6 Decisions That Changed My Blogging Career. One Still Scares Me.

63 amazing comments

blogging decisions

A career in blogging. What a weird thing.

It’s taken me a long time to get to the point where my blogging-based online business is solid enough to justify some of my “interesting” earlier life decisions.

I really love sharing experiences and strategies in the hope that it will help other people out there who are looking to grow their own blog, or just pursue something that they think will make them happier.

In this post I want to show you six decisions that changed my blogging career in a big way. I hope that if any of you are going through something similar it will show you that you’re not alone.


NOTE: This post contains an affiliate link. If you purchase a hosting package through my link I’ll earn a small commission at no extra cost to you (in fact it will save you money!). Thank you for your support.

Some big blogging decisions that changed my career

I’m really curious to know whether anyone else has experienced these ones as well. As always, drop a comment if you want to share.

1. Going from anonymous to VERY visible

The first two years of Blog Tyrant was written completely anonymously. I purposely decided to write under the name The Blog Tyrant and not show my face.

One day I had an email from the owner of ViperChill asking if I wanted to be the only other writer every to feature on his site.

Umm… absolutely!

The catch? He thought it would be a good idea to make my first post a big reveal that showed my identity. Luckily I also thought it was time.

The post went live and within a couple of hours it had received hundreds of comments and a lot of tweets and emails from people who had been reading the site for years and were happy to finally “meet” me.

blog tyrant

This was also the first time we debuted the “couch photos” which taught me some really interesting lessons about branding and standing out from the crowd.

It all turned out well but I’ll never forget how nervous it was. It still scares me when I go back to thinking about it.

Since the unmasking I noticed an immediate jump in reader interaction and brand loyalty. I’m really glad we did it and encourage other bloggers to think about ways in which they can make their own websites more human and approachable.

2. Migrating from a free blog to a paid hosting environment

When I first got started with a blog I played around for a few months on a Blogspot site. It got pretty popular and at some point I realized that I needed to get my own domain name and host.

Well, that turned out to be pretty stressful for a new blogger – especially when you realize that all of your permalinks will be changing and you’ll need a new theme, design, blogging platform, etc.

This is one of the main reasons why I encourage new bloggers to sign up for a domain name and hosting package right away. And I continue to recommend BlueHost because it’s cheap, reliable and they have great 24/7 staff who can do things like migrate your website or help you get set up with WordPress.

Without your own blog host and domain name your progress (in my opinion) will be forever stunted. I am yet to meet a single professional blogger or online company owner who uses a free blog.

QUICK INTERRUPTION: I’m very happy to let you know that BlueHost is giving readers of Blog Tyrant a massive discount rate of $2.95 per month on the 12 month starter plan if you sign up for a new web hosting package this month only. This is a really good offer from a company that I feel very comfortable recommending.

3. Utilizing the occasional (very) controversial title

In the last few years I’ve written some posts that have had somewhat controversial headings.

There was the one called Why Blogging is a Waste of Your Time and a just this week we had another called Don’t Build a Blog.

But the biggest of all of these was a post called Why I Hate Copyblogger.

And it featured as a guest post on Copyblogger…

As we learned later in a follow up post they wrote about that title (yes, that happened…) the article almost didn’t get published. Luckily Brian Clark had my back and though it was worth giving it a shot.

While I do get some flack for these titles I always try extremely hard to make the takeaway in the post useful and as helpful as possible. And I’ll never write a title that in and of itself could cause problems if someone read it and then didn’t take in the post.

The interesting thing is that whenever you write one of these and it goes well, especially as a guest post, you see a huge jump in subscribers and new readers who start to see your blog as a bit of an authority.

4. Getting rid of all of my clients

I’m going to write a whole post dedicated to this one day because people ask me about it a lot.

Around a year and a half ago I made the decision to get rid of all of my direct clients. I was still managing a lot of customers from the days when I used to do consulting and web design and, as much as I loved some of them, it was taking a toll on my business.

