A Failosophy talk I gave in Tijuana that touches on inclusiveness and failure


Failure means something different for many minority leaders and entrepreneurs.

It’s often viewed catastrophically, something to be avoided at all costs. It is the ultimate shame, the abscondment of your limitless potential. It is the collapsing nucleus of your family’s hopes and dreams. Though we all learn to fear failure in this culture, it has a much more pointed meaning if you don’t identify as a rich, white, heterosexual, male.

Lest you think this is purely a social justice cause, the effects of the difference in perceptions of failure can dramatically alter people’s fortunes and societal outcomes. Take the recent research published in the Journal of Personality and Social Psychology focused on the overconfidence and resulting incompetence of the wealthy. The researchers observed that high-status individuals were more confident than their actual ability, and this projection made others believe in their ability even more.

Though the paper doesn’t really address the potential causes, I believe this phenomenon (which we’ve all observed at one time or another) is rooted in the radically different failure experiences of rich, white people. Fundamentally, they don’t fear failure as much, perhaps because the “worst case scenario” is not that bad due to wealth, or because they have examples in parents/grandparents who wagered big and won. Either way, the effect is the same: loss aversion seems to express itself more readily in high-achieving minority leaders.

There are a number of reasons why this may be the case. From my own personal experience (as a Gay, Jewish immigrant), and in my research with entrepreneurs, innovators and leaders across domains, I’ve found a few common themes that color our perceptions of failure by class/race/gender/etc. Perhaps you can relate to one or more of these:

  1. You have to work twice as hard as the majority. Almost every high-achieving minority person I’ve met has heard this from their parents, grandparents or mentors early and often. Though it is intended to motivate, it can retard positive risk-taking behavior. When people believe that their opportunities are constrained, they may be less likely to take a chance and risk the success they have achieved.
  2. You never really know if you’re winning/losing because of your ethnicity, race, gender, sexual orientation or disability. Many leaders can relate to a career with both setbacks and achievements that left them feeling deeply out of sorts. It’s that creeping suspicion that you have either won or lost because of your background and not on the merits of your work that can undermine confidence and trust. If you feel that the outcome of your effort is capricious or random, at some point you might find it comfortable to stay in your lane, perhaps to the detriment of your actualizing your desires and potential.
  3. Your family is depending on you. Many high-achieving minority folks can relate to the pressures of having disproportionate opportunity and/or ability in a family that has sacrificed a great deal to further your advancement. Whether it’s driven by guilt or genuine need, if you are supporting your family’s dreams (and/or finances) it can be hard to follow your heart and risk their investment.

Of course everyone’s experiences are different, and one can imagine these influences being either motivating or demotivating in their own right. But the fundamental issue remains: your attitude towards failure is influenced by your background. And yet, we need to give people permission to make appropriate mistakes, to follow their hearts/minds and to lay things on the line when they matter.

Though there is no one size fits all, I believe that you must begin by acknowledging the biases that hold you back. If you come from any of these backgrounds, and have experienced the loss aversion I talk about here – know you are not alone. Each of us is going through it in our own way, and sharing stories can be very valuable.

The second part of changing this equation rests with those straight white men in power. To create an environment that fosters innovation and excellence in all people you must begin by understanding that everyone’s definition of success and failure is affected by their background. They may not be able or willing to take the same risks, to make the same mistakes and to communicate in the style of someone with greater means and clearer role models.

I’m reminded of an experience where I was hiring an engineer for my last startup. We had been introduced through an uber driver I met, and I was super excited to meet her, as female software engineers of color are exceedingly rare in the tech industry. During our first interview, I asked her a seemingly innocuous question:

“How do you see yourself in your career in 5 years?”

Pretty standard, right?

Her response caught me off guard.

She said, “Sorry, I don’t want to sound arrogant, but I am hoping to become a kick-ass software developer.”

My initial reaction was to really dwell on her lack of confidence. My mind immediately went to a place where I was concerned about her ability to hold her own with the highly opinionated cast of characters on our team. How would someone that timid, someone so unsure of herself, be able to achieve the great things we needed?

And then I remembered – this was a pretty risky conversation. She had few role models, and even fewer jobs in tech. We were her first startup, and she definitely didn’t arrive at coding with any particular leg up. I realized her hesitation was a coded way of saying that she was excited to have this opportunity and really wanted to do her best.

Of course, she could hold her own, did great work and has seen her career rise since the failure of my startup. But it was nonetheless a stark reminder: even folks with crucial skills, an entrepreneurial spirit and tons of intelligence can be unsure and risk-averse.

To truly unlock this potential, we must be willing to let everyone fail on their own terms.

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