“There is only one success – to be able to spend your life in your own way.” – Christopher Morley
“Upon graduation, my primary driver was freedom. I remember thinking that at the time. I would like to be anywhere, anytime I wanted and have a lot of money.”
That’s an excerpt from an interview I did after finishing The End Of Jobs. After I heard it, I nodded and thought, “Yep, sounds good to me too.”
Across time periods, across cultures, across genders, there are no lines that a desire for freedom hasn’t crossed.
Why do we want to be free?
I’ve no idea.
However, the phenomenology that every individual fights to exercise a greater degree of freedom in their life is crystal clear.
We, as a species, always want freedom. And once we get it, we always want more.
But, how do we get more freedom?
How To Have A Lower Acceptance Rate Than Harvard
Over the past two hundred years, since the dawn of the Industrial Revolution, the amount of wealth available in the world has increased dramatically.
Even as the population has gone from 978 million to over seven billion, the GDP per-capita has gone from $300 to over $20,000 in Western democracies.
We’ve had a population explosion, but the increase in wealth hasn’t just kept pace—it’s raced ahead.
Whether on an individual level or a societal level, as we have more and more access to resources, we have to choose what to do with them. It’s clear that one of the ways we choose to allocate that wealth is towards a greater sense of freedom.
People often take large salary cuts to move into flexible or remote work arrangements. Given a very clear cut case between more money and more freedom, they pick more freedom.
I spent two years working with a small entrepreneurial company, and starting in a position that, at the time, meant a 50% pay cut and a demotion from project management to grunt work.
When I told my former boss I was leaving, he came back the next day and said he wanted to make me a counter offer, including a raise. I walked because I wanted two things that it was next to impossible for him to provide, given his company structure: freedom and meaning in the work.
I wanted the freedom to travel, to work when and where I wanted, to leverage my best energy and best work.
The company I was leaving to go and work for ran a publishing business, one that has since grown into hosting conferences and meetups around the world.
I had been reading their blog and listening to their podcast for over two years at that point, and I resonated with how they ran their company.
I bought into the show hook, line, and sinker. I believed in “building businesses to create more freedom and wealth in my life, the lives of those I loved and the world at large.”
The way they ran the company reflected it. They plowed excess profits back in to grow the company and to enable them to create more freedom and wealth in their lives, the lives of their team, and the lives of their customers.
That company has a substantially lower acceptance rate than Harvard.
Escape The City is a job board targeted at highly successful corporate types and lawyers who are fighting for an opportunity to dump their six-figure corporate salary for an entry level one that dramatically cuts their salary but gives them more lifestyle design and meaning.
The Silent Revolution of the 20th Century
Over time, as the West has advanced and more wealth has been created, more and more people have claimed that wealth in the form of freedom. Remote working and lifestyle design is the latest incarnation, but certainly not the first.
Martin Luther led the Protestant Revolution which gave substantially more freedom to Christians compared to the Catholic Church. The freedom to interpret religious scripture was no longer left to a single man, but distributed to individuals.
The founding fathers of the U.S.—Jefferson, Franklin, and Washington, among others—led the American Revolution, creating the first republic government in the Modern West. This gave more freedom to more individuals than the Parliamentary monarchy they had previously suffered.
These “revolutions,” however, are small fries compared to what we saw happen in the 20th century.
What has gone quietly unremarked in history books is that the 20th century marked the greatest expansion in freedom in human history. The emergence of the modern middle class in liberal democracies during the 20th century led to more people acquiring more freedom than all of history up to that point.
The founding fathers distributed power from a monarch and a parliament to a group of rich, white landowners. From a few hundred to a few thousand.
It was, at the time, revolutionary. It sparked and inspired the French Revolution.
The level of freedom enjoyed by the average middle class individual in the West today is beyond the wildest imagination of anyone alive in the 19th, much less 18th, century.
Freer than John D.
The Baby Boomer generation built the knowledge economy, which gave them more free time, and the discretionary income to enjoy it with, than their parents’ generation ever imagined.
At work, what they think about requires problem-solving and creative thinking. Unlike the mass of factory and agricultural workers a hundred years ago, the bulk of the middle class today is engaged in knowledge work, more interesting and stimulating than mass manufacturing.
At home, they have freedom to pursue hobbies and more free time to do so. The average work week dropped from almost eighty hours a week in the late 19th century to around forty in the mid-20th century, where it’s stayed since.
