A collective sigh of sympathy went out to Leonardo DiCaprio when he failed yet again to win an Oscar for The Wolf of Wall Street. I was shaking my head in empathy. Hang on. Did I say empathy? Yes, I was reacting to what I thought he must be feeling. Okay, it’s not  easy to put myself in his shoes, much less see the world through his eyes, but you know what I mean.

We’ve all experienced a painful loss – a job promotion, admission to a dream university, a much needed scholarship, a financial investment or a lasting relationship. The big difference is Leonardo DiCaprio’s losses make headlines.

He most probably is disappointed over his latest Oscar miss. But I bet he is already moving on to his next project in film, philanthropy or environmental activism.

Skeptical? Let his words throughout his career support my bet, and let’s pick up lessons along the way too.

“My mom, Irmelin, taught me the value of life.  Her own life was saved by my grandmother during World War II.”

DiCaprio grew up with his mother who remained friends with his father after the couple divorced when Leo was a toddler. Both parents shared in his upbringing and encouraged creativity. His mother was born in Germany, moved to the U.S. in the 1950s and worked as a legal secretary. DiCarpio remains close to his mom. She was his “date” at Oscar night.

Leo knows about valuing life. Dwelling on loss would be a waste of precious time. 

“Brothers don’t necessarily have to say anything to each other — they can sit in a room and be together and just be completely comfortable with each other.”

An only child, DiCaprio has a close friendship with fellow actor Tobey McGuire, which began when they were auditioning for the same child actor roles in the 1980s. He also keeps a regular close group of friends.

Leo’s enduring friendship with a professional rival shows no grudges over missed roles or awards.  Friendships and relationships carry more weight than personal loss.

“Don’t think for a moment that I’m really like any of the characters I’ve played.  I’m not.  That’s why it’s called acting.”

DiCaprio’s portrayals of fictional and real life characters are not easily forgotten. Frank Abagnale, Jr. (Catch Me if You Can) and Danny Archer (Blood Diamond) are, to me, the most poignant. He chooses film projects not by genre but based on how interesting the character is.

Leo has no attachments to roles or awards. Devastation over a loss comes mostly from a perceived attachment. 

 “I’m not the kind of person who tries to be cool or trendy, I’m definitely an individual.”

A maverick is how he is described. While other leading men get comfortable working for years in an action franchise, DiCaprio does not mind doing supporting roles and is not afraid to play hateful protagonists and villains. He knows what moves him and does not go with the crowd.

Leo will not allow the Oscars to define who he is. Self-awareness keeps you centered in who you are.

“Drugs?  Everyone has a choice and I choose not to do drugs.”

DiCaprio has had his share of drinking and partying in the 1990′s but states he has never done drugs. Seeing drugs at an early age and growing up poor helped him make the decision not to go in that direction.

Leo used a difficult situation to make a wise choice. Wisdom comes from awareness, courage and commitment to a decision.

“I just really love doing what I do. I know every career is fleeting and there will be time periods when I don’t get the opportunities that I’m getting right now, so I’m taking advantage of them.”

DiCaprio is also a film producer and has worked with respected directors James Cameron, Steven Spielberg, Martin Scorsese and Quentin Tarantino.

Leo understands the financial and creative aspects of the film industry. Losing an Oscar will not stop him from finding — or making — the next big opportunity. With purpose and ideas, a loss becomes irrelevant.

“I’m just starting to scratch the surface of what really makes me happy and it’s taken me a while to admit that acting like a little child and being a jerk and a punk is fun.”

These words may have come when DiCaprio was younger but it shows maturity — wanting to learn about himself, accepting his discoveries, and not taking himself too seriously. He has stayed connected with his parents and he has real friends to relax and act like a child with.

Leo has other pursuits beyond movie making, and losing an Oscar will not make a big dent in his life. Developing all areas of life enriches perspectives, making any loss purely incidental.

“You can either be a vain movie star, or you can try to shed some light on different aspects of the human condition.” (and) “Raising awareness on the most pressing environmental issues of our time is more important than ever.”

DiCaprio is among the first actors who has put fame to meaningful use by bringing public awareness to environmental and humanitarian concerns utilizing media projects, campaigns and grants. The Leonardo DiCaprio Foundation gave a US$3 million grant to Oceana, an advocacy group working for the world’s oceans.

Leo’s philanthropy and environmental activism seeks to positively affect large parts of the world population. Losing an Oscar is trivial. Being aware of a greater need makes you realize how much you actually have and cuts your disappointment down to size.

What about his Oscar-losing streak?  Statistics-wise, a series of losses means he is close to winning.  But law of probabilities aside, the fact remains:  losing an Oscar is not an obstacle for Leonardo DiCaprio to continue living a highly successful and meaningful life.

So the next time you think “Poor Leo” (or the more common variation, “Poor Me”), think again.

Featured photo credit: Izzie August 344 via flickr.com

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