Cater to Your Personal Pathologies

Managing your time, I’ve found, is mostly a psychological problem rather than a logistical one. Many books lay out a particular system – from the Covey quadrants to David Allen’s 43 folders to a sea of nifty acronyms. What I’ve found from trying them out, and watching others try to use them, is that a system only works if it matches your particular needs. More specifically, if it caters to what I call your pathologies.

We all have some idealized version of ourselves that we aspire to be. This paragon of virtue may never procrastinate, or always rise above temptation .. whatever takes your fancy. Then there is the actual, flawed, imperfect person we actually are. Many people try to use a system that ought to work, rather than one that does work (for them). Hence a sea of unused DayTimer notebooks, mountains of abandoned organizational gear, and endless hopping from one To Do app to another. If cosmetics are “hope in a jar”, then organizational tools are “hope in an app” (or for the traditionalists, “hope in a binder”).

So what do I mean by pathologies? I don’t know what yours are, but I’ll share some of mine.

I Hate Clutter

Some people feel comfortable surrounded by things. They naturally keep papers in piles and leave lots of things lying out on desks. Not me – I like a spare and streamlined work environment. How does this relate to being productive? A friend of mine built an elaborate set of rules for sorting his email. Messages were passed automatically to a lovingly organized cascade of email folders. It worked well for him and was really cool, and I thought I’d give it a try, too. Result: disaster.

All my mail would come in, be sorted into the appropriate category, and I would look at it and be soothed by its orderliness. The problem is that I achieved this calm and pleasing result without actually doing anything. I had to throw away the whole thing and go back to having everything pour into my inbox and annoy me. Then I would be motivated to clean it up, by actually looking at the mail, making decisions, and taking action.

I Like To See My Whole World in One View

When I’m figuring out what to do, I like to see everything that matters all at once. I get stressed out when there are things I need to be thinking about, but they aren’t in front of me so I’m not sure I’m remembering all of them.

I like to plan out my week every Monday morning, and for many years, I have used two facing pages in my notebook to show: the big projects I’m responsible for, any deadlines for the week or in the near future, active to do items, key appointments, top priorities for the week, and top priorities for each day. It is a challenge to capture all that in two pages, but I’ve found it to be a really good exercise – it forces me to think about what’s important and distill it. Each time I have a new kind of role, I have to change those two pages. What I needed to capture when I managed a big team was radically different than when I’m a team of one in a startup and mostly work by myself on a set of projects. I keep those two pages open on my desk most of the time, so I’m always reminded of the most important things that I’m supposed to do that day and that week.

I could keep going for a while (I like to write and draw on paper, I can’t use bound journals because pages can’t be inserted or rearranged, ..), but I’ll spare you, because the important thing for you is to figure out what your pathologies are.

Sleuthing Them Out

A good way to start is to ask yourself:

  • What system has worked well for me? What did I like about it? Why did I like using it?
  • What didn’t work? Did it fail (you kept forgetting to do something important), or was it too much overhead, or did you just stop bothering with it? Why?

Remember, this is not about some idealized vision of yourself, or what works for somebody else – this is all about you. When you answer these questions, especially the second one, try to avoid value judgments – it’s not constructive to beat yourself up with things like “I’m lazy” or “I suck at organization”. Stick to thinking about what you have tried, what worked, and (for the things that have not) why they failed you.

The answers might be psychological (“I like writing things on paper because it is more visceral and I feel more committed to getting it done”) or mundane (“I didn’t carry around the binder because it was heavy and didn’t fit in my bag”). Don’t scorn the details – your whole system can founder if you just don’t like using it. If the color of the notebook bugs you, or you have a fetish for fountain pens, pay attention. If you are using an app, the details of the user experience matter a lot. “This app made me set up all these categories and I just got lost – I need something simple.” Or “I hate looking at the interface – it’s ugly”.

Your “system” might be very informal – maybe you like post-it notes on your monitor. Or piles on your desk organized a certain way. As long as it works for you, that’s what matters. Try to figure out how to eliminate any friction that prevented you from using (or wanting to use) some solution. Try to enhance any quality that you really like.

At the end of the day, the measure that your approach works is that you know what is important and you get it done. Then you have created a magical accelerant for your life.

Congestive Meeting Collapse – Scheduling Gridlock

I used to spend most of my day in meetings.  At one point, when I was managing a large team, I routinely had weeks where there were a total of 2 hours between 9 and 5 that I wasn’t in a meeting .. for the entire week.  Anything I needed to work on that didn’t involve other people had to happen early or late.  Such as answering the crushing quantities of email that stacked up while I was in meetings and actually paying attention.

