Getting To Freedom by Working the System

by Stephen Mills on February 22, 2010


For some of us, myself included, there is an internal battle going on between our natural inclination to go with the flow of unstructured thinking and living and the real-world of dealing with the necessary details of life.

By nature I’m not a planner nor an organizer.  My world is one of increasing disorder.  Whenever I get a wild hair and decide to get organized, the change is only temporary.  Things quickly return to an equilibrium of disorder.  I seem to have a set point of disorder.  Despite repeated attempts I can’t seem to change that set point.

I’m a big picture person.  I don’t like to work the details.  After a few minutes in a spreadsheet I want to commit suicide. I’m a tinkerer and I like to try things out and see if they work rather than trying to plan them out ahead of time.  I don’t like to schedule my day.  I like to work on whatever feels right at the time.  I love the freedom of going with the flow.

The problem with all this is that for most of us, life insists on a whole lot of details.  You have to take care of food, clothing, shelter, hygiene, pets, kids, bills, taxes, regulations, meetings, email, work, writing, relationships, etc.  Even when we have to deal with those kinds of things, some of us tend to approach them in an unstructured way.

I’ve finally settled on something that really seems to work.  I first got the idea from a wonderful book called Work the System: The Simple Mechanics of Making More and Working Less.  It can be applied to your business and work life or your personal life.  I don’t go the whole way with what is described in the book because it is just too much for me.  However, the ideas in the book were the inspiration for what I am putting into place.

The bottom line is that for those things you have to do, those things for which a repeatable process can be used, you create a system that is deadly efficient and as automatic as possible.  In this way you burn through those necessary tasks with maximum speed and efficiency and that frees up the rest of your time to do what you want.   In my case that means no planning and no organization.  Instead I do whatever I feel like doing and in the way I like to do it: playing, tinkering, and creating.  I expect to get much better at this as I continue to work these systems.

A Suggested Approach

Seeing the world as a set of systems and subsystems

You start looking at your world and realize that to a large extent it is made up of systems and subsystems.  Think about the human body.  It’s a number of subsystems; digestive, pulmonary, circulatory, immune, etc. put together to make up one primary system – you.  You can take some area of your personal life such as your health and break it down into subsystems like sleep, exercise, diet, regeneration, screening and checkups (for those of us in the older crowd).  Your morning routine could be considered a system that might be made more productive and efficient freeing up time for you to do something else.  I’ve identified online systems for myself like email, blog reading and commenting, blog article research and writing, and social media.  Your work is undoubtedly made up of many such subsystems.

Selection of systems to work on improving

You probably should only tackle one system at a time.  I’ve been working on the online systems mentioned above.  Obviously the most broken, most problematic, most time consuming areas are where you will get the most initial return on investment.  However, don’t just ignore smaller areas.  If you could attack 4 systems and save 15 minutes a day on each, your end result is one hour a day free for you to do something else.  I consider that a big payoff worth a lot of investment.


If you’ve read this blog for long, you’ll know I’m a big proponent of elimination.  Take an axe to what you think you need to do and then take another cut at what you think you have left.  Identify the Essential and Eliminate the Rest.  You can eliminate whole subsystems this way.  When you are first looking at improving a system look at what you can eliminate from it first.  For example in my email system I unsubscribed to a whole bunch of stuff that I never read, but that cluttered my inbox and had to be processed.


You may or may not always have this choice but I implore you to let go of the control and get creative to see if you can take advantage of delegation.  The work may be essential and maybe can’t be eliminated, but you may be able to eliminate it from your task list by delegation. From your perspective that accomplishes the same thing. In my household I earn the money so the deal I have with my wife is that she takes care of the household details.  I don’t pay bills, deal with insurance, taxes, clean, garden, mow, schedule repairmen, or any other of those messy things I’m not good at and hate to do.  It’s wonderful.  I don’t even think about them.  My female friends are jealous and joke that they want a wife like mine :-).  The same thing applies to your work.  Wherever you can, delegate tasks to others and free yourself for better things.

Analyze and document the process

Whatever system you have chosen to work on needs to be analyzed in detail and the process articulated in some way.  Unfortunately there is some heavy lifting here that cannot be avoided.  If you fail to analyze exactly what you are doing and how you are doing it, you will not have the foundation you need to dramatically improve the process.  I hate this part, but it is necessary.  You have to pay the price here to get the big payoff later.  I choose to document very lightly and only to the point of making sure I remember and understand every step I am taking.


