‘Stay hungry, Stay foolish’ is a quote from Steve Jobs commencement speech at Stanford in the year 2005.
As per Quora, it means that one should never be content with what is, nor consider oneself an expert. There is always more to do/gain (“stay hungry” for knowledge) and more to learn (“stay foolish“, meaning never consider oneself an expert but a fool to learn more).

There are two kinds of people – those who look for the next challenge and those who are content with where they are. There is no right or wrong type – it’s a personal preference. For some, it is a way of life.
For example, I love to challenge myself – I am a doer. I am one of those people who get the butterflies before doing something challenging – lose themselves while doing it – look for another one when its complete.
For the longest time ever, I never knew this is what I did until I met somebody in my team who was perfectly happy doing the same role they are doing forever. Once I became aware of it, I wondered why I am the way I am.
This year so far, I published a book, got two certifications at work – finished a couple of tight timelines driven projects and I am still rearing to go. I have this intense desire in me to do – challenge myself. I do get bored very quickly, as well. If it is routine, then I have to work extra hard to motivate myself.
A lot of people would describe me as being ambitious. And there was a point when I took offence to it – not anymore. I have learnt to accept who I am and use them as strengths and bring awareness on how it can be a weakness as well. We all have qualities which could be a strength or a weakness. There are two sides to a coin always. There is still another side of the story.
I realized that by not accepting who I am, including my flaws and imperfections, I was cutting away parts of myself. The hardest thing for me to accept was – ‘I am Human. Being human is being imperfect. May I be kind to me.’ This is the tenet of self-compassion, which is loving yourself.
And a poem I had read a long time ago has always haunted me, and now I am beginning to understand what it might mean. It is a poem by Derek Walcott.

Have you spoken to the stranger that is you?