Freedom, financial and otherwise

These days, there are a lot of people pursuing “financial independence.” They want to retire at 40, they want to build “generational wealth,” they want to “never work another day in my life.” The spirit is everywhere, with inspiration from people like Tim Ferriss and The 4-Hour Workweek and the startup scene. The idea is that you hustle really hard and then you can stop hustling and start living, or you figure out a hustle to give you nothing but leisure.

Why do people want to have total financial independence and retire at forty? They want to get to the good stuff. They want to see the world. They want to spend all their time with friends and family. They want to pursue their hobbies and interests. You can get rich and then do that, but there is another way to have that life.

Some people pursue their passions and spend their time with their friends, but are willing to do it broke. One of the best places to see this lifestyle at work is in the surfing and climbing communities. Long before living in vans and climbing was cool, people were sleeping in cars and climbing and living off occasional work and occasional meals. People spent months or years living that way. They called themselves “dirtbags.” In the 1970s, it became a more recognized subculture. 

The surfing world is another example of people pursuing their passion and “chasing the stoke,” without necessarily “getting anywhere.” Plenty of people who weren’t and aren’t professionals, especially decades ago, worked a little, traveled a little, and sought out the best waves they could ride with their best friends. William Finnegan’s Barbarian Days: A Surfing Life is an excellent biographical narrative documenting the phenomenon and offering a compelling coming-of-age story.

Sometimes people spend years living off the “path to success” and get there in the end, sometimes they don’t. They’re not necessarily in it for the outcome. Foam Dust—25 Years of FCD is a Patagonia film about Fletcher Chouinard Designs. Fletcher Chouinard is the son of Yvon Chouinard, Patagonia’s founder. But the younger Chouinard didn’t get his start by fitting into the corporate mold. In the mid-1990s, Patagonia was looking to get into surfboards and they started working with a small, largely amateur operation: Skunkworks. The goal was to produce boards which would last and use more sustainable materials. That evolved into Point Blanks in Ventura, California. At first, Patagonia was their only customer and they were a small subdivision of the company. Fletcher joined the crew until 1998.

What was Point Blanks like? It was a tin shed building, operating as a factory for surfboard shaping. The young guys who worked there also lived there. There were bunkbeds in the office. One guy slept on chairs. They didn’t have shower facilities. If the surf was good, they often closed the shop. As one of the guys says in the documentary, “It was pretty rugged back then. It was fun.” They didn’t start off knowing much about shaping boards or glassing, they kept getting better and adding more people to the team.

If the dream is doing what you love and spending time with people you care about, these guys had it. What lured Fletcher to Point Breaks? A friend explains: “He loved working with his friends. He loved surfing. He loved building stuff.” As one of the early shapers says, “It was literally the best time in my life. I had no money, no worries.” They could barely pay their bills and they had scorpions coming into the building at night, but “surfing came first.” 

The company evolved, becoming Fletcher Chouinard Designs in 2005 and becoming fully independent from Patagonia. But the old ethos built the brand. It got bigger, in part, because they teamed up with Kohl Christensen, a self-proclaimed “dirtbag traveling surfer.” He had no sponsorship, had once traded a surfboard for a horse, spent his time chasing big waves, and sometimes made money doing drug trials. That’s the last person some companies would want, but he helped design boards for bigger waves and take the boards into the bigtime.

The thing is, if you’re willing to accept the downsides and risks, you can pretty much spend your time hanging with friends and pursuing your hobbies right now. The “dream job” just may not come with a dream paycheck. There are subcultures around that show us some people are already living that way. They don’t wait to get rich. Most of us are just too cautious or too busy waiting to “cash out” to get to that life. 

You don’t have to care about surfing or scaling walls to live a bit differently. So much of our mainstream culture is built on consumption and excess, we can’t imagine being happy with less. We say we want to spend our time doing what we love with the people we love, but we’re putting a lot of effort into acquiring stuff and securing housing and vacationing in the right spots. It’s not all bad, but we can remember that these are actually choices.

An extreme alternative lifestyle is shown in the countercultural classic Possum Living, by Dolly Freed. First published in 1978, the subtitle is: How to Live Well Without a Job and With (Almost) No Money. Dolly and her dad did what they could to imitate Diogenes, a Greek philosopher who lived in a wine barrel and eschewed possessions. “The central theme of Diogenes’ philosophy was that ‘The gods gave man an easy life, but man has complicated it by itching for luxuries.’” Based on her actual experiences as a teenager, Dolly describes all kinds of alternative approaches to building a lifestyle. They fish and cook fish and turtles, raise rabbits for meat, sell homemade candles at the farmer’s market, bake their own bread, use the library for all it’s worth, distill their own moonshine, and get housing through foreclosures. It’s one version of “financial independence.” Fortunately, there are many steps between what most of us are doing now and what Dolly Freed can coach us through.

Possum Living doesn’t advocate much in the way of traditional work, but the guys at FCD just picked work that they loved, even though it wasn’t initially lucrative at all. There’s a lesson there. We can spend our whole lives chasing enough money to make our dream life possible, or we can have our dreams by living on less. There are a lot of ways that might look. We can choose jobs that leave us more time or keep us in a location we love. There are things that we would have to give up, but there are things that we might gain.