I had all these goals for my own company but I’d spend all day working on their projects or setting up new emails for them – it never ended.

Well, I got the the point where I realized that I was making a good living without the client-base and decided to let go of that “security blanket”.

And it was a solid move.

Now I literally only work on projects I want to work on. I’m free to devote my time to the Blog Tyrant brand and just build up my own assets. It was incredibly liberating and has allowed me to really grow a site that I hope lasts a long time and helps a lot more people.

5. Trusting people to take over my business

This is a really hard thing for any small business owner or entrepreneur (why can’t I ever spell that word correctly?) to do.

We become addicted to our own procedures and insecurities.

And it can really cripple your productivity.

One huge breakthrough moment for me was when I had an issue with the comments section here on Blog Tyrant while I was away. I couldn’t fix it myself, freaked out, and ended up sending access to a coder friend of mine.

The issue was fixed in five minutes and I’ve been using him ever since for all sorts of different tasks. It saves me a lot of time and he is an absolute wizard so I get a better product than I could ever produce.

Now I’m more likely to open up and let people take over aspects of my business. Once you give up that little bit of control you open yourself to a whole new world of expertise and lovely people who actually want to do good work for you and your business.

6. Dropping out of college when my degree was nearly done

I absolutely don’t advocate this for everyone.

In fact, there have been times when this self-employed stuff hasn’t been going so well where I wished I’d stayed in university.

That being said, I hated it.

I used to catch the bus into class, wait for the lecture to start and then leave and go and work on blogs. It was while this was happening that I sold my first blog for $20,000.

Life changing.

I soon dropped out to give the whole blogging thing a solid crack. It’s been a long and winding road but I think college gave me a taste of a life I didn’t want and really gave me the impetus to do something dangerous and see how it worked out.

The lesson here is not to drop out of college but to make sure you follow your gut and try different things with your life if you aren’t satisfied. As long as you take care of your family, debts and responsibilities there really isn’t anything stopping us from taking a few calculated risks now and then.

Have you made any massive decisions in your career?

I’d really like to open up the comments and hear about any big decisions you’ve made in your career. Did you end up regretting it or was it a choice that has led to more success and happiness?

Please leave a comment and let me know.

Photo: Joshua Earle.


Hi, I'm Ramsay. If you enjoyed this post you might like to check out:

Finally, hit the button below to get a free report and email updates so you're never out of touch.


63 Comments. Join in. *Closed after 30 days*

  • Mohit

    Have done #5. There is awesome power and freedom you get when you trust others to do what needs to be done.

    And plan to do #4 in 2016. It’s scary to even write it. Let’s see.

    1. Ramsay

      What’s your plan after they go?

      1. Joe Yobaccio

        HI, I just joined your blog after reading one about a topic I was looking into. I wanted to comment there so that I am not off topic trying to reply on a different topic, but I know you close older posts. As I go through that topic and others and want to ask a question, is there a way to still ask or reply?

        1. Ramsay

          Hey Joe. You can always shoot me a tweet.

  • Marcus

    No 4 is really crazy. But seriously, you did that??

    1. Ramsay

      Yep, best business decision I ever made. But I was very ready for it. It wasn’t like I had nothing else going on.

      1. Hamayon

        It’s a tough decision but this is the quality of the artists. They are the moody people and work on their own projects and do what they want and I believe you are a great artist in the field of “blogging” 🙂

        1. Ramsay

          Artist is not a term I’ve hear before. Ha. Thanks.

  • chris

    1. Several years ago, giving my “blog” one last try to build a decent following. I didn’t feel I was making my mark in the niche. If it didn’t work, I was going to give up. It’s been year after year of success since then.

    2. The biggest decision I’ve ever made is the one I haven’t made yet. I have a full-time job separate from my web biz. If I can get certain things accomplished and some goals met, I’m looking at leaving my nine-to-five job in a year or two. It doesn’t get much bigger than that!

    1. Ramsay

      If anyone can do it, it’s you. One of the most methodical, hard working people I’ve come across.