The average middle class worker in liberal democracies of the West today is freer in how they spend their how and where they spend their best energy and time than John D. Rockefeller was one hundred years ago, when he was among the ten richest men on Earth.
Modern communication technology alone could let you bring down Standard Oil in it’s heyday. The internet and technology all enable entirely new dimensions of freedom that Rockefeller couldn’t have imagined.
The insider information Rockefeller used to gain key advantages for Standard Oil during its rise would be entirely undercut by a smartphone with access to live market data.
If you own a kindle and a smart phone, you have access to more books and knowledge than Rockefeller could have even imagined possible, much less had access to.
Ideas and concepts which never even entered Rockefeller’s consciousness are now almost ubiquitous. The rise in Zen Buddhist and Stoic philosophy in the modern West is entirely linked to the rise of technology and the internet. Rockefeller simply never had access to those concepts.
Rockefeller only left the United States once in his life. Getting on a boat is an affair. Getting on a plane is an afternoon. You can buy a roundtrip ticket to Europe now for less than $1000.
He spent days riding trains between his expensive summer homes and the Standard office in New York.
We spend hours riding planes between AirBnB apartments. A level of freedom that cost him millions to create can be recreated today for a few hundred.
Rockefeller, compared to his peers, was incredibly free. Compared with a typical Standard Oil employee, Rockefeller enjoyed a degree of autonomy in his time and location that was unprecedented one hundred years ago.
For much of the middle class, the level of freedom Rockefeller enjoyed is now blasé.
It is this natural desire for increasing amounts of freedom that has been one of the main drivers in the advancement of civilization.
We’ve gone from one man, Luther; to a small group of men, the Founding Fathers; to a whole segment of society, the middle class Baby Boomers. And in each case, not only has the size of the group increased, but their degree of freedom. The professional middle class individual today has far more freedom than John D. Rockefeller, much less Thomas Jefferson.
Finishing the Row
Because freedom is a fundamental driver, a fundamental motivator of human action—your action—we always want more of it.
Despite having access to more freedom today than Rockefeller may have had a hundred years ago, large sections of the American and European middle class feel trapped or unsatisfied.
Older generations call us ungrateful. But past generations generally don’t see the whole phenomenology. Each successive generation wants freedom in a way their parents couldn’t have imagined, but can’t see that the next generation wants the same thing.
While our parents frequently see the success that long-term, stable employment and careers brought them and want the same for us, they fail to recognize that for them, that was a stretch. An ambitious goal, freely chosen, that they grabbed.
You can imagine King George getting the petitions of the colonists and blowing them off. They’ve got it good! They’re landowners, aristocrats, with access to a vast new continent. And they want to save a little money on taxes? They want representation? Bah, humbug!
Most of our grandparents lived through the Great Depression. They were, in many ways, the last generation of the industrial economy. Our parents were the first generation of the knowledge economy. An economy that has led to a magnificent amount of growth in the West.
I spoke with someone recently grew up on a rural farm the Southeast United States—we’ll call him Jack.
Starting from age ten, Jack worked in the fields.
When the harvest was bad, the dinner table was empty.
His father had survived the Great Depression and, more than anything, he wanted to avoid the real deprivation he had gone through and so he instilled in his children the ideal that overcoming material scarcity and being able to provide for their family in abundance was what mattered.
They had a saying when you were working the fields called “finishing the row.” Even if it started raining or the sun was going down, Jack always finished the row.
Finishing the row is the story of Jack’s life and of many of our parents’ lives. He worked on that farm in the mornings and evenings and went to school during the day. He got a science scholarship to get an engineering degree. He went to University to get a biotech PhD. He got done with the first year and realized the professors of the department were keeping the PhD candidates in school for as long as possible to do research for them. Because the field was so new, they needed a small army of researchers.
Sitting on his roof watching the race riots after MLK’s assassination, he realized it was going to take him ten plus years to get out of the program. He left to pursue Medical School. When it was time for him to choose his specialty, he chose Orthopedics over Cardiology. What he wanted from a professional perspective was to be a heart surgeon, but he didn’t do it because he knew that it was demanding, and he was married by that point and knew he wanted to have a family.
His decisions to drop out of the biotech PhD and to do Orthopedics are fundamentally representative of his life and of the lives of many of our parents. Many people in our generation would view that as “quitting on your dreams.”
I can see the new age career counselor asking with a hyperbolic degree of earnestness, “Why didn’t you follow your passion?”
