On the coast of Carmel, Annie Free watches the albatross and heron take flight and dreams of big-eyed, pastel-toned characters she’ll later manifest through watercolor, acrylic and ink. She’s admired this coastline since she was a child, but today, she relies on it as an escape — a place to recharge her creativity and take a step back from the digital world.

Behind her dreamlike depictions of imaginative creatures is a storied career rooted in the skateboarding industry. She began her journey in clothing manufacturing and went on to co-found the legendary skateboarding brand, HUF, in 2002, with her late ex-husband Keith Hufnagel. Simply put, Annie knows the power of a good graphic: As she says, “Whoever has the most creative eye candy wins.”

After decades of entrepreneurship, Annie opted for a life centered around creative expression. “I didn't intend to become an artist,” she says. “It just exploded out of my brain.” Making art — whether it’s with acrylic on canvas, watercolor on paper or a yarn-haired doll — is how Annie copes with loss, works through grief and celebrates life: “The bright colors you see and the humorous characters I paint are my effort to always return to the light,” she says in the interview that follows, “to find joy and to soldier on with gratitude, celebration and a smile.”

You have deep roots in the skateboarding world, having co-founded HUF. How has skateboarding culture influenced your life and creativity?

From the moment I saw a Zorlac skateboard arrive under our Christmas tree for my older brother, I became obsessed. I was probably 12. In a sea of drab earthtones and primary colors a completely Neon Monster head entered into our home. The artist who drew those early graphics for Zorlac went by the name of Pushead and seeing his artwork changed the course of my life. He did album cover art for Metallica and the Misfits. In a time where there was no internet, TV was limited and the only print media that showed up at our house was the town paper, images like the ones I began to see on the bottom of skateboards were incredibly impactful. I wound up working in Skateboarding Apparel Manufacturing, beginning with a part-time job at a silkscreening factory while in college. Unlike what you do at MOTHER, where fit, quality and construction are at the heart of what matters, skateboarding apparel is all about two things: the athlete that endorses the item or the art that has been applied to the item. The same silhouettes are offered by every skateboarding company in the market, from boards to hoodies to tees... so sales are often driven by graphics. Whoever has the most creative eye-candy wins. Every skateboarder and fan of skateboarding can tell you their favorite graphics of all time. Art drives that industry. I was able to see the world by tagging along on skateboard tours. Guess what professional skateboarders do for fun when they go to cities overseas? They go to art shows, they create art shows, they engage in creating illegal street art. In all my years owning a skateboard company I very rarely attended an X Game event or structured contest event. I found them to be incredibly boring. I liked to be in the part of skateboarding where there are no rules. In street skating, it's a form of performance art, at least that is the way I felt about it.

What inspired the shift from a career in business to becoming a full-time artist?

My art career came as a mid-life surprise. Out of nowhere and with no instruction I began to draw for hours on end at the age of 41. Until that point, I had spent my life in business and entrepreneurship and was truly bewildered there was so much art inside of me. I didn't intend to become an artist. It just exploded out of my brain.

What has it been like teaching yourself to create art across different mediums?

I've put myself through my own “trial and error art school.” For me, this has meant that I would go to Blick, buy supplies that looked like they might be fun to try, and then try to figure out how to use them. Consequently, I have explored pastels, acrylics, oils, all sorts of pens and pencils and different canvas types and papers. I always seem to gravitate back to the magic of watercolors. There is something in using watercolor that makes so much sense to me, even though they are sometimes a bunch of nonsense when you try using them. They are hard to control, so you have to let go a bit and let them surprise you. This year, while exploring grief, I worked my way into doing more watercolor collage. For whatever reason, these new pieces attracted the attention of gallerists. I now have two shows this year. One at And Friends in Santa Cruz and another at Cruise Control in Cambria.

Have there been any artists or creative influences that have guided you, especially when you were just starting out?

Yes! When I was early in my career as an entrepreneur there were people I knew that were further along in their journey that were incredibly supportive and generous with sharing advice or sources. There were also people that were dismissive and guarded. The irony is, the more supportive, open and helpful someone was to me in business, the more successful they became on their own journey. There is nothing about not sharing and hoarding that helps you have more. I was lucky to find two really generous artists that helped me understand how to work with watercolor and gouache. I took workshops from both Ana Victoria Calderon and Lindsay Stripling. I would encourage anyone that has not been able to go to art school but wants to explore how to use materials to look for help online. I never had trouble expressing my style, but I didn't have a clue how to mix paint. Both Ana and Lindsay are truly generous with their knowledge and encouragement.

Can you share what it was like to showcase your artwork for the first time?

The first art show I ever had was in Lela's kitchen. I had made about 25 drawings and was encouraged by her husband's bestie Jon Rosenberg to bring them to our next gathering and "show" them. We laid them across the kitchen Island and had a "show.” Everyone (as in about 5 of us) oohed and aahed and picked their favorite. I received lots of encouragement, and it helped me to keep going. I highly recommend a kitchen art show at your best friend’s house if you are just starting out as an artist.

What are the themes or emotions you find yourself exploring most through your art?

