Keep Going: On Creative Process & Art Direction

How do you know when you're finished creating something and ready to release it to the world?

This is a question I get asked by other creatives. It's often one of the hardest parts of the creative process for me. And it's one of the (many) reasons I have Laura.

If you don’t know the full story: Laura and I met 14 years ago when she was working as a full-time wedding photographer and I was on staff at my church. It was friendship at first sight, and she’s been one of my closest friends ever since. I hold her opinion on everything—work, parenting, faith, marriage, decorating, etc.—in very high regard.

Also, we’re VERY FUNNY together, which just delights me. She’s like my sister. She's like that younger sister who's somehow also bossier and wiser than you.

Laura was the first female entrepreneur I ever met in real life. It was a pre-Pinterest, pre-social-media-business-era, and I didn’t know that a “regular girl” could start a business and be successful, like little Laura had. She was like: it’s not that difficult. You just work really hard and be good at what you do and treat people well and keep your receipts and file taxes.

(It’s safe to say this is an oversimplification of entrepreneurship, but it was enough to encourage me to start Lindsay Letters, and for that I’ll forever be grateful.)

Laura shot our first shoots for me completely free of charge. I had zero capital and paid her in props and art—which, for a minimalist like Laura, got overwhelming really fast. Finally she was like your friendship is enough and I started paying her in money as soon I could.

Business Tip 1: Yes, know your worth. But the things I have received and done for free have made some of the biggest impact, and have paid dividends in the end.

At a time when there weren’t any other non-big-box online art stores, I knew that photography and styling would be key to casting vision for my print-on-demand art across a webpage. (Something art.com, for example, hadn’t been doing).

I’d actually never seen a styled photo of art or an art print before. I had seen images of art in rooms, like in catalogs, but the idea of flat-lays and styled images and prop switching was something that I’d never seen before.

I was so inspired by Laura’s detail shots from weddings (something that’s expected now, but was ahead of its time then) that I just knew Laura’s unique photography, story-telling and styling skills would be a key ingredient in the success of my brand. I was right, and it’s one of the wisest choices I’ve made.

Business Tip 2: if you find someone who has that special something that you can’t place your finger on, that inspires, delights, and surprises you, do whatever you can to hire them. Even if it’s for a role that feels weird or undefined. I've done this with every member of my team, and it's one of the decisions I feel most confident and proud of.

Over the years, Laura’s grown in her own skills and transitioned from weddings to more interior design and interior styling, which has only made her more of an incredible blessing to my creative process and our team. After Eva’s accident, Laura stepped in as Art Director for LL (in addition to doing the photography) and that has been such an incredible asset and gift to me.

From the very beginning, I’ve always sent Laura images of what I was working on, or one-off texts with an image of my work, and questions like how’s this? and am I crazy?! 

Over time, I began to notice that the more ownership and insight she had into my work prior to actually shooting it, the more successful and cohesive the shoots became. When she became the official Art Director, it made that ownership and cohesion the goal and not the lucky exception. It’s been wonderful and so fun for me, because I love collaboration. It’s truly a beautiful partnership. We make each other better, and we make really good art together. 

Laura and I start every collection with a mood board. (This actually started in 2015.) Either it will be something that sparks a collection idea for Laura, or for me—usually about half and half. It might be a pillow, a piece of marble, a photo of a woman in a flowy dress, whatever. And then we build out a mood board from there.

We use Pinterest to create these secret boards, and we really try not to pin any other artists' work. I take pride in trying to offer a good variety of styles within my work, and I want to protect myself from ever unintentionally taking too much inspiration from any other artist, be it calligraphy or painting.

For me, this means that I really can’t follow many artists that are peers, and I try to glean inspiration from places that aren’t art. Which is actually a really fun challenge! The exception to pinning other artists' work is if it’s within an in-room vignette (like a photo of a living room, for example) that we really like the interior design of, or if it’s a vintage piece that’s public domain. So in the mood board, we’re describing visually how we want the art to feel and look, without using art. 

Above: the mood board for our next collection, which I'm actually en route to KC, MO to shoot with Laura (as I write this)!

Once the mood board is ready, I’ll start painting/drawing/creating. Because Laura lives outside KC, MO and I live in Wisconsin, we communicate through FaceTime and text until we’re actually together at shoots. This usually means me texting her shoddy phone photos of wet paintings and waiting for her to thumbs up them (crushing) heart them (satisfying), send heart eyes (jolt of pride for each emoji), or tell me in words how brilliant I am (be still my tender heart).

Sometimes I even paint with her on FaceTime, which can be hilarious.

Usually Laura’s critiques of my work come in one or two words, and it’s very simple stuff. I love being Art Directed, but I appreciate that she lets me do my thing and she knows she’s there to inspire and enhance the work, but not to change it or me, if that makes sense. Her responses look like: pretty, or more blue, or YES.

This is usually all fun and helpful. But there are two things that she says that I HATE.

(Ha! Bet you didn’t see that coming.)

The first is when she says stop... but I’ve already kept going.

Let’s say I send her an in-progress picture, and then I keep painting and she hasn’t gotten back to me because she has a life or whatever, and then she responds four hours later with perfect!

Little does she know that I HAVE BEEN CONTINUING TO PAINT ON IT FOR FOUR HOURS WHERE HAVE YOU BEEN IT’S TOTALLY DIFFERENT NOW.

