Failure #1: You’re Not Late. You’re Alive.

Welcome to the first issue of the Learning to Fail newsletter. I was supposed to send it out two weeks ago on Friday, June 13th. Clearly, I’ve already failed.

It felt like a perfect launch date. Friday the 13th — the unluckiest day of the year — subverted by a newsletter about rethinking failure. It was poetic. Meta. A little cheeky. The kind of calendar coincidence you don’t ignore if you live in my head.

But here we are… not Friday the 13th. Barely even June, honestly, and my perfect plan didn’t happen. Instead, life happened. Kids. Work. A few too many deadlines stacked on top of each other like unstable Jenga blocks, and this one fell off the top. Quietly. Softly. No explosion. Just... didn’t happen.

For a few days, I felt the kind of quiet shame that’s familiar to anyone who’s ever been in school: I missed the deadline.

The “missed deadline” programming that school teaches us runs deep. After all, missing a deadline in school wasn’t just a scheduling issue. It was a character flaw that meant you were irresponsible, lazy, disrespectful, unmotivated, or…. the real dagger: not living up to your potential.

When I was a student, deadlines felt like they had the weight of divine law. Whatever was in the syllabus was what I had to follow no matter what, and it never occurred to me to wonder why the deadlines are what they are. Who created them? What are they meant to accomplish? And do they achieve those goals?

Fast forward a couple decades, I’m on the opposite side of the classroom, and I realize deadlines are just logistical necessities. They help teachers manage grading and keep a class moving forward at a reasonable pace. Heck, some of my deadlines exist simply because I don’t want to be stuck grading things over Spring Break.

But when you’re a student, you can’t appreciate the haphazardness and artificiality of deadlines. Instead, deadlines take on a moral weight. Did you meet the deadline? Great! You’re a responsible, maturing adult. Did you miss it? Sorry! You’ve failed. It doesn’t matter why. Doesn’t matter what else was going on in your life. It doesn’t even matter if you know the material. You’re late, and so you’re penalized.

The implication is subtle but powerful: success means aligning your life to the schedule someone else made. If you can’t do that, you’re not good enough.

To be clear, I’m not suggesting deadlines don’t matter. If you have a deadline to pay a speeding ticket or you’re going to jail, you should adhere to the deadline. But remember that deadlines aren’t divine pronouncements. They’re human creations to keep the world moving forward, and their purpose is to help you accomplish valuable things, not make you feel bad when you don’t.

Unfortunately, teachers don’t usually do a good job of making this distinction, and, as a result, from an early age we all learn to equate missed deadlines with failure. When nobody ever reminds us otherwise, we carry the same feelings of failure into adulthood. We bring them into our jobs, our relationships, our creative projects, our inboxes, and, most importantly, our ambition.

Then one day, you miss your “perfect” newsletter launch date, and you feel that familiar twinge in your chest. Not disappointment. Not frustration. But shame. Like you let someone down, even if that someone is just an imaginary reader in your head who doesn’t know this thing exists yet.

But the truth about deadlines isn’t what school teaches us.

Missing a deadline isn’t failure. It’s evidence you’re human.

Missing a deadline isn’t proof of laziness or poor time management or self-sabotage. It’s proof you have other priorities. That your life is complex. That you’re not a machine.

Sure, deadlines are useful tools, but that’s all they are: tools. They’re not truths or tests of character. And they’re definitely not the final word on your worth or ability.

You’re not late. You’re on time for the version of your life that actually exists.

That’s the part school never really taught us. School taught us that “on time” is an external standard… a line drawn in someone else’s sand. But real life doesn’t work that way. Life has curveballs, traffic jams, sick kids, angry bosses, broken printers, canceled flights, and big ideas that take a little longer to form. And the things worth doing don’t always fit neatly inside someone else’s calendar. Sometimes they don’t even fit inside your own.

That’s not a flaw. That’s a feature.

So here we are — this newsletter, this experiment, this new thing — not launching on a perfect day, but on a real one. A slightly messy one. A later-than-planned-but-still-worthwhile one.

And honestly? That feels exactly right.

I’m glad you’re here. Let’s keep going, even if we’re a little behind. In fact, let’s keep going especially because we’re behind.

- Dr. Dinin

This Week's Failure Challenge: Celebrate a Missed Deadline

Think of a deadline you missed. Maybe it was yesterday. Maybe it was last year. Maybe it’s still hanging over your head, quietly judging you from the bottom of your to-do list.

This week’s challenge is simple:

Celebrate it.

Seriously. Take a moment and reframe the missed deadline not as a failure, but as something that made space for a different kind of growth, learning, or life.

Maybe missing that job application helped you realize you didn’t want the job.

Maybe you forgot to RSVP to a wedding and ended up with a magical solo weekend.

Maybe the delay made the work better.

Maybe it just meant you were tired, and that’s okay, too.

Once you’ve identified the deadline, write a short note — just a sentence or two — about the missed deadline and what came from it, then send it to me. Better yet, share it on social media as a post or a video and add the caption:

“This week’s #LearningToFail challenge: I missed this deadline… and I’m celebrating it.”

Tag me — @AaronDinin — so I can celebrate alongside you. (And respond to some of my favorites.)

And remember… you’re not late. You’re alive!