The Dysfunctional Guide to Blogging (and Business) Success

The Dysfunctional Guide to Blogging (and Business) Success

Reader Comments (93)

  1. Fantastic information Demian! I am just starting to get asked to guest blog. I am a wife, a mother of three, a grandmother of nine, and great-grandmother of 1 1/2. And I’m pretty…my husband thinks I’m very pretty! I wear classic styles and get my nails and hair done regularly. I drive a sweet pale blue Mini-Cooper. My goldendoodle Emma is one of the great loves of my life. I am a psychotherapist. I write a blog. On my blog I talk about my experiences in juvenile hall, almost getting pimped out, the mental hospital, being gang-raped, doing drugs, sleeping around, and being beaten, and becoming a mother at seventeen. I’m almost at the part where I became very seriously mentally-ill…for years! After that I’ll write about breaking my neck, and being given one year to live with a huge brain tumor at the base of my brain-stem. Because the truth is, I’m still here. I’m not only here, I’m thriving! And when a young mother who has had all of her children removed comes into my office for treatment, I can look her in the eye and say very truthfully, “I could have been you. Let’s get to work.” And we do.

  2. A lot of my favorite blogs are listed here, and I found myself nodding along. I have seen many personal finance blogs that share their net worth, debt, etc. I think that kind of transparency is something that works well in that niche, but you don’t always have to lay it all out that way if it doesn’t make sense for you and your family.

    Personally I take into account the fact that my family is a huge part of my story, so I have to be mindful of how they feel about sharing certain things. While brutal honesty is a wonderful, wonderful thing, we also have to be mindful of the relationships in our lives. We can still be honest and share our story without hurting the ones we love.

    • I agree, Kelly — even if you’re going to be quite radically transparent, I think we can all set boundaries about what we will and won’t talk about.

        • Very important to set the right boundaries, I agree. Too little, and you are one blog among millions. Too much and its either too exhibitionist or you risk hurting people who accidentally stepped in front of your train wreck.

          But the right balance is magic and delivers value.

          Great post, btw. I plan on checking out all of the blogs you mentioned. And thanks for mentioning me, Demian. I really appreciate it.

          • James: Did you ever write a post that you feel went too far? If so, please share it. I’d love to see an example. As someone with a very tiny audience testing just how far I can push it, I’d be curious what someone at your level considers the “right balance.”

            Thank you!

    • Hey Kelly, love your examples about financial writers opening up their financial lives to us. That’s an example I didn’t think about, but it really shows vulnerability.

      And I agree: brutal honesty is a wonderful thing when it doesn’t damage someone else’s life.

    • Kelly – I also agree about being “too” transparent because we still have family to think about. I waited to begin writing my story until after most of my family passed away. No matter what happened, my healing includes forgiveness and no desire to hurt them. And for the family who are still here? I leave a LOT out. Damage is something we’ve all had enough of. Great comment.

  3. That was a super post.
    Who would have thought that blogging like this can trigger the success factor? I truly enjoyed the post.
    Also the post proved to be useful to me because I got to know about a lot of blogs that got successful by not following the typical blogging tips that we read every now and then. They are what they are on their own.
    Superb post man. I got more inspired knowing that I am not the only one failing now and then.
    Keep this up as I can use a lot more inspiration.

    • Hey Arbaz, thanks for the great comment. And while radical transparency was a key to these bloggers success, a lot of them also use tried-and-true methods to attracting attention like compelling headlines, working the social media pump, etc.

      Glad you got inspired brother! Rock on!

  4. My blog is all about transparency in an environment where Christians stumble dangerously close to perfectionism. I tell people, “I screw up; the whole world knows about it.” Some have called my blog unique. And you’re comment reminds me that I need to get more interviews. Too much talking about me. This post though really helped me feel inspired and introduced me to new inspirations.

  5. It takes a lot of guts to be “radically transparent” and not many companies are comfortable going to such lengths, especially since you can’t really hope to hide and build your brand at the same time. But I go agree that people respond to honesty and humanity. Your company is made up of people and those people have thoughts and feelings and opinions and faults and your audience wants a peek at them every now and again.