  • Melissa

    Great post Ramsay and having just started my blog it’s great to hear some of the background to your blogging career. I’ve pinched a few ideas from your posts over the last few weeks x!

    1. Ramsay

      Glad it’s helping! Pinch away!

  • Alex Garner

    I got right on that A game and went straight for a paid hosting and WordPress setup. Glad I did that. But I don’t think I’ve had any extremely big life changing scary moments. Maybe I’m not pushing the boundaries enough? Maybe I could be doing so much better if I took a few more leaps of faith?

    1. Ramsay

      That’s a hard one. You’ll probably know when you encounter one worth taking because it often keeps you up at night. Well, me anyway. Ha.

  • Gabriel

    Hi Ramsay, excellent article! I have a question about #1:
    I am thinking of starting an anonymous blog because my job requires that I must stay on the low and avoid any public exposure.
    I am also very passionate about writing books and I would also like to write e-books for my blog in anonymous.
    I plan to eventually reveal myself if I reach enough passive income to stop my bog.
    What are you advices concerning anonymity? Do you have some tutorials or articles that explain how to successfully set an anonymous blog? Is it really worth it?

    1. Ramsay

      Hi Gabriel.

      No I don’t have any articles but it might be time to write one. Thanks for the idea!

  • Cameron

    I need to get better at #5. I do so much on my own and when you have other writer’s managing, editing and, hyperlinking, promoting, all their content takes a toll. It’s even harder when they are currently working for next to nothing as I’m new and can’t pay them much yet.

    My time is already stretched thin so eventually I’m going to have to get to this place. Hard to find good people though.

    1. Ramsay

      It does take a long time. Let me know if you need any recommendations.

  • Linell Vonkeman

    This is an awesome article, Ramsey! Thank you!

    I found the first point to be very intriguing and I am on the fence about this. I just started a blog; very elementary and still in the process of really finding my niche, which is why I don’t feel comfortable being that exposed I guess.

    When is the right time? How long should you ghost write before you become public?

    1. Ramsay

      Personally if I was starting over again I would have my face on my blog from day one. But it’s a decision each individual needs to be comfortable with.

  • Wendy England

    I can relate and this has prompted me to finally comment on one if your post – I often read but don’t bother commenting.

    I was running my first mlm business (don’t hate me, it was Avon) but found I couldn’t progress as my full-time supermarket job if 8 years was taking up my time. I decided to quit, as I hated stacking shelves, but a mere 2 months later found my self in debt and unemployed.

    Do I regret it? No. Would I do it again? Yes.

    I’ve learnt a lot from the many jobs I’ve had since then and met some amazing people. It’s made me grow as a person. Had I not taken the plunge and quit I’d have missed out on living my life.

    I’m still trying to find the one job I care about; I’ve been job hopping for 3 years now. I am happier though and that’s the important thing.

    Blogger of Bumpkin, Broke & Reading

    1. Ramsay

      Hi Wendy. You sound like a very brave woman. I wish you the best of luck with the next step.

  • Scott Kindred

    Thanks for sharing these examples, Ramsay. Your story in #4 has parallels to what I’ve been working on for the last 18 months, for my own business; a departure from project-based work. As you said, it’s never ending. And when I use the measuring stick of “Is this life-giving or is it life-draining?” I sometimes have to give the latter answer. WordPress has been that security blanket you mentioned. But my transition into dependance on recurring revenue versus project-based revenue has been deliberate and I am just now starting to see some of its fruits.

    By the way, when you laid out the whole timeline of being anonymous for 2 years before VC convinced you do de-cloak (…Romulans!), it made me realize I’ve been around since “way back then.” Bravo on your success!

    1. Ramsay

      Hey Scott.

      Yep, you’ve been around since the beginning. It’s been a pleasure having you here deconstructing my photo choices and leaving value-adding comments. Honestly speaking, you and a handful of others have made it so much more enjoyable for me.

      Thank you.

