14 years ago today, we lost Steve Jobs. I’ve been thinking about his Stanford commencement speech lately - I’ve probably watched it 20+ times over the years. Still hits different every time.
Three stories. That’s all he told those graduates. No grand theory of success, no step-by-step playbook. Just three stories from his life. But man, they pack a punch.
Here’s why this speech still matters.
Connecting the Dots
Jobs dropped out of Reed College after 6 months. Seemed like a disaster at the time, right? His working-class parents had saved their entire lives to send him there, and he just walked away.
But he stuck around campus and took a calligraphy class - just because it looked interesting. No plan, no career path, just curiosity about something beautiful.
10 years later, that “useless” class became the foundation for Mac typography. The first computer with beautiful fonts. And since Windows just copied the Mac, it’s why every computer today has decent typography.
The thing is - you can’t connect the dots looking forward. You can only see the pattern looking back.
That random interest you have right now? That weird detour in your career that doesn’t make sense to anyone, including you? They might be the most important decisions you’re making, you just don’t know it yet.
I think about this one a lot. All the projects I took on that seemed like dead ends at the time. The skills I picked up that had nothing to do with my “career path.” Years later, they all connected in ways I never could have predicted.
Trust that the dots will connect. Because they will.
Love and Loss
At 30, Jobs got fired from Apple. The company he started. In his parents’ garage. With his best friend.
Think about that for a second - how do you even process being rejected by something you created? The board sided with the guy they brought in to help run the company, and Jobs was out. Very publicly out.
But here’s what got me: he said getting fired was the best thing that ever happened to him.
It freed him up to start NeXT and Pixar. To fall in love with his wife. To be a beginner again, less sure about everything, but more creative than he’d ever been.
Sometimes life hits you in the head with a brick. The question isn’t whether it’ll happen - it’s what you do after.
Jobs kept going because he loved what he did. That’s it. The rejection didn’t change that. He was still in love with the work.
Keep looking for what you love. Don’t settle. And when you find it? Hold on tight. Because your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work.
Death
Jobs asked himself every morning: “If today were the last day of my life, would I want to do what I’m about to do today?”
If the answer was no for too many days in a row, he knew something had to change.
This was BEFORE his cancer diagnosis. He was already living with that urgency. Already using the awareness of death as a tool to cut through all the noise - the external expectations, the pride, the fear of embarrassment or failure.
“Your time is limited, so don’t waste it living someone else’s life.”
Don’t be trapped by dogma. Don’t let other people’s opinions drown out your own inner voice. Have the courage to follow your heart and intuition.
A year before this speech, Jobs was diagnosed with pancreatic cancer. The doctors told him he had three to six months to live. He spent a day preparing to die, trying to figure out how to tell his kids everything he thought he’d have ten years to say.
Turned out it was a rare, curable form. He got the surgery. He lived another six years.
But that day - that clarity you get when you think you’re about to die - that stayed with him.
Stay hungry. Stay foolish.
Why It Still Matters
What makes this speech work isn’t just what Jobs said - it’s that he lived it.
Dropped out. Got fired. Faced death. Came back stronger every time.
The dots connected. The love sustained him. The awareness of death clarified everything.
14 years later, I think that’s the real lesson: life doesn’t happen in a straight line. It’s messy and unpredictable and sometimes brutal. People are going to reject you. You’re going to make decisions that look insane to everyone around you. You’re going to fail, publicly and painfully.
But if you stay curious, if you do what you love, if you remember your time is limited?
Those dots will connect.
The calligraphy class will matter. Getting fired will free you. The awareness of death will clarify what’s actually important.
You just have to trust it. And keep moving.
Stay hungry. Stay foolish.
If you’ve never watched the full speech (or it’s been a while), it’s 15 minutes that’ll hit you right in the chest: Watch it here
RIP Steve Jobs.