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 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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Henry R. Kravis Financier; co-founder of Kohlberg Kravis Roberts & Co.
I think one of the most important things that I’ve had to overcome is jealousy from the outside. Of learning that not everybody is going to be my friend.
Recorded Academy of Achievement, 12 February 1991 source ↗
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 ↗
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 ↗
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 ↗

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