I remember on launch day, it was February of 2013.

I was sitting at my desk, we launched mailbox,

we had a waiting list of almost a million people waiting

for our app, and I there and then saw this,

what I now call the crossroads of should and must.

It was this moment where I could see my entire design career

and the startup career I'd worked on the Uber app.

I'm sure most people are familiar with Uber.

I worked at all these amazing startups,

and I done all this stuff that all had led me

to this amazing point of launching this product,

but I had no idea what any of that had to do

with my dream of painting in a white room.

And I think that's really the gist of where I am

in my journey and the story that I'm sharing

is that this crossroads of should and must arrives

in all of our lives, over and over again,

all the time in big and small ways.

And let's look at that day, peak of a startup,

and also this kind of fledgling, bizarre expression

of wanting to paint.

Those worlds were both equally appealing,

...