Changing Your Operating System

How do you change not just your habits, but your entire life routine? How do you lift yourself out of comfort and tackle something completely different than what you’re used to? Derek Sivers recently posted a transcript of an interview he did about this topic, and while it’s a long read, it’s well worth your time. Some highlights:

I felt like I needed to shatter my habits. So my little mini slogan was, “Wherever you used to say ‘yes’ say ‘no’ and wherever you used to say ‘no’ say ‘yes’.” Reversing all of the things you used to do and trying the opposite… I would use that even on a little micro level. I see the gorgeous girl across the room and I’m like “Ahhh!” terrified to talk to her! Then I remember, “Whatever scares you go do it! So here we go..” and I would just walk up to the girl that intimidates me and say hello. Then of course she’s wonderful or not, whatever it is, but I walk away no longer scared. Now I just have that approach through life. I think whatever scares you go do it, because then it won’t scare you anymore.


I wanted to make it impossible for me to get stuck in a rut. So my mission was to spend the rest of my life outside of the US, mainly because I loved it too much. Santa Monica in particular. When I got to Santa Monica, I just felt “This is it, I have arrived. Like I love this place. I love these people. I love the food. I love the weather. I love everything. This is it. This is my home. This is where I belong.”

But that feeling kind of scares me, because it’s like that thing when people get to a certain age and say “This is who I am. This is how I like my eggs. This is where I live.” I didn’t feel it was time to stop progressing, even in my physical location. So my challenge to my self is to live the rest of my life outside the US, because I love California too much.

I went to New York City for 3 days, passing through for a friend’s wedding, and I met this gorgeous girl and we had this great first date, we’re all swooning over each other. So on our second date I said, “How would you feel about leaving the US and never coming back?” She looked at me for a second, kind of squinted and said, “Yeah, I could do that.” And so then we had a third date and that’s my wife.

She’s joined me on this mission to spend the rest of our life out of the US, even if it’s uncomfortable. Even if it’d just be the easy and comfortable thing to just go back to Santa Monica to what I know well. It’s the idea of kind of forcing yourself to keep progressing.


It’s really tempting to think it’s the exciting quick fix adventure thing of hopping on a plane and quitting your job and breaking up your relationship. That’s fun but be really honest with yourself that maybe the thing to get you out of your rut is finally acting on the thing that you have been avoiding for years.

While reading the transcript all I could do is nod my head. I share a lot of beliefs with Derek, and even though we lead separate lives, the main drivers behind them (adventure, avoidance of comfort, tackling new challenges) are the same. I remarked upon this when I reviewed his book

I met the author of this book in Rio, after already having been a fan of his blog. We talked a little about life, business, and travel, surprised that so many of our beliefs were similar yet our paths so different. He poured his energy into music and business while I poured mine into women and writing. I hold him up to be a business role model, a guy on the same page as myself who brought value to his customers over several years and was greatly rewarded for it.

So it’s no surprise that when Derek speaks, I listen.

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19 thoughts on “Changing Your Operating System”

  1. You can only make a difference by doing an action in the present to change the future. Past experience doesn’t have to hold you back as it is the past and cannot be changed only percieved differently to fit your ego.
    By not identifying yourself with your ego (created by your enviroment and past experiences etc and is not you) it’ll become easier to make a change that you want as you know that past experience or the feeling of inadequacy doesn’t define who you are and doesn’t have to affect your actions right now.
    A little experiment of thought, try to record for yourself all the thoughts that you have during one day, write them down after the day is finished. Then do it another day and see what they say. It’s kind of funny to do that exercise and you will realise something doing it.
    There’s tons of literature on the fact but you don’t really need that. You don’t need the guidence as you just have to let go and believe in yourself to live in the present and not letting your ego (identity) define you. It’s as hard as you make it, unfortunately.
    (Hard to truly explain it as it has many hard to get things and could come of as rather “hippie-like”, it’s also a contradictory subject)

  2. I like the direction this article is taking the though process of change. It’s a very ‘meta’ view, to envision the mind as having an “operating system,” as in the default behaviors & actions we use to operate on autopilot most of the time.
    Another metaphor that has helped me: consciousness is like a heavy flywheel–it has a lot of momentum, which stabilizes its directionality, and also requires a LOT of energy to change its direction or vector. Every behavior that is different from the old vector nudges the flywheel in a new direction.
    Great stuff, Roosh. I’m looking forward to listening to that Sivers piece, I just downloaded it.

  3. The message is timeless, and the ethic rings true. Too many people allow themselves to stagnate into a mind-numbing, stultifying conformity that looks very much like sleepwalking. Better to fall on the field of glorious battle, engaged in any transcendent purpose, than shuffle about quietly in our suburban prisons.

