“Was I deceived, or did a sable cloud
Turn forth her silver lining on the night?”
John Milton wrote that in 1634.  Silicon Valley offers a ramped up version of looking for the silver lining. It starts with the dark part of the cloud:
“It is probably Silicon Valley’s most striking mantra: ‘Fail fast, fail often.’ It is recited at technology conferences, pinned to company walls, bandied in conversation.
“Failure is not only invoked but celebrated. Entrepreneurs give speeches detailing their misfires. Academics laud the virtue of making mistakes. FailCon, a conference about ‘embracing failure,’ launched in San Francisco in 2009 and is now an annual event, with technology hubs in Barcelona, Tokyo, Porto Alegre and elsewhere hosting their own versions.
“While the rest of the world recoils at failure, in other words, technology’s dynamic innovators enshrine it as a rite of passage en route to success.”
“Silicon Valley’s Culture Of Failure … And ‘The Walking Dead’ It Leaves Behind,” The Guardian (June 28, 2014)
This article’s title takes the mantra even further — “Fail Fast, Fail Often, Fail Everywhere,” it urges:
“In the United States, talking about failure is something of a cottage industry. Though Americans frequently profess, per Yoda, that we are a nation of achievers, from another perspective we are a nation of failures—folks who gave up on a way life somewhere else to start a new one here. Talk regarding the subject is far from verboten; indeed, it is often celebrated as a means to a greater end, notably in Silicon Valley, where “fail fast, fail often” is basically a mantra. We like discussing failure so much that Cassie Phillipps, a founder, with Diane Loviglio, of FailCon, an annual conference devoted to the experience, which began in San Francisco, in 2009, took a break last year because she felt that the subject had become so commonplace as to render the gathering superfluous.”
Can we apply the mantra to advice like do what you love, follow your passion, find your calling? In 1989, I was in the grip of associate disillusionment when a book came out called Do What You Love and the Money Will Follow. I’m sure there was more to the book than the title, but that’s all I took away. The notion that there’s some kind of link between doing what you love and making money was irresistible, and a few years later I took the plunge. The experience was magical alright, except for the money part. Years later I tried again — another magical experience, another financial bomb.
Lesson learned: if you need to make money from your big idea, marketplace rules will apply, and the odds are good you’ll fail. Silicon Valley understands that well enough to believe that failure is good for you if you can learn from it:
“‘I think we’re very lucky to work in an industry where people see you spent a year trying something and it didn’t work out and they ask, What’d you learn from that?’ said Christine Yen, cofounder of software company Honeycomb.io.”
“Finding Positivity In Failure: Silicon Valley Leaders Talk About Past Setbacks,” UC Berkeley Sutardja Center for Entrepreneurship and Technology (Apr. 4, 2018)
Failure done right is transformative, but it still hurts. Which is why some people would dissuade you before you ever try — like this writer in Forbes. And here’s more caution from The Guardian article cited above:
“Most startups fail. However many entrepreneurs still overestimate the chances of success – and the cost of failure.
“But what about those tech entrepreneurs who lose – and keep on losing? What about those who start one company after another, refine pitches, tweak products, pivot strategies, reinvent themselves … and never succeed? What about the angst masked behind upbeat facades?
“‘It’s frustrating if you’re trying and trying and all you read about is how much money Airbnb and Uber are making,’ said Johnny Chin, 28, who endured three startup flops but is hopeful for his fourth attempt. ‘The way startups are portrayed, everything seems an overnight success, but that’s a disconnect from reality. There can be a psychic toll.’”
But for each voice of caution, there’s another — probably coming from somebody else in the tech starup world — that’s chanting “go for it!” Before you do that, you might read Fail Fast, Fail Often to be better prepared. Here’s the Amazon blurb:
“Bold, bossy and bracing, Fail Fast, Fail Often is like a 200-page shot of B12, meant to energize the listless job seeker.” New York Times
“What if your biggest mistake is that you never make mistakes?
“Ryan Babineaux and John Krumboltz, psychologists, career counselors, and creators of the popular Stanford University course “Fail Fast, Fail Often,” have come to a compelling conclusion: happy and successful people tend to spend less time planning and more time acting. They get out into the world, try new things, and make mistakes, and in doing so, they benefit from unexpected experiences and opportunities.
“Drawing on the authors’ research in human development and innovation, Fail Fast, Fail Often shows readers how to allow their enthusiasm to guide them, to act boldly, and to leverage their strengths—even if they are terrified of failure.”
More coming up on the joys and sorrows of failing on the road to career satisfaction.
 “Every Cloud Has a Silver Lining,” Know Your Phrase.