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The question

What is the biggest professional obstacle you have faced?

Originally asked

The American Academy of Achievement, to its honourees, its oral-history interviews

The Academy of Achievement repeatedly asks honorees to identify a major professional obstacle or challenge and describe confronting it.

You answer as yourself. Nobody on FLAPSS answers as anybody else.

Steve Jobs

Co-founder and chief executive of Apple; co-founder of NeXT; chief executive of Pixar

Recorded said elsewhere, not written here
At Pixar when we were making Toy Story, there came a time when we were forced to admit that the story wasn't great. It just wasn't great. We stopped production for five months.... We paid them all to twiddle their thumbs while the team perfected the story into what became Toy Story. And if they hadn't had the courage to stop, there would have never been a Toy Story the way it is, and there probably would have never been a Pixar.

Betsy Morris, Fortune interview, Kona, Hawaii, 7 March 2008 source ↗

Others on this question

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Philip Johnson Architect; first winner of the Pritzker Prize
Then you have the clients. The care and feeding of clients is really one of the main obstacles, because you always have a client with some preconceived idea of what a house looks like, and all you want him to do is leave a check and go to Europe for a couple of years. Or leave two checks. But alas, life isn’t simple. If it were, more people would be better architects.
Recorded Academy of Achievement, Academy of Achievement interview, New Canaan, Connecticut, 1 April 2000 source ↗
David Vélez Co-founder and chief executive of Nubank
Sí, empezamos desde cero. Pedimos una licencia de financiamiento comercial, pero es difícil comenzar porque la banca se basa en confianza, regulación y escala. Hay barreras regulatorias que dificultan la entrada de nuevos jugadores. Es un sector históricamente cerrado, que favorece a los incumbentes. Aun así, logramos construir una marca fuerte y generar confianza en los consumidores.
Recorded Alejandra Rico Muñoz, interview, La República, 25 March 2026 source ↗
Tony Judt Historian and essayist
This cockroach-like existence is cumulatively intolerable even though on any given night it is perfectly manageable. “Cockroach” is of course an allusion to Kafka’s Metamorphosis, in which the protagonist wakes up one morning to discover that he has been transformed into an insect. The point of the story is as much the responses and incomprehension of his family as it is the account of his own sensations, and it is hard to resist the thought that even the best-meaning and most generously thoughtful friend or relative cannot hope to understand the sense of isolation and imprisonment that this disease imposes upon its victims.
Recorded The New York Review of Books, 14 January 2010 issue, 14 January 2010 source ↗
Mellody Hobson Co-chief executive and president of Ariel Investments
We would constantly have to move because we couldn't quite afford the places that we were living. And sometimes we got evicted. And it was just very, very difficult as a child to try to understand that.
Recorded Farai Chideya, News & Notes, Leading Ladies series, NPR, 22 March 2007 source ↗

More from Steve Jobs

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Question How would you want people to remember you? Death & what remains
I think the work speaks for itself. I don't think that people have special responsibilities just because they've done something that other people like or don't like. I think the work speaks for itself. I think people could choose to do things if they want to but we're all going to be dead soon, that's my point of view. Somebody once told me, they said "Live each day as if it would be your last and one day you'll certainly be right." I do that. You never know when you're going to go but you are going to go pretty soon. If you're going to leave anything behind its going to be your kids, a few friends and your work. So that's what I tend to worry about.
Recorded Daniel Morrow, Smithsonian Institution Oral and Video Histories, for the Computerworld Smithsonian Awards Program, 20 April 1995 source ↗
Question When did you last change your mind about something important? Change of mind
I used to think that technology could help education. I've probably spearheaded giving away more computer equipment to schools than anybody else on the planet. But I've had to come to the inevitable conclusion that the problem is not one that technology can hope to solve. What's wrong with education cannot be fixed with technology. No amount of technology will make a dent. It's a political problem.
Recorded Gary Wolf, Wired 4.02, February 1996 source ↗
Question How does a new piece of work usually begin for you? Craft & work
Creativity is just connecting things. When you ask creative people how they did something, they feel a little guilty because they didn't really do it, they just saw something. It seemed obvious to them after a while. That's because they were able to connect experiences they've had and synthesize new things. And the reason they were able to do that was that they've had more experiences or they have thought more about their experiences than other people.
Recorded Gary Wolf, Wired 4.02, February 1996 source ↗

More on craft & work

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Sundar Pichai, David Vélez, Hilary Swank, Mellody Hobson, Shinya Yamanaka, Mario Molina

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