Why I Moved My Website Away From Squarespace

Wordpress vs. Squarespace is a common on-line debate, so why did I decide to move my website from Squarespace to Wordpress?


I decided to move my website away from Squarespace.

When I started my blog on February 23rd, 2016, it was on a total whim. In 48 hours I created the logo, bought the domain, designed the site, and wrote four blog posts. I was an emotional woman on a mission. I felt confident in my Squarespace skills, and while I had used WordPress many times over the years, I never loved the interface and how easily things could break. While I knew enough about coding to get by, I wanted to get TCM up and running and didn’t want to deal with finding a host, template, coding, and all that jazz. I wanted to drag and drop my vision onto a white screen and have it up and running in minutes, which Squarespace provided me with. Squarespace rarely had any down time, was always secure, and… well it was simply put: easy.


I know the great debate in the blogging world is WordPress vs. Squarespace, too which I always rolled my eyes.

  • Silly WPers, Squarespace has great built in SEO! My site in 7 months began ranking around 70,000 in the U.S. and 500,000 in the world. While note exactly where I wanted it to be, in 7 months it was pretty good without ever spending a penny on ads.


  • And sure, I can’t customize my Squarespace site like you can your WordPress site, but I had found a nifty hack where I simply created pages for my categories to look just how I wanted it too…


But then it happened, I got the notification that I could not create another page without upgrading my account… So I deleted a page and re-tried. Again the notification that I had too many pages and needed to upgrade my account… I deleted 5 more pages and tried again… Only to receive the same notification.

Hurriedly I counted my pages, I had around 30. Squarespace’s basic plan allowed up to 20 pages for $96  per year (normally $120 per year, but I signed up with my student account to get a little extra discount). The upgraded account would cost me $18-26 per month. At that time, I thought it was insane to spend basically $200 a year just to host my site since I always see people in Facebook groups talking about hosting for $3 per month and with Squarespace there was a significant time investment per post for me formatting each post to look just right since they weren’t really a part of the template.

What I didn’t realize, was just how expensive hosting would be to match the security level and size of Squarespace… and that in time, I will likely be paying more than $20 per month for hosting and other services that were simply included with Squarespace (seriously, I cannot believe how many plugins cost money and that stuff was simply free on Squarespace!).  But, that’s in time, and right now it’s definitely cheaper to be on WordPress than Squarespace.

Also, a little back story, a month or so prior I had made the decision to fade out my career coaching services. I am simply put, not passionate about it anymore. I work with some amazing career coaches and can gladly still make referrals, but it doesn’t light me up the way it once did. So if you all heard me talking about a mini-rebrand coming to the blog at the end of the year, I was referring to phasing out rachelritlop.com, revamping my services, and bringing those contents in-house to TCM. I certainly did not expect to move my site to WordPress, design a new logo and site, and well have a panic attack the week before Thanksgiving.

But here we are, with a new site, which I have grown to love and I hope you will love too. In the last two weeks, I spent 16 hours a day working, researching, and trying to fix things… and breaking a few things.

While breaking those things and feeling like I was in a digital sea of confusion and desperation – I got to a point of “F* it! I am just going to revamp my Squarespace site, screw this!”



I came across this blog post, which basically says Squarespace can terminate services and leave you high and dry without notice or penalty. Pretty scary if your blog is a major source of income for you like it is for me.

For that fact alone, I feel better about my decision to move. While I still strongly recommend Squarespace to new digital entrepreneurs and bloggers, because the likelihood they will just shut down or shut you down is pretty slim, it simply wasn’t for me anymore as I grow my site.

And the switch to WordPress from Squarespace was SO easy – it was only complicated because I didn’t love the template and was hacking the look of my site together with funky root url’s, gallery boxes, and grids to get it to look just right – which led to a lot of clean up and all of my comments not auto-populating from Disqus right now! GRRR – if anyone knows how to fix this let me know! All of the comments are on my Disqus channel, but just aren’t showing up in the posts here! How frustrating! Also for some reason, the font I uploaded still doesn’t seem to be sticking all the time. So if you are seeing any serif font, that’s not actually part of my final design. But I know I need to take some deep breaths because the design and comment kinks will work themselves out soon!

If you guys notice anything is broken, wonky, or simply have tips or suggestions, feel free to drop me a comment or e-mail me!

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  • Candy Kage
    November 26, 2016 at 11:30 am

    Didn’t know squarespace had that clause in there. I love my wordpress and haven’t had any problems.

