owners Association, a volunteer effort with far-reaching possibilities down the road
  • blog/consult/elance” tracks my time developing this blog, doing ad hoc consulting, and learning how to use elance both as buyer and seller.  They’re grouped because these activities happen under the same entity.
  • the “bagpack” is the BagPack for Hands Free Groceries, a consumer product that was able to get off the ground. (We’re still looking for a real model.)
  • search” includes the wide variety of projects with which I’ve had some contact, including apps for local search, hardware and software for robotic vision, and just over a dozen other concepts pitched to me.  It also includes my networking time before I started representing ArtistBomb exclusively.
  • business of life” is my catch-all for things like “getting new tires” or “getting new cell phone.”  They directly benefit my productivity but can’t be allocated fairly to any project.

I find it interesting to look back and see how my attention has shifted hither and thither.  Some projects require constant nurturing, some develop wings and fly off on their own, some have to be taken around back and shot.  But that’s the risk with any new venture.  Good time management ensures that you’re getting the most out of yourself, even if sometimes you head down blind alleys.

If you’re interested in knowing how I track my time like this, check out my previous article.

What do you think?  Have you pivoted your time away from some things and onto others in the past year?

Busier than a one-legged man at a butt-kicking contest

Yes, I guess I am, but I don’t feel that way.  Below are some fun statistics from my personal task list, and one big surprise at the end.

(For those of you that don’t know, I follow David Allen’s Getting Things Done to stay in control and Making it All Work to keep perspective.  The gist of the first book is simply that you should write down everything that occurs to you and keep this all in one place.  That way you never panic that you’re forgetting something.  The gist of the second book is that you should keep a separate, shorter list of bigger things that matter.

I also follow Andrew Grove’s  High Output Management, which is what inspired me to start taking data on this stuff.)

This first graph shows task completion since I started tracking data last winter:


My collection habit means I go through phases, like May to early June, where I add much more to my list than I can remove.  If the blue line stays above the red line indefinitely, my task list will expand forever, and that’s bad.  So I want that red line up high.  Overall, the red line makes it looks like I only do five things a day.  I guess most of what I do is so spontaneous and isn’t on the list.

This second graph shows the quality of my tasks.  One of the things David Allen goes on about is making sure that your tasks have a context.  So I want that green line down near zero.  Most folks would also want that purple line down near zero, too, because that would mean they could retire (nothing left to do).  But for me, always thinking about what could be better, I’m okay with letting it pile up until I get some help.


You can see the effect of tracking metrics in these first two graphs.  When I first started back in December, I saw literally hundreds of task list items that had no context and appeared undone.  I reviewed these all until they had moved to wherever they belonged. Some of them were given contexts and/or set status = “complete.”  Others were set status = “maybe someday,” which means I still might get to them.  For instance, some day, maybe, I want to dedicate a statue in a park.  Doesn’t need to be on next week’s “to do” list.

This final graph speaks to my ability to follow-up.  David Allen defines a “tickler” as a reminder to do something.  As of yesterday, there were about ten ticklers overdue.  The red line indicates that I’m waiting for something and I haven’t set a tickler date.  That’s not helpful, so I want that down near zero.


So what’s the big surprise?  Since I started tracking data in December, I’ve completed 937 tasks and 23 major projects.  That’s about one project a week.  Here’s a sampling:

  • Win my first freelance consulting job.
  • Prove that some physics we were testing in one program works.
  • Rent out one apartment.  And then another.
  • Help Team #1 launch a consumer product (Hands Free Groceries).
  • Write a business plan for XYZ (didn’t start).
  • Help Team #2 launch a tech startup (ArtistBomb).
  • Help Team #3 rewrite the bylaws for a non-profit (had some help on this one).

And I’m not breaking a sweat.  Thank you, David Allen and Andrew Grove.

