It Takes Two – A Look Behind the Scenes of wit & whimsy

September 21, 2020

wit & whimsy

I started wit & whimsy in 2006 and for the better part of the last 14 years of its existence I largely did everything by myself. I had some contributors do a handful of posts between 2007-2009 from time to time (back in the day this was very popular for bloggers to guest post on other blogs!) but other than that I have largely maintained the site myself. So when my part time editorial assistant Kate approached me in 2016 asking if I may need help with wit & whimsy I said… “I’ll get back to you” – ha!

But fast forward four years later and Kate has become the best behind the scenes wing woman I could ever ask for. And an even better friend!

Truth be told, Kate and I met three short weeks after I had left my corporate job to become self employed so my life was very influx. It took me about four weeks to think about whether I was ready to bring someone onto the team part time but the more thought I gave it, the more I was willing to try it. And after we got coffee one morning I loved her so much & saw a lot of my self in her and clearly we hit it off as she’s been a part of the wit & whimsy team ever since August 2016!

wit & whimsy

wit & whimsy

wit & whimsy

wit & whimsy

wit & whimsy

Kate and I snapped these photos in Soho last year while I was shooting this post and this post with Jackie Clair. I just recently re-discovered the photos and figured it was high time to properly introduce my right hand woman behind wit & whimsy.

So what exactly does Kate do for wit & whimsy? Kate does a little bit of everything for me! She helps source pieces for various blog posts that I review before they go live (she is the queen of finding the best picks on Amazon Fashion!), she helps run quarterly Analytics reports for me, she does all the collages for the site (I was so happy to offload this task – I hate making collages!!), she helps a ton with graphics for Instagram Stories and a variety of other things that inevitably pop up.

I think one of the biggest misconceptions about bloggers and digital content creators is that it’s just taking photos and sharing links. But there is truly so much that goes on behind the scenes in order for sites to operate and posts to come to life. On average every blog post takes me between 3 and 10 hours. (The higher end being those related to collaborations so there’s a lot of coordination between the brand and myself related to negotiating, contracting, selects, post conception, invoicing, etc.) And I do five blog posts a week! (And sometimes six during the holiday season.)

By now you know I am very particular about what I share. I don’t just post to post or just post to make money. I put a great deal of thought into the links and pieces I share and as my brand has evolved, it’s meant greater attention to detail to build the brand and it’s meant more strategy behind the scenes.

In addition to just getting posts written + live, I shoot all the photography for them (including editing, resizing and naming each image), I maintain each of my social channels, work with an SEO specialist to draft + update SEO-friendly posts, work with a tech team to tackle the inevitable IT issues that pop up nearly weekly (newsletters not firing! being locked out of your site! formatting issues! broken widgets! spam! security compromises! I could go on and on…) I have elements of my site I work to keep fresh + updated regularly like The Shop, I am constantly obsessing over my analytics to inform future posts based on what you guys are clicking on and buying and there’s the constant stream of emails and reader DMs to keep up with. It’s a lot. I absolutely love it, but it’s a lot.

So having someone who has been able to provide stellar support the last four years along with being a sounding board and brainstorming partner has been so valuable.

I thought I’d have Kate answer a few questions so you can get to know her better!

What made you want to work for wit & whimsy?

I’ve been reading blogs for over 10 years and have always been fascinated by the industry of influencers. When I met Meghan at an event, I’d been reading wit & whimsy daily for a few years and loved the site as a resource for beauty, travel and fashion content. I chatted with Meghan for a few minutes at the event and after grabbing coffee at Ralph’s the next week, realized we had more in common than I knew. I really liked the idea of getting to see a little more behind the scenes of a blog I loved and everything that goes into keeping a site like wit & whimsy running. I never knew it would turn into a great friendship also!

What’s your favorite thing you do BTS for wit & whimsy?

I love putting together the collages! They feel like a puzzle – making all the items fit together just perfectly.

What’s something that surprised you about the blogging / content creator world working in it?

I thought I knew how much time went into keeping a blog running but I was seriously mistaken. The hours that go into shooting outfits (I’ve had the chance to join Meghan on a couple shoots!), linking all the products, setting up a post on the backend of WordPress, updating old posts, assessing analytics, doing SEO… it’s so much more work than it appears to the readers. And that is just one platform – I have so much respect for influencers like Meghan who balance a blog, Instagram, IGTV, Pinterest, etc.

Any highlights having worked with wit & whimsy?

I had the honor of traveling to London last year with Meghan for a press trip and it was the most incredible experience. We had the best time and I’m so grateful that she asked me to go. And of course, having Meghan as a friend is a highlight that I know will continue for many many years!

What’s something about Meghan that people may not know?

This question was so hard for me to answer because I think Meghan is so authentically herself that she comes through just as I know her on her blog, but the first thing that came to mind that may surprise people is that Meghan LOVES Shark Week! But really, who doesn’t?

What are your favorite blogs to read day to day?

My daily reads are Carly the Prepster, Atlantic Pacific, Hello Adams Family, The Style Scribe, The Stripe, Jess Ann Kirby, Carrie Bradshaw Lied, Damsel in Dior, Julia Berolzheimer and of course wit & whimsy.

Who are your favorite follows on Instagram?

In addition to following all my favorite bloggers, my favorite follows lately have been  @thegoodcarmablog (love her style & everything she shares on social justice), @mystylevita (newer follow but never miss her Stories), @ashleyspivey (love her book recs), @heathermcmahan (she is hilarious), @venitaaspen (her style & Charleston content are perfection), @tarynnewtown (her kids are adorable & loving following her home build), and @bethereinfive (for her pop culture deep dives).

. . .

I hope you enjoyed meeting Kate as part of today’s post and were able to get a better sense of wit & whimsy behind the scenes! Kate, thanks for all you do! I’m so grateful to have you as my w&w better half!


On Meghan: Sezane Blouse (similar here) // Agolde Toni Jeans (size 27) // Chanel Slingbacks (similar style for less here)

On Kate: J.Crew blouse (similar here and here) // Mott & Bow Jeans // Gucci Loafers (similar style for less here)

p.s. things I’ve bought and loved recently and my favorite flat.

[Jacqueline Clair Photography]

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