Now that I’m in a startup, where I’m typically in a traditional “meeting” for a couple of hours a week total, it is amazing how much gets done.  When I touch base with people from my previous employer, the scheduling overhead can become darkly humorous.  Routinely somebody will ask to get together, and then schedule it for a month later.  That slot then gets stepped on by some other meeting, often more than once (and typically at the last minute). It’s common for it to take two to three months to set up a conversation with more senior folks (!).  Really?

I think there is an interesting analogy to the performance of networks.  When the amount of traffic reaches a certain fraction of a network’s capacity and the scheduling protocols are not optimal, the network achieves what is called congestive collapse.  It means that the network is in a stable state of low throughput.  Is your company permanently in “congestive meeting collapse”?

The Damage it Does

When everyone is so hyper-scheduled

  • There is no slack in the system.  If something important comes up, you have to step on an existing meeting to get everyone together.  When one meeting is moved, that causes a cascade of rescheduling among all the attendees, which moves other meetings they were in, and on outwards like ripples in the water.
  • Everyone is in meetings all the time, so they are frustrated, bored, and don’t have time to work on individual projects except outside normal hours.  Anything “optional” (like thinking deeply about the state of your world, the future, and what you need to do about it) gets squeezed out by something “practical” but often much less important.
  • A huge amount of time is wasted scheduling and rescheduling.
  • “Medium importance” decisions take forever.  Big ones get attention; the medium ones that require a number of key people to get together and resolve something, but aren’t a crisis, get rescheduled and rescheduled and take much longer than they should.  This gums everything up and makes the organization inefficient.

Why Does This Happen?

Clearly the problem is that there are too many meetings, but why is that?  There are some obvious kinds of inefficiency, such as:

  • The Serial 1:1 – Some meetings are a lazy way for a manager to talk to folks on their team.  Everyone else sits glumly listening, doing email and/or propping up their eyelids with toothpicks, as the manager talks in turn to each person.  Now and then something relevant to the whole team comes up, but mostly it is a series of 1:1’s with bystanders.  Regular team “status” meetings are often like this – ugh, don’t do it!
  • The Inefficient Mess – There is no clear agenda, things wander along without being well managed, and action items aren’t captured efficiently.  Something that could have been handled in 15 crisp minutes takes 90 minutes, and often bleeds over to another meeting because people weren’t clear about what they were and weren’t accountable for doing afterwards.  This is lampooned by John Cleese in a fun training video called “Meetings, Bloody Meetings”.

But annoying as they are, bad meetings like these are just one-off problems that can be fixed with some coaching.  The much more insidious villain, I’ve found, is too many stakeholders.

As organizations grow, and as more groups are needed to be successful, every important decision develops a long list of people who legitimately have a stake in how it is made.  For example, consider a major shift in the strategy of a particular product.  It affects the people who design the product, build the product, communicate with customers, sell the product, and support customers.  It might also involve legal issues, HR issues, and resetting the expectations of senior management.  In a matrixed world, even one stakeholder can drag in multiple people – sales organizations often have somebody who owns the worldwide quotas for a particular product, for a particular market segment (“enterprise customers”), and/or for a particular regional market (“Germany”).

Thus, two things tend to happen.  One is that many stakeholders get involved in the decision.  They participate in meetings to discuss it, commit to it, implement it, learn about it, and review progress on it.  They all try to get invited to the most important meetings, so they are “in the loop”.  As you scale up, this leads to madness.  The other result is that it is so hard to get things landed that only the most senior people in the organization have enough authority to drive key decisions.  So more and more things land in their lap, disempowering everyone else and slowing things down to a crawl because nobody can get the meeting scheduled with them(!).

Sometimes you can dodge the problem by keeping teams small – the so-called “two pizza team” approach.  But if you are successful, eventually things tend to get big.  And at scale, I think the only solution is to cleanly and aggressively delegate authority and to be absolutely hard-core about defining a minimal set of people who get to influence a decision before it is made.

Both of these are hard and involve risk.  Sometimes, the decision-maker will screw up.  Bad decisions will get made that could have been avoided by involving other teams or more senior people.

But the price of avoiding those mistakes is to live constantly waist deep in mud.  Everything you do, every decision you make, is a slow-motion struggle to make progress.  The cost may be less apparent, but in a world moving at lightning speed, can you afford to carry that kind of a burden?  As Teddy Roosevelt said, “in any moment of decision, the best thing you can do is the right thing, the next best thing is the wrong thing, and the worst thing you can do is nothing.”

