Business, Blogging, and Broken Windows


This is the follow-up to last week’s article on Product Launches. The series deals with the business side of blogging and social media – a topic that some will be interested in and others won’t.

This article will look at site comments, scheduling, organizational structure, and taking control over where your paycheck comes from. My goal is not to provide a comprehensive overview of everything related to business and blogging, but rather a close look at a few specific topics.

The analogy I’ll use is a variation of the broken windows theory. This sociological theory comes from the study of crime and deterrence. Roughly stated, it means that when a neighborhood window is broken, the property owner should fix it as quickly as possible. Otherwise, another window may be broken, then another, and pretty soon the whole neighborhood goes downhill.

In terms of crime and deterrence, the theory has sparked a lively debate among politicians, the justice sector, and academics. As we’ll consider it here, I think about broken windows in terms of issues that need to be addressed within an organization or community. Most organizations have some kind of public front that needs to be maintained. Continuing with the analogy, when one of their windows is broken, the organization can choose to ignore it or fix it.

Like other writers and entrepreneurs, I’m in the business of sharing information. Here are a few specific “windows” to be aware of when trying to build an online business or non-profit community.

Public Comments

Especially when you are first starting out, public feedback is emotionally addicting. “I love getting comments on my blog,” a number of people have told me. I love them too– but I’ve also learned that comments aren’t everything, and it also takes a lot of time and attention to monitor what people are saying.

Some blogs open the floodgates and let anyone have a say, even if what is said is harmful to other posters or people who just feel differently. If you have a blog of your own and ever get depressed after receiving a negative comment, you can cheer yourself up reading the comments on most posts at TechCrunch. It’s like going to the zoo, except there are no cages for the monkeys.

My belief is that a well-run blog is not a democracy. I have a “no asshole policy” on the site – in other words, I welcome constructive discussions, but I don’t welcome rudeness, name-calling, or just general troublemaking. Like the broken windows, once a popular blog opens the door to assholes, it’s hard to take back control.

Of course, the internet offers numerous other platforms where anyone can share their views. If someone wishes to, they can publish their opinions elsewhere. In reality, most assholes are not that motivated, so they will rarely take the time to set up a blog just to complain about someone else.

Lastly, I always remind new bloggers that the most readers almost never participate in the public comments section. On average, less than 1% of the readership will participate. The rest will happily read along without feeling the need to publicly respond. Therefore, bloggers have to be careful about focusing entirely on the response they receive in the comments section, since it’s not always representative of the whole community who reads.


If letting comments go to the dogs is one broken window, slacking off on the publishing schedule is an even bigger one. I’m a big fan of schedules, mostly because they promote consistency and self-discipline.

Over here, I have tried hard to keep the schedule sacred. In 2008 it was every Monday, Wednesday, and Friday, and in 2009 it is Monday and Thursday for main articles with a short update on Sunday. As I said in 279 Days, this rule is not so much for everyone who reads as it is for me. The problem is not that I feel so self-important that I think a lot of people would be upset if I slacked off. The problem is that I know myself, and I know if I missed a day, I’d be prone to missing another day, and before long the whole house could come crumbling down.

Therefore I keep the schedule: 547 days and counting so far without a broken window. I’m not saying it will never happen – I don’t post many articles in advance, and there is the real possibility that something could go wrong while I’m traveling and I find myself offline on a post day – but so far, so good.

One question that frequently comes up about scheduling is: “What do you do if you find yourself slacking off?” I think the best answer is to ask yourself if you’re doing the right thing. Are you still passionate about the work? Do you still derive personal meaning and help others when the work is actually done?

If your answer is yes, then you probably just need to improve your environment, say no to other things, and find a way to complete the work. In other words, you just need some self-imposed ass-kicking. If your answer is no, then you have a bigger broken window and therefore a bigger problem to address. You may need to make a bigger change or move on to something else. These things don’t usually get better on their own.

