Advance The Pawns
Depth vs Breadth
If you’re anything like me, you’re always stretched for time. For all the things you’d like to accomplish, it takes time to do each well.
You’re faced with a constant tension between depth and breadth.
Go too wide and you’ll be spread thin, making only marginal progress towards each goal. Go too deep and you’ll develop tunnel vision, neglecting other priorities because you’re lost in the details.
As an ambitious perfectionist, I know both these failure modes all too well.
One Step At A Time
“Advance the pawns” is my strategy for striking the delicate balance between depth and breadth.
The idea is this: you don’t achieve any goal in one fell swoop. Instead, you chip away at it with small bursts of progress. There’s no such thing as overnight success. It requires consistent, deliberate effort across several fronts.
Your pawns only move one square at a time. They can’t leapfrog to the other end, but they can make incremental advances towards it. Real-world success requires the same bite-sized approach - there are always intermediate milestones to hit along the way to your end goal.
Save Your Progress And Move On
But it’s not enough to only advance a single pawn. You need to move other pieces too. Winning requires a balanced approach, not a singular line of attack. If you overinvest in one dimension, it leaves you vulnerable in another.
The same is true for getting things done. You need to diversify your effort. Make progress on a priority and move on. This is where perfectionists slip up. Tantalized by the promise of perfection, they get trapped in its endless pursuit. They don’t realize there’s no such thing as done - perfect is a direction, not a destination. As a result, they chase diminishing marginal returns in one area while entirely neglecting the others.
Advancing the pawns is a useful reminder that progress happens in discrete steps. Perfect is a direction, not a destination. As long as you’re gaining ground on your goals, your energy is well-spent. This also helps you visualize how to diversify your effort - move the ball forward, “save your progress” and move on to the next priority. You can always pick up where you left off.
This allows you to advance on several fronts in parallel through step-change improvements. As a result, you balance depth and breadth - meaningful progress on all your priorities.
How I Apply It
I put this principle in action through the Pomodoro Technique. It’s a time management method to break work into intervals - I do 50 minute sessions followed by 10 minute breaks. By timeboxing my effort, it lets me work on many projects in parallel.
For example, I use it to write these posts (and measure how long they take). Instead of completing it in one stretch, I do one writing session every day. The scheduled interrupt prevents me from getting lost in the weeds. If it weren’t for this, I’d surely spend all day writing and agonizing over the smallest details. While that may create a better piece, it would steal time from my business. Also, I can always come back to refine them. In fact, I hope to write a book one day - this may very well be the first iteration of it.
As I predicted earlier, this became a keystone habit:
This will form my keystone habit of time management. In my Year 1 reflection, my goal was to experiment with the Pomodoro technique. Since I’ll be using Pomodoro sessions to timeblock my writing, I hope to extend it to other tasks as well.
Once I began using it for writing, it bled over to the rest of my life. Now I schedule my day in Pomodoros, i.e how many work sessions to spend on each workstream. This allows me to allocate more time for high priority tasks, but also ensure I’m moving the ball forward on all fronts.
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