It may seem obvious, but it is often missed.  There are undoubtedly ways you can simplify the process.  If you have to go from point A to point B, the shortest distance is a straight line.  Eliminate any unnecessary steps and look for shortcuts.  If you get good with keyboard shortcuts in working email for example, you can eliminate a lot of moving the mouse and clicking around.  It can dramatically speed up the process.  The main thing is don’t take three steps to do what can be accomplished in one.

Make it repeatable and rigorous

Come up with at process that is rigorous and reliable by making it repeatable.  If you just wing it every time, that may “work”, but it is inefficient and makes it more likely you will spend more time to get less done.  Why do I need a repeatable process for reading and commenting on other blogs?  At first thought that seems ridiculous to me, but I have realized I’m neglecting that task because I do it haphazardly.  I start reading something when I feel like it and then I get distracted and/or bored and end up going off on a tangent or procrastinating.  A rigorous repeatable process allows me to allocate time and get things done that are important to me in as little time as possible.


If you make a process within a system repeatable, you have a lot of opportunity for automation.  Automation is the mother lode of payoff.  Automated tasks are like eliminated or delegated tasks – you are no longer doing them.  Email is a perfect example.  I’m creating rule after rule in both Gmail and Outlook to process email automatically and send emails to predefined folders or just automatically delete them.  Some of those folders I review and some of them I keep for records.  For instance, I get a lot of emails saying something was automatically paid or shipped.  Those just automatically get filed for record keeping.  I have blog or newsletters going to other folders, some of which are high priority for review and some which I almost never look at.   The latter should be candidates for elimination.

Time limits

For someone who tends to be unstructured like me, time limits work great.  I’m setting time limits on many of my systems for two reasons.  First to motivate me to accomplish something important to me such as “Read and comment on five favorite blogs”.  And second to finish it “in 30 minutes” and ensure I’m not getting distracted and wasting time.  That is not preventing me,  in my free flow time, from reading and commenting on more blogs, it’s just that by having a system with a time limit, I know I’m getting something important done and not just when the mood may strike or not in my more unstructured time.


This is nothing more than maintenance and continuous improvement.  As I discover new tools, have new ideas, or as conditions change, I tweak the system and make it better.

The Future

I’ve only been working the systems like this for a short time, even though I had the idea from reading the book over six months ago.  I really think it has great long term potential to allow me to get the things done I need to get done in a structured way, while allowing the rest of my time to truly be my time.  That is time without the stress and pressure of incomplete tasks.  Sam Carpenter has this to say about his Work the System methodology.  I think he is on to something:

“If you pay attention to the mechanical details of your world and make proper adjustments to the key systems that compose it, you can construct a life that is unencumbered with fire-killing, a life seldom dictated by urgency.  Flexible, strong, and resilient, it’s a life of smooth, calm days; days that have lots of room for thinking and planning, for friends and family, and for just being yourself.

What do YOU think?  Leave a comment and join the conversation.


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Systems Mindset Newsletter
February 23, 2010 at 11:02 pm

{ 29 comments… read them below or add one }

Hulbert February 22, 2010 at 1:37 pm

Hi Stephen, like you, I also like to go with the flow of things. I don’t like to schedule every minute of my day because I don’t want to feel as if I’m a robot. But sometimes, we need to create a schedule (it can be a mental schedule) for ourselves to follow because, at the very least, it makes sure we are not wasting valuable time and doing something productive. Your tips here have helped eliminate what we shouldn’t do, and they have also focused on the things that matter most in order to get productive results during our day. Thanks for this.
.-= Hulbert´s last blog ..My Brother Got Pulled Over by the Police – Part I Interview =-.


Stephen Mills February 26, 2010 at 9:28 pm

Hello Hulbert, its interesting the different personalities people have. I know people who are micro-organized and like a list and a schedule for everything they do. Then there are others of us who can’t write down something to save our life 🙂


Cheryl Paris February 23, 2010 at 7:05 am

Hello Stephen,

I am early morning person and I like to be organized and I do not beat it if I miss something. I personally liked the Sam Carpenter’s Work Methodology.
One more thing, to be organized cannot happen the very next morning, Yes but it can definitely begin the next moment and is a Process.
I loved the tweaking point, as it is very much required when learning new technology or process which can help us getting tasks delegated and/or organized.