  • Ron Stewart

    Great post Ramsay. I’m thinking about giving up my part time home business for blogging. I tried blogging before to create an online presence for my business, but it didn’t work out too well. I couldn’t give it the time it needed because of other business obligations, but if I make the blog my business I can devote all my spare time to it. I want to create an online store & use a blog to drive traffic to it. Plus, I’ve got a couple other idea for websites that I would like to set up at a later point.

    Thanks for all your great wisdom.


    1. Ramsay

      Hi Ron.

      I really think it’s a good idea to keep that part time job while you build it up. It takes a lot of the pressure off. I used to clean a gym from 6am to 10am and then come home and work on my blogs.

      Let me know how you go.

  • Laura

    Hi Ramsay,

    I just recently found your blog after deciding to get into the blogging world. I just signed up with a host and got a domain name this week. I’m actually planning on starting two blogs.
    #1 was interesting to me because I’m planning on showing my face for my first blog (a beauty blog). I think for that genre it is especially important to brand yourself, and show yourself to be friendly and approachable.
    However, for my second blog, I’ve decided to remain anonymous for awhile at least. It’s going to be about quality reading and thinking, about living a better, more mindful life (Farnam Street, and Darling Magazine are my main inspirations for the blog). I really need to work on my focus and niche for that blog. I’m a little unclear about where it’s going to go.
    I’ll feel better writing anonymously while I’m still figuring out that blog’s niche. Also, I’m basically totally new to social media (I don’t have a Facebook account or anything), so I think I’ll have enough on my plate figuring out that for my beauty blog.
    So it’ll be an interesting experiment to see if there are any differences in growth of the two blogs.
    Do some anonymous bloggers still make use of social media?
    And since I’m new to it, do you have any recommendations for info on utilizing social media (for blogs)?

    1. Ramsay

      I think if you’re anonymous you’d make your social media accounts as if they are owned and run by the website itself – sort of how multi-site authors do it. It’s all a bit of a guessing game though – every site and niche is different.

  • Daniel Daines-Hutt

    Hey Ramsey,

    Number 4 is the scariest and definitely the most important.
    We are not fully there, instead only taking on premium clients in industries that we are interested in working with.

    This means more time to work “on” our business and not in it.
    I think it also signals a move that you are now treating the blog as a professional business.

    Recently found your site and powering through the content!


    1. Ramsay

      Glad the content is helping. Thanks for the feedback.

  • Jess Thomson

    Great post Ramsay. Nice to hear about your journey and the lessons you’ve learnt along the way. It’s valuable to hear that success is a winding road for everyone. Keep it up!


    1. Ramsay

      Thanks, Jess. How’s your stuff going?

  • Linda

    Hi, I also wanted to blog anonymously and started out that way (even under a different name), but that did not go on too long. Along the way somewhere I came across an article on Google h-cards and realized to be anonymous is not going to get me anywhere.
    That is why my gravatar is not fixed yet – should probably fix it sometime.
    Thanks once again for a great post
    Keep well,

    1. Ramsay

      Thanks for commenting Linda.

  • Saqib Ahmad


    Ramsay, Well You wont believe that I showed my face to my reader on the first day of blogging 😀 that Becuease I also do video blogging. I have started my blog last month and already received the great resposne. As I am currently on blogspot platform so things are limited for me. But, I will going to continue in it since for now I am focusing on bulding blog readership.

    Thank You

    Best Regards,
    Saqib Ahmad

    1. Ramsay

      Best of luck!

  • Vitaliy

    Interesting insights, Ramsay! I have always been cautious about the length of my page titles but I admit I don’t pay that much attention to it. (for example I don’t double check with MOZ)

    Although using a catchy title is something that everyone does here and there, I like how you put the importance on making a purposely controversial title, while systematically backing up your views. It’s no surprise why a post like “Why I hate Copyblogger” would get featured on a place like Copyblogger itself! Of course this pales in comparison to the more extreme things you can do such as getting rid of your clients to focus on your blogging efforts and deciding when/how to provide identity to your posts (including adding the picture and so on)

    1. Ramsay

      The length of page titles is very important once they are ranked in Google, but before that it’s not so important.

