The question

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.

Alessia Cara

Canadian singer-songwriter

Recorded said elsewhere, not written here
It was very challenging at first, as I came straight out of high school where my lifestyle was so different to that of a professional musician. I lived such a secluded life – I went from school to home, school to home, and never travelled anywhere. I hadn’t figured out who I was, as I hadn’t explored anything yet. To jump into the completely opposite lifestyle so quickly and so young was difficult – I was very afraid, and didn’t know how to say no.

Cordelia Lam, The Forty-Five, 30 July 2021 source ↗

Others on this question

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Ernst Mayr Naturalist and evolutionary biologist
Very often I had to fight for the recognition of my ideas, particularly since, in those earlier days, I wasn’t in any prominent position where people would listen to me.
Recorded Academy of Achievement interview, 5 April 2001 source ↗
David Herbert Donald, Ph.D. Historian; twice winner of the Pulitzer Prize for Biography
I have generally had few setbacks and few obstacles. I have been very fortunate in that things have been handed to me rather than my going out after them. There are a few roads that I didn’t take that I maybe could have. When I was a graduate student, maybe a second-year graduate student, I worked frequently at the Illinois State Library in Springfield, and one day, the director of that library called me into his office and said, “I have some news to tell you that is still very hush-hush, but I’m resigning from this job. I’m going to the Chicago Historical Society, and I’m going to recommend that you be appointed in my place.
Recorded Academy of Achievement, Academy of Achievement interview, Cambridge, Massachusetts, 1 April 2005 source ↗
Alice Sheppard Dancer, Choreographer
Everything. Theatres are ready for disabled audiences, more or less, but they aren’t ready for disabled artists. An example I always give is: theatres don’t always have an accessible toilet backstage, so you can’t pee before the show, or if you do you’re halfway through make-up and you have to run to the front where the audience is. The main issue is physical access, but it is improving.
Recorded Sophie Griffiths, DIVA, 9 April 2020 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 ↗

More from Alessia Cara

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Question What advice would you give your twenty-year-old self, and what should they ignore? Time & hindsight
To just chill out and not worry. Growing up, I worried about every little thing. I was like, "oh I'm not good enough, I'm not confident enough, I'm not pretty enough, I'm not this and that." I would cry about my appearance, and cry about a bunch of things that don't matter to me now. I would just say, the stuff that matters now won’t matter in a few years, and just chill out and enjoy your life.
Recorded Danielle Sinay, Teen Vogue, 13 September 2016 source ↗

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