A "Learning to Fail" Preview
Entrepreneur Office Hours - Issue #288
Note from Aaron: By the time you’re reading this, I’ll have officially launched my new Learning to Fail newsletter. This week’s issue of Entrepreneur Office Hours is a preview of what to expect. If you enjoy it and want to subscribe (it’s also free!), you can do that here.
Also, I’ve decided to publish Learning to Fail on Friday mornings, and I’ll be moving the weekly publication day for Entrepreneur Office Hours to Tuesdays. See you next Tuesday with a full issue.
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.
Why did missing an imagined deadline feel so much like a failure?
School, Deadlines, and Dread
The “missed deadline” programming school teaches us runs deep. 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?
Do they achieve those goals?
Fast forward a couple decades, I’m on the opposite side of the classroom, and I realize school 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 a teacher's 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. The reason why doesn't matter. 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.
What Deadlines Really Mean
To be clear, I’m not suggesting deadlines don’t matter. If you have a deadline for paying a speeding ticket or else 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.
And 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.
-Aaron
If you enjoyed this issue, be sure to subscribe to my new Learning to Fail newsletter. Based on my popular entrepreneurship class at Duke University by the same name, each week I’ll share a lesson and a failure challenge to help reframe how we think about failure and its potential as a tool for learning, growing, and becoming more resilient humans.
Great read
Thank you for this! And Cheers for getting your email out even though it wasn't on the 13th. I really enjoyed the read.