Values and Organizational Structure

The organization structure of what I do is hard to define. I write for free and still make a good living. Most of the people who read don’t buy any of my products, but enough do that I’m doing just fine. It’s simultaneously a career, a non-profit community, and a small business. Next fall it will be a book, then a book tour, and then a few other things I have planned.

The upside of this hybrid structure is that I love what I do. I don’t believe in life / work balance and I want to love everything I do. I feel like I’m in at least the 90th percentile of happiness. If I could get to the 98th, that would be great, but I’m not too worried.

The downside of this kind of structure is that it can get messy, and without careful attention it can become a broken window. Overall, I don’t really mind messy. It suits my ADD brain and my disdain for a structure that is imposed by others. To assuage the messiness, however, it helps if the values and mission are clear.

Not being clear about values or intention is a (very big) broken window. Get them right and you can make plenty of other mistakes with only minor consequences. Get them wrong, and you’ll be hard-pressed to sustain your project over time.

Even though I thought about what I wanted to say for two years prior to beginning AONC, I’m glad I didn’t start it when I first began outlining. I think my values were less clear then, and I’m not sure I could have sustained the pace or managed the growth even just a couple of years earlier.

Money-Making and Dependence

The last broken window is sneaky one. It reflects more of my philosophy on employment in general, and the principle is that I think working for someone else is riskier than working for yourself. People in traditional careers for big employers are sometimes afraid of going out on their own. Contrary to conventional wisdom, I believe the greater risk is in relying on someone else (a person or an organization) to take care of you.

As applied to online careers, I’m fortunate to have met a number of other successful authors and full-time bloggers over the past year, and I’ve also met a great many more who aspire to be more successful than they are– perhaps a nice way to say that things are not working out as well as they’d like.

As I’ve said before, success is entirely relative. However you define it, there is no single secret to success and I still believe that hard work over a long period of time is the best predictor, but one other element that I think is critical is to take ownership of the process.

Many forms of online work rely on other parties for success. By owning the process and building my own business, I’m able to control many more aspects of the money-making side of things. I am not dependent on an employer, Google, advertisers, sponsors, or any other single person (or group of people). All of these relationships seem to me like windows that are breakable. They might remain stable, but since you don’t have ownership of them, you can’t be sure.

It doesn’t mean that I have no dependence at all – but having it spread around, I have a lot less dependence than almost anyone I know who has not acquired enough wealth to not worry about making a living. Generally speaking, wherever you can take ownership over the process of how you get paid, it’s in your best interest to do so.

You Are an Entrepreneur

The implications for the bloggers and online entrepreneurs who have read this far should be fairly clear. Let’s say, though, that you’ve made it to the bottom and you don’t define your career in business terms. Personally, I think that everyone who takes responsibility for their own life is effectively an entrepreneur. Congratulations! You are the CEO of a corporation of one — or a sole proprietor if you prefer.

Perhaps you don’t have to deal with hundreds of blog comments or maintaining a regular schedule of posts, but chances are, you have your own windows to look after. Take a close look at what you do and ask yourself if anything is problematic or unsettled.

Broken windows are traditionally thought of as problems that need to be fixed, but they can also be seen as opportunities for growth as long as you recognize them in enough time to patch things up. Where are your broken windows?


Broken Window Image by Josh

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  • Scott Webb says:

    I am hoping that I don’t have to announce my no-asshole policy; however, it is sitting in my draft box. Tim Ferris of the 4 hour work week made me think about that from one of his presentations. I am not leaving room for the negativity.

    I know what you mean by ADD Brain and it’s why I have a few projects on the go, many books on the go and so on. I also have been diagnosed with high anxiety, depression and recently realized that it my be bipolar. I have started looking at my life differently and never know when a bad day or stress storm may go crzy. I can have insanely productive times, and then be down for the count for a other days. Although when working on my passion, I feel that I have less of those days. Thus I am pushing myself to cut the cubicle umbilical cord and move towards being location independent.

