n LEADERSHIP
H
enry Ford dreamed of mass-producing cars. So he
started the Detroit Automobile Company … and it
flopped. Oprah Winfrey was fired from her first job at
a TV station. Before she dominated the world of fash-
ion, Vera Wang failed to realize her original dream —
making it as an Olympic figure skater. And before he rallied
the world to fight Adolf Hitler, Winston Churchill was fired in
1915 as head of Britain’s navy.
Examples like these are everywhere. Success is built from
the blocks of failure. “Failure can be the greatest gift,” says
Michelle Payne, a leadership coach and CEO of Sacramen-
to-based SEE Strategies. “I see this with all my clients. Maybe
someone gets laid off, or the job gets eliminated. It’s painful,
but fast-forward six months or a year later, and they’ll look
back and say it’s the best thing that ever happened to them.”
Yet most of us dread failure. We’re embarrassed by it, al-
most like a body odor. So what, exactly, makes failure useful?
Clearly not every failure is a blessing in disguise. (Try saying
“Look on the bright side!” to a resident of Chernobyl.) But fail-
ure can have power if we learn how to respond to it, and that
involves a mix of psychology and grief — and lots of spaghetti
and marshmallows.
USEFUL FAILURES
We toss around the word “failure” as a catchall, but not all
failures are created equal. “When corporations say they want
to ‘fail fast’ or ‘fail hard,’ they don’t really want … to lose $30
million,” says Payne, laughing a bit. “Failing fast” is a way of
piloting — testing, tweaking, taking lots of smart risks.
Consider the spaghetti experiment. A decade ago, Peter
Skillman, then an executive at Palm, arranged volunteers
into four-person teams and gave them a goofy mix of items:
20 sticks of spaghetti, 1 meter of tape, a piece of string and a
single marshmallow. The teams had 18 minutes to build the
tallest structure they could, and it had to have the marshmal-
low on top. He gave this challenge to hundreds of people, in-
cluding CEOs, lawyers, engineers and business students.
The winning group? Kindergartners.
“The engineers had years of schooling and work experi-
ence to teach them how to build sound structures,” explains
Megan McArdle in the book “The Up Side of Down: Why
Failing Well Is the Key to Success.” “But the kindergartners
had something even more powerful: They were not afraid of
failure. By trying and failing, they learned what didn’t work.”
This is the bedrock of science — you create a series of exper-
iments, and each time you “fail,” you apply that learning to
your next attempt.
Yet, if we’re not careful, these small, useful failures can
snowball into a catastrophe. “Failure can be like boiling a
frog in hot water,” says Payne. “You get used to the tempera-
ture so much you don’t notice that you’re being boiled alive
until it’s too late.” For this we can blame our mind’s penchant
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for confirmation bias — we welcome data that supports our
views, and we put less stock in contradictory evidence. For
an example, let’s consider the case of an entrepreneur named
Jontae James.
OUR STUBBORN BRAIN
James had what he thought was a killer idea: a startup called
YOOO, short for Your Out of Office, a platform to promote
work-life balance. James had connections. He was a popular
guy and had been since he played basketball for Saint Francis
University (he was good enough to make NBA training camps,
but didn’t crack a roster).
So, in 2013, in Silicon Valley, he launched YOOO, leverag-
ing his connections to arrange deals for employers, offering
them out-of-office perks they could give their employees as an
HR engagement and retention tool — a free happy hour on a
Tuesday night, or maybe VIP access at a club. He wooed cor-
porate clients and envisioned a $100 million valuation, but he
needed more users, so he kept giving away freebies to grow the
base. This cost money. He dug in deeper.
“I ignored the hard truths,” he says now. Looking back,
years later, James acknowledges a confirmation bias — he had
focused on every nibble of interest and glossed over the many
rejections. “The truth is that I had the wrong business model,”
he says. “It just didn’t add enough value for the employers. It
was a nice-to-have; it wasn’t a need.” In a desperate Hail Mary,
he decided to throw an epic 10,000-person party to salvage the
business — converting partygoers to users and convincing
corporations that YOOO was legitimate.
James put every nickel into that party. “I borrowed money
from people I shouldn’t have,” he says. The night of the par-
ty came. Fewer than 2,000 attendees showed up. YOOO was
dead. “It was rock bottom,” he says with pain in his voice. “Just
total despair. The biggest failure ever. I literally felt like I want-
ed to kill myself.”
Those negative thoughts shadowed James for years, and
for this, we can thank neuroscience. Alison Ledgerwood, a
psychology professor at UC Davis, studies how information is
framed — whether in a “loss frame” (glass half empty) or “gain
frame” (glass half full) — and then how the brain responds to
changes in that framework. In a TED Talk that went viral (4.2
million views), she shared this example: One group of people
is told a new surgical procedure has a 70 percent success rate
(a gain frame), and another group is told that a new surgical
procedure has a 30 percent failure rate (a loss frame). Same
procedure, same data, but people liked the procedure more
when it was described positively.
That part isn’t so surprising. Here’s the twist: She then
went back to the first group (the positive frame) and told them,
“You know, you could think of this as a 30 percent failure rate.”
Suddenly, they didn’t like the procedure. They changed their
minds. She also went back to the second group (the negative