Lessons from a Russian Prince in Exile
Serge Obolensky’s autobiography is a riveting tale of reinvention that even non aristocrats can learn from
It’s a cliche, but sometimes a life story is too incredible to believe, it’s comprised of twists and turns a fiction writer would consider too implausible.
I came across Serge Obolensky in a roundabout manner. An anecdote in one article, a mention in a book. Blogs listing the real “most interesting man in the world” often include him. Eventually curiosity got the better of me and I went looking for a copy of his out of print autobiography on PDF Drive. One Man in His Time, which came out in the 70s, is Serge’s attempt to tell his compelling and complicated life story. If half of what’s written is true he deserves, his place on those blog lists.
Let me give you a brief, non comprehensive, biography.
Serge was born a Prince in late 19th Century St. Petersburg to a family with close ties to the imperial household. In this capacity he was raised to follow the life of a landed aristocrat, but fate had other plans. After studying at Oxford and serving with valor in World War I he became a legendary guerilla fighter in the White resistance against the Russian Revolution. Obviously that did not work out so he eventually escaped to England where he married an Astor and lived the life of a 1920s playboy.
When his marriage floundered, Obolensky relocated to America to try his luck. Quickly he showed a knack for hotel PR and real estate development including relaunching the Plaza hotel and St. Regis to great acclaim. When World War II arrived, even though he was in his 50s, he did not sit it out. Serge joined the OSS and led parachute operations behind enemy lines in missions to liberate Sardinia and later Paris. After that he retired to a relatively relaxed life as a hotel executive.
I enjoyed his writing style and also felt there was more to take away from the autobiography than just an interesting tale. Oblenskey approached life with a sort of ease and natural fluidity, there was none of today’s ubiquitous hustle culture which seems to be a prerequisite for success in the modern world.
Serge is also one of the strange 20th century figures who inhabited two worlds, the aristocratic 19th century as well as the capitalist late 20th Century. The closest comparison I can come up with is fictional, Carlos Fuentes’ masterpiece The Death of Artemio Cruz.
Instead of a traditional review, I want to try something different. Let’s take a look at some of the life lessons that you can takeaway the Prince’s world view and experiences.
Not all Rich Kids are Wimps
The conventional wisdom in America today is that inherited wealth is some sort of basic moral peril. More than just fostering inequality, unearned money brews festering weakness in the person who receives it.
Easy cash rots the Weberian soul, right? From Bill Gates declaration that he only plans to give his children $10M to business gurus like James Altucher who glibly expound this logic, many assume its veracity is self evident.
Serge’s life contradicts these ideas.
He was raised as a literal prince. He had chefs, coachmen, private tutors. The family estate encompassed hundreds of thousands of acres of some of the world's most fertile farmland. The wealth and privilege he had is hard to comprehend by modern standards. According to today’s conventional wisdom, he must be something of a wimp, right?
Serge Obolensky became the opposite. The prince volunteered to serve on the front lines of World War One. When he lost his fortune after the Russian revolution he did not fold but instead took on a new way of living. He was not lost without wealth even though he had known nothing but privilege his entire childhood.
Both poor people and rich people fail. Serge is an example of someone who gained strong values from a high social position. The broader takeaway is to never judge a book by its cover and don’t make snap judgments based on faulty popular wisdom.
It’s always easy to cherry pick anecdotes that fit a cynical world view but they often tend to be the exception rather than the rule.
Your Network is More Valuable Than Wealth
Again this is a cliche, I think one that most people say but don’t really believe. In Serge’s case it turned out to be true. Money comes and goes, but a strong network of friendship and connections can help you weather any storm.
While he was not entirely penniless after the Communist revolution in Russia, Serge needed to make some money fast and construct a new life.
It was impressive how his social skills helped him find housing, work, and romance relatively quickly without any particularly defined skills. His first job in exile in England was selling agricultural machinery though a connection he made in Russia. This took him to Australia where again he used his considerable charm to forge an entire new network. He enjoyed a lavish life and felt confident to pursue risks because his network gave him a form of safety net.
Serge knew how to connect with people and how to help them connect with others. He developed a social ecosystem which constantly brought in new people who could assist him in the future. He didn’t ask for anything at first, Serge understood that with enough connections doors would open when he needed to pass through them. This goes beyond the crass form of quid pro quo networking people do today. His first thought was how to help others, the rest followed.
I think there is a case to be made that you should put as much, if not more effort, into cultivating your network as your direct career and family. It’s easy to let this slide but when I’m down or looking for a change it’s these diffuse connections who come to the rescue.
Avoid this “Dostoyevsky” Sort of Personality
We live in a woke world and the tendency is to assume that this is a recent phenomenon. The truth is the wokster has existed in various forms for a long time.
In the memoir one passage hit me over the head like a ton of bricks. Serge describes a certain type of person who came to prominence after the revolution. I will just quote him here, because he does a better job describing them than I ever could.
“One of the trying aspects of that time was the sudden rise of the Karamazov type of Russian intellectual I had known in my college days. Under the old society these embittered individuals were just avoided, as far as possible, because they were rude or provocative and tiresome. But now they were incredibly dangerous. They flourished under the Bolsheviks. They were glib and quick, and they knew politics. The atmosphere of terror that made everyone afraid to speak up gave them a field day. Many of them became Bolshevik agents. They would wander around trying to provoke arguments, twisting the most casual remark into something that had a political meaning. Nothing could be done except to suffer in comparative silence. Not too silent, though! That also would be held against one.”
Notice any parallels? I sure do. Throughout the memoir we get a sense of the terror of a world where these people take over. Fighting back against the insidious worldview is the only way to get through life without losing your mind or your country.
It’s also important to develop an understanding of the distinction between being clever, intelligent, and wise. Like the talent on MSNBC, the type of person Serge describes is indeed very clever, always with a quick comeback or the ability to jujitsu your words back in your face.
They tend not to be that intelligent, otherwise they’d be writing novels or doing astrophysics, or wise, none seem to be that happy. Don’t be like these people.
Don’t Be Afraid, with a Good Attitude you can Reinvent Yourself
This is probably the most important takeaway from the book, and is the underlying theme for the first three lessons.
Counting on my fingers Serge had five or six almost entirely different lives, going from Russian prince, to soldier, to London playboy, to hotel executive, to Spy. When you read the book you get a sense of his excitement for all of these roles, like an actor looking forward to a challenging new character. He took the world on not with grim fortitude but active enjoyment.
I have been thinking about motivation and personal growth a lot recently. Trying to find more personal motivation, the modern approach to grit and grinding seems like it's missing something.
I really connected with Serge because his story shows the power of optimism.
It’s much easier to have grit and determination when you’re optimistic about the outcome. Many Russians gave up on life after the revolution, but not Serge. His optimism is what pushed him to go on. From a near death experience at the hands of Red captors, to a bad divorce, to failing hotels, optimism is the through-line.
Sacrificing in the present for something in the future requires optimism.
So if you’re like me and looking for a change cultivate optimism and good things will come to you. The struggle will not be so hard if you can envision the positive future.