The deadline I knew about all year (and still almost blew)
Published 18 days ago • 2 min read
The Proactive Risk PM Weekly
Issue #25
June 22, 2026
Hi ,
My wife's birthday was yesterday. Yes, the same day as Fathers Day!
I knew that her birthday was coming. I've known it for... well, every year. It's not exactly a surprise on the calendar. I even had the big gift handled early: a new bike she'd been wanting, so she could ride around the neighborhood with the kids.
Done. Wrapped up before I could even feel good about it.
So I told myself I had time. Cards, cake, prepping the kids for birthday morning... that's the easy stuff. It happens every year. I've got this.
And then summer happened.
Kids out of school. Summer activities firing off in every direction. Me heads-down in course development, filming YouTube, teaching back-to-back PMP® and PMI-RMP® courses.
The "easy stuff" quietly slid down the list, day after day, until I looked up Friday night and her birthday was 48 hours away.
Nothing bought. No cards. No cake. Just a list and a wave of guilt that I'd let this, of all things, sneak up on me.
Now, let's get Proactive Over Reactive!
"We suffer more often in imagination than in reality."
~Seneca, Moral Letters to Lucilius, Letter 13
Lesson of the Week
The most dangerous deadline is the one you're sure you'll hit
Here's what got me thinking after the dust settled.
A birthday is the most predictable deadline on earth.
Fixed date.
Same day every year.
Zero uncertainty about when it's coming.
And it still almost ran me over.
Not because I forgot. Because I was so sure I had it handled... that I stopped watching it.
That's the trap.
On your projects, the risks that bite hardest usually aren't the wild, unpredictable ones. They're the obvious deadlines and dependencies you're confident about... so confident you stop managing them.
In the video this week I call this your project's Mile 20, the predictable wall that wrecks people who didn't plan for it.
The fix isn't a 40-page risk register. It's three questions... the same three I run on every project:
What could go wrong?
What will I do about it?
How will I know it's happening?
If I'd run those three on "her birthday" back in May, I'd have spotted the obvious: summer is my busiest season, and the easy stuff always gets crushed first.
That's not bad luck. That's a known risk I chose not to look at.
Your most predictable deadline right now is probably the one you're not watching. Go look for it!
The Bearded Risk PM on YouTube
Watch the full video on:
"Psychological Barriers Are Killing Your Projects | Marathon Insight"
What Two Marathon Records Teach Us About Risk
Don't Forget to Like the Video, Subscribe to the Channel, and Leave any Questions You Have in the Comments!
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