    • Good comment, Nick. The company that immediately comes to mind when I think about radical transparency is Best Buy. I believe they have something like 3,000 employees tweeting for the company. That’s risky, and I understand that they are using it for customer service/tech support, but still, I guarantee they aren’t micro-managing those accounts–that shows trust for their employees which I think translates to credibility.

  6. Some of my favorite sites and blogs were included in this post. I appreciate when people are as honest and open as I am. Some writers shy away from that in fear of being “found” on the web making commentaries on their job, sex life or pets. I say why not? Sometimes it’s okay to use an alias, but when people can have an honest conversation through blog comments about serious topics like depression, I can’t think that that is anything but a good thing.

    • The nice thing about the web is that you can hide–and write about the things you really want to write about without getting busted. I guess that is a nice thing. Depends on what you want to do with that anonymity. There are lines that shouldn’t be crossed. Ever.

  7. This post rocked!! thank you. I try to speak in my own voice in my blog but do find myself holding back, as to not offend anyone. I’m so over that now. I needed this kick in the ass. thanks again.

  8. Excellent post about blogging success. I think many of us are looking for the secret. It’s often not very formulaic…just gutsy real human connection, redemptive stories, and outrageous stories have their appeal. One of the things I’ve found is whether blogging or speaking, many of us appear more together than we are. People are encouraged by the reality that we are all so darn flawed and cheered by the fact that we keep trying anyway.

    • I think you pretty much summed it up with this line: “It’s often not very formulaic…just gutsy real human connection, redemptive stories, and outrageous stories have their appeal.”

      Thank you for sharing.

  9. Nice article, and you are right, there is something sweet about learning from others’ mistakes that can make an article truly compelling. We get to pretend that ‘I would never make *THAT* mistake’ and learn from it at the same time.

  10. Great points made here, and great examples! (I’ll have to check out some of those blogs I’m not familiar with.) There are so many blogs out there that I’ve enjoyed in the past but have become bored with because they’re not willing to be imperfect. Every post is, “This is what I’m up to! I’m so lucky and happy! Here’s a pretty picture.” Not that they’re not allowed to be happy, but I’m suspicious of anyone who claims to be happy the majority of the time.

    I’ve definitely noticed that my posts that show me a little vulnerable and a little exposed get the most feedback. People appreciate honesty, plain and simple.

    • I couldn’t agree more, Cassie! I prefer a humorous, self-deprecating blog to one that is all flowers and pink and cupcakes and cashmere. There is a blog called Pepper Steak and Polyester that pokes fun at those gorgeous (WordPress) themes and ladies.

    • I agree. I like taking risks in writing. I find the posts I hesitate to publish are the ones that get more responses. I like taking risks.

  11. Hi Demian.
    Transparency is very powerful, admitting to your mistakes makes you more human and not just a blog designed for affiliate scraping and Google AdSense. People love to identify with people ‘warts an all’ as we say here in the UK.

    Admitting to your mistakes also helps others to avoid making the same mistakes and when someone finishes reading a post and walk away feeling connected to a person, identifying with the author and having learned something that they didn’t know before they read the post will have them coming back for more and being grateful to you for writing the post.

  12. To say that I’m impressed with this post is an understatement. Superb writing and such a relief after reading so many posts elsewhere that (as you mentioned) aren’t exactly grammar food.

    I’ve been thinking a lot about this very topic. Marla Cilley of is one who turned her dysfunction into a successful business. My more successful posts have also been self-revelatory in nature. But I think you make such an important point: there has to be more to it than that. After all, I was fascinated with Hoarders for a while, but when you’ve seen one house full of 60 dead cats, you’ve seen them all. The blogger has to offer help and hope in addition to the opportunity to rubber neck for a while.

    Thanks for something to think about as well as a list of great blogs (including yours) to check out.

  13. Outstanding post. I’m really excited to see two of my favorites here: @blogdangerously and @redneckmommy They are awesome beyond description.

