20th Anniversary of Steve Jobs' Stanford Commencement Speech

In 2011, the same month Todd and I decided to start Test Double, Steve Jobs had recently died, and we both happened to watch Steve Jobs' incredible 2005 Stanford commencement speech. Among the flurry of remembrances and articles being posted at the time, the video of this speech in particular broke through and became the lodestone for those moved by his passing.

The humble "just three stories" structure, the ephemera described in Isaacson's book, and the folklore about Steve's brooding in the run-up to the speech became almost as powerful as his actual words. The fact that Jobs, the ruthlessly focused product visionary and unflinching pitchman, was himself incredibly nervous about this speech might be the most humanizing thing any of us have ever heard about him.

Well, it's been twenty years, and the Steve Jobs Archive has written something of a coda on it. They've also released the e-mails Steve wrote to himself in lieu of proper notes (perhaps the second-most humanizing thing). They've also spruced up and remastered the video of the speech itself on YouTube.

Looking through his e-mails, I found I actually prefer this draft phrasing on the relieving clarity of our impending demise:

The most important thing I've ever encountered to help me make big choices is to remember that I'll be dead soon.

In 2011, Todd and I ran out of good reasons not to take the leap and do what we could to make some small difference in how people wrote software. In 2025, I believe we're now at an inflection point that we haven't seen since then. If you can see a path forward to meet this moment and make a meaningful impact, do it. Don't worry, you'll be dead soon.

I've never regretted failing to succeed; I've only regretted failing to try.