5 ms·

Why did you quit Apple at such a prime time?

dunstanorchard 4d ago
It was very exciting to work at Apple. In one way it felt like I was at the center of the creative world (despite not being in the hardware or software division). But the interesting _web_ stuff was all happening elsewhere. Stewart Butterfield kindly kept asking me to join the Flickr team, and eventually the pull of that outweighed the allure of Apple. I spent the next four and a half years at Flickr and it was foundational to the rest of my working life. The people I was lucky enough to be around and learn from there were extraordinary, and the environment and opportunities were second to none. In retrospect another six months at Apple, further taking advantage of their employee stock purchase program, would have been life changing. Shares were about $7 each back then after the discount. But you do what you think is right at the time, and I'm grateful for every moment I got to spent in Cupertino.
- rconti 4d ago
  > But you do what you think is right at the time, and I'm grateful for every moment I got to spent in Cupertino. It often surprises me when people express deep regret for things like this, because if you feel you made the correct decision at the time, it's hard to feel that it was a mistake. But I suppose this comes from a position of the relative privilege of having savings.
  - gambiting 3d ago
    How do you know if it was a correct decision, if not through hindsight? I stayed for over 4 years with my first girlfriend, and it felt like the correct decision at the time to try and make things work. In hindsight I really really wish I hadn't and I regret doing so. Is that any different?
  - dunstanorchard 4d ago
    I’ve always been happy I left when I did. It was the right thing for me at that time and it led to a great adventure and a new set of friends.
  - bookofjoe 3d ago
    >There is no such thing as a good decision https://bookofjoe2.blogspot.com/2026/09/there-is-no-such-thing-as-good-decision.html https://bookofjoe2.blogspot.com/2026/09/there-is-no-such-thi...
- bradly 4d ago
  > But the interesting _web_ stuff was all happening elsewhere. Were you writing WebObjects? Internally, how was WebObjects viewed at the time?
- dosisking 4d ago
  [flagged]

It was very exciting to work at Apple. In one way it felt like I was at the center of the creative world (despite not being in the hardware or software division). But the interesting _web_ stuff was all happening elsewhere. Stewart Butterfield kindly kept asking me to join the Flickr team, and eventually the pull of that outweighed the allure of Apple. I spent the next four and a half years at Flickr and it was foundational to the rest of my working life. The people I was lucky enough to be around and learn from there were extraordinary, and the environment and opportunities were second to none. In retrospect another six months at Apple, further taking advantage of their employee stock purchase program, would have been life changing. Shares were about $7 each back then after the discount. But you do what you think is right at the time, and I'm grateful for every moment I got to spent in Cupertino.

rconti 4d ago
> But you do what you think is right at the time, and I'm grateful for every moment I got to spent in Cupertino. It often surprises me when people express deep regret for things like this, because if you feel you made the correct decision at the time, it's hard to feel that it was a mistake. But I suppose this comes from a position of the relative privilege of having savings.
- gambiting 3d ago
  How do you know if it was a correct decision, if not through hindsight? I stayed for over 4 years with my first girlfriend, and it felt like the correct decision at the time to try and make things work. In hindsight I really really wish I hadn't and I regret doing so. Is that any different?
- dunstanorchard 4d ago
  I’ve always been happy I left when I did. It was the right thing for me at that time and it led to a great adventure and a new set of friends.
- bookofjoe 3d ago
  >There is no such thing as a good decision https://bookofjoe2.blogspot.com/2026/09/there-is-no-such-thing-as-good-decision.html https://bookofjoe2.blogspot.com/2026/09/there-is-no-such-thi...
bradly 4d ago
> But the interesting _web_ stuff was all happening elsewhere. Were you writing WebObjects? Internally, how was WebObjects viewed at the time?
dosisking 4d ago
[flagged]