    • Rachel Ritlop
      November 28, 2016 at 9:00 am

      Right! Super sketch. That’s good to know there haven’t been issues! Change is always scary haha

  • Brittany L Carson
    November 26, 2016 at 11:38 am

    i’ve been with WordPress from the beginning. I haven’t had any problems. Hopefully you will grow to love it just as much as SquareSpace 🙂


    • Rachel Ritlop
      November 28, 2016 at 9:01 am

      I am slowly already! I think my anxiety is just high with how many things there are to consider and pull together, but I am really liking it so far and it’s not as scary as I thought! What plugins do you recommend/use?

  • Yana | Smile Is It
    November 26, 2016 at 12:13 pm

    I love WP. I already had an eCommerce website with unlimited hosting for about $20/month, so my decision to stick with WP was natural. I don’t know anything about Disquis comments, but I fixed font in my blog through WP Add Custom CSS plugin. See if it can help you.

    • Rachel Ritlop
      November 28, 2016 at 9:01 am

      Yeah I had an extra } in the code! It’s all fixed now! Thanks!

  • Melissa Chee
    November 26, 2016 at 3:04 pm

    Very interesting post. I’m currently on squarespace because it’s so easy for me.

    • Rachel Ritlop
      November 28, 2016 at 9:02 am

      Yeah I still love it! Haha but after being on WP this last week, it’s not as scary or difficult as I had built it up in my head thankfully!

  • Becky @Disney in your Day
    November 26, 2016 at 3:42 pm

    Really interesting. I’ve never used Squarespace but I didn’t know all of that stuff about it.

    • Rachel Ritlop
      November 28, 2016 at 9:02 am

      What is your site on Becky?

      • Becky @Disney in your Day
        November 28, 2016 at 7:41 pm

        I’m on wordpress. I started with a free wordpress.com site and then transitioned over to paid one on wordpress.org.

  • Seersucker Sass
    November 26, 2016 at 4:09 pm

    I’m so excited for you in making the switch! i’m trying to block out some time to move my blog over to WordPress, and I’m terrified, but I know it will be worth it in the end.

    XO, SS || Seersucker Sass

    • Rachel Ritlop
      November 28, 2016 at 9:04 am

      Haha thanks girl! It’s all done and I am really happy! I think it’s definitely worth it. Have you chosen your template yet? For two weeks before I made the switch, every blog I went to whose template I liked, I would open the designers site and book marked it until I narrowed it down. My template comes with 6 months of support which totally sold me on it! That helps make the transition even easier than I could’ve ever imagined! I have some posts coming up about it over the next few weeks!

  • Annissa Slusher
    November 26, 2016 at 7:17 pm

    We started our blog in WordPress.org and I’m so glad we did! Congrats for making the change!

    • Rachel Ritlop
      November 28, 2016 at 9:04 am

      I am totally happy I made the change too! It was way easier than I thought

  • Kaitlyn Fickle Killebrew
    November 27, 2016 at 2:26 am

    I recently switched from WordPress.com to WordPress.org and the decision has changed my experience completely! Congrats on the switch 🙂

    • Rachel Ritlop
      November 28, 2016 at 9:04 am

      Thank you! And congrats on your switch too!

  • Kari Jonard
    November 27, 2016 at 10:06 am

    Interesting. I’ve never heard of squarespace. Hopefully you will start to enjoy wordpress even more. There are a ton of great plugins.

    • Rachel Ritlop
      November 28, 2016 at 5:57 pm

      Thanks Kari! I am definitely enjoying it, I need to figure out how to speed up my site though! Any suggestions on plugins for that or security would be awesome!

  • Amelie
    November 27, 2016 at 11:56 am

    I’ve heard a lot of things about WordPress vs Squarespace. I personally cannot really tell you which one I think is better because I’ve never experienced Squarespace! But I do love WordPress and I find it pretty easy to use. Congrats on the switch!

    • Rachel Ritlop
      November 28, 2016 at 9:05 am

      It really is a lot easier to use than I thought it would be! And Thank you! Do you have any “must have” plugin recommendations?

  • Claudia H. Blanton
    November 27, 2016 at 1:34 pm

    before moving my blogs from the free wordpress.com to wordpress.org I dabbled a little with Wix.com, which is slightly like Squarespace, but not as good, and I hated it. I guess being used to the interface of the free blogging site, the switch to the self-hosted wordpress sites was much easier and intuitive for me. I thought for a breath to go to Squarespace, now I am glad I didn’t I also depend on the income of my websites. Blessings!

    • Rachel Ritlop
      November 28, 2016 at 9:06 am

      Yeah I’ve used wix for some temporary stuff (wedding website). I actually like it, but could never imagine running my blog on it. And truth, #blessed! do you have any “must have” plugin recommendations?