  14. Thanks for sharing all of these kick ass, raw and ultra-talented bloggers. I agree completely with the idea that transparency = connection. Through blogging and performing, the work that has resonated most with my audiences has always been the same—the painful truth. It’s been especially true these last two months. After getting sh*tcanned from my day job, I went to town on my blog. At first, I was euphoric…actually forgiving of my employer and my boss, who I thought was a saint.

    Then I woke up. And I let that fu*cker have it. (I swear, I’m not bitter!)

    The response has been fantastic: a significant boost in site visitors, support from friends, and more importantly, unsolicited comments from people who’ve said they “love” what I’m writing about. I’ve only received this kind of feedback from two prior posts: one honoring my “super dad,” and another about my mom’s death. And I mostly write humor. Go figure.

    So, seeing others crank out their dark side inspires me to both continue what I’ve been doing and do so with even more vulnerability. I only hope I can shut up my stupid censor inside and let it all hang out.

    Thanks again for sharing.

  15. I do think you can be too transparent, but it’s important to show the ‘real’ you. Let’s face it; no one is perfect. If you can share your trial and errors regarding “fill in the blank,” your readers will know that you’re not perfect and that you stumbled and fell a long the way. Be real and cut out the B.S. (most people can see through it anyway). Just be you.

  16. I can’t believe you left Penelope Trunk off this list. Tweeting her miscarriage? Putting up a nude photo featuring the bruise her abusive husband gave her?

    • Penelope Trunk is one of the first people I think of when we talk about this, I agree. But she gets enough traffic already. 🙂

      The Bloggess is another one. And Dooce. And Mrs. Woog. And, and, and.

      • Yet Penelope Trunk is may be the most bizarre of the lot – and mesmerizingly intrigueing. I agree with ‘Blog reader’ – and not just because of the miscarriage. Many of her posts make me cringe – and then smile, or shake my head, and wheter Penelope is downright crazy or not, I applaud her.

  17. I would add Tucker Max to this list. Self-proclaimed asshole who blogged about his drunken escapades and sex life and landed book deals and made his own movie as a result.

  18. I believe in AUTHENTIC because it works in my own life [after nothing else did].
    So I make my blog authentic. Transparency is the detail needed to make it authentic. When is little to little and much too much – still finding my way.

  19. First time to read this site and it has given me lots to think about….Thanks!!! More thought to titles and what works and what doesn’t…..mine has seemingly been making the rounds in Europe and I am in the US….not sure how that happened but it is fun. Hoping to build a following to help with marketing my book coming out in a few weeks and so much to learn. Writing the book was the easy part. “Climbing Out of the Box, My Journey Out of Sexual and Spiritual Abuse Into Freedom and Healing………

  20. I LOVE this article Demian and I’ll be subscribing now to read more!! I’ll also be checking out the blogs you’ve mentioned here as many strike a chord and look like they’ll be fun to follow. My own blog is about me, and when I began writing I doubted that anyone would read such self indulgant nonsense about a woman’s experiences running a small business. My most popular posts were about a skirt that fell down as I presented a training course and a case of (mistakenly!!) being arrested for soliciting… It’s good to see that we’re all a teeny bit crazy. Thank you for showcasing these people – looking forward to your next blog!

  21. Hi..this is a very detailed, very impressive post. As a blogger, talking about my personal opinions or my life has always been very tough for me. I think ‘radically transparent’ only works for some people, but after a while, it gets old! I have experienced that myself while reading some blogs that seemed too narcissistic after a while. Gradually, a pattern emerges that shows the reader that most posts are self-serving, and that’s a huge let down.

    I wonder if it is possible to sound genuinely dysfunctional without being so? In that case, you would be writing fiction! What do you think about that?

    I seem to remember another Copyblogger article in my email recently that advised the ‘be yourself’ mantra, and suggested that bloggers should not profess to know anything or be expert at anything until they build up an ’empathetic’ following! Does this mean people will relate to you only if you’re dysfunctional?