Good post!

Cheryl Paris
Cheryl Paris Blog
.-= Cheryl Paris´s last blog ..To People Who Want To Get Stress Of Your Chest — But Can’t Get Started =-.


Stephen Mills February 26, 2010 at 9:30 pm

Hi Cheryl. For some of us it definitely can’t happen the next morning. I may be one of the hopeless cases for whom it will never happen 🙂 Thanks for stopping by to comment.


Jean February 23, 2010 at 10:32 am

Gosh Stephen! In your opening section all I could think was, that’s me! Totally me! I feel so disorganized, I begin to think I have adult ADD~if there is such a thing. My husband is the one who is Mr. Organized.
I’m the ‘idea person’. Problem is, I have too many of them.
I’m trying to get organized enough to start my own blog. I need a really simple one! So far, Typepad seems the most suited to my brain-type, but it still is very time consuming to me and I get bored with it and put it back on the backburner.
I’m taking my first online writing class, though~something I’ve been dying to do~and can only hope that will help in the organizing enough to get me started on something meaningful. I am in the enviable position of having enough time to do this at the moment. (It won’t always be this way.) This is my best chance to get things ‘up and running’ so that I can take it to wherever we move next.
Thank you so much for your helpful tips.


Stephen Mills February 26, 2010 at 9:43 pm

Hello Jean, actually there is such a thing as adult ADD. I’m sure I have it just a wee bit 🙂

I wish you the very best on your blog adventure. Be sure and come back here and tell us about it.


Tracy Todd February 23, 2010 at 1:25 pm

I’d just like to give you another perspective and hopefully some food for thought. I don’t think you should be too hard on yourself about not living a more ordered and structured lifestyle. Rather enjoy the freedom that comes with that kind of mindset. I’m in an unfortunate position where I broke my neck and was forced into a strict routine, ordered and structured life which I find exceptionally limiting and confining. It can be extremely frustrating! I miss the freedom of being able to do what I want, when I want, as I want.

However, I have learned that the human body works at its optimum and is healthiest when operating in a strict routine.

Enjoy your free, uninhibited, boundaryless, disorderly moments as often as possible. Always be spontaneous and most importantly just have fun.
.-= Tracy Todd´s last blog ..A Letter from a Soldier =-.


Stephen Mills February 26, 2010 at 9:42 pm

Hello Tracy! First off I’m sorry to hear about your accident, but I hope you found the positive in that situation.

I do enjoy my unstructured life. But on the other hand the lack of structure causes me problems. I hope I have found the happy medium where I apply structure where it is needed and that leaves the free time to just be whatever I feel like being at that moment.

Thanks for the thoughts 🙂


patti February 24, 2010 at 10:16 am

As ADD artists, my husband and I could both benefit from your column(s). The book that you read – I wonder if it’s effective for the self-employed? I ‘retired’ early due to a chronic illness so my time is somewhat structured for me. My husband, though, who now runs our graphic design/advertising/etc. company is steeped in stress, even though I handle most of the same duties as your wife:) I tell him that we are better off than 90% of the population because of the strength of our marriage, our creative abilities, and our relatively stable financial situation… any other suggestions?
.-= patti´s last blog ..A Grand Night for Hopping =-.


Stephen Mills February 26, 2010 at 9:37 pm

Hello Patti. Definitely the book is effective for the self-employed. It’s really geared toward entrepreneurs, but can also be applied to your personal life or work life.


Tess The Bold Life February 24, 2010 at 11:46 am

I think you have X-ray vision right into my life! I’m exactly like you describe yourself. My husband is a neat freak and I’m Tess the mess. ADHD is me…hyper and distracted. I’m going to think about this further and see how I can fit it in my life. I like what Patti says about her assets. Great way to look at it.
.-= Tess The Bold Life´s last blog ..A Priceless Gift =-.


Stephen Mills February 26, 2010 at 9:38 pm

Hi Tess, I love that: “Tess the mess” 🙂

Thanks for the comments as usual!


Armen Shirvanian February 24, 2010 at 12:04 pm

Hi Stephen.