  • Nicole Parise
    November 27, 2016 at 2:00 pm

    I started with wordpress, so I can not relate, but glad that you are happy with the switch! Sounds like it is better financially 🙂
    xx nicole

    • Rachel Ritlop
      November 28, 2016 at 9:06 am

      Thank you Nicole! Definitely happy about the switch. Do you have any “must-have” plugin recommendations for wp?

  • chevyd80
    November 27, 2016 at 5:51 pm

    Congratulations on moving your website to wordpress for better. I learned the hard way that if you want to start a blog use wordpress.org and not wordpress.com, Rachel

    • Rachel Ritlop
      November 28, 2016 at 9:07 am

      Haha yeah that would’ve been a frustrating lesson! I’d been on WP both .com and .org over the years so luckily that was easy haha. Thank you!

  • Jessica Lam
    November 27, 2016 at 10:01 pm

    A company I was working for used Squarespace, and I didn’t like it at all! I’m a total WordPress girl as well haha, I’ve used it while working for a few companies and I use it for my own blog, it’s great!


    • Rachel Ritlop
      November 28, 2016 at 9:08 am

      Haha why didn’t you like it? You definitely have wayyy more freedom with WP which is fun! Any plugin recommendations that are must haves?

  • Sara
    November 28, 2016 at 7:42 am

    I moved from Blogger to WordPress a few years ago and had a hard time getting used to it, but I was never a huge Blogger fan. I’m sure the switch has been trickier for you if you love Squarespace! Your site looks great, though, and I hope that you’ll one day find the perfect set up. (:

    • Rachel Ritlop
      November 28, 2016 at 9:09 am

      The switch was actually super easy and I do like the site. I think it’s just change that freaks me out haha Thank you!

  • Miss ALK
    November 28, 2016 at 8:58 am

    I’ve been on Blogger for over four years and am still happy, but this was an interesting perspective on Squarespace!!

    xoxo A

    • Rachel Ritlop
      November 28, 2016 at 9:10 am

      I know so many people who love Blogger! I’ve never used it! I always thought your site was on WP and realized today actually because of your commenting system that you were on blogger lol

  • Lecy | A Simpler Grace
    November 29, 2016 at 9:10 am

    These are things about Squarespace that I did not know but am glad to. I’m still a Blogger girl but will likely make a switch soon, so any info about the other platforms is helpful. Thanks for sharing!

    • Rachel Ritlop
      November 30, 2016 at 6:18 pm

      You’re welcome! I have a few more posts coming about the switch and tips on choosing a host and theme that I hope will be helpful too!

  • Tawni Sattler
    November 29, 2016 at 9:42 am

    I think the Disqus issue is actually just a Disqus issue. I’m having the same problem with comments not auto-populating to my site. I’ve tried to get help but, alas, nothing. Anyway though everything looks great and I’m glad you’re happy with your decision!!!

    • Rachel Ritlop
      November 30, 2016 at 6:17 pm

      Thank you so much Tawni!

  • Siow Chei Lew
    November 29, 2016 at 10:39 am

    Thanks for sharing your experience. I know of bloggers who had been sitting on the fence between WordPress or Squarespace would benefit from this. Looking at your analysis, I think WordPress would be better for most bloggers because they charge by pages, while business owners may benefit from the quick set up and ease of use.

    • Rachel Ritlop
      November 30, 2016 at 6:17 pm

      The blog posts aren’t counted into SS “pages” – I had a 150 blog posts, and 30 pages. They get counted into as one, so it’s actually a great set up for bloggers! It’s just if you are generating income from your site – its scary they could shut it down and you could have nothing in the end with no recourse based on their TOS!

  • stefanie schoen
    November 29, 2016 at 11:59 am

    wordpress is hard to get used to but SO MUCH better in the long run!


    • Rachel Ritlop
      November 30, 2016 at 6:16 pm

      I am really liking it and it hasn’t been as difficult as I thought it would be!

  • Kristie McCollum
    November 29, 2016 at 1:11 pm

    I never used Squarespace, I started with WP so I can’t say I agree lol. But I do love WP! Hate that you had a not so great experience before converting.

    • Rachel Ritlop
      November 30, 2016 at 6:15 pm

      Thanks so much! I am liking WP!

  • Greta Hollar
    November 29, 2016 at 1:29 pm

    I started using WP and learned a lot when I first started blogging. But now that I took classes and figured it out I love it!

    Greta | http://www.gretahollar.com

    • Rachel Ritlop
      November 30, 2016 at 6:15 pm

      Yeah I am really liking it so far!