    Another thing I have noticed is that people/bloggers prefer to downplay themselves or plead ignorance just to ‘relate’ to the multitude. Playing dumb seems to be the fashion.

    Appreciate any thoughts you have on this.

    • Uh, to sound dysfunctional without actually being dysfunctional…I’m thinking that’s a possibility. I think it’s called acting. I don’t know about your second question. You would need to link to it. And regarding your last thought, it definitely is in vogue to not be be a know-it-all.

      Great questions. Thanks for asking.

  22. Hi Demian, well put together and interesting piece.

    Just thinking about your notes on blogs that break the rules but succeed; there is one blog I read, that is very popular among a certain group of people.

    The man writes like a demon, vast swathes of extremely dense material, sometimes thousands of words on a very sophisticated tangent, complex intricate thinking, not for the average reader for sure, but he does have an extremely loyal following to the extent that if the guy wrote on toilet paper his fans would read it, he shuns all social media and yet his readers set up a fan club for him.

    What you notice about his writing and why it succeeds (he is a very fast writer, but all his stuff is carefully edited) is there is not much self consciousness in it, it’s not contrived and he writes from passion, real interest, no compromise.

  23. This article should garner 10 points in a scale of 1-10. The extremes of things (success and failures) are excellent areas to talk about. When one can communicate his thoughts as if one is in his shoes, the rest will come out unexpected. We can sense a good deal of honesty to the writer when he/she talks about something that he/she had undergone. A vivid presentation of the struggles, failures or successes he/she had experienced can be most appealing to the reader.

    I will visit this site regularly and read more about the articles and the references mentioned. Thank you so much!

  24. This post makes you think! We all like to naturally be as good as we can be, but if we are not up to our own expectations in any area, then we don’t like to shout about it publicly. However,within blogging it can have a beneficial effect, as you say. We are all human and we are not perfect and others will relate to that as they are human too.This could be called the foundation stone of blogging – building trust. Why should people trust us? Because we tell it like it is.

    • Couldn’t agree more with your comments Laurie.
      And wow what an incredible post! A great lesson is ‘Transparency works because you are vulnerable.
      You show people you are just like them — a human with endless faults.’
      This is where the engagement, empathy and connection comes from.
      I’ve done a lot of public speaking and my most successful presentations, that helped and inspired people, where when I talked about all the mistakes I’d made and what I’d learnt. Yep we all stumble and fail!
      I’m currently writing a guest blog where I put myself out there and it’s really difficult to write but I’m hoping it will help others so it will be worth it.
      And I totally agree, getting that all important balance is a real art form.
      Thanks for sharing this

  25. When I first began doing this line of work and writing my own blog at the same time, discovering you was the single most encouraging thing that happened to me. This insightful, well-written article carries your voice so strongly; your level of transparency in your personal work inspires me with your bravery and honesty. I’ve been living in the northeast too long; the dissonance I feel wears me down and creates huge barriers for my own transparency. What a nuisance. Stay who you are. You light the way for us.

  26. Thank you for a lot to think about and a terrific post.I have spend several days mulling it over. 😀
    It’s true, people flock to witness struggle and discontent. The blogs you mentioned are terrific and I enjoyed exploring many of them for the first time. If I stick around I’m sure that I will be a faithful reader and begin to care about their families and their mental health just like I do about Dooce and her children. I will feel compelled to comment and offer support.
    Now here comes the but….my own discomfort.
    I would love to write as well as these women but I have no intention of writing a “reality blog.” I know if I wrote more about my husband sudden death and how it effected my teen my number of comments would grow as would the clicks. When I have written about being offended, hurt, or snubbed my readers flock (a small flock) to comfort me but since this takes energy away from their own lives, I think carefully before I hit the publish button.
    I noticed you did not mention blogs that grow from being silly or interesting lifestyle like The Pioneer Women. If you did mention them…I’m sorry If I missed them. You also didn’t talk about these blogs effects on the bloggers family members, friends and community. The solution for some it seems is to write anonymously. How really is anonymous. I like real names.
    For reasons I will keep exploring, growing a blog through strife, discontent, and mental illness seems very self serving at the expense of the reader.
    Thank you again for the food for thought.