    I must say that I like your outlook on the dependence of others for your income. Diversity is a big thing and if Google were to have a massive fart, you’d still be ok.

    I’ve been inspired to fix the broken windows of the soul. I believe that my blogs have helped me to fix the windows of my own soul and I’ve began to find meaning and value in my life again. A lot of people, new bloggers even, don’t realize that the blog or online outlets globalize their voice. I hope to fix their broken windows by starting up blogs for them and allowing them to focus on their message.

    Congrats on your 547 days and counting.

  • Colin Wright says:

    Great analogy.

    I hold the same ‘no-asshole policy,’ though fortunately I haven’t had any trouble with it so far…I don’t think my kind of content really appeals to that audience, fortunately 🙂

    Keep up the good work! Nice to have more insight into your structure!

  • Seth Baker says:

    I think this broken window business extends to people in all creative endeavors. Painters, sculptors, musicians, writers, they’re all entrepreneurs whether or not they realize it.

    Unfortunately, many don’t. Rather than build their own lists and online store fronts, they become dependent on universities, publishers, galleries, and clubs to showcase their work.

    One club shuts down, one gallery rejects them, one publisher doesn’t market them like they promised, and that single broken window ends up tearing down the whole neighborhood.

    If they’d created their own marketing infrastructure, they could just shrug their shoulders and keep on peddling their creations.

    Here, their dependence has fail them. Had they been only marginally dependent, or interdependent, on these outlets, fixing that broken window would’ve been far easier.

    Maybe the old cliche of putting all your eggs in one basket is more accurate. I’ve seen too many do it, and when the basket is taken away, all the eggs break, and nobody even has the heart to make an omelet.

    BTW, loved the pictures from Bhutan.

  • Akila says:

    As a new blogger, I face a lot of broken windows because we are still building up our site, getting it going, and developing an audience. I think one of the hardest parts of developing a site is prioritizing the problems that need to be fixed. It is so easy to get bogged down in one aspect — say, the design of the site — that you lose focus on the remainder of the things that need to be resolved. To handle that problem, we set aside about 1/2 an hour about once every two weeks to do a full run-through of our site and identify all of the things that we see that needs to be fixed or resolved and then work through that list slowly over the next several weeks. This helps keep us from burning out from trying to fix all the broken windows at once.

    I really like the idea of scheduling posts. I have set an internal goal of writing three posts per week but only publishing two of the three posts so that we have a backlog of posts to publish when we are traveling.

  • Mike CJ says:

    Nice one Chris. I scanned and read the “no assholes” part and thought it was going to be a preachy post, but I then started at the top and read it properly. Good post and the broken window thing is a great analogy – the only problem with blogging full time is that there are so many damn windows!

  • Sean says:

    The question “What do you do if you find yourself slacking off” is one I have been thinking a lot about lately. I have found that I have not been as consistent as i should in certain aspects of my life, and I really think it comes down to an environment change. I need to put myself in a place where I know I can be productive, and as you mentioned, that just takes a little bit of self-imposed ass kicking!

  • Tyler says:

    I first read about the Broken Window Theory in The Tipping Point by Malcom Gladwell. I’d wager that a lot of the subjects brought up in that book would be valuable to people like us trying to convey an unconventional message.

    In working on my own projects, I’ve found that I maintain excitement about them, but can quickly bog down when trying to work on them exclusively before or after my day job.

    Fortunately, I have a (somewhat) flexible work schedule and an understanding boss. We negotiated that I can use a reasonable amount of time during business hours (when I need to be here) to work on outside projects in return for time spent at home working on work projects.

    This allows me to alternate the use the most productive part of my day, which is really nice. As long as my projects at work are going well, there are no raised eyebrows or questions asked.

  • Hilary Gardner says:

    This is so timely! Your comments about scheduling being central to your own productivity are very well-taken. And amen about the no-asshole policy! Lively discussion: good thing. Disparaging, small-minded meanness: totally unnecessary and unwelcome.

