Name: Caroline Kelso Winegeart
Claim to fame: Designer and founder of Made Vibrant, an online community and resource shop for creatives. The mind behind the #BetterLetteringChallenge.
Wise words: "I’ve been blessed and cursed with this very high standard for my own happiness"
Instagram has gotten a bad rap in the last couple of years for being a "filtered" version of our every day lives. Less wrinkles, more rooftop rose parties. Less "wow, my account balance is low", more #blessed.
But amidst the posturing and the posing, I have found a colorful sanctuary where reality shines through in a beautiful, inspiring, wow-I-don't-feel-so-alone-anymore kind of way: Caroline Kelso Winegeart's Instagram account.
A few months ago, a member of my girl gang introduced me to Caroline and her work by tagging me in a comment on one of her images (probably one of her stunning hand-lettered images) and Caroline was immediately inducted into my girl gang, too. I was moved not only by the beauty of her work, but by the honest reflections on life and work that accompanied each piece.
Caroline, an entrepreneur and creative, is one of my vulnerability role models, as she shares openly about everything from credit card debt to the joys (and challenges) of getting back into shape with her community.
This interview is no exception when it comes to Caroline's courageous vulnerability, and I'm so thrilled to be able to share stories from this special woman's life with you.
On the long, messy process of honing your intuition
I’m sure that, if prompted, we can all come up with a thing or two that our college romance(s) taught us about ourselves. Personally, I learned a thing or two about what a healthy relationship does -- and doesn’t -- look like. Maybe yours illuminated a new interest, taught you something new about your body, or, on the other end of the spectrum, helped you to identify a gaping blind spot in romantic judgement. We’ve all been there...amirite?
Collectively, Caroline’s college boyfriends taught her something else entirely, a skill she uses to this day in all aspects of her life: the ability to determine whether something feels right, and the courage to act on it when it doesn’t.
“In college I would date these guys for about a year, enough time to understand the relationship, and then break up with them.” Each boyfriend, she explained, was so different than the last, leaving her friends absolutely baffled about her ‘type’. “The second I would realize that we were not creating the better versions of ourselves together, I would break up with them the next day,” she told me. “My girlfriends thought I was cold-hearted, but it wasn’t about that. The second I realized that the relationship was not right for me, every moment after that was a limited moment.”
As we’re talking, Caroline effortlessly draws connections between these romantic experiences and her entrepreneurial career, pointing to the role that intuitive decision-making has played in all aspects of her life.
“It’s so similar to my business life in that I have to try on these different sides of myself and give myself time to understand how I’m responding to it,” she offered, “you have to experiment and then really sit with what’s happening inside to understand it and make a decision.”
Caroline’s intuition was put to the test in a big -- and painful -- way during a brief stint in a non-creative role at an advertising agency. “Every day of that job, I would come home and bawl,” she recounted, “I would feel this strain in my chest -- even telling you about it now has me rubbing my chest.” In the first few months, Caroline was overcome with what she described as a full-body knowing that this job was not right for her. “It [her time at the agency] wasn’t even that long, but just the idea of spending my days not feeling like the true person that I am, I felt the implications of that day after day after day.”
Although, in the end, acting on that inner guiding voice has led to feelings of satisfaction, liberation, and joy for Caroline, she acknowledges that making the choice to move on from a situation that no longer serves you can be a painful thing to do.
“I always focus on what it’s going to feel like on the other side.”
“I’ve been blessed and cursed with this very high standard for my own happiness,” she explained with a small laugh. “It’s hard because the second that I decide something mentally, I just have to do it right then,” she continued, “but I don’t want to have hard conversations, I don’t want to feel uncomfortable.” The easy part, she said, is when she makes the internal decision, the hard part is what comes next. “But in those situations where I’m thinking ‘this is going to suck’,” she offered, “I always focus on what it’s going to feel like on the other side.”
