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.

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Recorded Sundar Pichai said elsewhere, not written here
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

Stanford University Commencement, Google (The Keyword), 14 June 2026 source ↗

Others on this question

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Clive James Critic, essayist, poet and broadcaster
What I’ve got doesn’t hurt. I’ve been lucky. The treatment has been benign. I don’t know if I could concentrate if I was in pain. I’ve never had to stop.
Recorded Robert McCrum, Interview at James's home in Cambridge, published in the Observer New Review, The Observer, 15 March 2015 source ↗
John Clauser Experimental physicist; Nobel laureate in Physics, 2022
The hard part was getting around this, this was a religion among physicists, and in fact even in the Bohr-Einstein debates, and with Schrödinger also, the universal religion was quantum mechanics makes correct predictions, period, no, off the table. What Bell's theorem and in particular our version of it, the Clauser-Horne-Shimony-Holt experimental prediction, showed that either that had to be wrong, nor Einstein's whole legacy had to be wrong. I think at the time people who were critical of doing the experiment didn't realise really what was at stake, that it was that cut and dried between two religious icons, if you will, the field of physics. Since I kind of was the inventor of the CHSH inequality and the CH inequality and all that, I knew exactly what it was all about. But it took a long time for that to filter in.
Recorded Nobel Prize Outreach, Nobel Week interview, Stockholm, 6 December 2022, Nobel Prize Outreach, 6 December 2022 source ↗
Mike Krzyzewski Basketball coach at Duke University, 1980-2022; winner of five NCAA championships
In ’91, we were playing Nevada Las Vegas, and they’d won 45 in a row. It was almost like it would be okay to lose. Everybody would say, “Oh, that’s all right.” That, to me, was the biggest obstacle. I was most proud of that game, because, as a leader, I helped my group overcome rationalization at the highest level. When we beat them, and then beat Kansas for the National Championship, everyone was saying, “Boy, you won the National Championship,” but for me, it was amazing because I got over that final hurdle, as a leader and a teacher.
Recorded Academy of Achievement, Academy of Achievement interview, Durham, North Carolina, 1 May 2001 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 ↗

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