    Thanks, as always, for the common-sense advice and motivation!

  • Aaron says:

    Love the “no asshole” policy on your site. It’s good advice for everyone else to keep things under control on their sites, as well.

    Good advice in this post, too. Your writing is so clear and to the point. Keep up the great work!!!

  • James Nicholls says:

    Definitely agree with the broken windows idea. I’ve let a fair few problems get out of hand and it takes ages to get things back on course. Ah well, every mistakes brings me closer 😀

  • Peter Mis says:


    Thank you for posting. As a relatively new blogger I initially awaited comments to my posts like a kid on Christmas Eve. I would excitedly click on my WordPress admin page and the first thing I would look at is the comments section. It was, and still is, a thrill to get comments on something you’ve poured your heart into. It feels like all the hours I put into building my site is suddenly worth it.

    I still enjoy getting comments, but what I’d much rather have is my reader’s support. My posts primarily deal with (hopefully) inspiring people to realize their true capacity for living their greatest life. My hope as a writer is that the reader will in some way be even a little bit inspired by the words I have crafted. I hope that my words make even the slightest difference in the life of my reader. That’s really what my blog is supposed to be about…it’s not about me, it’s about the reader.

    Secondly, if my reader thought my post was meaningful, the hope is that she/he would spread the message on to others, either through Twitter, Facebook, StumbleUpon, e-mail, or any other way that my reader connects with others. For me, it’s the message, not the messenger. Spreading the message, to me, is far more important than posting a comment on my blog.

    Although, I’ll take both!!

    Thank you for sharing the gift within you!


  • Robert Granholm says:

    Great peak into your administration “box”. I perked up when getting to money and your mindset on dependance. I fumble when it gets to entrepreneurship. I’m at the critical mass point where I can almost feel myself willing things into action in search of success. I’m had enough partial success failures. Sometimes it feels like I enjoy pretending to be an entrepreneur instead of actually making things happen.

    I’ve worked for a few companies, I’ve been solely self-employed for a couple years, and now work 40-50 hours, am running a side business, and looking to create another one that will hopefully free me from both the others…yet don’t have an LLC or anything more than a self declared branding name and my good old will power. I suppose my broken windows when I really analyze past failures are not pushing through in launching an idea to an audience, or doing the research to do so properly. I perhaps for the first time will admit I might be getting lost in the execution, paying too much attention to the processes. Hoping I patch that window this time around….looking forward to more administration type posts!

  • Conrad Walton says:

    Schedules. That’s where I fall down. I get excited and write a bunch, then get distracted and slow down. I’m going to try to write posts in advance and schedule them out in the future. That worked once before, then I slacked off on doing that too.

    Oh, well. I keep getting back up.

  • Playstead says:

    Great post, hope to read more about the business side of what you do.

  • Jon Buscall says:

    Nice post!
    I’m all for schedules. It’s important to know where you’re going and also build a sense of familiarity for your audience. I like knowing that when I check my newsreader my favourite blogs will have updated “today”.

    Comments were perhaps more thoughtful, more engaging a couple of years ago. Nowadays I see less quality in the comment field across the blogoshphere but if you work hard and keep the windows tidy good people stop by and engage. Like here.

    Great site. I’ll be back.

  • Rich Dixon says:

    Broken windows is a great analogy. I’d add another piece–one person’s broken window is another’s ventilation system. We often allow others to define the problems and what needs to be “fixed.” Using your messiness issue: if your yard’s a disaster area and the paint’s peeling from the exterior, it impacts others and probably should be fixed. If the mess is in your office–your business.

  • Terry Gearhart says:

    As always, right on point, Chris. Keep up the good work!

  • Ashley says:

    99% of the time I do indeed happily read your posts without feeling the need to comment. “No Assholes” triggered the 1 percenter in me today.

    Well done.

  • Daniel Richard says:

    I just got called to this post via the email newsletter. 🙂

    You know… I sorta just realized that I’m suddenly unemployed. Hmm.

