To Portland and Back
I’m writing down some memories.
You can start at Chapter One if you like or just keep reading here.
— 2008 —
When Agitar shut down, almost everyone I knew went to work for Google or Apple but I decided I’d had enough of Silicon Valley and went to work in Portland. A friend of mine hired me at WebMD and I took a huge pay cut because living in Oregon was so much cheaper than living in Silicon Valley.
I drove up to Portland and left my family back in California for a few months so the kids could finish school and we could sell the house. Matt from Alphablox had moved up to Portland a few years before and we hung out together almost every day.

My family came up to see me for a few days in April and the first day was wonderful. We had glorious sunshine and strolled around the market by the Willamette River.
As we wandered through the Pearl District, Mrs Clown said,
“This is so lovely we shouldn’t even bother going back to California. We’ll take the kids out of school and let the real estate agent take care of the house.”
The next day it poured with rain. The day after that there was sleet. Then it froze. Then it snowed.
Mrs Clown said,
“I am going back to California now. If you want to stay married, you’ll come with me.”
I told my boss at WebMD that I had to move back to California but he said I should continue working remotely.
“You can come up and see us every month and we’ll have telephone meetings when we need to talk to you.”
So I worked remotely for a few years.
WebMD was my first job where I wasn’t writing software. They were stuck in the old days when product managers churned out specs that nobody read and the QA folk weren’t allowed to talk to developers in case it affected their objectivity. They were in a different part of the building.
I’d been hired as Chief Software Architect and helped a couple of hundred developers transition from a traditional engineering organisation to a modern agile organisation. The first thing we did was tear down the walls and make little self-contained teams, each with its own set of developers, product managers and testers who worked together every day.

This was the time when Portland was re-inventing itself and reinventing the IPAs that would soon take over the world. Every pub had a Top Ten Beer Board showing how hoppy the IPAs were and Matt and I set ourselves a goal to visit every pub in Portland. Even at the airport, they enjoyed a beer and the barmaid in The New Old Lompoc would start pouring my Condor Ale as soon as she saw me turn the corner each month.
— 2012 —
Hanging out with Matt was cool but working remotely was less cool and I spent most of my time on the phone. I barely left our house in San Jose for a couple of years and my mental health started to suffer.
Suddenly, out of the blue, I got two random job offers on the same day. One was from Netflix. Netflix was just down the road from where I lived, so I went to see them.
The Netflix office was the most beautiful office I have ever seen. It was like walking into Steven Speilberg’s guest house. Larger-than-life movie posters on the walls. Lush armchairs. Enormous coffee table books on enormous coffee tables. It was just gorgeous. And they promised me a fortune in salary.
The other was at a brand-new start-up with no money and no office yet. They didn’t even have proper desks. I told Rian about my dilemma over coffee.
“You seem like a start-up kind of guy to me,” said Rian.
I took the startup job and an even more massive pay cut.

I’m writing down some memories.
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Thank you, Rian!!
Thank you for taking the pay cut, Ragged!!
From a happy SmartPatients.com member
Hahaha I love Mrs. Clown. And you sum up the west-side PacNW climate dilemma perfectly. It’s like living with a charismatic, fickle, untrustworthy lover. When things are good, it’s so good! But how can it betray me so?!? Over and over again. How lucky for you that she saw its true colors on that first visit.
I’ve spent my whole adult life with it! I also can relate to your remote work tale. I earned my library degree via one of the first programs to offer a fully remote option. My first year I had no job so took close to a full load of classes and planned to finish in two years. My husband and kids trotted off to work and school each day and I sat in the family room in front of the family PC (it was dial-up then!) all day, then again after everyone went off to bed in the evening. It took a similar toll on me and I found a .75 job before the next school year started. It took six years to finish but being out in the world again was fantastic! I am glad you were able to get out of that grind.
Glad you took the start-up, Ragged!
And apparently Mrs. Clown was OK with it…
That took some guts as well as foresight!
We had the year’s worth of seasons in one week. Even England is more predictable than that week in Portland. If I remember correctly it was April when we came. Probably Spring Break…spring my **** :).
Haha I believe it. I call that season “sprinter” and it runs from February 14 when the daffodils come out until July 5 when the cold rains stop. Then 8-10 weeks of summer, which seduce visitors into thinking they’d like to live here. But now I just call that “smoke season.” You’re missing nothing, trust me. Am glad you escaped before you started putting down roots!