Planning to (not) Fail

Planning to (not) Fail

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Failing to plan

is planning to fail

It’s a rather straightforward idea, and I’d bet most of us have heard that quote at some time, but it seems like many of us don’t really understand it, or at least we don’t put as much energy into it as we should.  Planning is one of those things where you can do TOO much of it; indeed, many daily tasks don’t really need much, if any.  That said, anything bigger, or more complex, definitely benefits from more planning.  To help keep things simple, I try to break planning into three areas… from smaller to bigger - my week, projects and my career.


For your week

Before the week begins (generally on a Sunday) I take time to review what’s coming up.  This involves going over my calendar, project tracking system (e.g. Asana, JIRA, sticky notes, etc), emails, etc. to see what’s coming up.  I spend a bit of time reviewing my recurring meetings (one on ones, team meetings, etc) just to ensure I’m up to date on the agenda and plan, but I particularly go through my non-recurring meetings.  These can sneak in over time, so I’ve found it’s very important to dig into them.  Where possible I rearrange things to make better sense of my time, for example I cluster 30 minute meetings to give me more blocks of time to work, or I bow out of things I”m not needed for.  This helps me better focus my time during the week, and lets me identify areas that need particular help.

For a project

Individual projects also get their own planning attention.  This can range from scheduling out meetings with vendors, to thinking through how to handle various stakeholders, to mapping when deliverables are needed.  While it can be annoying and a bit time consuming, the energy spent on continually improving project plans has consistently paid off in terms of better outcomes, less stress and avoiding mistakes.

I make a point to put project planning onto my calendar on a weekly basis as an event.  This ensures I’ve got the time blocked off, and also lets others know I value and prioritize this work.  I also send out weekly project updates (depending on the project these can be as short as a one-line update or as long as a page).  Writing these not only keeps everyone up to date (assuming they read them!), but also forces me to look at my portfolio and really understand what’s going on.  Time time helps support my overall project planning as I’m constantly examining what’s going on

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If you don’t know where you are going, you’ll end up someplace else.” ~Yogi Berra

For a career

Planning where we are going in our career is one of the longest things we can plan for.  These types of plans generally span years, if not decades, and can seem very daunting to put together.  I try to break them down into very distant, fuzzier plans, and slowly bring up the clarify and focus as I get closer to today.  I tend to not get any closer than 1 year from now, as project or weekly planning can handle that time frame, but understanding the bigger picture is critical to the rest.  How can I decide which project to go after if I don’t know where I want to be in a year or five?  Having that knowledge gives you a lens to focus your efforts, something that helps sort through everything and provide guidance on what you should do to attain your goals.

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