  • Ryan Biddulph

    Hi Ramsay,

    Before you showed yourself I thought BT was a shadowy figure blogging from a basement in India or something. No joke. I also thought that, although I wanted to believe your 20K share, at that time, well, I doubted it on some level. Only because I could not see your face. I could not see you were human.

    Far and away that was one of the best moves of your career. You went from clever guy who posted on ProBlogger a few times to branded, human, beyond likable star. So glad you made that choice.

    As for me, trashing 3400 posts from my old blog, and deep sixing that bad boy, to make room for Blogging from Paradise was the life changing decision for me. It took some cajones but I knew deep down it was the right choice. Your intuition always knows the way.


    1. Ramsay

      Interesting how adding the face to the site changed your perception of trust, even though none of the facts changed. I had often wondered about that. Thanks for sharing mate.

  • Marla Russell

    Hi Ramsay,
    Just started a blog a couple of months ago and found Blog Tyrant while researching. You have been invaluable and I’m sure will continue to be. Wanted to comment on number 5. I find it wonderful to have other eyes looking and minds sharing ideas! It’s the old “whole is greater than the sum of the parts” adage. You just have to find the right minds.

    1. Ramsay

      Absolutely. I do have a few friends who I see regularly and we chat about all of our shared online business experiences. Uni definitely wasn’t that inspiration for me personally, however.

  • Cathy Mayhue

    I have seen couple of people doing this, cultivate a mystique around themselves by writing under a pseudonym, build up the suspense about the identity and one fine day expose themselves, thus getting maximum attention. You pulled it off similarly and in a big way. You blogging on the couch presents a very impressive picture.

    1. Ramsay

      Thanks Cathy!

  • Slavko Desik

    You had some serious turning points man. When I think about my career (first time calling it for what it is btw) I see how most of my decisions were rather slow to make, and almost always helped by circumstances. Say what you will but you man have the guts.

    Leaving college, and deciding to abandon your client part of the business, takes a very determined mind.

    Here are few of my game changing decisions.

    -Partnering up with the right person.
    This one is being lucky more than anything else. The guy I work with is a friend of mine, and we go way back- elementary school. More than three years back I came up with this crazy idea to make a site and earn money out of it. Nothing was ever the same.
    He runs the technical side of things, and shares the weight of every business decision along the way. I often times joke that what I do is writing and content strategy only.
    Advice for those starting now- partner up if you can. Not only you will share the load of responsibilities, but you will grow your online biz way faster, and much further. And between talking business with your partner and allowing him to step up when you are obviously reluctant to take the lead, passion almost never dies.

    -Another huge decision that we made is attempting to monetize when it made sense. This is different for everybody, but try to do it early, and you might never learn what it takes to do quality work (will be obsessed with searching for easier ways to scale); postpone more than you should, and there lays the danger to never start earning and quit. Luckily we made it just in time, by starting to rank workout reviews and earn affiliate commissions. Today, they pay the bills for both of us, and then some.

    -Few changes in design and content strategy, but this came natural over time; outsourcing for things like guest articles and PBN’s was a huge step though.

    -Finding the right affiliate partners. Making the same number of sales, but increasing the percentage. Our paycheck nearly doubled just by finding the right network and vendors.

    -Forgetting college altogether. I haven’t dropped out yet, but having in mind that more than a year passed and I forgot what the building looks like… It’d be a wonder if they still keep my documents in file. This boils down to fear of failure. When you stop be afraid of your business breaking apart, such decisions are far easier to make. Like when you decided to forget clients altogether.
    For me this was the moment when I earned enough money to realize that college will never match what I have going now. If you have a B plan it is distracting as hell. Find the perfect timing when you can ditch it. There is time for hesitation, and there is time for decision. Know which is which.

    -Decide to create and sell something. By far the most exciting turning point. Still doing the turn though, so I cannot predict things ahead but trying to look at it objectively, this can be huge.

