From Sailing To Art: Building a Creative Business From Scratch

When I decided to start painting again, I was 37 and hadn’t picked up a brush in a good 12 years. I also hadn’t had a job in 8 years and was the mom to 3 small boys. My youngest was just 10 months old and my oldest was 5. And somehow I knew I didn’t want to just paint as a hobby—although this is a wonderful thing too. But for me I knew from that first moment that it was my path to build this “painting thing” into a real business. How did I know? I knew because I really wanted to do that, and it sounded fun. 

Sounding fun is great, but of course so much work went into this. And I had zero idea, at that point, what I was getting into. All I had was this dumb confidence that I could somehow “figure it out.” And I did…but of course in hindsight so much more went into “figuring it out” than I ever could have envisioned at the time. I wanted to put this all into a blog post, and detail the steps I took to really build a creative business from scratch. 

For starters, and I’d say most importantly, I committed to the practice of painting. I mean fully committed to the practice. (And of course this applies to whatever your path is.) Meaning I painted every day, no matter what. This was 2018, and I was still traveling a lot, with kids in tow, and spent many days sailing and many nights on our sailboat. I brought paint with me. I skipped Netflix and painted after bedtime. I started skipping that glass of wine and started going to bed earlier and waking up early to squeeze in some painting. I put painting first in my (admittedly limited) extracurricular time, and that was non-negotiable. 

To be totally honest, I’ve never been great at committing to something so fully in the past—I have a ton of interests that are all over the place and I can get really excited about a lot things and then eventually move on to the next (Gemini rising with most of my planets in air signs, and if you’re into human design I’m your classic MG!)—but it’s like something in me knew I needed to do this. It was bigger than me, and that made it easier to commit to. It was like I had to. That’s as well as I can explain it. 

Once we moved to the vineyard and I got myself a real studio, I kept this commitment going. I remember painting with the flu, pausing to lie down every few minutes on the filthy floor. I painted on the phone with my divorce attorney. And when Covid came I just moved the whole operation into my kitchen and painted while single-mom homeschooling 3 kids. When I tell you something larger than me was driving this show, I really mean it. I think when we decide to commit to what we truly want to do, the universal forces show up en masse to carry us forward. 

The second thing I did was start listening to business podcasts and investing—in small courses at first and then larger ones—in programs to build my business knowledge. I invested in courses that would make me a better businesswoman, from finances to branding to marketing oneself. I learned about using all the social channels, I listened to Jenna Kutcher explain how to leverage a Pinterest page, and Amy Porterfield explain online courses, all from the treadmill at the Martha Vineyard Y. I took courses on money—energy courses and practical ones—and I joined an accountant’s membership to learn more about the practical, accounting side, of running a business (Sunlight Tax by Hannah Cole.) 

Third, I said “I am an artist” and I put myself in the company of artists. Thanks to social media, this is really easy to do. In real life it can happen too—it just takes naming yourself as that which you hope to be. If I hadn’t started saying “I am an artist” I doubt I would have met other local artists. This brings up the common point that we can’t wait for someone else to label or choose us. There is no lucky “anointed few”. We get to decide who we are and what we do. I still cringe a little thinking of the first time I called myself an artist. It did not come out confidently at all. But I did get the words out, and each time I said it, they felt more and more natural. 

On social media it was simpler—I followed tons of artists, and I put myself in the conversation. I commented on posts, messaged those I admired, either with comments or questions, and so on. I still do this. I love my artist friends I have met online and highly value our connection, conversation, and friendships. I took this one step farther by joining artist communities online. I joined several, then stuck with the one that spoke to me the most—The Art Queens which was started by artist Ekaterina Popova. I have a wonderful “sub group” that I’m a part of within the Art Queens and we have such a supportive community. Within groups like these you not only find support, you find friendship and the chance to support other artists on their journeys. You also get countless opportunities for educating yourself further. 

Fourth, I read a ton of books, listened to the audio versions, or played youtube tutorials in the background that were helpful in building my business. There is just so much free advice and knowledge out there today, there is no excuse not to educate yourself. I had genuinely no idea what I was doing in the beginning of this journey, but I had the confidence to know I could figure it out as I went. The next post will be on the specific books and podcast channels that I found the most helpful…there are too many to list out here!

Fifth, I recognized the importance of creating mental space for creativity. This is easier said than done, especially in today’s world. But I kind of quickly started to feel over-saturated with information from all the podcasts and so forth. In early 2019, I took a trip to Costa Rica for a month with my kids, followed by a month home in Florida, and I was really forced to slow down and quiet my mind. I was reminded of all the mental space I enjoyed while living on our sailboat. I started painting in my head again, and when I returned to my studio the results were well worth it. I was amazed at the progress I had made, skill-wise, even though the majority of my painting practice for two months had been inside my own head. 

Going forward, I consciously created that space in my everyday. And this may sound silly but when you have three kids, you have to be really intentional about this. Really, I think in today’s noisy world, whether you have kids or no kids you have to be extra intentional with your mental space. The universe abhors a vacuum—and so does the “real world” around you. Keep that space clear for the universe to come in and fill you with creativity or else the world will fill it with nonsense first. 

I really believe in the paths we take being the perfect path we need to walk. If I had continued with my graduate work in the Middle East, or working with refugees, or any of the other interests I had, instead of taking off on a sailboat, would I be here today? I don’t know. Living on the sailboat gave me that space of long stretches of boredom. Of feeling a little lost. And what filled that space was a longing to return to some form of creativity. Eventually I started dreaming every night that I was painting the scenes I saw around us every day. It amazes me, now, how long it took me to listen. We are slow to respond in this dense world, but we get there eventually.