My freshman year at college, neck-deep in starting my first company, I got an early taste of worrying about work/life balance.  How much time should I spend on the company, I wondered, versus on classes and homework, or on boozing, socializing, and pulling crazy pranks with friends?

At that point, I had also just re-read Lewis Carroll’s Alice in Wonderland, and I still remember being struck by the exchange between Alice and the Cheshire Cat.  When Alice asks the Cat for directions, he asks her where she’s headed.  “I don’t much care where,” says Alice.  To which the Cat replies, “Then it doesn’t matter which way you go.”

With that in mind, I set out trying to envision an ideal future life, a clear sense of where I wanted to end up, so that I could choose the right roads going forward.  By the time I turned 50, I asked myself, what did I want to be doing?  What did I want to have already accomplished?  Who, really, did I want to be?

To keep things structured, I broke my life down into four broad categories: Work (the things I did for a living, and to make a broad impact on the world), Play (things I did just for my own enjoyment, like writing, playing music, or travel), People (friends, family, and eventually building a family of my own), and Self (mind, body, and spirit).  And, for the better part of a year, I tried to work out a vision for each of those areas that seemed right, that excited and inspired me.

It’s now some 20 years later, and though the age of 50 has inched closer (I’m now just 12 years off), my vision has changed surprisingly little over that time.  Which is excellent, as those long-term goals serve as the basis for my short-term planning, too.  I work backwards from them to 5-year goals (where do I need to be in 5 years on a given goal, to be on track to hit the overall goal by 50?), then to 1-year goals.  And then I translate those, in turn, into either habits for the year (like daily meditation, a monthly museum visit, or a quarterly weekend trip) and projects (big but finite things, like building the Composite client app, which I sort into a long ordered list, then knock off by focusing on one at a time for the first couple of hours of my day).

Most days, I can just get down to work, knowing that, if I stick to those projects and habits, I’m on track to my longer-term goals.  But twice a year – once on my birthday (which happily falls on the middle of the year, in July) and once at year’s end – I stop and take stock.  I look at the big picture.  If I spend the rest of the year climbing the ladder as quickly as I can, those two times, I pause to make sure the ladder is on the right wall.

I start by reviewing my goals – the age 50 ones, as well as the 5 year, 1 year, and project/habits that stem from them.  And then I take a careful look at where I am right now.  During the week between Christmas and New Years, I write in-depth reviews of the four areas of my life – Work, Play, People, Self.  For each, I summarize where I stand, how I fared the past year.  And, for each, I give myself a letter grade, and then see if I need to make any tweaks to my upcoming projects and habits to do better in the year ahead.

Sure, it’s a pretty wonky and time-consuming approach.  But as the world basically shuts down this week anyhow, it’s easy to fit in.  And, for me at least, it pays dividends in purpose, productivity, and sanity for the next twelve months.