Five Reasons why Entrepreneurship Isn’t Quite Business


Good entrepreneurship eventually leads to good business.  But here are five reasons why the two start out different:

1. Framework

Startups may be inventing either a new product or a new service, but quite often they’re also reinventing a business model.  Good businesses, on the other hand, already know how they’re going to make money.  Good businesses therefore always have this framework in which they can adapt to changing circumstances, but startups usually search for a bit before they figure out what it is that they’re doing.

2. Customers

Startups have no customers.  Businesses focus on the omni-present “voice of the customer,” but startups have to go to extraordinary lengths to find this.  They have to develop a product, get it in front of possible customers, and get their feedback.  Sometimes, the first “customers” you talk to turn out not to be your customers at all.

This “lack of customer” means many startups have under-developed or non-existent sales and marketing teams.  Many high tech startups bet the farm on a single big product unsupported by secondary revenue.  If this is the case (and that’s a capital-intensive strategy), you’re much better off thinking about the “company” as a product development team than as a business.

3. Processes

Startups have no established ways of doing things.  Good businesses have written processes and procedures AND, less commonly but even more importantly, built-in rules for changing the process.  This is at the heart of why so many startup investors place so much stock in “the team.”  Good businesses make it possible for ordinary folks to do extraordinary things.  Good startups almost always rely on extraordinary folks.

4. Resources

Startups have what seems like too little time and usually no money.  Good businesses operate on long timescales with the ability to forecast, budget, and invest.  If you’re at a startup, you have to be extremely adept at balancing long-term goals with immediate needs.  Many of the building blocks of a real business will seem unaffordable at a time when maybe you should be paying for them.

5. Independence

When you start something new, no one tells you what needs to be done.  If you fail to do what matters, your venture fails.  In good businesses, there are mechanisms whereby individual accountability is reinforced from the outside.  Customers call you back to find out why you haven’t finished their project, your boss tells you what your goal is this week, the manufacturing floor tells you what you need to fix, etc.  But when you’re in a startup, you really don’t have a lot of buttressing.  Everyone must be highly accountable to themselves with good follow-up techniques and task list management.

Where does all your time go?

It’s winter in Boston and it’s dark by 5p.  When it’s night already and you didn’t get much done, you can feel like the day just escaped you.  Here’s a trick to keep a sharper look-out on your time: keep a time log.  All you need is a small, reporter-style notebook and a pen.  Here’s how it works.

Your First Time Log

Just for a couple days, every time you switch from one activity to another, jot down the time and a short description of what you were doing.  Then, when you have a couple of days’ worth of data, look at where you spent your time.


Oftentimes, the simple act of paying attention to what you’re doing is enough to help you use your time more effectively.  But sometimes when you look back over a day’s work, you’ll see surprising things.  When I first tried this, I was amazed at how much time went to helping coworkers figure things out.  I had previously thought of these drop-in tasks as interruptions, but when I realized how much time it took, and how important it was, I started thinking about it as my major job responsibility.

That’s a good example of where time tracking can eliminate a stressful perception about “wasted time” that really isn’t.  It can also shed light on the timesinks.  Email, for instance, is crazy-inefficient compared to high-bandwidth phone calls or face-to-face meetings.  If you find yourself spending a long time in a general bucket, like “email” or “errands,” try to rephrase it in terms of what you’re actually accomplishing.  If the email is related to that new product launch, then that time spent emailing counts as “product launch” time.  If you thought about “product launch” as your goal, would your first action be to check email?

To summarize your activities, you might take a clean sheet of paper and write down in one column “activities,” and then in another column write down “blocks of time.”  You can get very sophisticated with this, and in fact, it’s the essence of cost accounting for professional attorneys and hourly contractors.


A few tips

  • There’s no need to be very precise, just put down times to the nearest quarter hour.
  • Try to make the activity descriptions useful for your review.  For instance, if you split your time among three projects, better to write down “project A” or “project B” rather than, “typing report”
  • If you’re focused just on time management while at work, leave out out-of-work activities.

I’m curious to hear whether you find out anything surprising.  Drop me a note, or leave your comments below!