You probably wouldn't see it, if I didn't tell you, but there is quite a bit of grief, sadness and even sometimes despair in my work. When I sit down in the space I create work, it's where I connect with my loved ones that are no longer here. I have photos of my two siblings, my precious dog Bones, my partner in Huf, Keith, and my Dad who was my sun, moon and stars on my wall where I create. I love to remember them, to miss them and to have conversations with them when I make my art. I'll stop what I'm doing sometimes and play the music box my Dad gave me a few months before he died. It plays "You are my Sunshine.” He knew what he was giving to me when he gave me that music box. I get into a real flow state when I make my art and the barriers between earth and the heavens seem to disappear for me. The bright colors you see and the humorous characters I paint and draw are my effort to always return to the light, to find joy and to soldier on with gratitude, celebration and a smile. Sometimes you can see sadness leak through in my work, but it's not my intention. I hope if you have a piece of mine on your wall that it makes you laugh, smile or feel warmth.

What has been one of the most unexpected lessons or challenges you've faced as an artist?

Internet trolls! One time a quite famous person put some of my artwork up on their many millions of followers Instagram account. They were expressing how much they loved my art, and the internet came after me with their torches lit. Most of the comments were about how my art looked like a five-year-old made it. I was really hurt initially because I thought that meant I wasn't a "good artist" (whatever that means). In time I was able to reframe it. Of course my artwork looks like a 5 year old made it. At the time of this internet witch hunt, I had less experience making art than your average 5-year-old. I'm now grateful to be free to create however I feel like creating, just like a 5-year-old does. I don't have the critics of art school or some professor's words in my head telling me my work is "too flat" or has used "too many colors.” In my head I'm totally free, and ultimately, that freedom of the mind is probably what made so many people come after me and say, "How dare she!" I'm not going to lie though, internet trolls are the meanest bullies around and for about three days I felt like quitting. Damn trolls.

Are there any daily rituals or creative practices that help you stay grounded, especially when life gets hectic?

I live on a river, so it's completely cheating. All I have to do is make a cup of coffee, walk out and sit by the river in the morning... watch the ducks, the fish, the birds and little crawdads do their thing. Instantly Grounded AF. Nature is a full lifehack.

You’ve mentioned how much dogs mean to you. What is it about them that inspires you?

Well, first of all, I think we can all agree that dogs are the greatest creatures to ever be invented and humans are the luckiest creatures on earth that we somehow domesticated them to become our companions. Obviously, dogs are called a DOG because GOD made them in her image, so they are truly a mirror image of the mightiest spirit in all of the sky… I like to stop and meet and pet every dog that passes me if an owner will take the time to let me. If you meet 10 new dogs in a day and pet them, you've met God 10 times that day. I have 4 dogs, so my house is basically a church.

How does living in a place like Carmel influence your creativity?

I love cities so much. I've lived in LA, NYC and SF. Cities are filled with endless amounts of creative inspiration because you are feeding off of the energy of so many creative people in your surroundings. But Carmel, oh my gosh it is magical. The scenery literally never gets old. I've been staring at the same coves and beaches since I was a kid and I swear they just get more beautiful. A city can fill you up with creative ideas, but then the stress of living there can deplete you of the energy it takes to execute your ideas. Nature will never do anything but support you. It will never steal your energy. For me, I feel it's easier to stay connected to my creativity because I have chosen to live in such a quiet place… There is something in the air, that's for sure. You'll feel it if you come to visit.

Are there any hidden gems in the area that you find especially inspiring?

I like to go to the beach at Stillwater Cove in Pebble Beach. If the tide is in too high, I'll just hang out on the pier and watch the sailors and kayakers. I go to Moss Landing a lot too. The estuaries there are pretty special. I don't know what it is about aging that makes you suddenly appreciate birds. Moss Landing is a great place to watch Heron being Heron, Albatross fly by with their gigantic wing spans and little sandpipers piping away for teeny crabs. Did you know that Birding is a sport/hobby that is based entirely on the honor system? I bet there are some big liars out there claiming they saw the blue-footed boobie or a snowy owl. Anyway, that's another conversation entirely. In Moss Landing you're going to see some cool-ass birds and won't have to lie about it.

What drew you to open SOMEWHERE? What was your vision for the space, and how has it evolved since?

I've been in retail since I was 14 in some capacity or another. Opening stores is almost like a reflex at this point. Carmel is one of those coastal towns that is lucky enough to have not changed since I was a kid. It is also cursed enough to have not changed. Some of the same old dusty knickknacks that were for sale 40 years ago are still for sale today. Thankfully, there has been a wave of new and youthful energy infused into the little village. Our shop is just one of many that opened in the last few years that are modern concepts. Initially, we set out to sell housewares, but we quickly found out that tourists don't have room to stuff a decorative pillow in their suitcase. We evolved into a cleverly curated collection of California and Carmel tchotchkes. (Too bad tchotchke isn't spelled with a "c" or that would be the best sentence using the letter "c" I ever came up with.)

What advice would you give to someone looking to reinvent themselves and follow a creative passion later in life?

It's later than you think. You don't have to wait for permission or for it to make sense. When you are on your deathbed, I can promise you that you won't be thinking, "I'm so glad I never tried to be an artist.”