    Oh well. Back to working on the process!

  • Sarah Robinson says:

    Chris, when I first read 279 Days, I took your adherence to a schedule to heart. Sticking to a schedule does not come naturally to me – but it is the critical key I think to keep me focused on what I am about on my blog. Still working on the makin’ money part – but it’s comin’ along.

    Oh – and I am a total bouncer. People can disagree with me, but they can’t be mean in any way shape or form. I have to deal with enough assholes in the world without allowing them onto my blog. 🙂

  • giulietta nardone says:

    Great post Chris. I like the business model you offer your readers. Give them good info and some will buy. It’s refreshing and never feels icky! I’m probably going to buy your new product before the price goes up. So, this honest approach does work.

    Enjoy your week!


  • Jeffrey says:

    I’ve struggled with the comments section in my blog. I am still a new blogger, and haven’t yet built a large readership.

    For years my blog was very personal, and only friends read it. I typically posted challenging, controversial topics (religion, philosophy, politics), and my comments section (while somewhat friendly), always resulted in long strings of debates between people that weren’t open to changing their mind. I recently decided to move away from this style, and make my blog more friendly, uplifting, and whatnot.

    For me, this means moving away from the acerbic and contrarian mode I lived in for many years. I’ve kept the comments open (for now), but have considered the option of closing them, as I know many great blogs without comment capabilities.

    Thanks for the post and congratulations on no broken windows.

  • Tyler McCann says:

    Another entry I have enjoyed.

    It is truly so important to address problems or issues when they arise. Otherwise the ignored conflicts will inflate into monsters or breed more monsters that seek to destroy your progress!

    Just as there is no get-rich-quick scheme that is foolproof (or even in existence?) working or writing on your own takes lots of responsibility. I hope for all that the responsibilities and freedom achieved as an entrepreneur are worth the effort! It certainly is possible 🙂

  • jake says:

    Hi I like this post. Especially because I’m at a point where all my windows feel broken.

    I’ve been out on my own for several years now, first creating a community for artists, I even got government funding but lost steam because I don’t know how to monetise it, therefore I’ve been taking on client work for the last year and a half which has distracted me from what I really want to do, run a website that creates income.

    I eventually had enough of doing client work and tried to get into a company I admired for a while, they lifestyle the job offered would rival my current work-from-home status. I spent about 2-3 months fostering the relationships needed to get that job, right when I thought it was clinched the boss went overseas for a month and I’ve had trouble getting hold of him since. In the meantime I turned down several projects on the belief that things were about to happen with this company. In the last day or so I’ve realised that things just aren’t happening with this new job.

    I’ve run out of money and need to do something quick. And here’s the problem. I’m now likely to rush into something unfulfilling basically to keep myself a float. I know there are ways out there for me to develop my ideal lifestyle, (humbleness aside, I’m pretty damn good at what I do)

    Time to re-evaluate my focus. I started building a new site and I have ideas for monetizing it but I fear I will be swept into the bosom of a regular wage

  • Mike Turitzin says:

    Completely agree about sticking to a schedule — I left my job about a year ago, and I’ve been unemployed and following a daily schedule (of writing- and music-related activities) since then. I’m not 100% consistent, but I’m pretty close.

    I love most about schedules that (1) they eliminate the constant procrastination and time-wasting that happens if you don’t use them and (2) they eliminate the need to “psych yourself up” for creative actitivies (because when you’re on a schedule, you have no choice but to start).

  • Alison says:

    Great post, thanks for the insights. I know there are broken windows with my site and this gives me some excellent perspective.

    I think a schedule is the first thing to get started on. I’m learning that consistency is key for both me and for gaining a broader audience. Thanks again!

