Originally presented at DevopsDays 2015 as an Ignite talk. The text is my original script, somewhat idealized over what actually made the cut. :)

1. Four Jobs in Four
Years
A Devops Empathy Tour in 5 minutes
Presented in Ignite format at DevopsDays SV, November, 2015
Charles Johnson, Product Manager, Chef

3. The first time I saw Willy Wonka and the Chocolate Factory I
was five years old.
There’s a scene where some rich businessmen try (and fail) to
use a computer to cheat at the search for a golden ticket.
Other kids might remember the creepy-ass boat ride scene,
but I remembered the computer guy, and thinking that I could
have made that computer do what it was supposed to.
That early, even before I had a word for it, I knew: I wanted to
be a sysadmin.

5. I disassembled my parents' first Apple ][ when I was 7.
As I got older I got really into computer games, but I had way
more fun taking them apart than I did actually playing them.
I loved getting those early games running, even more than I
loved playing them.
Some of the best memories of my middle school years are
about getting Ultima 7 to run on a 386SX with 2 megs of RAM.

7. When I was 15, I got my first paid sysadmin job.
Over the next 20 years I never stopped working. Together with
my peers, we built the internet. It was an amazing time.
But in 2010, at the age of 35, I found myself
with a 20-year sysadmin career already under my belt.
And by then, I had gone full-blown feral BOFH.
I was fed up. I was bored, frustrated, lonely, and angry.

9. When I was at my lowest, I discovered Chef, and through
Chef, the Devops Manifesto. I’m here to tell you: CAMS saved
my sanity.
The idea of Culture, Automation, Measurement, and Sharing
resonated so strongly. The idea of Continuous Delivery
resonated so strongly.

11. I wanted to be a part of this new movement.
After years of burnout, my work was fun again. It became
imperative to spread these ideas to my colleagues, people
who were hurting like I was.
I worked hard to evangelize these ideas. I started writing, and
speaking at meetups.
The people at Chef saw one of these meetup talks, and they
hired me as a consultant. Thus began job #2.

13. I never thought that I'd ever work for a tools vendor.
But it turned out that being a consultant instead of a staff
sysadmin was great! Consultants are constantly meeting new
people, encountering new problems, learning about new ways
we can help each other.

15. By teaching, I learned that the problems I faced weren't just
unique to the organizations I had been a part of, but rather
were endemic to the profession as a whole.
My job was to help people in bad work situations heal
themselves, and my toolkit was CAMS.
It was an empathy bomb!

17. It was around this time that I read The Phoenix Project, which
I’m sure this audience is familiar with.
At the end of the book, the IT manager hero goes on a quest
to embed in all the other divisions of his company, to find out
their unique challenges and build empathy not just within his
IT organization, but to build empathy with people who do jobs
he’d never even considered.

19. This led me to an uncomfortable truth!
Because even though I was saying that spreading Empathy
culture was part of my goal, a true culture of empathy meant
finding common ground with people I was not equipped to
understand as human beings.
There was an entire class of colleagues that I had long
avoided, because to me, they were aliens:

21. SALES PEOPLE.
I didn't understand sales people at all. I didn't understand the
reasons behind the pain they inflicted on consultants. I didn't
understand the rewards that fed their brains dopamine. I didn't
understand the pressures that drove them.
If I wanted to live my ideals and be the best person I could be,
then I would have to find a way to relate to them.

23. So I became a sales engineer. Job #3.
Let me tell you: Being a sales engineer for a product you
believe in is GREAT.
First, the money is amazing. Second, you get to build
prototypes all the time, so it’s engineer fun times. AND! People
get excited about the possibilities you present to them. They
want to believe in you, they want you to succeed.
Also, there’s nothing so satisfying as closing a huge deal.
Nothing.

25. But the pressure on the sales team? It's enormous.
If you don't do your job right, not only are your customers
unhappy because they didn't buy the thing that they need,
but your colleagues and friends will be out on the street.
You have to provide the right thing, to the right people, at
exactly the right moment, or nobody’s happy. It's not just your
livelihood on the line.

27. And while the travel is great at first, after a while it becomes a
grind.
Once you own every Ingress portal at multiple airports (GO
ENLIGHTENMENT!), and you know all the people working at
your home terminal on a first-name basis, it's no longer
fun like it used to be.
My family life was suffering. Eventually, I just wanted to get a
deal closed and get home.

29. No matter how hard you work in sales, there is always a huge
gap between what the customer wants to buy, and what you
actually have for sale. And no matter how you try to close
that gap, it's never totally erased.
And the people who come by behind you and have to deal
with it after you? That's right: The consultants.
It was this gap between what people wanted to buy, and what
we actually had to sell them, that was causing all the
problems.
When you’re in the field, the gap is SO OBVIOUS. But it
seemed like the people who could fix it weren’t aware!
We had to bring even more people into the conversation:

31. ENGINEERING.
In many organizations, engineering was treated as a silent
giant, armed with translators for the rest of the company.
How could we bring developers who lived in the abstract into
conversations about the things they built?
So when the opportunity arose, I became a product manager.
Job #4.

33. My colleagues in field engineering were ecstatic. Over and
over again, as individuals and as a group, they let me know
that they expected me to go in and lay down the law.
They viewed their own colleagues as an enemy, the same way
I had viewed sales.
But guns blazing is a sure fire way to make sure you never
build rapport with anybody. Instead, I have spent a lot of time
understanding the challenges faced by brilliant
engineers.

35. I’m afraid that many of them may still view me as a great
disappointment.
It turns out that to a person, every developer I met craved
those conversations about the things they made. They didn’t
always like the answers, but they never once shied away from
the discussion.

37. After so many years as a systems admin, I thought
engineering and I were kissing cousins. I thought
understanding the motives of engineering teams would be
easy.
I knew they were driven by a creative urge, but I didn’t
understand how many of them felt constantly stifled in their
creation.
I didn’t understand that many of them wanted their work to
connect with an audience as strongly as any artist or
performer.

39. I am learning about the challenges created by the simple
inability of personalities to understand each other.
I am learning that the job of product management is, at its
core, about bridging that gap between what people want to
buy, and what you have to offer them.
I am learning that it is maybe the hardest option I could have
chosen at this point in my career. But at the age of 39, it’s both
great and terrible to be brand new at something again.

41. When sysadmins view themselves as the keepers of truth,
engineers view themselves as the keepers of creativity, and
sales people view themselves as the Real Fucking World, we
can't communicate beyond the roles we define for ourselves.
In the last four years, I've learned Devops isn't just about
breaking down the silos in your IT organization. It's about
breaking down all the silos, finding ways to understand each
other, even when that person is completely different. Even
when their incentives make you an obstacle. Even when your
incentives make them an obstacle.

42. Four Jobs in Four
Years
A Devops Empathy Tour in 5 minutes
Presented in Ignite format at DevopsDays SV, November, 2015
Charles Johnson, Product Manager, Chef