What is the biggest obstacle you have faced professionally?

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.

Recorded Steve Jobs 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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Sundar Pichai Chief executive of Alphabet and Google
The second filter is to gravitate towards working on hard things. I’d love to tell you I was an immediate success after leaving Stanford… I wasn’t. Even a decade later, I felt like I wasn’t on the right path, and it took me a while to find my footing. Until I applied to Google. I had my final interview there in 2004, it was April Fool’s Day and the day Gmail launched. So when my interviewers asked me about it, I wasn’t sure if it was a joke or a real product. That’s because at the time, one gigabyte of free storage for everyone felt super ambitious, and almost impossible. A couple years into the job, I got my chance to work on a seemingly impossible problem, too. It was around this time that the internet was moving into a new phase. The web was evolving from simple web pages to rich applications. There was a group of us that felt we could reimagine the browser to be much better and faster, and we had an early prototype that we thought was pretty good. Internally there was a consensus that building a browser would be incredibly difficult, requiring hundreds of engineers; we had a group of about ten. The consensus was right. It was going to be really hard. In some ways we were naive, and it's good to be a bit irrational when you approach new things. And in 2008, we launched what we thought was a great browser. We had eight million users in the first twenty-four hours, and the reviews were really positive. And then user growth stagnated. After a year, we had around two percent share. I remember Steve Ballmer, the CEO of Microsoft, made fun of Chrome in an interview and called it a rounding error. It could have been demoralizing. But with that California optimism, I told the team that the fact he went out of his way to dismiss us meant we were doing something right. We kept going, setting highly aggressive stretch goals to keep the team pushing. We rapidly iterated, shipping the browser every six weeks while others shipped one maybe every six months to a year. Success began to follow. Working on hard things has taught me a lot: It typically attracts other great and optimistic people. And even if you miss meeting the high goals you set, you’ll still achieve something great. So when you have the choice to work on something hard — say yes. Do what excites you
Recorded Stanford University Commencement, Google (The Keyword), 14 June 2026 source ↗
John M. Martinis Physicist; Nobel laureate in Physics, 2025
I would say there are many challenges, and that's kind of what's hard about it. And my particular thesis, since leaving Google and doing my own company, is that building a quantum computer is a little bit harder than the scientists think about because of the system engineering. Building a powerful computer is hard. So what we're particularly working on is the manufacturing of qubits and doing that much better than what people are doing right now. I really enjoyed being in academia, and even at Google working on that. But I really enjoy right now trying to think very practically about what we have to do to get this to work. And what kind of people we have to collaborate with in order to put all the pieces together and build a quantum computer in a cost effective, economic way that makes business sense.
Recorded Adam Smith, Telephone interview recorded shortly after the prize announcement, October 2025, Nobel Prize Outreach, 1 October 2025 source ↗
Christopher Hitchens Essayist, critic and journalist
Myself, I love the imagery of struggle. I sometimes wish I were suffering in a good cause, or risking my life for the good of others, instead of just being a gravely endangered patient. Allow me to inform you, though, that when you sit in a room with a set of other finalists, and kindly people bring a huge transparent bag of poison and plug it into your arm, and you either read or don’t read a book while the venom sack gradually empties itself into your system, the image of the ardent soldier or revolutionary is the very last one that will occur to you. You feel swamped with passivity and impotence: dissolving in powerlessness like a sugar lump in water.
Recorded Vanity Fair, First Person column, September 2010 issue, 4 August 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 does a new work 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 ↗
Question What is the most important lesson life has taught you? Time & hindsight
I'm convinced that about half of what separates the successful entrepreneurs from the non-successful ones is pure perseverance. It is so hard. You put so much of your life into this thing. There are such rough moments in time that I think most people give up. I don't blame them. Its really tough and it consumes your life.
Recorded Daniel Morrow, Smithsonian Institution Oral and Video Histories, for the Computerworld Smithsonian Awards Program, 20 April 1995 source ↗
Question How has a failure, or apparent failure, set you up for later success? Do you have a favourite failure? Failure & regret
I didn't see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.
Recorded Stanford University 114th Commencement, Stanford News (Stanford University), 12 June 2005 source ↗
Question What do you do when you feel creatively blocked or stuck? Craft & work
We called that the 'story crisis,' and we never expected to have another one. But you know what? There's been one on every film. We don't stop production for five months. We've gotten a little smarter about it. But there always seems to come a moment where it's just not working, and it's so easy to fool yourself - to convince yourself that it is when you know in your heart that it isn't.
Recorded Betsy Morris, Fortune interview, Kona, Hawaii, March 2008 source ↗

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