Essays
Living a Thousand Lives
Business of Happy Customers
Willingness to Fail
Every Product's Signature
Change the Problem
A Letter to My Younger Self
Keep going.
It's 1999.
You're about to open Macromedia Flash 4
It will change your life.
You'll go deep into design and
programming.
You'll fall in love with both.
High school won't be so bad.
You'll make the senior soccer team, but
barely play.
It happens.
Your sister will buy you a Samsung Yepp
YP-55 MP3 player.
It will hold glorious 18 songs.
You're blessed to have her so don't
annoy her too much.
You'll be fortunate to attend the
University of Waterloo.
It will be really, really hard. Keep
going.
You'll walk out resilient. Waterloo will
shape you.
You'll work at BlackBerry.
See how great Canada can be when it
dreams.
You'll learn to
change problems when you can't
solve them.
And see firsthand how quickly companies
can disappear.
Keep going.
You'll move to Seattle to work at
Amazon.
Learn what it means to be
in the business of happy
customers.
Come to terms that growth requires
a real willingness to fail.
Keep going with the puns.
You'll make a bad fantastic math
joke.
And be stunned when your (future) wife
actually laughs.
That's how you'll know.
After school, you'll start your own
company.
It will fail. Don't beat yourself up.
(You will anyway.)
Keep going.
You'll join Maluuba.
You'll
work on AI assistants
a decade before they're cool.
The product will be
too early and wrong.
Keep going. It will be a lesson you need
to learn.
You'll move to San Francisco.
The Bay Area really is a parody of
itself.
The people, though, will surprise you
with their kindness.
The outdoors
are more beautiful than you can imagine.
You'll join Amplitude as their first
designer.
Spend 4 years imagining
analytics as a social product.
You'll help people play with their data
for the first time.
You'll join Quora.
Learn the power of questions.
And how important context is in order to
understand an answer.
You'll join Airtable.
Spend 4 years building interfaces
designed to be endlessly customized.
You'll learn a product's neurotic and
obsessive users show the way.
You'll realize makers leave a signature on their products
These years will pass in a blur.
Keep going.
Through it all, you'll wear many hats.
Software engineer, founder, designer,
product manager.
Others will see differences between
these roles more than you do.
Keep going.
Remember this: the late nights, the launch emails, the celebrations, all of those will pale in comparison to how blessed you'll feel to work with some of the smartest, kindest, most earnest people.
And all the typical life advice?
Almost all true.
Call your parents more often.
They will always be your biggest
supporters.
Floss regularly. Go to the gym more.
You probably don't need to buy another
domain name.
Your kids want your time more than
anything.
Make more messy crafts,
more baked goods.
They'll grow up even faster than people
warn you.
Tell people you love them more often.
Keep going and you'll soon be ready to
start your next company.
You'll try again what you wanted to do
now—except it will feel different.
Right now, you create because you're
surprised you can.
Because new is exciting.
Because you love being the first to see
something before others.
Those reasons will no longer matter to
you.
After all these years, after all these experiences, you'll learn to love building because it's a way to live a thousand lives.
Keep going.