I am a fan of Steve Jobs’ 2005 Stanford commencement address. He talks about his own university experiences, and in particular, his decision to drop out. This was a big thing for him (he describes it a ‘pretty scary’), because his biological parents had stipulated that whoever adopted him had to agree to send him to university.

Jobs talks about the need to trust himself, to ‘trust that it would all work out OK’. He hung around campus for 18 months after dropping out, taking classes that interested him.

Here’s how he tells it:

‘I decided to take a calligraphy class…I learned about serif and san serif typefaces, about varying the amount of space between different letter combinations, about what makes great typography great. It was beautiful, historical, artistically subtle in a way that science can’t capture, and I found it fascinating.

None of this had even a hope of any practical application in my life. But ten years later, when we were designing the first Macintosh computer, it all came back to me. And we designed it all into the Mac. It was the first computer with beautiful typography. If I had never dropped in on that single course in college, the Mac would have never had multiple typefaces or proportionally spaced fonts. And since Windows just copied the Mac, its likely that no personal computer would have them.

If I had never dropped out, I would have never dropped in on this calligraphy class, and personal computers might not have the wonderful typography that they do. Of course it was impossible to connect the dots looking forward when I was in college. But it was very, very clear looking backwards ten years later.

You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.’

It’s worth reading Jobs’ speech in full.

And it’s worth thinking about trusting yourself, going with your hunches sometimes, even if you can only connect the (logical) dots with hindsight. When I think about my career(s), I particularly remember my fierce sense that corporate law was not for me – and how long it took me to trust my instinct and actually do something about becoming a writer and an idea sharer instead. I fully appreciate the need for reflection and planning, but there does come a moment when you have to move into the unknown.

What would you change if you really trusted yourself?