    • Hey Katybeth, I think it is wise to think through before you hit publish. I have a friend who writes nasty Facebook posts, shows them to his wife and then deletes them. He gets it out of his system without hurting people. I wish I had that kind of discernment at times. 🙂

      Pioneer Woman was on my short list but I pulled her in the end. I forget why. :/

  27. Up until very recently I ran a technology blog. As I’d also been involved in politics I ran a reprinted article on the resignation of a physicist. Said scientist (now deceased) resigned from an eminent organization due to his views on the miscarriage of science regarding global warming.

    427 (published, many to vicious to permit) comments that, to my mind display the dark side of the environmental movement. NB: At that time I’d passed no comment on the veracity of climate science, ran a political campaign that was reasonably pro action etc. A taste of how vile the individuals can be can be seen in the comments section here:

    I was pretty disappointed and admit I had a rethink on “transparency”. Surprising for a decade long veteran Usenet Moderator (now retired Moderator).

  28. WOW I had to re-read that jon morrow article again. I forgot that it was one of the most inspirational posts that I had seen to really make me take this blogging thing seriously.

    Still haven’t seen too much dysfunction from copyblogger though just great examples of making it happen. How about sharing some TRUE FAILURE stories. Talk about posts or launch ideas that failed and why, etc?

    • You remember how Demian talks about two strategies? We do the first one. 🙂

      Copyblogger’s never going to be a “confessional,” personal Dooce-style blog. But we do sometimes run stories wehre we learn from things that didn’t work, and once in a great while we run more personal posts that talk about how we got where we are now.

  29. This is such a great discussion and i am learning so many things, not only from the post itself, but all of you! I am glad it keeps coming back into my “in” box because I want to print the original post off and then have those addresses handy. Thanks so much for this Demian!

  30. Everyone,

    After reading your excellent comments, I thought of something else: Why are companies so afraid of showing personality in their blogs? For example, in my last job, I wrote a post about personal disruption, which involved my week-long attempt at sporting a mustache. I realize this may sound silly, but there was a connection back to the company’s overall mission (i.e., helping people with health issues).

    The post garnered the highest number of visitors *ever* to the company’s blog, a lot of positive comments, and yet the CEO made us take it down. Why?

    He said, “I don’t like it.”

    The marketing director told me, “It’s highly entertaining and a great post…it just doesn’t make a direct connection to our products.”

    Really? Does everything we do always *have* to sell? I believe our followers liked the post because it was funny, truthful, and did *not* try to sell them something. If anything, it was selling something even more important to building relationships: that we’re people who, like you, struggle with stupid sh*t.

    I would love to hear what others feel.


  31. This is an excellent post. When I first started my blog, one of my readers contacted me and we became friends; when I met him and his wife for lunch he told me that reading my blog always left him feeling raw and wanting to cry. Somehow that sounded wrong to me and I thought writing personal stories was bad. Business school had after all taught me to seperate my personal life from my business life. It took me 3 years to understand why my blog traffic dropped drastically – I stopped telling stories and there was no me in the content. Reading this confirmed how important it is to be authentic in all aspects if your life, including writing. What I got from this post is to find the balance between quality content and telling your own story by being transparent. Thank you for such an insightful post.

  32. I keep coming back to this blog post and reading it…I’m almost addicted! My own blog is very personal, and I am always fighting with myself about how much to reveal and how much to keep to myself. I recently read Cheryl Strayed’s “Wild,” which was fantastic, but she revealed some things about herself that I was not sure she would want her children to read. It left me wondering about my own blog and how much to reveal. A previous commenter wrote something about that…that we need to be cognizant of hurting people in our lives with our words. I am a therapist, and I also need to think, “if one of my clients found out this was my blog and read it, would it be helpful or hurtful. It’s a quandary, but I cannot help but write. My latest post deals with the suicide of my brother. I just found out that it’s “National Brothers Week.” Did anyone know this? Have a fantastic week everyone!