It is this beautifully messy practice of getting to know that little guiding voice that lives within each of us that Caroline is trying to illuminate through her offerings with Made Vibrant. “People come to me saying ‘just tell me what to do!’, but I always tell them, if there’s one thing to invest time and energy into, it’s understanding yourself,” she shared. Caroline herself admitted that it was only once she stopped looking to external sources for validation that her business really took off.
“It’s a cultivated skill that you constantly have to bring your mind back to every day. But I think that that is the number one key to happiness and fulfillment.”
On anxiety, confidence, and embracing your worth
When you visit Caroline’s website, you are greeted by beautiful artwork in vivid shades of blues, pinks, and yellows. Scroll a little further down and you’ll see a slideshow of images featuring a beautiful young woman smiling and making faces at the camera. Click through a few pages and you’ll find beautiful illustrations and inspiring quotes.
In short, Caroline makes business look blissful! And, by her own admission, most days it is. But she is also quick to note that there are moments -- some short, others long -- in which running a creative business is anything but bliss.
Driven by a desire to support her fellow creatives, Caroline is keen to shine a light into the darkest corners of entrepreneurial life -- including her own struggles with anxiety. “Some people might have the perception that I have it all figured out, and boy, do I not. I wish that people knew more of the neurotic struggle.”
“I hit a low point six months into my [freelance] client work,” she shared, “and in the Spring of that year, I started feeling this deep, lingering anxiety.” Her experience was a very physical one, she described waking up every morning feeling as though an elephant had been sitting on her chest all night. Worried that she might be sick, she went to visit her doctor, who asked if she had recently made any life changes. Caroline’s response: “oh, you mean like being solely responsible for my own income?”
This anxiety, which she worked on with the support of a therapist, also began to affect her creative output and productivity. Even though her clients were thrilled with her work, she began to worry that they were unhappy. “There were days I couldn't even work, I wasn’t making any money and I managed to rack up $7,500 worth of debt,” she told me, “it was a really low point.”
Around that time Caroline and her partner, Jason, took a trip out to San Diego to visit some friends. During their visit, her friend lent her a copy of a book about confidence, which she quickly devoured. From that book came a revelation that helped change the way she saw herself and her business: her anxiety had knocked her confidence for a loop, and it needed to be built back up.
“It’s something I know a lot of women struggle with,” she remarked. “My boyfriend Jason would say things like ‘I wish you had more confidence in yourself’ and it hurt because I felt confident, but I was afraid to articulate that to anyone for fear that I would be viewed as arrogant and full of myself.” Caroline realized that she needed to find a way -- her way -- of projecting her inner confidence to the world that didn’t feel slimy or fake. Once she was able to make that shift, she noticed an uptick in her business, and in her mood.
Although she has come a long way since those early freelance days, Caroline is candid about the fact that she still experiences feelings of overwhelm and anxiety as she grows her business. “I see many people that struggle with the idea of worth, but I struggle with worth in a different way,” she shared, “I think without realizing it I felt that my mom’s message to me growing up of ‘you deserve happiness’ came with a condition that I must excel, that I have to be the best. I have to get up and fight that battle of perfection every day.”
One her favorite ways to cut through mental chaos of entrepreneurship and reconnect with her inalienable worth is by flexing her creative muscles: “My art was my way out of my excellence thing that I was stuck on. The more I do my art, the less I feel like my worth is tied to these external things. The more I feel my worth is inherent and by showing up as myself, flaws and all, I get to claim that worth.”
Caroline also derives a tremendous amount of inspiration and motivation from the thriving community that she has created through Made Vibrant, “these days, I get the most joy from getting an email from a mom whose kids went off to college and reconnected with the creative self she had forgotten. Those are the connections and stories that light me up.”
But regardless of how her day is going, Caroline knows that it isn’t about the hand you’ve been dealt, but how you decide to play it. “I’m really proud of the daily commitment that I make to being the brightest version of myself,” she said, “it is the thing that guides my entire life.”
One day at a time, Caroline is choosing brightness over dark, ease over toil, and what feels right over what feels easy.
And the good news is that we are all free to do the same.