Book Review and Interview – Job Free: Four Ways to Quit the Rat Race

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:

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?  



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  1. Thanks for the review. It looks worthwhile to check out……

    It just goes to show you that there are so many ways into today’s economy to structure your career, finances and life. Truly the 30 year job is unrealistic today (at least for the vast majority of us). It’s encouraging to read about so many viable alternatives!

    Thanks again,


      1. While working, I somehow managed to remain oblivious to the whole freelance/side hustle economy that’s been going on for quite a while. Had I known about all these possible ways to make a decent buck outside of a 40 hour/wk job I might have stopped working full time sooner!

    1. For sure. For a newly minted college grad, the 30 year career at 1 company is obsolete (excepting perhaps government jobs that have a decent chance of offering a pension in 30 years).

  2. I’ve listened to Jake’s podcast for a little while now and actually just listened to his interview on Radical Personal Finance. I like the fact that he stresses no way is right or wrong on this path, and everyone needs to figure out what’s best for themselves.

    1. Absolutely! I think most of the folks that read this blog (and similar blogs) are planning on the save and invest then retire path in some form. The book does a good job of fleshing out that path to ditching your job, but also nails three other ways to escape the 9 to 5 that I see very little of in the PF blogosphere.

  3. This sounds like a book I definitely need to read, especially it contains lessons from other early retirees. 🙂

    It’ll be very interesting to read the book and get some ideas for ourselves.

  4. I’m really hoping to check this book out. Since starting to care about personal finance, I’ve seen the pros and cons of each of these. I think personally, I’ll try some of each in my life. I had a year or two as an extreme saver, and now I’m about to jump onto the unjobbing bandwagon. Later on, hopefully I’ll start a business, and maybe when I’m old I can do a lifestyle business.

    Each choice has a lot of merit to it, but I think they make sense at different points.

    1. Yes – one size doesn’t fit all. And like you say, over time your focus will shift. I think the extreme saving method is a good early start on the path to FI, and then pursuing one of the other routes is much less risky once you have an asset base to rely on and use to support your living expenses if necessary.

  5. mmmmmm its a sliding scale on the financial prep side. I see lots of job free guys around our town….hanging out at the beach all day….and sleeping under the trees at night. :o) No money but maybe the same feeling of freedom from work.

    1. They aren’t Job Free, they’re homeless!

      I’m sure it’s a liberating feeling until the lack of a roof over their heads becomes untenable. In any event, Jake’s book provides a few good routes to not working a traditional job while keeping a roof over your head. 🙂

  6. Justin,

    You know my stance on leaving work behind. Never quit, get laid! If you quit, you don’t get a severance, your unvested stock options go bye bye, you don’t get any of your deferred cash, there’s no health care COBRA benefits for usually 6 – 12 months, and you certainly won’t get 26 weeks of unemployment benefits.

    I’m not sure why people don’t want to negotiate a severance. Without negotiating a severance in 2012, I would have felt a lot of pressure to try and make money online, and not write the posts I wanted to write that clearly won’t make me any money (e.g. today’s How To Get Your Parents To Pay For Everything). Besides me, so many people have been able to negotiate a severance to have the financial breathing room to do what they want.

    Why do you think more people don’t negotiate a severance? Everyone who works at a corporation has at the minimum, usually a 2 month “severance” in the form of the WARN Act if they get laid off.

    But I’m glad a book like Job Free is encouraging people to think about new ways to live and earn!


    1. I never got a severance when laid off, and in fact, my current company did not provide severance for the most recent layoff.

      WARN act or no, it’s not a guarantee. My first layoff was a restructuring bankruptcy. Should have been covered under the WARN act. In fact, there was a class action lawsuit, which was was settled out of court. Instead of getting paid that $10k, I got stock in the new company, worth approximately $75 at the time. Now worth nothing.

      If you are leaving on your own terms, that’s one thing. But severance is by no means a guarantee. And when it does happen, in my experience, it’s 2 weeks pay at best.

      1. Exactly! Which is why it behooves everyone to proactively figure out how to get that nice severance. 4 years later, I’m still getting over $40,000 a year in severance money.

        Those who negotiate early and get laid off early get the biggest severance. You don’t want to be the laid off employee who gets jack!


        1. I’m guessing by leaving and getting a severance you are referring to trying to get your company to ‘force’ you out rather than leaving on your own?

          If you leave on your own you don’t give yourself much of a chance of getting anything.

    2. Go for the severance if you can get it!

      I got let go back in 2013, and wasn’t eligible for anything other than unemployment (and it was only 20 weeks in NC at the time, so $7k total). Still better than nothing, but not much. I was working for the state government without any real employment rights (totally at will, exempt from our state’s Personnel Act), so they didn’t have any severance deals of course!

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