    Been a while since I opened up my RSS feed. Your articles always make me rethink a lot of stuff.

    1. Ramsay

      Always a pleasure to have you here, mate. Your comments are always very insightful. Sounds like you’re making some brave decisions too!

  • Dewald Swart

    Your site does indeed help allot of bloggers. The content you write about is so intriguing that you just have to read it. Not only is it interesting to read but has practical applications.

    1. Ramsay

      Thank you.

  • Vishal Ostwal

    “Getting noticed” has always been a problem for me, since I wasn’t much comfortable with it.

    People slowly notice, observe, and judge my work. And that’s where I might feel a bit of nervousness.

    For first few initial months, I didn’t feel like posting and sharing my work due to some kind of insecurity which I faced. But slowly I realized that there was a need for me to exist out there, instead of hiding in my corner of world.

    It has taught me a lot.

    Anyone should really dare to open up, and try to be their own brand. More than that – Don’t fear. Everything becomes alright very soon.

    Also, every good thing ultimately follows your hard work. (Great to experience that it works!)


    Don’t fear to be what you want to be.

    Focus on work, more than results at the beginning.

    Be like you.

    Keep creating stuff, even if it isn’t perfect.

    That’s all..I guess that we all bloggers feel and learn the same kind of things, isn’t it?

    (Maybe I got a bit more touched by this topic, or else why would’ve I written such a long comment)

    Bless you, Ramsay!

    1. Ramsay

      Epic comment! Lovely to see you here, friend!

  • Richard Huckle

    I just wonder what advice you would give the whipper-snappers out there about planning for the day your retire?
    Yes, it does happen – you grow old & decrepit! Just visualize the day you begin to struggle to get off that lovely couch of yours.
    Scary, hey?
    So what about pension plans, investments and hiring a financial adviser?

    1. Ramsay

      That all sounds like very wise actions to take, but it’s not my area of expertise so I don’t cover it here on Blog Tyrant. Thanks for the reminder, though.

  • Sarah Beeson

    Wow Ramsay, you’ve made some pretty bold decisions over the years!

    I left uni too after having that moment of ‘this is not what I want to do’ and it wasn’t an easy decision but definitely a good one! It’s awesome to see that others have had that moment too.

    I think my biggest life changing decision was moving to the other side of the planet. Man I love Australia, but there’s a whole different world out there and leaving it wasn’t that hard, but deciding not to return permanently was tough.

    I haven’t come across any life changing decisions yet with my blog but I’m really looking forward to that point where I can. There’s nothing like a scary decision to energise you and propel you forward!

    Thanks for sharing =)

    1. Ramsay

      Do you get back here much?

      1. Sarah Beeson

        Only been back once in 5 years (my family come over here loads thankfully) but coming home to Adelaide for a visit in October. Counting down! =)

        1. Ramsay

          Shoot me a message if you want to catch up.

  • Srikanth

    thanks for sharing your experiences
    it will be helpful..
    thanks again

    1. Ramsay

      Thanks for commenting!

  • Hammo

    Great Post! My biggest career move was to quit a 6 figure job, so I can work on being more creative. I’ve tried the grind and it’s way too slow a process.

    Quitting work gives my more time on the things I love to do. I now just need to learn how to make a living doing them.

    1. Ramsay

      Do you regret that change to a blogging/online career?

  • Linda

    I have done 1,2 &3 and am now seeing great results! Including being asked for an interview on a New York radio show. Thanks for all the gems! And for encouraging the unmasking! You are a star.

    1. Ramsay


  • Donna McDonald

    I feel like something is missing in my life.Being a parent and being home with my family was amazing but they are beginning college and I desperately want to earn my own money and respect from my husband but more for myself.i don’t have anything to sell but I have things to say to help others.without selling anything and by blogging about life in general, how can I earn money or where does my money come from.i feel led to do this and really want to try.please help me by answering my questions.id like a few examples of what people who make money blog about.