  • nicole simonetti
    November 29, 2016 at 2:28 pm

    I’ve always used wordpress & blogger but have a few friends w/ squarespace sites so it was super interesting to read your feedback knowing what they’ve told me about squarespace! so scary that they can just turn your site off without any notifications though… x, nicole // http://www.nicoleeigh.com

    • Rachel Ritlop
      November 30, 2016 at 6:14 pm

      Right! And you never think to back up your site when you’re on SS – so scary!

  • Anna Moore
    November 29, 2016 at 3:07 pm

    Hi Rachel! I’m glad my article was somewhat helpful for you! I, myself, thought about trying out Squarespace when it first came out, but after reading the TOS there’s no way I wanted to go anywhere near them. I just couldn’t risk that for what puts the food on my table, ya know? It doesn’t make sense to me for business that rely on their income to be on that platform.

    I’m glad WordPress is working out for you! The site looks great 🙂

    • Rachel Ritlop
      November 30, 2016 at 6:13 pm

      Thank you so much Anna! And thank you for writing such a helpful post!

  • mckenna bleu
    November 29, 2016 at 3:59 pm

    I use WordPress and I love it! Im also just used to it becuase i’ve used it for so long. It sounds like your gonna like being on WordPress!

    • Rachel Ritlop
      November 30, 2016 at 6:13 pm

      I am definitely enjoying it!

  • Jenny
    November 29, 2016 at 4:01 pm

    I was never on Squarespace but I switched over from Blogger over a year ago and never looked back. WP has a bit of a learning curve but I have been able to learn so much over the past year.

    • Rachel Ritlop
      November 30, 2016 at 6:13 pm

      And your site looks awesome! I am liking WP a lot so far!

  • DwellBoxes
    November 29, 2016 at 5:56 pm

    I went from Blogger to WP. Blogger was so nice because everything was done. But the learning curve that comes with WP is exhilarating! Every time you need a new plugin its like getting a shiny new toy. I love it! 🙂

    • Rachel Ritlop
      November 30, 2016 at 6:12 pm

      haha I love that word choice! It is exhilarating! haha

  • Silvia Marquez
    November 30, 2016 at 12:56 am

    Great post! I never thought of other websites but WordPress (mainly because it felt like everyone was throwing them in my face!) and it’s quite easy for me to use.


    • Rachel Ritlop
      November 30, 2016 at 6:12 pm

      haha yeah if you start with it, I think it’s super easy. I had a designer do a site for me a few years ago and he scared the be-jezus out of me that I would break something that I became super scared to use it in the end!

  • Berniedette PetiteAndToned
    November 30, 2016 at 1:47 am

    I absolutely love wordpress! But I made the mistake of initially hosting with wordpress, but moved over to site ground.

    • Rachel Ritlop
      November 30, 2016 at 6:11 pm

      I didn’t even know you could host with WP! Is that WP .com vs .org?

      • Berniedette PetiteAndToned
        December 1, 2016 at 12:16 am

        Oh I know self hosting OUTSIDE of WP is .org. So I think hosting with WP is .com… anyways, I had to switch to the .org version because there were so many themes that required the .org hosting service. So I totally “wasted” $100 with WP. Oh well

        • Rachel Ritlop
          December 1, 2016 at 5:46 pm

          Lol ok that’s what I thought! haha Oh man! That learning curve stinks!

  • Shane Prather
    November 30, 2016 at 8:49 am

    I honestly don’t know much about square space but my transition from blogger to WordPress was tedious upfront but well worth it in the end!

    • Rachel Ritlop
      November 30, 2016 at 6:11 pm

      Oh gosh talk about tedious! I had to remap so many urls because i had done some dome ish on SS. Your blog looks great now! Totally worth it!

  • Ashley Vickney
    November 30, 2016 at 9:08 am

    This was so informative and in-depth Rachel! I used to blog on Blogger, but wanted to move to WordPress when I re-branded at the beginning of this year! I really like all of the things that I can do with it, and it’s so easy to use! I’ve heard of sqaurespace but never thought of it as a blog platform until I saw that you were moving from it!
    Also, everything looks great on your site!

    • Rachel Ritlop
      November 30, 2016 at 6:10 pm

      Thank you Ashley! Yeah WP is surprisingly easier than I thought it would be!

  • Kristine Circenis
    November 30, 2016 at 10:25 am

    Thank you for this post. I am in the process of making my blog a more steady revenue stream for myself, which inevitably comes with self-hosting and all of the fun things that come along with that. I have been doing research about switching to a new platform and it’s reassuring to hear that I’m making the right move by choosing WordPress moving forward.