We Pace Within The Bars of Our Own Imagination

Have you ever heard somebody say, “I wish I could <do something or other>”, with a wistful look in their eye?  And you want to grab and shake them and say, “you CAN.  Do it NOW!”  And it is just so obvious to you that what they wish for is right there in front of them, ready to be seized if only they would have the gumption to reach for it.  Well, guess what: a lot of the time, you are that person.

We are the biggest buzzkill and the harshest critic standing between us and our dreams.  We shrink back from the echoes of old failures, from carping and doubting voices that ring inside our heads.  “I’m not the type who starts a company.”  “I’m not a natural leader.”  “I’m not creative.”  “I’m not a good writer, or an artist, or an athlete.”  We fence ourselves in behind these imaginary barriers, looking wistfully at the banquet of delights that we think is permanently locked away from our reach.

So What do You Want?  Really Want?

A fun way to start breaking through is to do a little fantasizing.  Try finishing these sentences:

  • “Of course it isn’t practical, but I’ve always wanted to …”
  • “I don’t do it any more, but when I was a kid I always loved to …”
  • “The times in my life when I was most exhilarated and at my best, I was …”
  • “In my dream job, I …”
  • “In the life that I daydream about, ….”

Get something down that you can look at.  Maybe write a journal entry on paper or on a computer, mindmap on a white board (with an encouraging friend, if that works for you), or draw on a big piece of paper, or collage a poster full of pictures.  Find some cool images on the Internet.  Whatever gets your juices flowing.

We’re not trying to be practical here, we’re trying to dream a little.  Always wanted to be an astronaut and explore other galaxies? You are five feet tall and walk with a cane, but fantasize about being an NFL running back or an Olympic athlete?  It’s all good.

After you’ve had a shot at this, and you sit back and take a look, you might suspect that some of your fantasies are a lot more fun in your imagination than they really would be in practice.  That’s probably true.  There is a reason that the phrase “it reads better than it lives” comes up a lot in adventure tales.  But you’ll never know until you try something, whether you will really like it.  And you may stumble across some related activity that is even better.  I backpacked quite a bit when I was in school, living out some fantasies that I had when I was a kid.  I discovered that backpacking is fun, but what I absolutely loved was rock climbing.  And I did quite a lot of it, in some amazingly beautiful places, and had adventures that I still often think about.

It takes a bit of work to figure out what will make you happier and more fulfilled.  You don’t have to – there are intelligent and highly paid people working hard to take care of that for you.  Their siren song is everywhere – how great your life will be if you have a fancier car, a bigger house, more fashionable clothes, and glamorous vacations.  There is overwhelming evidence that these things won’t make you happier, but perhaps you are the exception.  Run, hamster, run .. maybe you will get there, if only you can make that wheel spin a little faster!

Life Isn’t All or Nothing

One of the traps that I see people fall into all the time is being much too black or white about their dreams.  “I want to be an Olympic downhill skier, but I’m 40 so obviously that’s not going to happen.  So instead, I’ll have beer and chips on the couch.”  Uh huh.  Or, somebody is working full time and is a parent so they decide that their dream to be an artist is hopeless.  But you don’t have to be a full-time artist in order to make art.  If you are fascinated by outer space, you can study astrophysics, go to lectures, paint scenes set on other worlds, go to space camp, build your own telescope, and visit observatories.

If you love something, then weaving aspects of it into your life can be richly fulfilling, even if you can’t do it all the time or do it to the level that you fantasize about.  After all, even an Olympian only gets to compete in the games for a couple of days every four years.

Just Take a Step

Now you come to the crucial all-important step that so many people leave out.  They have dreams, but they don’t turn vision into action.  A grand goal like “become an artist” or “write a book” is great, but you can’t sit down on Monday afternoon at 2pm and become an artist.  You have to turn those ideas into concrete actions you can do right now.

To become an artist, maybe you need to research art classes at a local school or get an instruction book on some techniques you want to learn.  If you want to start a company, attend a local get-together of entrepreneurs or read a book about it.  I like to think about this as “just take a step”.  Write down everything you can think of that you know exactly how to do and can get done in less than an hour.  A big goal may seem impossibly daunting if you think of it as a whole, but surely you can spare an hour?  And then, after you’ve spent one hour, pick the next thing and spend another one.

Magic of Starting

There is a wonderful quote, which is commonly attributed to Goethe.  Sadly, that’s not exactly true.  But it’s great anyway, even if it has a mixed ancestry, and I have repeatedly found it to be true: “Whatever you do, or dream you can do, begin it.  Boldness has genius, power, and magic in it.  Begin it now.”