I recently had the opportunity to chat with Jake Desyllas, another very early retiree. Jake hosts The Voluntary Life, a podcast about entrepreneurship, financial independence, and freedom. In 2000, he founded Intelligent Space, an award-winning consultancy in the UK, that led innovation in the field of pedestrian movement simulation and analysis. In 2007 he sold his business and in 2010 he retired early, at the age of 38. He is the author of Becoming an Entrepreneur and his new book is called Job Free.
Since achieving financial independence, his adventures have included becoming a perpetual traveller, going minimalist, playing in a band, writing books, and creating a podcast. He currently lives in Panama with his wife Hannah.
You just released your new book Job Free: Four Ways to Quit the Rat Race and Achieve Financial Freedom on Your Terms. What’s it all about?
It’s a book demonstrating that a job-free life is possible and there are multiple ways to achieve it. I’ve interviewed many people who live free of jobs and presented their real-life stories in the book, along with my own journey to financial independence and early retirement. The book provides a framework to help understand the options for living job free.
There are four basic strategies to escape the rat race of jobs. I call these strategies extreme saving, unjobbing, lifestyle businesses, and startups. By reading the book, people can choose which of these strategies (or combination of strategies) is right for them.
Is becoming job free the same thing as reaching financial independence and retiring early (reaching FIRE)?
That’s a great question. They are not quite the same—job freedom is a broader concept than financial independence and retiring early (FIRE). FIRE is a great way to live a job-free life, but it is not the only way. I think it is helpful to consider why you want FIRE. Most people want it because they want more freedom in life. They especially want to be free of the dreary, unfulfilling obligations of their jobs. For example, they don’t like having a boss, having to show up at set times, having to commute, having to wear a suit, having to follow someone else’s vision and not their own, and so on.
One way to free yourself from these dreary obligations is to save for FIRE, and I cover this strategy in a chapter called “extreme saving.” But there are other ways to free yourself of bosses, commuting, and all the other crappy aspects of jobs. For example, you can start a lifestyle business and be your own boss, so you never have to answer to a boss again. Or you can found a startup and build the company of your dreams. You don’t have to spend your working life building someone else’s dream. There are ways to achieve great freedom in life without FIRE. And many job-free lifestyles can lead to FIRE in the end too, as mine did.
What led you to write Job Free?
The idea came from interviewing fascinating people on my podcast about how to get more financial freedom in your life. I’ve interviewed many people (including Mr. Root of Good himself) who achieved FIRE in different ways to me. I’ve also interviewed people who are not fully financially independent, but have achieved job-free lifestyles that give them the freedom that they want. I noticed that although these stories were very diverse, they could all be understood within a framework of four essential strategies.
I wanted to explain these four strategies using the stories of the people that I’ve interviewed, to show that it is possible to live job free and there are options for how to do it. Many books about lifestyle design convey the message, “my life is awesome and you should live like me.” I’m not advocating for one particular lifestyle; I am explaining the available options and encouraging readers to choose the life that’s right for them.
Who would benefit most from reading Job Free?
The book will be most helpful to those at the beginning of their journey to job freedom, because it provides an overview of the entire journey ahead and all the options available. However, readers who already know a lot about one strategy for quitting the rat race can also gain a lot from understanding the alternative strategies.
I’ve found that there is not much crossover between different communities interested in job freedom. For example, there isn’t much overlap between the extreme saving community and the startup entrepreneurship community. Yet, I think they each have a lot to gain from learning about the other. I hope my book encourages crossover learning between different job-free communities. Although these lifestyles might look different, they share many goals.
When did you first decide that becoming job free was a main goal in your life?
When I was a teenager, I was lucky to meet a mentor who had the explicit plan to start his own business, reach financial independence, and retire early. I learned a huge amount from watching him successfully implement his plan, and from seeing how he changed (I tell his story in Job Free). His example inspired me to create a job-free life for myself. I did a PhD, and as soon as I had finished studying, I started my own business. Eventually I sold it and retired early. I’ve spent very little time as an employee.
What are the biggest hurdles encountered while trying to escape the need for a job?