  • Angie says:

    Do closed comments work? I would really like to operate with closed comments because my heart really isn’t in a workload of comment moderation. And also, if I’m really honest, because I’m not sure I wouldn’t end up scared to post anything in an effort to please everybody.
    I know closec comments can be seen by some as not being open to criticism, or being less genuine. Would showing that I’m happy to read email help mitigate the idea? Would closing comments reduce the interactivity so much that people will connect less with my blog?

    Ahh, I just don’t know what to do, but I definately feel like comments are a thorn in my side.

  • tippy says:

    Hey Chris! Thanks so much. Keep on writing! I always go to your site when I feel down. I find comfort in the fact that there’s someone out there, working on his goals & just has enough optimism & determination to complete it despite the speed bumps here & there 🙂

  • Caron Margarete says:

    Hi Chris, great post! Great analogy! I also appreciate the insight into the business side of your work.

    I know that you put a lot of energy into making sure your information is free and not pushing the sale for the ebooks and I know that I’m supporting you for the right reasons so I think you can feel safe in the knowledge that talking about the business of making an income with your site is not going to put you on the persecution chopping block.

  • Douglas says:

    Excellent post, Chris!

    Some real truisms here.

    Instead of the broken window analogy, I often likened the same theory to cancer. In previous roles as a business owner and a business executive, I had to be aware of cancers that could or did develop within the organization. It ranged from negative employees, unresolved customer complaints, unresolved employee issues, concern about the direction of the company in troubled times – each were a cancer that had the potential to spread to others if they weren’t dealt with quickly causing a real unhealthy situation.

    Now as a solo entrepreneur, I have to monitor the cancer within, whether it is a at times a lack of focus, an open project, outside distraction, whatever – most of them are often benign issues because I treat them very quickly. However, if I don’t, they have the potential to become malignant. And as a solopreneur, no one else is going to watch out for or help with my health.

    Thanks again for putting together a solid post.

  • Raam Dev says:

    Wow, fantastic post. I really loved this:

    “Not being clear about values or intention is a (very big) broken window. Get them right and you can make plenty of other mistakes with only minor consequences. Get them wrong, and you’ll be hard-pressed to sustain your project over time.”

    When you’re unclear about your values or intentions, making the decisions that will contribute to progress becomes a lot more difficult. If you don’t know what your destination is, how can you make choices that will lead you in the right direction?

    “I think that everyone who takes responsibility for their own life is effectively an entrepreneur.”

    That’s exactly how I feel about life. Everyone has a responsibility to take full responsibility for their own life. Doing otherwise is being reckless, selfish, and throwing away what it means to be human.

  • Ryan says:

    Thank you for the inspiring post!

    I’m a beginning blogger who initially intended to post every day, but quickly realized I couldn’t keep up the pace without creating many “broken windows.” I’m going to implement your posting schedule idea and see if that helps me patch some up!

  • windwriter says:

    I have been very much enjoying your blog and I find it very useful. I like the broken window analogy but what really resonated with me was this:

    “Contrary to conventional wisdom, I believe the greater risk is in relying on someone else (a person or an organization) to take care of you.”

    This reminded me of a time when I was taking a course that had a rock climbing component. I have a mortal fear of heights when staying on that height depends on my actions or when it defies reason that the high thing should be there so the idea of climbing was terrifying. I did do the climb and found that I love rappelling. All experienced climbers dislike rappelling because success leaves their control and rests on the equipment. I, however, am light enough that I have to hand over hand myself down the rope until I am within about 25 feet of the ground at which point gravity can overcome the friction of the rappelling brake against the rope. I could sit on a rappel line for as long as it holds out; I could read Tolkien’s Lord of the Rings cover to cover up there. This gives me a false sense of security. I am entirely dependent on the equipment although if it fails the results could be catastrophic. Still, I trust it more than myself. Interesting insight.

  • Tamara G. Suttle says:

    Hi, Chris. I’m new to bogging and new to AONC. What a treat to find your voice! And, yes, yes, yes you are so on target for mending my broken windows! Thanks for paving the way for us newbies and sharing your info so generously. You ARE making a difference.

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