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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

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 13d 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.
- dunstanorchard 13d 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 13d 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...
- gambiting 13d 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?
bradly 13d ago
> But the interesting _web_ stuff was all happening elsewhere. Were you writing WebObjects? Internally, how was WebObjects viewed at the time?
- dunstanorchard 12d ago
  Apple was a very segmented company back then (I've no idea what it's like now) and the online store had three groups that contributed to it: my team, which designed the pages; an engineering team, which took our designs and transformed them into WebObject templates that ran the site; and a content team, which controlled the database that spat out the images and prices. I did my work in HTML/CSS/JS (and some PHP for the imagemagick stuff in this case), which the engineering team then had to adjust to fit the code their templates could output. I don't recall much detail about how WebObjects was viewed. I do remember that at the time the store used a version of WebObjects that could only run on old hardware, so there was an impending deadline for a total re-write before the hardware stopped being available. I've no idea if they did that rewrite or swapped to a different system altogether.
  - bradly 11d ago
    Thank you for the reply. Yes, the lore of the store code is what I'm thinking of. I made my way to Apple from 2017-2021 and it was still quite segmented. No morality in the segmentation, though. I enjoyed my team feeling like its own thing and we got to use Ruby because we all really liked it.
dosisking 13d ago
[flagged]

rconti 13d 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.

dunstanorchard 13d 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 13d 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...
gambiting 13d 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?

bradly 13d ago

> But the interesting _web_ stuff was all happening elsewhere. Were you writing WebObjects? Internally, how was WebObjects viewed at the time?

dunstanorchard 12d ago
Apple was a very segmented company back then (I've no idea what it's like now) and the online store had three groups that contributed to it: my team, which designed the pages; an engineering team, which took our designs and transformed them into WebObject templates that ran the site; and a content team, which controlled the database that spat out the images and prices. I did my work in HTML/CSS/JS (and some PHP for the imagemagick stuff in this case), which the engineering team then had to adjust to fit the code their templates could output. I don't recall much detail about how WebObjects was viewed. I do remember that at the time the store used a version of WebObjects that could only run on old hardware, so there was an impending deadline for a total re-write before the hardware stopped being available. I've no idea if they did that rewrite or swapped to a different system altogether.
- bradly 11d ago
  Thank you for the reply. Yes, the lore of the store code is what I'm thinking of. I made my way to Apple from 2017-2021 and it was still quite segmented. No morality in the segmentation, though. I enjoyed my team feeling like its own thing and we got to use Ruby because we all really liked it.

dosisking 13d ago

[flagged]