    1. Changing the OS is usually more difficult than at first face. If nothing else, because wiping out the existing OS will kill the system entirely. Best to make incremental adjustments over time in the form of new habit formation.
      They say that forming new neural pathways over time involves clearing out the overgrowth and underbrush of old habits. First, though, you have to identify where the weeds are to extirpate them, then turn over the soil to plant something new.

  4. George Costanza discovered this in a famous “Seinfeld” episode where he resolves that no matter the situation, he will do the exact opposite of his gut instincts. He instantly starts becoming successful in life and with women, even after telling some chick “I am unemployed and live at home with my parents”.

  5. While this guy certainly has a greater sense of adventure than most American men, he first made the ultimate comfort-seeking maneuver of locking up a steady supply of pussy to take with him before embarking on his adventures.
    I’d personally be more comfortable banging a my hot wife/girlfriend in various third-world locales than I would rolling solo dolo in unfamiliar bars on the other side of town.

  6. Thought provoking. However, I was a bit turned off by Silver’s relativism and, although I admire Silver’s work ethic, feel that his advice regarding comfort needs to be qualified more. As it stands, his advice is bad.
    “But I felt like I needed to shatter my habits. So my little mini slogan was, “Wherever you used to say ‘yes’ say ‘no’ and wherever you used to say ‘no’ say ‘yes’.” Reversing all of the things you used to do and trying the opposite.”
    Applying this logic literally would be insane. Normally, when someone makes me angry, I don’t lash out and punch them in the face, even if I feel like it. But according to Derek,
    “I’ve had this slogan ever since I was a teenager. “Whatever scares you, go do it.””
    Robbing a rich man’s house and killing witnesses would scare me. Should I go do it?
    Now I understand that I’m pushing his logic with extreme examples, but the relativism and lack of moral clarity just made his advice feel like he was saying whatever he needed to say in order to make people feel good about whatever decisions they’re about to embark on. He’s just gaming the public with vacuous feel-good statements in order to get more pageviews/downloads/free-publicity from whoever.
    And although he was merely describing his own thought processes, that’s just the thing – if I couldn’t see myself living in his own shoes for a day, how am I supposed to take him seriously? So I just write it off as nonsense.
    The above isn’t to say I did not find any value from the transcript. Derek’s biggest source of success appears to be from this belief he has:
    “Do the work. Shut up, sit down, fight the temptation to do other things, to follow your distractions, and just work.”
    This is the only kind of no-bullshit attitude I think appropriate for a masculine man.

    1. He is just another quack. Come one, bringing your wife around the world, what a bitch seriously. Defeats the entire purpose. It’s like a diabetic going to candy store.

  7. Which Santa Monica did he flee to? According to wiki there is a city of Santa Monica in the Philipines, and another in Mexico. I certainly hope he doesn’t mean California, USA.

  8. I like the timeliness of this article and the theme of “avoiding comfort” because I’m actually considering a brief (4-6 year) stint in the military, before ultimately relocating to a foreign country in SE Asia. It would be going right into the belly of the beast for a few years to plot a new course in life.
    Why in the world would I want to join the über-conformist military? Partly, for the challenge. Partly, for the money. I’ve realized – if I can’t BEAT the system, I must USE it to my advantage to build a bridge to my new life as a expatriate.
    The pros seem to outweigh the cons:
    I need to lose about 30 lbs to pass the physical fitness standards. I’m in my 30s and would also need to develop the physical conditioning to keep up with the 18 year olds in basic training. I know I can do it if I focus. Plus, being in excellent physical shape will give me side benefits in other areas.
    I’m making chump change in my career. My prospects for advancement and even a steady job look to be waning as the field I’m currently in steadily deteriorates and is taken over by women. (Men are being driven out of this field through attrition.)
    Not only that, but I hate it more and more each day as we stoop to new levels in order to turn a profit.
    I’d get paid considerably more as an entry-level, first-year Officer than I’m now making with 12 years experience in my field, when including the housing allowance that kicks in after a couple of years. Best of all, I could pay off my student loans with the government’s money because of the education benefits.
    Joining the military would also allow me to leave the “plantation” and get out of my employment contract. Sure, I’d be joining another plantation but – importantly – I would end up in a much better place in the end. My current path is simply going to lead me to a dead-end road.
    I have been pondering this major move for over a week now.
    Whether or not a the military ultimately factors into my exit strategy, my mind is made up. I want out of the United Feminized Police States of America.

    1. Two things, based on friends who were in the military:
      1. If you lose the weight and stay in shape, while eating healthily, you’ll be way ahead of the 19-21 year olds who enlist nowadays, and who were bred on junk food, video games, and inactivity. My one buddy, whom I referenced in my one post on Matt Forney’s blog, was in his late 20s when he enlisted and managed to beat out a lot of guys ten years younger than he was. His secret? He was always physically active. Basic training made him even more so, but he had far fewer bad habits to overcome.
      2. The military is less conformist than you might think — depending on your branch of service. The same buddy reported that many in the military were “mercenary” and not “patriotic.” “Mercenary” in the same sense that you are — in it for the money and the education.
      Finally, the best that you can hope for in the military is to put yourself in a much better position, six years hence, than you are now. That will depend on how much advantage you take of the opportunities (e.g., school, training) that are available to you. As you’re in your 30s, you know yourself better and know where you want to go, unlike the 18 or 19 year old who’s clueless and needs more direction in his life.