I like how you broke things down here, in a scientific fashion. That point about selecting certain systems to work on does make sense. We have to pick a few that we want to bring to a stable level of success, such as our exercise regimen, or social ventures, or business practices, or educational absorption, or so on. Each of these is separate, although they combine to make up our presence, and so we should handle them as separate areas of effort expenditure.

Automation is an advanced one that requires even more long-term thinking than regular effort toward a goal, which is already longer-term thinking than not putting in effort towards a big goal. The few who do automate fly ahead.
.-= Armen Shirvanian´s last blog ..Others Won’t Create The Perfect Circumstances For You =-.


Stephen Mills February 26, 2010 at 9:34 pm

Hi Armen. Yes, I agree that the few who really work on automation have a big advantage. I find that there is almost nothing else that frees up my time besides elimination than automation.


Mike February 26, 2010 at 7:22 pm

This is a great site – glad I discovered it. Automation is one of my personal favorite systems that I love to play with – and wish I had discovered a long time ago! It’s funny how life can becoming so much richer, full of meaning and full of interesting experiences when you eliminate 80% of the idle activities that derail you. (Watching TV being a huge one, IMO.)
.-= Mike´s last blog ..6 Friendly Cities for Entrepreneurs =-.


Stephen Mills February 26, 2010 at 9:32 pm

Hello Mike, thank you so much for that comment. Those kind of comments about my site really make my day! Thank you for joining us here.


Mike King February 26, 2010 at 11:31 pm

Hey Stephen, this is a really cool way to look at a problem. I read your description of the way you think big picture and struggle with planning simple events and such, and I completely align with that as it is exactly like me in that area of life. Anyway, the whole article is great and certainly adds some tools for me to apply with an area I can certainly use the help in myself! Thanks so much!
.-= Mike King´s last blog ..Book Review: 42 Rules of Employee Engagement =-.


Do You Dave Ramsey? February 28, 2010 at 6:06 pm

Stephen – this is a great article and I’ll certainly add this book to my list of ‘to read’.

I’m curious as to examples of your sub systems. I like the idea of having a ss for your morning routine and for your blog work. I’d like to delve to the patterns and principles you put into place to design and refine your sub systems.

This is an interesting topic. I want to spend more time with it.

Thanks for sharing.
.-= Do You Dave Ramsey?´s last blog ..I Want That Feeling Again =-.


Judith March 1, 2010 at 11:39 pm

” After a few minutes in a spreadsheet I want to commit suicide. ”

As a survivor of a loved one’s suicide, respectfully, I would like to ask you to consider the unintentional but hurtful result this glib comment has. Suicide is very complex and fraught with secondary wounds for survivors. The combined effect of “commmit” and “suicide” imparts a sinful connotation that is not deserving. Many people today say their loved one died by suicide, just as they would say they died from cancer or a car accident. Are your frustrations seriously enough to make you want to end your life. I truly doubt it. Finding another analogy would be helpful to ending the stigma of suicide.


Stephen Mills March 2, 2010 at 7:57 pm

Hi Judith, thank you for commenting. First of all that was not “glib”, and secondly it was not analogy. It was rhetorical hyperbole. Of course I don’t literally “want to commit suicide” and nobody would think I did. So to try and tie this in somehow with the topic of literal suicide is uncalled for and quite frankly ridiculous in my opinion.

This is the way I speak and I refuse to be an enabler to the self-victimization of people who are looking to be offended. I’ve wrote on this very topic several times in this blog. I’m not nor do I recommend others give in to the control of victims who are looking for offense where none is intended. This is a slope which you will never get off. There will always somebody who can create some offense out of something that is said. My writing would be so bland and would take so much time to create in such a bland and unnatural manner. I’m not interested in that.

Your request was respectful so I will just respectfully decline to take your advice. Despite that I’m sorry for your situation. I would recommend you don’t make it worse by picking up unnecessary rocks like being offended by the harmless rhetorical devices of people like me.


Judith March 3, 2010 at 8:24 am

I am not a victim and am surprised to be labeled as one on your blog. I simply wanted to point out to you and your readers the negative impact the use of your rhetorical device “commit suicide” has. It may be a part of the common lexicon but through history there are developments of understanding and compassion that lead to society agreeing that certain terms are no longer accurate. I want to point out that few religious institutions consider suicide a sin. Yet the stigma from the historical perception of the sin prevails. The next time you use this rhetorical device I know you will remember my comment and the fact that I have pointed out to you there is not a rhetorical phrase “I want to die of cancer”.


