Steve Jobs on Following Your Curiosity and Dealing with Uncertanity

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The 5 to 9 Job

Raymond kirungi

113 episodes

4 days ago

Welcome to The 5 to 9 Job—my journal on growth, failure, and figuring life out. I started this show because I felt this deep need to help people like me…People trying. Failing and rebuilding. The idea was to use the hours between 5pm to 9am to grow. Slowly, my vision expanded and I wanted to do it all, to build a platform to raise others, reflect and share my interests and soon I hit a wall. Now It’s back to the basics; fewer better episodes. Each week, I share a few reflections, conversations, and stories from guests so make sure you don’t miss out on any episode. Welcome to my workshop.

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Personal Journals

Society & Culture

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Steve Jobs on Following Your Curiosity and Dealing with Uncertanity

The 5 to 9 Job

9 minutes 51 seconds

3 weeks ago

Steve Jobs on Following Your Curiosity and Dealing with Uncertanity

“You can’t connect the dots looking forward; you can only connect them looking back.”

In this episode of The 5 to 9 Job, we break down one of the most powerful stories from Steve Jobs’ 2005 Stanford commencement speech—the calligraphy class that changed everything. From dropping out of college to shaping the future of personal computing, Jobs shows us that trusting our curiosity and following the unknown can lead to life-changing outcomes.

If you’ve ever felt lost, uncertain about the future, or overwhelmed by choices—you’ll want to hear this.

What You’ll Learn

How Steve Jobs’ detour at Reed College shaped Apple’s design legacy.
Why following your curiosity—even when it doesn’t “make sense”—matters.
The importance of trusting your gut when the path ahead feels uncertain.
How today’s small decisions may shape tomorrow’s breakthroughs.

Resources & Acknowledgments

Steve Jobs, Stanford Commencement Speech (2005)
Credit: Steve Jobs & Stanford University

Call to Action
If this story inspired you, share it with a friend who needs encouragement right now. Don’t forget to subscribe, leave a review, and tune in to future episodes as we explore more of Steve Jobs’ lessons on life, creativity, and perseverance.