How Justice Scalia Broke PayPal Founder Peter Thiel's Heart Long Ago

We will all experience failure at some point in our lives, but we can develop incredible grit and resilience by reframing these encounters into learning experiences.

Peter Thiel (photo by TechCrunch via Wikimedia)

Peter Thiel (photo by TechCrunch via Wikimedia)

“All I have in life is my new appetite for failure / And I got a hunger pain that grows insane / Tell me do that sound familiar?” Kendrick Lamar

What do David Lat and Peter Thiel have in common? They both applied to be Supreme Court clerks for Justice Antonin Scalia. And both were interviewed and rejected (albeit with nice letters).

Many know Peter Thiel as the co-founder of PayPal and Palantir Technologies or as the first outside investor in Facebook. But before these achievements, he attended Stanford Law School and did well enough to interview with Justice Kennedy and Justice Scalia for SCOTUS clerk positions. Just as David Lat failed to receive a SCOTUS clerkship offer, so too Peter Thiel failed to secure a clerkship offer. So what can law students and young lawyers learn from these setbacks?

In Harvard’s Success-Failure Project, Lat reminisces about his rejection:

In September 2000, I interviewed for a clerkship with Justice Antonin Scalia. I thought to myself: if only I can get this, then my life will be perfect. I had thought the same thing about getting into Harvard College, and then Yale Law School. Of course, each time I snagged a brass ring, a new one materialized.

Alas, I didn’t get the clerkship… Little did I know that my feelings of dejection and inferiority would come in handy.  Several years later – while working as a federal prosecutor, after a few years at a New York law firm – I started a judicial news and gossip blog called Underneath Their Robes. I wrote under a pseudonym, ‘Article III Groupie’ – a young lawyer whose failure to secure a Supreme Court clerkship gave her an amusingly unhealthy obsession with federal judges.

The rest is history – of a bizarre and perhaps trivial nature, but history nonetheless. Underneath Their Robes became a runaway hit.  After I was featured in the New Yorker magazine, I received an offer to blog full-time, for the politics blog Wonkette. After gaining that experience, I launched Above the Law, a blog about law firms and the legal profession. Today it is one of the country’s most successful (and profitable) legal blogs, receiving over 10 million page views per month.

Although I never got a Supreme Court clerkship, I suspect I’m more professionally satisfied now, as a blogger, than I would have been as a lawyer. Sometimes failure in achieving one goal is merely a way station for success in achieving another.

In his book Zero to One: Notes on Startups, or How to Build the Future (affiliate link), Thiel also reflects on being denied an opportunity to clerk for the Supreme Court:

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The highest prize in a law student’s world is unambiguous: out of tens of thousands of graduates each year, only a few dozen get a Supreme Court clerkship. After clerking on a federal appeals court for a year, I was invited to interview for clerkships with Justices Kennedy and Scalia. My meetings with the Justices went well. I was so close to winning this last competition. If only I got the clerkship, I thought, I would be set for life. But I didn’t. At the time, I was devastated.

In 2004, after I had built and sold PayPal, I ran into an old friend from law school who had helped me prepare my failed clerkship applications. We hadn’t spoken in nearly a decade. His first question wasn’t ‘How are you doing?’ or ‘Can you believe it’s been so long?’ Instead, he grinned and asked: ‘So, Peter, aren’t you glad you didn’t get that clerkship?’ With the benefit of hindsight, we both knew that winning that ultimate competition would have changed my life for the worse.… It’s hard to say how much would be different, but the opportunity costs were enormous. All Rhodes Scholars had a great future in their past.

Justine Musk, Elon Musk’s ex-wife, has stated that extremely successful people (like Elon Musk) do not fear failure – or they do, but they move ahead anyway. “They will experience heroic, spectacular, humiliating, very public failure but find a way to reframe until it isn’t failure at all. When they fail in ways that other people won’t, they learn things that other people don’t and never will. They have incredible grit and resilience.”

Many of Justice Scalia’s former clerks have gone on to do remarkable things. I’d venture to assert that just as many people who have been denied the clerkship opportunity by Justice Scalia have achieved spectacular success as well. Indeed, “sometimes failure in achieving one goal is merely a way station for success in achieving another.”

The top five regrets of the dying are: (1) I wish that I’d let myself be happier; (2) I wish I’d stayed in touch with my friends; (3) I wish I’d had the courage to express my feelings; (4) I wish I hadn’t worked so hard; and (5) I wish I’d had the courage to live a life true to myself not the life others expected of me (the most common regret was this).

The legal universe will miss Justice Scalia and his eloquent opinions. Whether you agreed with him or not, one thing cannot be denied: he left an indelible mark on the legal profession. Justice Scalia always had the courage to express his feelings. I bet he left this world with little regret.

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We will all experience failure at some point in our lives. But we have the opportunity to develop incredible grit and resilience by reframing these encounters into learning experiences. Our greatest failures can become our greatest teachers. Few of us will ever be so fortunate as to be interviewed for a SCOTUS clerkship. Even fewer of us will develop the grit and resilience to bounce back from failure and achieve success beyond all expectations. The most fortunate of us will encounter many failures, but harbor few regrets.

R.I.P. Justice Scalia.

Earlier: Justice Scalia And Me: A Love Story


Renwei Chung is the Diversity Columnist at Above the Law. You can contact Renwei by email at projectrenwei@gmail.com, follow him on Twitter (@renweichung), or connect with him on LinkedIn