That’s neither a true nor a fair question.
Dreams and ambitions for everyone and every generation are different.
Many Baby Boomers that were raised in an environment where they couldn’t afford food at some point. The idea of finishing the row, of building a life and family that they could provide for in material abundance, was deeply motivating, meaningful, and fulfilling to them.
It was a new level of freedom. Jack did just that. He worked incredibly hard from the time he was seven to seventy to fulfill that dream and provide for his family in abundance.
If Jack and others like him hadn’t done that, we would all be sitting around trying to finish rows. That was the promise for the generation of the Baby Boomers and (minus some accumulated debt) they fulfilled it. The growth in wealth and quality of life after WWII is unparalleled in human history.
And so it’s quite natural that many Baby Boomers would wish the same for our generation. They want their children to be safe, to enjoy material abundance, and to benefit from long-term, stable employment.
However, that was not because of the exact nature of jobs, but because it was an expansion of freedom beyond what they could have imagined.
The career counselor asking that question is asking it now because that’s the nature of the human desire for freedom. We want more of it.
Lifestyle Design > Choice
Who has the power in a democracy? Who is the most free? The obvious answer would be the voters, right?
Who has the power in America: the voters?
Or the people that control who the voters get to choose from?
The people who really have power are those who decide who shows up on the ticket we vote for. They’re able to create the options you choose from.
In reality, there are a nearly infinite number of ideological choices for president or senator, but we get stuck in a Republican/Democrat paradigm because that’s what we see as citizens and voters.
Our role there is not to design, but to choose from a set of options designed for us.
In a world of vast possibilities, we focus all our attention on a relatively tiny portion because the most powerful people are structuring the consciousness of everyone else.
The power in a republic is more dispersed than in a monarchy, but it isn’t totally free.
One way our generation has fought to distribute freedom and to gain more if it can be seen in the culture around protesting through movements like Occupy Wall Street.
What the protestors are missing is that we, today, our generation, have more opportunity not to ask for power, but to wrest it from the structures that exist.
If our generation chooses it, if we seize it, the degree of freedom we can create is likely beyond the capability of human imagination two decades ago. It’s entirely possible that the level of freedom you can create in your life within two decades will be beyond the imagination Steve Jobs had during his lifetime.
Instead of choosing from a set of available jobs, we can create our own. It’s the triumph of design over democracy. Instead of choosing from a set of options at the buffet, we can become the cooks.
It’s important to think about what you want your average day to look like.
Another friend of mine was given the choice between going into entrepreneurship and going into academia as a PhD.
He had a passion for reading and books and interesting ideas.
While most people don’t think of entrepreneurship as the path to those things, it’s worth playing out the scenarios.
A good scenario for a PhD is 7-10 years in school and ending up on a tenure track in Idaho. If you do make that happen, which is highly competitive, you’re going to spend twenty hours per week teaching classes, twenty hours per week grading papers, and twenty hours per week managing administration.
The reason professors work so much is they don’t get to start doing the research and writing they got into academia for in the first place until sixty hours into their week.
If you have freedom of time, that’s not the case. Richard Branson and Paul Graham are freer than any academic philosopher to actually do Philosophy.
The difference between Branson or Graham and a PhD is that they didn’t choose any of the options available to them.
They designed one that didn’t yet exist.
A Slightly Better Blackberry
Why is it that more and more freedom and autonomy creates even more and more freedom and autonomy?
Edward Deci, the founder of self-determination theory we discussed earlier, noticed in his experiments and observations that great work emerged when individuals had more freedom. That is, when they were allowed to be more entrepreneurial.
If we think of the great contributions made to human society, they were all made by people that were free to do whatever they wanted but used the freedom to create amazing things.
Pablo Picasso wasn’t obligated to paint; he freely chose it. He, in fact, struggled early in his life seeking work:
“One of the reasons why I’m now without a position, why I’ve been without a position for years, it’s quite simply because I have different ideas from these gentlemen who give positions to individuals who think like them.”
Imagine someone telling Steve Jobs that he had to design a new phone. Given that sense of obligation, he likely would have made a slightly better Blackberry.
Great work—the kind of work that will create wealth in our lives and the lives of others is not the product of obligation—is the product of freedom (and hustling).
By seeking more freedom and building it into our lives, we not only improve our ability to create more material wealth and make more money personally, but we also create more of it in the world at large.
Last Updated on July 30, 2019 by Taylor Pearson