    • Asking yourself if you would want your children to read what you wrote is a great principle (my children read my posts and I used the word “crap” and my daughter said Daddy, that’s a bad word.” I was embarrassed and haven’t used it since.). And clients finding out what you wrote…that’s huge, too. That’s why some people go anonymous. There is always your journal.

  33. Hi Demian,

    I do use a pseudonym for my blog, although with all the connecting social media stuff it would not be hard to figure it out. My children, all grown, know my story and are following my blog, but I leave out lots of details for their sake. There are a lot of things that do not add to the point of the story anyway, and my point is to give hope to those who have gone through similar traumas…there is light at the end…the details don’t matter. Thanks so much for responding to my comment!

  34. These posts have given me a lot to think about. My blog reveals a lot about myself…as a matter of fact I use a lot of my own “stumblings” to share about my spiritual journey. However in my soon to be released book, “Climbing Out of the Box, my journey out of sexual and spiritual abuse into freedom and healing,” I tell it all with nothing held back. It has actually served to answer my children’s many questions about not only my past, but theirs as well, and encourages them to move forward, knowing we are breaking all generational patterns. I feel it is our journey and if it can help one soul to have hope for their future then I tell it as it is………..

  35. Thanks for asking Linda!! It will soon be linked to Amazon. When you read it be sure and rate it on Amazon!! My latest posting on my blog tells the story of how the book came about……..I so enjoy your life’s journeys you share on “A Light At the End”…..I eagerly await every new posting…surely a book in process!!! Blessings

  36. My favorite post of yours so far…easily.

    I have found that they posts I make that are the most brutal, the most guttural, the most honest, garner the most interaction. I personally am careful to talk about my personal hiccups in a humorous way because there are few things I hate more than a comment at the end of a really heartfelt blog that begins with, “I’m so sorry”. I’m not. Shit, had it not been for the catharsis that occurred because of whatever that big thing was, it wouldn’t have ever been worth writing about anyway.

    One of my most popular blogs was titled “And sometimes I just suck at stuff” and I think people loved it because they could really relate. I had another post that was just brutal for me to write, about overcoming homelessness, living without furniture, about my dead cat…(I won’t link you unless you ask me to because it’d be tacky) but people really flocked to that thing. Most of them emailed me directly because they had some soul pouring to do with a tinge of stagefright, but whatever, they still let me know they were there.

    My biggest struggle lately is F-bombs. I want to use them sometimes because hey, I’m speaking conversationally, but I’ve been told by my design buddies it’s a no-no and I should offend my Christian Housewives. But hey, I’m a Christian and God still loves me, but I get it. I do.

    Decisions, decisions…

    • I’m tempted to use F-bombs, too. Sometimes it’s like adding that filthy adjective just drives the point home in such an exquisite way. And forceful, too. Email me through my website and send the link to your homeless post. Would love to read the story.

  37. Great post Jeremy,

    I agree with your opinion that almost all of the successful people on this planet mostly were the people that gained many failures in their past. And that’s the truth. They are really independent, extremely persistent, super stubborn and fully passionate with what they do.

    Writing can be really fun to express our feeling to other people. But sometimes, we need to be really confidence with what we are writing. We have to write contents not only to inform readers, but also to make them interested or attached to our articles personally. And that is the one that i’m really struggling to learn right now. lol!!

  38. Great article and some great bloggers to read! You’ve given me some really good food for thought. I’ll admit, I’ve gotten a bit bored with my niche but you’ve just given me a new idea twist. I did have some really great success with a couple of posts and you’re right, it’s because they were pretty transparent. Recently, on a mission trip to Haiti, part of our team experienced something very few in America would be able to wrap their minds around and that’s been my most popular post (Yep, it’s linked to my name here in the comments). And another favorite on my site, I’m Breaking Up With You – that got a lot of response and got me in a little hot water with my mother-in-law. Thanks for the great advice! I always enjoy reading here!

This article's comments are closed.