    • Rachel Ritlop
      November 30, 2016 at 6:09 pm

      Definitely! I am going to be sharing a few posts about the transition (choosing a host, choosing a template, blogging checklist) over the next few mondays! Also working on bringing back the wedding wednesday series this month! What questions can I help you with specifically? I was planning a post on how to choose a venue (this post is gold, not to toot my own horn but I am really excited about it), as well as how to choose details, grooms gifts, bridesmaids gifts, etc.

  • Alex
    November 30, 2016 at 10:39 am

    Wow, this is so interesting! I currently use blogger, but really want to transfer over to wordpress

    • Rachel Ritlop
      November 30, 2016 at 6:08 pm

      I definitely have been liking it more than I thought I would! I am going to do a series in the coming weeks about the move more in detail with some helpful guidelines to make it easy!

  • Autumn Dickens
    November 30, 2016 at 12:20 pm

    I just moved to Squarespace last month and so far it’s okay. TBH I was expecting more but it’s definitely allowed me to be more creative compared to my Blogger blog. I’m honestly terrified to move to WordPress. It just seems like a bunch of coding work and confusion and I’ve read so many horrific stories of peoples blogs just erasing themselves. So I guess there isn’t really one perfect platform out there yet. Haha. But WordPress is definitely still a future option for me, I’ll just have to hire someone to do it so I won’t break anything. lol. LOVE the new layout btw. 🙂

    • Rachel Ritlop
      November 30, 2016 at 6:07 pm

      Yeah I noticed you were on SS now, I actually sent your site to a reader who is using the same template as you to show her an example on the header/menu bar! Lol – And I am going to do a series the next few weeks about the switch in more detail – it was honestly SO much easier than I could’ve ever expected! I do have a little coding background, but not a ton, and felt really confident. I moved everything and cleaned it all up in under two weeks!

  • Katie
    November 30, 2016 at 3:42 pm

    I am currently on Blogger but loved hearing more about the difference between Squarespace and WordPress as well as your personal experience with it!


    • Rachel Ritlop
      November 30, 2016 at 6:05 pm

      Thank you so much Katie!

  • sandsunandmessybuns
    November 30, 2016 at 5:57 pm

    We’re our own worst critics when it comes to our blogs, aren’t we? I haven’t noticed any wonky links on your site and I’m seeing a sans serif font on my end. Wish I could help with the comments, but I don’t know of any solution. I loved your opener about being a woman on a mission. lol
    xoxo, erin | sandsunandmessybuns.com

    • Rachel Ritlop
      November 30, 2016 at 6:05 pm

      Lol thank you! and it’s because I fixed the fonts 🙂 It just took a day haha And I am still sorting out the link and comment stuff, but oh well! IT will get fixed in time! Patience is a virtue they tell me lol

      • sandsunandmessybuns
        November 30, 2016 at 6:10 pm

        One I’ll develop someday, I hope! lol I post in the FB groups whenever I’ve tried everything on my blog and can’t find a solution. There’s usually someone out there who has experienced something similar and figured it out. That’s always my last step before hiring someone to just fix it for me. xo, e

        • Rachel Ritlop
          November 30, 2016 at 6:19 pm

          That’s so smart! thank you for the suggestion!

  • Latasha| Arts and Budgets
    December 2, 2016 at 10:55 am

    Oh, wow! I also switched from Square Space to WordPress! 🙂 I truly loved Square space!!! It was so easy to set up and get things going.

    Since, moving over to WordPress I love it too- after I got over the learning curve, lol.

    Great post!

    • Rachel Ritlop
      December 2, 2016 at 8:37 pm

      That’s awesome! The learning curve has been fun! haha What made you decide to switch?

  • Finja
    December 4, 2016 at 6:00 am

    Wow. Ok, So there is a reason why I’m on WordPress even though I was actually thinking of moving to Squarespace, it just looks shinier from the outside. Glad I came across this post though.

    Cheers from London & Happy December!
    xx finja / http://www.effcaa.com

  • Arin Agase | Heart of Chic
    December 6, 2016 at 8:57 pm

    Good for you, girl! I made the WP switch a couple of years ago, and I’m so glad I did! Definitely over my head sometimes, but it’s so worth the headache 😉 http://www.heartofchic.com

  • allie blaising
    December 31, 2016 at 2:00 pm

    Okay, here I go–I think it’s time to transition to word press 🙂

  • Ashley Mason
    February 10, 2017 at 2:35 pm

    I’m on SquareSpace so this makes me want to reconsider! Thanks for sharing this!

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