Have you ever wondered why your iPhone has an ‘i’ at the front? The iPod, the iMac, iPad, iTunes? Allow us to introduce you to Ken Segall, a veteran creative director and manager of Apple’s ‘Think Different’ campaign, who worked with Steve Jobs for 14 years.

When Jobs was looking for a name for the 1998 computer that would save the Macintosh company, he wanted something that would connect instantly with the Macintosh brand, and show that this computer was built for the internet – for the future. Ken Segall pitched five name ideas, and among them was his personal frontrunner, iMac. Segall pitched it to Jobs twice, but never heard back on a formal decision until the name was printed onto the product, ready for unveiling. There are rumors that Jobs initially wanted to call it the “MacMan”, and what a different world we’d be living in if that was the case. Segall’s simple, effective formula gave way to the entire ‘i’ product suite and lifestyle, and at the core of its success was a beautiful plainspoken-ness, which has become synonymous with his work.

But how to you do simplicity? Where does simple come from? Ironically, simplicity turns out to be quite a complex beast. Segall explains that in business and art, what might look short, quick and simple – whether it’s a product, a business, a work flow, a philosophy, a website, a store – has probably been through a long distillation process; a smooth, nice thing that’s chiseled out from a bulking block.

One practical tip for steering towards simplicity is perspective. Steve Jobs took something seriously that many managers only think of as a pesky obligation: the user experience. Segall says that Jobs put himself in the shoes of the nightmare user – critical, brutal, unforgiving. He focused on the experience of the product, from the first ad you would see, to what the store you bought it in looked like, to the packaging, to opening the box, to reading the instructions, to intuiting its functions. That was his amazing strength as a visionary. The difference between that mindset and a regular attitude is the phrase, ‘Well, that’s close enough.’

This critical mindset is as useful in business as it is in a person’s social life – and here we can perhaps no longer be inspired by Jobs. The kind of self-analysis Jobs embodied in business can translate to self-awareness in friendships and relationships too. What’s the perspective you’re not seeing? Consider people’s experiences with you and how they could be improved. It also extends to the design of the space in which you live. Can you crystalize your home into a simple state? Segall leaves that branch of simplicity more up to Marie Kondo, but he has a lot of wisdom on the art of simplicity. Watch above and learn.

Ken Segall’s most recent book is Think Simple: How Smart Leaders Defeat Complexity.