We recently connected with Maddison McKinley and have shared our conversation below.

Maddison, thanks for joining us, excited to have you contributing your stories and insights. Can you open up about a risk you’ve taken – what it was like taking that risk, why you took the risk and how it turned out?

Back in October of 2019, I went on my first trip abroad, to Barcelona, by myself. I distinctly remember sitting on the rooftop of my hotel and asking myself: “What do I want to do with my life?”, and the answer bore itself right on the sheet of paper I was writing on.

I want to help women feel Clothing Confident.

Less than a year later, in September of 2020, I decided to make it a reality.

I sold my condo, packed up my tiny little sedan, and traveled the United States. For 2+ years, I’ve been on the road interviewing women across the country for my Seeking Inspirato series on DailyInspirato.com.

I have written a book on how to live a Clothing Confident life (though not published yet), and continue to speak about the impact clothing can have on our self-esteem.

While traveling the country, I stayed in Nashville for a month, and on the last day of my time there, I booked a studio session via an Airbnb experience. The song the producer, Caleb, and I created together (I See Us) sparked something in me to write music again.

The whole experience was so fun and riveting, that I couldn’t stop thinking about it. Though I grew up singing (anything from Shania to Shakira), I was always way too painfully shy to actually sing in front of people (even writing and recording I See Us was difficult!). Crippling stage fright.

However, something about traveling thousands of miles by yourself for a couple of years might just make you a little more confident in your abilities, including fear of rejection and what other people think.

With this newfound and renewed sense of self-confidence, I booked multiple studio sessions with Caleb again in September of 2022 and created my EP, Cowgirl Serenade, which is set to release in the Spring of 2023.

And none of this would have happened, meeting the love my life, visiting and seeing so much of our country, meeting amazing people, writing about Clothing Confidence, and rekindling my love for music, if I hadn’t took the risk of leaving Portland behind and seeing what the future held.

Maddison, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Maddison is a 7th-generation Texan who ventured up to Portland, Maine after graduating from the University of Texas at Austin. Quite the shock to her never-leave-Texas-family, but they still kept her in the family :)

In Maine, she started her career in marketing and has worked in both a creative agency serving clients, as well as in-house in the global center of excellence at a Fortune 1000 veterinary tech company as their lead/global inbound digital marketing strategist.

While all this was interesting and fun, it never seemed to scratch the creative itch she felt.

Once she started to hear other colleagues of hers talk about fashion, and confidence, and how the two were difficult for them to grasp, Maddison as a lifelong clothing lover was intrigued.

Could it be possible that not every woman loved the way she dressed, most days?

Turns out, no. Thus, Maddison embarked on interviewing 100s of women and telling their Clothing Confidence stories on DailyInspirato.com & @DailyInspirato. She’s interviewed women from Vienna, Austria, Australia, and within the states. The vision is to share the stories of Clothing Confident women so that other women can see that not every woman is born into Clothing Confidence, they grow into it.

For you, what’s the most rewarding aspect of being a creative?

Being creative is not something I thought I was, actually.

Growing up, there were so many creative people in my life, so I thought I was just “middle of the road”. I also was always an arts and music lover, so I would compare myself to musicians and writers I adored and say “well, I’m never going to be like ____”.

It turns out that comparing your creative output to what other people are doing is a fruitless endeavor because creativity is about the journey to creating something that *you* love, and you hope others do, too (or maybe not even that).

It’s about the JOY to truly create. To have a finished product you can read, look at, listen to and enjoy. You made it.

For me, it really mattered what other people thought of my writing for DailyInspriato.com, as well as my music and songwriting (the latter being the most terrifying).

But once I started writing music that I was jamming to, and preferred to listen to, I knew I was onto something.

As for the Clothing Confidence articles, I knew I was doing something right when I saw the organic search queries and traffic going up and up. I was addressing the needs of women, across the world, and allowing them to self-serve 24-7-365.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

Be careful who you are vulnerable to. Not everyone who loves you, are the right ones to be vulnerable to. What I mean is that once I shared my music with someone who I know loved me very much, but had some rather discouraging words. This was a long time ago, and it definitely impacted the way I saw myself as a musician. In fact, I stopped writing and playing music entirely.

I had to learn that who you share your work and art with *really* matters, particularly in the early stages.

It’s sort of like a little sapling. When I’m first working on a song, and looking for feedback, one little finger of tough criticism on my sapling root could prevent the tree from growing, or from writing the song.

As the song develops and grows, however, as does the tree, a little bark coming off here or there isn’t going to prevent the tree from growth.

I have become more thoughtful on the people I share my work with, and WHEN I share my work (too early).

When I feel really good about the work, it actually makes receiving helpful feedback more useful anyways. So I try to wait until that point.

I remind myself, often, think about how many people “don’t love” [insert famous artist here]’s latest song or album? There will always be haters, and there will always be people who don’t like what you’re doing. Don’t let them stop you.

Contact Info:

• Website: https://www.maddisonmckinley.com/
• Instagram: https://www.instagram.com/maddisonmckinleymusic/
• Youtube: https://www.youtube.com/channel/UCF3Q8ueUDeDKVora4lTR8Tw
• Other: https://www.tiktok.com/@maddisonmckinleymusic

Image Credits
By me!