Is Ridiculously Extraordinary Freedom Possible At A Day Job?


“Understanding that your job is to make something happen changes what you do all day.” – Seth Godin in Linchpin

The answer is yes, Ridiculously Extraordinary Freedom is possible with a day job.


Here’s why: Ridiculously Extraordinary Freedom means you are able to do what you want to do, but are not forced to do anything you don’t want to do. If you want a day job, if that is Freedom to you, then it’s all good.

A couple months ago I created a list on twitter:

It’s the only list I’ve created thus far and it consists of exactly one person: Mark Cuban, owner of the Dallas Mavericks, HDNet, Landmark Theatres, blogger at, and all around bad ass.

And when I mean I’d work for Mark Cuban, I mean if he wanted me to clean his house or scrub the floor of the American Airlines Center, as long as I had access to his brain in some way, I’d do it. (There’s the rub!)

I know I would learn a lot from him. I know I could execute a lot of ideas for his businesses that others wouldn’t be willing to try. And I also know it would be hard work, but fun as hell.

But let’s get off that for a moment because, well, although I would accept if Mr. Cuban contacted me, I’m not looking to get my first job since the year 2000. :)

Where this is coming from: I’m currently working on the anti sales letter for How To Live Anywhere and it starts with a story of two of my friends.

One of them, who makes a very nice amount of money online in only a few hours (usually less than 10) per week (*ahem* thanks to my teachings), doesn’t want to quit his job. I think that’s awesome. He has the option, the Freedom, but he likes his job, so why quit?

It’s almost the ultimate Freedom: knowing that the second he doesn’t like his job he doesn’t have to worry about what he’ll do. He can move on.

When To Stay and When To Kill a Day Job

If you have a business that is generating enough cash to live on and you hate your job, you quit.

If you have a business that is not generating anything, and you hate your job, and you have no savings, you stay. And you get your ass in gear to start generating that cash!

If you have a business that is generating some cash, but if you worked on it harder you could ramp it up, and you hate your job, you quit. And you get your ass in gear to start generating more cash!

If you have a business that is generating some cash, but if you worked on it harder you could ramp it up, and you love your job, you stay … and reevaluate that decision when your business is generating job replacing income.

Or if you’re Dave Navarro, you wait until your business is rocking so hard you’d be crazy not to quit your high level management day job.

Your Turn …

Seriously think about this: What is Freedom to you? I write so much about Freedom, but I don’t think I’ve ever directly asked you what your version of Ridiculously Extraordinary Freedom looks like. I’m excited to read what you have to write!


  1. “what your version of Ridiculously Extraordinary Freedom looks like” – hehe your definition from the interview is pretty similar to my definition: “do what I want, when I want, where I want and with whoever I want”. Just have the freedom to do everything my way. And I won’t stop until I achieve it!

    • Eugene, that rocks! I never really thought about how by having a day job every aspect of your life is scheduled for you, whether you like it or not.

  2. Karol,

    I can relate to this first hand. I have a day job that takes up my time 3 days a week. But I think I have the ultimate blend of freedom and guidance. I think there are some keys to getting ridiculously extroaordinary freedom in a day job

    1) Report to a Visionary or CEO: In your case, this would be Mark Cuban. I report directly to the CEO of my company. One of the advantages of reporting directly to the CEO is that you have access to an entrepreneur and the way he thinks. Another advantage is that your ideas go straight to him with no filters in communication. Personally, I think all aspiring entpreneurs with day jobs should try to report to a CEO (I’m working on an article about it :)).

    2) Find a day job that complements your Entrepreneurial efforts: Fortunately for me, running BlogcastFM and Skool of Life completely overlap with my day job. In fact some of the people I”ve interviewed for BlogcastFM are people I might end up hiring to contribute weekly posts to our corporate travel blog. So, if you can find a day job that aligns with your long term entrepreneurial interests than you can still achieve freedom.

    3) The Job Has to Be Flexible: While this is not a hard and fast rule, I find the fact that I’m only in my office 3 days a week makes a huge difference. While I techincally might make more with a full time job, it turns out that having a job 30 hours a week and working on projects on the side is much more lucrative. It also allows me to diversify my income streams. This also allows me to adjust my life based on surf conditions :).

    So, is it going to be the live anywhere, work anywhere, go anywhere whenever you want type of freedom. MAybe not in the first year, but it sure as hell is a great setup to get you there. That’s my advice.

    • “This also allows me to adjust my life based on surf conditions” hehe :)

      Your #2 is a great point. The fact that you already have a day job that suits your lifestyle is great, but I’m not advocating people go out and find day jobs to suit their lifestyles. What I’m trying to get at is, if you already have a day job that you love, there’s no reason you should quit just because I think day jobs suck … or because other people think day jobs suck … or because it’s not sexy to have a day job.

  3. SO happy you said this. I love the term “lifestyle design” but so many people think it’s equivalent to traveling full-time and for many of us, that’s not the case. It is about designing your life to work for you. For us, that has meant paying off all of our debt (except for a modest mortgage that we’ll have again as of next week) which gives us the freedom to do things we want to do – like quitting my job and spending the summer traveling w/my kids.

