Jenna Rainey


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I’m Jenna Rainey. 

I'm an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.



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A highly creative nerd with a unique breed of humor and the proud earner of a self-bestowed award for being the world’s most curious and driven human.

Hey I'm Jenna!

(with me)


It’s like Netflix-binging Bob Ross videos, but with a dose of dry + quirky humor and fewer happy little tree references. 

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biggest mistakes when creating a website

The Biggest Mistakes People Make When Creating a Website with Jen Olmstead

Business Resources


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What are the biggest mistakes people make when creating a website? Is it the images? The speed the website loads?

A well thought-out, beautiful website design is hugely important for introducing your brand to your customers.

My first website was a Squarespace site I designed myself that was almost all black and white (Have you seen my artwork?! There's nothing black and white about me.). For my second site, I had a custom-designed WordPress site and it worked, but there was room for more of my vibrant personality.

And then Jen Olmstead and Jeff Shipley from Tonic Site Shop came into my life in 2019. Jen designed the stunning, colorful, bursting-with-personality ShowIt/Wordpress website you see today and I couldn't be more thrilled with it. This isn't apples to apples but you get the idea:


Throughout the process of working with Jen and Jeff, I learned that there's so much more to website planning than color schemes and pretty fonts—you've got to have a clear brand story.

Related Post: 10 Killer Website Copywriting Tips

Because Jen is SO knowledgeable about intentional website design and killer About pages, I knew I had to bring her on the show and share her wisdom with all of you. (Plus, witty banter is her love language and so it's always a blast talking to her.)

Side note plug…If you're in the market for a new website—whether one that's custom designed or a beautiful drag and drop template for a fraction of the cost—go check Tonic Site Shop and see for yourself why their customers are raving.


Stellar insights

  • [05:17] “I realized that when you made something [website, magazine, newspaper] really beautiful, people paid more attention to it and they actually read it.”
  • [06:51] The biggest mistake Jen has seen people make is not starting their website with a thoughtful plan and intention.
  • [08:29] A brand interview is a great way to get clarity about what people most value and appreciate about your brand.
  • [12:34] Jen highlights the importance of authentic copy to go alongside beautiful visuals.
  • [14:41] Another huge mistake people make is not clearly stating on their site what they do and who they do it for.
  • [18:16] The About page is really about “how you can help the person who's on your website get what they want.” And remember, people want to connect with people.
  • [20:36] Include stories on your site that help people know, like, and trust you.
  • [25:37] Jen discusses the differences for desktop vs. mobile design and making sure you're giving plenty of content on both.
  • [28:46] Treat your homepage as a landing page with snippets of everything that's within your site.
  • [32:40] Jen weighs on on the ultimate WordPress vs. Squarespace debate (and why she loves ShowIt).


Rapid Fire Questions

What's your best time-saving hack? I love Slack. We use Slack all the time. It saves us from writing emails. Slack is like instant messenger. Um, but for your business and I didn't realize I was great at instant messenger in high school. That's like one of my primary life skills. And now that's translated well to Slack complete with these slightly emo song lyric away messages.

What is your best organization hack? Oh gosh. I don't know if I have an organization hack. I was telling Jenna before this podcast that I literally found my podcast mic at the bottom of my closet. I found the cord for it in our storage room and like the dongle, which is a terrible word by the way in my nightstand table. I'm the least organized person of life, but we do use Asana and I do think that Asana can be a great situation.

Oh, I do have an organization hack and that is I use this amazing app called Huckle &. Goose, this app for cooking. This is not an affiliate link, but I do love it. And basically it's like your friend, who's a really good cook, sends you five recipes each week that you should make some time. Huckle & Goose. It's amazing. I love the people that run it, Christine and Anka. And they're amazing. Huckle & Goose is incredible.

What is the best advice you've even been given? Okay. So we actually just posted it on our Tonic Site Shop feed because this is my favorite quote ever. I'm not going to read it cause it's really long, but it's basically Ira Glass, who is the person behind This American Life podcast. And he basically is talking about how, when you start out as a creative, you have something that makes you great and it's not really talent. It's your taste. And your taste is: you know what's good but your talent is not there yet. And so you're not able to create stuff good enough that your taste says this is good.

And basically he says that it takes time to close that gap. And essentially the way to close that gap is just to keep creating. And so I think a lot of people kind of burn out or get frustrated before that gap is closed and they're like, I just suck. Like that's what it is. I just need to stop. And I think what Ira says, I just love it. Cause I feel this frustration all the time. I'm arguably a good designer, but I can totally get trapped into like Pinterest comparison where like I just shut my computer. I'm like, I should never do this again. Cause there's so many better designers out there and I'm sure you've experienced this as an artist. Like you see other great art and you're like, I am terrible. What am I even doing? Like I'm going to stop now. Or drink tequila soda with lots of limes. And basically I just love that. He says like, keep creating, turn out work, give yourself deadlines, finish the stuff that you're starting. And slowly that gap is going to be closed. And you're going to be able to create work that feels in line with what your taste says should be good. And I think that that was just immensely encouraging.

What is the book you've recommended most to other people? Probably Building a Story Brand like I just mentioned earlier, that's definitely one of my favorites. I also love Steal Like an Artist by Austin Kleon and basically says you don't want to look like your heroes; You want to think like your heroes and kind of teaches you how to take inspiration without copying, which I love. And then most recently I loved The Dutch House by Ann Patchett, which is written by of what, sorry, which is read by Tom Hanks on audible. And I didn't realize that I wanted Tom Hanks to read everything to me, but I was like, this is like, You've Got Mail but 12 hours long. And I love it.


Subscribe & Review

If you had an ah-ha! moment or learned just ONE new valuable bit of information, I'd be so grateful if you would leave a 5-star review and tell me what you love most about this podcast. It's a HUGE motivator for me to keep creating this for you. In addition, it helps our raking in iTunes so that more people discover this show.

And to make sure you never miss an episode (including any pop-up bonus episodes), click here to subscribe on Apple iTunes!


Links mentioned

*This is an affiliate link which means that I may receive a small commission at no extra cost to you. This helps me be able to produce free, valuable content for you. Thanks for your support!


Related Episodes

Episode 43: How to Elevate Your Brand Through Visual Storytelling with Nick Onken
Episode 34: 10 Killer Website Copywriting Tips
Episode 41: “Should I Have a Blog?”
Episode 9: Tips for Overcoming Imposter Syndrome
Episode 11: Tips for Finding Your Artistic Style

by Jenna Rainey 

add a comment

  1. Reese Forêt says:

    Thank you. Thank you. Thank you! I think I found you through Pinterest and I’m never never going to let you go. Lol!
    Seriously though, I’m currently binge- listening to your podcasts and, boy are they full of golden nuggets! 🌟
    Thanks to you and all your friends, I feel the pandemic funk leaving my creative nest. Powerful stuff! 🙌👏👏👏💛

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