I often tell folks
that schools teach bad habits as well as good ones.

 

For one thing, your typical college course
habituates students into believing that everything consists of neatly packaged
problems that they can be graded on. 
Is that how people are evaluated in the real world?

 

Similarly, most college courses teach students to cram random bits of
information into their heads at certain intervals so that they can pass big
bang tests.  Is that how projects and breakthroughs succeed in the real world?

 

What is the actual
value of trying to memorize everything? 
Can we actually memorize everything we need to know?  I
think the answer is clearly no, or else search engines like Google
wouldn't exist.  Would you rather have access to your own memory for information, or access to Google?

 

Schools assume you
have all the information you need available to you.  Schools assume you
should be able to perform tasks and recall information without referring to a
book.  These assumptions are simply not correct. 
Perhaps that's why there's no shortage of stories of people who did well
in school but didn't in the real world, and vice versa.  The correlation is there, but it's not in
lock step like it should be.

 

Real life, of
course, is not simple.  Problems don't
fit into neat testable boxes.  The
information you need probably isn't in a book on your desk.  Sometimes problems solve themselves without
you even needing to lift a finger.  And
other times, the solution itself becomes unnecessary.

 

So, with that in mind, here are some questions I often ask when deciding when to stop planning and start acting.
 

What is the cost of
failure?

 

Failure has a rather
negative connotation associated with it in our society.  Nobody likes to fail.  However, it only takes a single flash of
insight to realize that it is not failure that one should be afraid of, but
rather the cost of that failure. 

 

Failure doesn't feel good to most people.  However, the amount of
planning you perform before acting should be roughly proportional to the actual cost of failure
and not to any psychological hang-ups related to failing.

 

Can the cost of
failure be lowered?

 

You will find that,
most of time, the cost of failure is negligible.  However, when failing is expensive, that's when you will
need to be on your toes.

 

When encountering a situation where failure will hurt, it's important to understand that you have two variables to
work with.  The first is to plan
more.  The second is to reduce the cost
of failure.  Call it the "walk before you run" strategy.

 

Reducing the cost of
failure has advantages over simply planning more.  Changes in the
problem to be solved or project priorities can quickly invalidate even the best laid plans.  Most importantly,
planning lacks a direct connection with reality.

 

The great takeaway here is that there are often ways
to reduce the cost of failure without changing the nature of what needs to be
done.  For example, releasing a buggy
software product can easily kill a company. 
However, if you restrict the releases of a product to a smaller
group of
users who are willing to deal with problems and provide feedback, you
locate more bugs but affect a much smaller subset of people who are
also more tolerant of those bugs.

 

Simple
changes in process like this can easily mitigate huge amounts of risk
at a fraction of the cost.  Try doing anything once or twice before you
do it a thousand times.  It's simple advice, in theory, but you'd be
surprised how often people still don't follow it.

 

What have you
learned?

 

The second important
point, after acting, is that you have to learn from what you've just done.  You might think that this is patently
obvious…after all, who does something and doesn't learn from it afterwards?  Trust me, people and teams repeat mistakes more often than you think.

 

In many cases, it's
simply enough to make a mental note and move on.  You're either the type that takes something
away from the process or you aren't. 
Unfortunately, I don't believe I can offer specific advice on how you
become the type of person that learns from everything happening around him.  So we'll move on.

 

However, as tasks
become larger in scope, the correct takeaway does become more specific.  I think that it probably comes as no surprise
to you that memories are quite fallible.  In software development, for example, an engineer often writes code to automate
all the little things that previously had to be performed by hand in order to
accomplish a task.

 

While writing code
to automate tasks is somewhat beyond the reach of most people, creating
checklists isn't.  In fact, writing
everything down that you have to do is one of the core tenets of the popular
Getting Things Done system.  If an activity seems to occur often, something anyone can do is create checklists.  That speaks directly to the entire point of acting quickly, which is to expose new information, remember it, and feed it back into the process as soon as possible.

 

Summing up

 

So there you go…three simple questions that tell you when to get over your "analysis paralysis" and get on with it.

 

I've
done a lot of background chatting here on the topic of planning vs
action, so let's wrap this up by summing up the general strategy.  My
general opinion
on deciding to act is as follows.  Most
of the time, the cost of failure is cheap or can be made cheap.  In these cases, you should favor a very brief
period of planning, followed by immediate action.  Make
sure to write down things as you act so that you retain the extra knowledge and
experience for the next run.