    • Thanks Shannon! (BTW, I actually don’t like the term lifestyle design. :) In 93 articles on this site I don’t think I’ve used it once. haha)

      Quitting your job and traveling with your kids = Living Anywhere to me. Even if you spend a lot of time at the home base.

      • I don’t like what people assume lifestyle design means but I love the idea that you can design your own life. What don’t you like about the term?

        • I like the term from the standpoint that it’s Tim Ferriss’s term and he came up with a great brand. I’m not Tim Ferriss and I don’t want to be.

          So …

          Part of it is I’ve never felt like a lifestyle designer. I’m a lifestyle liver (not the organ). ;) Part of it is it’s Tim’s term, not mine. He can use it, I’d rather not. (And I love Tim, no hate here. More on that Saturday.) Part of it is there are 18 billion cookie cutter “lifestyle design” blogs. I don’t think I’m better, I just don’t think I’m cookie cutter. :) (Or maybe I am and I just have a MASSIVE ego? ha!)

  4. Hi Karol,

    I’ve been hanging around your blog for a few months, but this is the first time I’m commenting.

    The nomadic lifestyle appeals to me. I play a lot of competitive chess so I travel a lot for tournaments. My idea of Ridiculously Extraordinary Freedom would be to hit the chess circuit, travel to far off places to play tournaments and use up my time in chess and writing. I’d probably be liked to be based in some far off mountain village with little interruption from the outside friend. A good looking European girl friend would help. ;)

    I’m just a teenager, so my ideas may change, but what’s Ridiculously Extraordinary Freedom if you can’t change ideas? ;)


    • Hey Ajay,

      Thanks for hanging out and thanks for making your first comment!

      Your ideas of Freedom are great. And you’re dead on, the beauty of REFreedom is you can switch gears on a dime. Booya!


  5. Hi Karol,
    I guess my idea of ridiculously extraordinary freedom would be the feeling of being able to stop whatever you’re doing at the moment, and pick up something else, whether that be quitting a job to go travelling, dropping out of uni to start a band or get a job, or dropping out of your band to open a café…basically, not being afraid to try out everything and having the means to chop and change at short notice.
    I got lucky with my ‘job’, I work shifts at my old Uni library so it’s ultimately flexible and well paid for wage work. I don’t even know if I have to quit per se, or if I just stop putting availabilty on the rota!

    • Thanks Amelia. I wonder if the library would notice if you didn’t put your availability on the rota for a few months. :)

  6. Freedom is all mental and only sometimes physical. Freedom, in my opinion, is something you have to strive for constantly. I equate it to knowledge, and I acquire knowledge through experiences. The more I experience the more free I become.

    Just the ability to take life as it comes and enjoying it to its fullest seems like the true definition of freedom. Being able to handle life on a case by case basis would be ideal. If you knew each situations worst case scenario and were able to live with that ending you would be light years ahead of us all. You would have the freedom to make mistakes without feeling guilty about the consequences.

  7. freedom to me is being able to stand wherever i want,have my own working times, and feel happy without anyone telling me what to do.

  8. Ridiculously Extraordinary Freedom to me means working for these reasons:
    1) To contribute to the world and improve others’ lives
    2) To express my creativity

    And not for these reasons:
    1) The money
    2) The status

    Pretty much, it means I am able to work for authentic reasons and not merely to keep up with the Joneses in either material or emotional ways.

    • Hi Damien,

      Wonderful. Thank you for sharing!

      I would submit that status is very important if you’re trying to improve others’ lives. Why? Because it’s much easier to help people if they see you as an authority as opposed to a “nobody.” People will listen to you as an authority, and maybe not otherwise.


  9. I totally agree on that Karol.

    If we only are selfish we miss the most wonderful things in life ^_^.

    Money comes and goes,Friends are for life.

  10. Macmillan Dictionary defines freedom as: “the right to do what you want, make your own decisions, and express your own opinions”. So Ridiculously Extraordinary Freedom could be something like: “the right to do all the Ridiculously Extraordinary things you want, make your own Ridiculously Extraordinary decisions, and express your own Ridiculously Extraordinary opinions” … so to speak ;)

  11. For me, freedom would be to be able to support myself enough to travel without having to be somewhere at a certain time. If that means working online, from home or at a flwxible day job, I’d do it. What restain me the most, I think, is having to be at work at a certain time, attend meatings at scheduled times etc. I need to be able to work on what I feel like that very moment, that is when I feel joy when working and that’s when I do my best.

  12. I actually work better with structure so enjoy that part of a day job but would love something that was interesting and dynamic but that I could walk away from for, say, three months of the year. I’m a ‘go-places-but-have-a-home-base’ kind of person so that rhythm would work in other ways too.
    I don’t in the least care about earning massive amounts of money, enough to not have to think about it would be perfect for me!!

    • Thanks for your thoughts Claire! It’s important to have a clear image of what Freedom means to you, and it seems like you’ve got that. :)

  13. Something that I have learned is that knowing yourself truly is a big part of the battle won. Often our underlying desires aren’t actually reflected in our named goals. Which means we can be fighting against ourselves…definitely not helpful in actually moving forwards!

    I only discovered your blog today but I’ll keep reading,


    • You put it so well Claire, thanks! When our underlying desires aren’t reflected in our named goals we really are fighting against ourselves. That is spot on.

      Thanks for reading! :)

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