Stephen Mills March 3, 2010 at 9:00 am

Judith, whether you are a victim or whether you are speaking on behalf of other victims, the intent was the same. You were clearly indicating victimization from such rhetoric. Let me quote your exact words:

“As a survivor of a loved one’s suicide, respectfully, I would like to ask you to consider the unintentional but hurtful result this glib comment has.”

“hurtful result” is the exact kind of self-victimization I am talking about. It’s there in your own words.


Stephen Mills March 3, 2010 at 9:05 am

Judith, Of course there is no such rhetorical phrase “I want to die of cancer”. It would mean something entirely different. The meaning of “I want to commit suicide” is clear. I will not refrain from using this because people are making themselves victims.

I may or may not remember it. But if I do it will be in the context of this self-victimization and not your attempt to bring into the discussion the literal topic of suicide. I’m pretty sure that is not what you wanted.


Judith March 3, 2010 at 10:49 am

No, I wanted to shine a light on stigma for you and your intelligent readership, and you have been very generous in allowing me to do that. I thank you for the space on your log.


Ronnie Walker March 3, 2010 at 4:41 am

(Stephen, in response to Judith, you wrote: This is the way I speak and I refuse to be an enabler to the self-victimization of people who are looking to be offended. I’m not nor do I recommend others give in to the control of victims who are looking for offense where none is intended.”)

Hi Stephen,

Was it really necessary to be intentionally insulting in your response? You write many intelligent things in your blog, but this response demonstrated a remarkable lack of empathy or understanding for the debilitating emotions and PTSD experienced by those who lose loved ones to suicide, witness suicides, and discover bodies. Most suicide grievers are strong and functional people, like yourself, who have been “brought to their knees” by an experience unlike any other. Grievers struggle long and hard to survive and go beyond just surviving and often move in a world that is clueless about their experience. This is not about being an enabler to self-victimization; this is about what you learned in kindergarten: consideration for others.

Ronnie Walker
Executive Director: Alliance of Hope for Suicide Survivors


Stephen Mills March 3, 2010 at 7:41 am

Hello Ronnie,

Consideration for others does not mean walking around on eggshells. Consideration for others means helping them live in ways that means they do not pick up rocks they do not need to pick up. I have written multiple times about this very issue. People who are offended where none is intended are people who are creating problems for themselves. I’m not being inconsiderate. I consider myself very considerate of others in real ways.

If people are looking to be offended where none is intended it is they who have the problem. They are creating problems for themselves. For me to change my behavior just enables this culture of “offense” victimization where everyone controls everyone else by being “offended”.

You made the exact same mistake she did. You start talking about suicide as if my rhetorical device has anything whatsoever to do with real suicide. It is people who try to equate something like that with actual suicide that are creating problems for themselves and others.

I’m not talking about real suicide and you have no idea what my personal situation is. Nobody but people who are looking to create victim situations for themselves or others would think otherwise.


Brandon Winters October 20, 2010 at 2:36 pm

This was excellent, I really believe in your suggested approach. It is eerily similar to mine 🙂 Thanks for the scientific breakdown!
Brandon Winters´s last blog post ..What is Lifestyle Design and Why Should It Mean Anything to You


Rachel March 1, 2013 at 12:15 am

I’ve tried the automation idea in another fashion and it really works! Here’s how I’ve applied it with my own twist! After I had children, I had so much to carry when I came in the house that I kept putting my car keys down in random places, and then not being able to find them. Well after having to rush somewhere one day, and not knowing where my keys were, I decided…enough was enough…I had to find a way to put my keys in the same place. So I installed a key rack by the garage door and I literally practiced walking in from the car and putting my keys on the rack. I did this 5 times until I could do it without thinking about it. Result, I almost always put my keys away, no matter how much I’m holding. If I forget, I literally go in the garage and come back in 5 times to help retrain myself. This might sound goofy, but it works! It allows you to put menial tasks on the back burner, while making sure they get done. Give it a shot…remember 5x…good luck!

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