So an example: I sent Laura an in-progress photo of Monarch and Laura responded later: it’s perfect! But it didn’t look like the photo I had sent her. It had became Monarch. Which she liked, we'll just say, significantly less.

Soooo, I tried to re-create the layer that I had sent her originally, and that painting became Daughter. And Daughter has sold, we'll say, significantly more than Monarch... and this is why I listen to Laura. 

Above left: Monarch | Above right: Daughter

(Since then, what I’ve learned to do is take a break, let the layer dry, and scan that layer before I keep painting on it. In the Girls House Collection, Mint Meltaway is actually underneath Icing on the Cake. Wild, right?)

Above Left: Mint Meltaway | Above Right: Icing on the Cake

The other thing Laura says that I hate? 

Keep going.

You would think that if I hated stop I wouldn't mind keep going, but I hate them both equally and for contradictory reasons.

When I send her something that’s (in my opinion) finished, and she tells me to keep going, it's her way of saying: you’re on to something but it’s not there and I’m not going to tell you how to fix it.

One year Laura was still doing lots of weddings and planting a church. Phoenix was still a baby. She and I hadn’t communicated much through the creation of that year's holiday collection, and we had a call to figure out our specs for placing the canvas order for the photo shoot. (These are usually my favorite calls—picking the sizes/finishing/etc.)

I sent her a PDF of all of the work I’d made for the collection, right there on the call, while we were getting ready to order. 

(As an aside, I was exhausted. I hadn’t hired Joy yet, I had just closed my brick & mortar shop, and I honestly wanted to be done with the collection. But it was for Christmas, which is an important collection financially, and so I didn’t really have a choice about whether to do it or not.)

I sent her the PDF and waited for her to open it.

Silence.

I was like, well?

And she said: "Linds... this isn’t there. Like, at all. You need to keep going.”

I was crushed. It was such an awkward call. I didn’t want to keep going. I wanted to be done. Done with the collection and, honestly, done with Lindsay Letters.

It might sound like Laura was being harsh, but she was right. The collection was pretty awful. I wasn’t in a good place. I wasn’t feeling inspired. I was deflated. But Laura knew what I also knew, which was that I literally couldn’t afford to release a crappy collection. At that time my business hinged on Christmas sales, and my family depends on my business. To fail at Christmas would mean that everything would need to change, in ways that would have significant impact on our home—my time with my kids, Dugan’s job at our church, etc. A lot was riding on the collection, but keep going in that moment of exhaustion felt like running a marathon and mistaking a water station at mile 20 for the finish line (if you’re reading this Jen, hi, and I love you).

I got off the phone, cried, went to bed, and picked up my brushes and pens the next day and made a way better collection. It wasn’t my collection de résistance, but it paid the bills and we didn’t lose our house and D didn’t have to quit his job at church to go and be the breadwinner. I’m so glad I kept going. 

Keep going pays off. It doesn’t answer any questions for us. It doesn’t tell us when we’re done, or what to do to be done. This is true in art, in work, and in life.  Keep going means that there isn’t an obvious answer like "more blue"—only that you’re not finished. 

I’ve come to expect Laura will say “keep going” to me every several pieces I send her, and they are always better for it. It's become a running joke with us, a mantra. And while I still think it’s annoying, the proof is in the pudding.

This happened again recently at the Girls House shoot. We were so well prepared, and when we were staging, it all came together as we planned. But as we stepped back and looked around at 2am the morning of the shoot, something felt off. It was executed exactly how we’d pictured, but it still wasn’t right.

After the rest of the team went to sleep, Laura and I stayed up, moving things around, trying to get a handle on what needed to happen... which would prompt this text from Joy in the morning, as she tried to piece together what had happened:

As we locked up that night, Laura and I both agreed: we needed to keep going. Exhausted, I laid my head on the pillow finally at 3:30 am, just trying to wrap my mind around the what didn’t feel right and what keep going actually meant, this far into the shoot. 

The next morning, I painted Fairy Garden.

As bright and bubbly and delightful everything else in the collection is, we had planned Gumdrop as the anchor piece for the collection, and it felt like too much. Beautiful, fun, quirky—but relatable only to the few people it was made for.

Leanne Ford says if things feel too cutesy, add black. And that’s what we did. That’s what it needed: something deep and grounded. We added black accents around the room and I painted over the square Gumdrop canvas, and that became dark and dreamy Fairy Garden. It's been the best seller of the collection.

ABOVE: Fairy Garden

Throughout the shoot, we couldn’t decide what design to create for the for the cream hoodie we wanted to release. But as we processed through the shoot on the way to drop Laura off at the airport, we mused at how that shoot was our finest example of “keep going” and how hard we had to push to get to the gold. Laura said: maybe that’s what we need to put on a shirt and I said done. And so here we are. And here’s the hoodie.

The Keep Going Hoodie

I’m so honored to have been able to share my creative process with you, as well as the multi-faceted meaning behind this sweatshirt design.

Whether you use this phrase as a cheeky "you’re not done yet," or as inspiration for a journey you need to keep walking, or as a nudge of encouragement on a day you need to power through: I hope it serves as a comforting reminder that you are seen and loved.

Keep going.

xo, L