There are many practical challenges when it comes to replacing the income from a job. However, I have found that the really difficult hurdles are the psychological challenges that face anyone who wants to live job free. For example, job-free lifestyles require you to take a far more active role in creating a community and support network for yourself. Secondly, you have the challenge of creating structure for your life outside the structure of a job. Lastly, the most important psychological challenge is in finding your own clear sense of purpose that can replace the default purpose that you got from a job. Many of the topics that I cover in my podcast are directly related to these psychological challenges, since they are issues that I faced myself.
What are some of the other most important books those seeking a job free life should be reading?
I think Root of Good readers will already be familiar with many of the good books on the extreme saving approach, like Your Money Or Your Life by Joe Dominguez. I recommend exploring some books about other job-free lifestyles. If you want to find out about unjobbing, the best introduction is Michael Fogler’s original book, Un-Jobbing.
If you are interested in lifestyle businesses, I recommend starting with The 4-Hour Workweek by Tim Ferriss, because it is still the most influential book about this approach. You may also enjoy Pat Flynn’s short book, Let Go, for a personal story of his journey into this kind of business.
If you are interested in founding a startup, then my own book, Becoming an Entrepreneur, provides an overview for beginners, and contains many suggestions for further reading on specific topics. Derek Sivers’s book, Anything You Want, is a fascinating personal account of his experience of selling a business.
Root of Good’s thoughts on Job Free
Jake provided me with a free electronic copy of the book for review and I liked it enough to share Job Free with all of my Root of Good readers. In Job Free, Jake does a superb job of conveying the multiple paths to ditching a traditional job, some of which lead to financial independence and some that are essentially lifestyle design on steroids. All four paths lead to the same objective – removing the necessity of a regular nine to five job.
The chapter most interesting to me was the chapter on Extreme Savers because it presents the path that I took to reach financial independence. Get a decent job, save and invest half or more of your income while keeping investment costs and taxes low. When you have enough to cover your annual expenses with a 3% to 4% annual withdrawal, then you are Job Free.
In the chapter on Extreme Savers Jake shares what he learned from interviewing or researching a number of early retirees that you probably recognize:
- me (you know where to find me)
- Jeremy and Winnie from Go Curry Cracker
- Jacob Lund Fisker from Early Retirement Extreme
- Pete aka Mr. Money Mustache
- Mike and Lauren from Mikeandlauren.com
In the Extreme Savers chapter, Jake also references Thomas Stanley’s The Millionaire Next Door where Dr. Stanley presents the patterns and commonalities observed after conducting hundreds of interviews of millionaires across the US. In Job Free, Jake follows a similar methodology as Dr. Stanley by compiling a summary of how numerous Extreme Savers under age 40 managed to save and invest their way to financial independence.
Job Free presents three more in-depth chapters on other ways to escape a regular job through unjobbing, lifestyle businesses, or founding a startup. Plenty of people balk at the idea of becoming an extreme saver, but might have no problem with one of the other three paths that involve pursuing a fun career at lower pay, developing a business that caters to one’s desired lifestyle, or in the case of founding a startup, growing a company and selling it for a large sum of money.
Jake draws on his practical experience as an entrepreneur and startup guy and on his interviews with dozens of others who have attained freedom from a job in different ways.
So far, I’ve had the opportunity to chat with Jake during two podcast interviews at The Voluntary Life and even though his intent was to glean some wisdom from me for his listeners, I have to admit that there was some information exchange going on in both directions. Jake is one of those guys that truly gets what it means to design your life so you can live in an intentional manner. His latest book, Job Free, is a great nugget of his wisdom.
Do you have any questions or comments for Jake?
Root of Good Recommends:
- Personal Capital* - It's the best FREE way to track your spending, income, and entire investment portfolio all in one place. Did I mention it's FREE?
- Free Travel* - We score $10,000 worth of free travel every year from credit card sign up bonuses. Get your free travel, too.
- Save more on travel with Airbnb and take $40 off your first stay*. We usually get apartments with 2-3 bedrooms plus a kitchen and living room for less than the price of 1 hotel room. Save even more with weekly and monthly discounts.
- Use a shopping portal like Ebates* and save more on everything you buy online. Get a $10 bonus* when you sign up now.
- Google Fi* - Use the link and save $20 on unlimited calls and texts for US cell service plus 200+ countries of free international coverage. Only $20 per month plus $10 per GB data.