      1. Agreed. I’m approaching this from a mercenary perspective. It’s simply the best option considering where life and the edumacation system brought me.
        In fact, I’ve started wondering why I’ve put up with all the things I have in life by avoiding the service when I saw how much good it did my sister to enlist. They really wanted me to join, but I had a nonsensical dream to chase after.
        Unfortunately, having such a specialized science degree like I have limits my options in the civilian world. Friends that graduated in my class are almost universally all doing something different, in many cases teaching.
        It’s time for me to start looking out for what’s best for me instead of listening to more of society’s pablum.
        The military is a means to an end and I’ve read that once you get past Basic it actually gets much easier.

  9. I’ll post some good quotes for those who didn’t read:
    “The one thing I mention in passing but I didn’t emphasize enough is the importance of reading books. Not just scanning articles. If you think about how many hours and hours you spend skimming articles and reading the news, that quick-fix kind of stuff. If instead, can you imagine if you didn’t do that but instead you put aside two hours a day to pick up some books that speak to something that you either don’t know anything about – like architecture – or to make you a deeper expert in something in an issue that you really care about? So often you learn so much more from that than you would just skimming around.
    The idea of thinking something through deeper and then putting aside time to reflect on your perspective. It’s one thing to just sit and read and read and read. Sometimes you need to put aside an hour and half to write your own thoughts about it. Internalize it instead of just taking it in and moving on.”

  10. Second good quote:
    But then the other way out of a rut – the last thing we just mentioned – is to finally have the willpower and discipline to do the thing that you’ve been avoiding all these years. You know what you need to do. To understand that you really need to do it now. That your life is going to get worse and worse and worse if you don’t act on what you know you should be doing.
    For some people that means starting a company. For some people it means joining a company. For some people it mean making calls that they’ve been scared to make, or confronting their parents about something. Whatever it is, it’s usually the difficult, often long thing.
    It’s too tempting to say that it’s going to be a short thing. It’s like “Hey, just make that call that you’ve been meaning to make.” No, you need to learn that programming language that you’ve been meaning to learn, and it’s going to take you a year, y’know? It can often be that really long, hard, difficult thing. How about like changing your eating habits? You’ve been eating crap, you need to start eating mostly vegetables, and it’s gonna be hard!

  11. Third:
    One thing you said that I really liked was how you hadn’t created. I think a lot of people have this hollow feeling in themselves where they know they could be creating – and some of them even attempt to do it through business – but it just doesn’t transfer. They fall prey to resistance. They don’t actually get it done. And that hollowness really ends up tainting their own world view. So how do you take that hollowness that you felt of not creating and turn it around, and actually make something from it?
    Do the work. Shut up, sit down, fight the temptation to do other things, to follow your distractions, and just work.
    Most of us know what we need to do. That’s what’s crazy! I think in any field, any person, what you need to do is usually painfully obvious. We’re all searching for distractions or reading yet another book with yet some more advice. But no, we’ve heard enough advice, we’ve all got enough advice. Really you already know what you need to do. It’s different for everybody.
    For me, it’s programming. In order for all of my ideas to happen, it has to start with the website. To me business is still art. It’s something that I create as a personal expression of something that I want to exist. So the idea of saying, “just hire somebody to program it,” is a little like telling the songwriter in the band to just hire somebody to write the songs for them. It’s like, “Well no, this is what I do. This is my art. I want to write the songs.” So, I still want to program my websites, my ideas.
    I’ve never learned JavaScript before. Talking about changing my operating system – I’ve been doing nothing but PHP for 10 years. Then learning Rails. I’ve never touched JavaScript. It always was kind of a silly decoration until a few years ago – it always felt a little like an unnecessary flourishes. Now it’s really become more core. So I picked up a 1200 page book that everybody says is the best way to learn JavaScript. And I’m going through it, chapter by chapter, jotting down everything I’m learning into flash cards and memorizing it all, and spending hours a day just making little exercises for myself. Learning JavaScript with the idea of applying it to programming those ideas that I was talking about.
    So how do I combat that emptiness and feeling? It’s just willpower. It’s almost like meditation. Again, I’m no Buddhist, but when you learn about mediation first thing you hear is that yes, all of these distractions come into your head, and you’ll be sitting there trying to stay silent and focused and all of a sudden you’ll think about something that somebody told you yesterday, and you have to just learn to let it go – to say “OK, that’s just a distraction. I can let that go now”, and to let it run back out of your head instead of doing something about it.

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