Welcome to Nights & Wknds, a weekly newsletter for ambitious professionals building successful careers and lives.
Honest reflections. Practical frameworks. Lessons learned the hard way, written by someone who's been in the trenches and is still learning.
Whether you're learning to manage a heavy workload or protect a relationship with someone you report to, this newsletter is here to help you play the long game.
This week…
The single habit that separates people who manage their workload well from people who don't. It has almost nothing to do with the work itself.
Let's get to it!
Aaron
One of the most common ways I see talented people hurt themselves is missing deadlines.
And almost every time, it isn't because they couldn't do the work. It's because they were silent at the wrong time.
They knew on Monday that the Wednesday deadline might slip. They said nothing, hoped they'd catch up, and (best case) let their boss know on Tuesday they couldn’t make the Wednesday deadline or (worst case) just missed the deadline.
The work was never the problem. Not communicating early was.
THE QUESTION I KEEP GETTING
"How do I manage deadlines I have so many competing priorities?"
Some version of this comes up a lot, usually framed as a time management problem. People want a system to stop falling behind.
But everyone falls behind sometimes (depending on your job, ‘behind’ is a constant state of being). That's not the thing that gets you in trouble. What gets you in trouble is being the person your manager has to chase.
The solution isn't never slipping an initial deadline. The solution is communicating upward before the slipped deadline becomes your manager’s problem too.
HERE'S WHAT I'VE LEARNED
A 30-second call beats the perfect email
When something is going sideways, a quick call with a timeline and flagging competing priorities is worth more than a long, careful email that takes twice as long to read.
It sounds like this:
"Hey, a fire drill just came up with [insert keystakeholder of fire drill] that has to be dealt with today. It might impact our Wednesday deadline. Wanted to flag it now. Is there flexibility to push the deadline to Thursday or Friday?"
That's it. That's the whole call.
You'd be amazed how much goodwill that buys. The person on the other end can now re-plan around you instead of getting surprised. You've turned a potential missed deadline into a managed expectation. Most people over-explain when they're behind. The move is to under-explain and over-communicate.
The call is only possible if you built the relationship first
Here's the part people underappreicate. The comfort to pick up the phone and admit you're underwater is built on top of a real working relationship. If that foundation isn't there, the call feels dangerous, so you avoid it, and you go quiet at exactly the moment you shouldn't.
So the communication habit and the relationship habit are actually the same habit. You invest in the relationship on the normal days so that on the hard day, the honest call feels easy instead of terrifying.
Build the relationship first. Then the hard conversations stop being hard.
WHAT I'D TELL YOU IF WE HAD 5 MORE MINUTES
The most reliable people aren't the ones who never fall behind. Everyone falls behind. They're the ones who let you know before it becomes a problem.
That's a reputation you can build starting this week, the next time you’ve got competing priorities. You don't need to be faster or smarter. You need to be the person who picks up the phone early.
Reliability isn't never missing. It's never letting someone get surprised.
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