We had the good fortune of connecting with Anna Dawson and we’ve shared our conversation below.

Hi Anna, every day, we talk about how much execution matters, but we think ideas matter as well. How did you come up with the idea for your business?
Growing up, I was that girl on snow days or weekends, who would grab a magazine and my mom’s makeup and attempt to recreate the looks I saw. How many times did I end up looking like Amy Winehouse with an overly large wing eyeliner… Fast forward to adulthood, where I worked in various administrative roles, juggling schedules, invoices, contracts and travel arrangements for others. It clicked—I had been busy building the businesses and dreams of others, but neglecting my own. I knew that nothing would be handed to me, no surprise there. Yet, if I didn’t try, I wouldn’t know what I could create on my own. So, I jumped!

Let’s talk shop? Tell us more about your career, what can you share with our community?

As a Makeup Artist and Content Creator, I invest significant attention and energy into all areas of my work. In my experience, I’ve found that the way I nurture my business often mirrors the care I’m giving myself. I’ll sit with something for a while to understand my “why” behind it and try my best to take action from that place. How do I want people to feel after they leave my makeup chair? I don’t want them to just feel looked after on a superficial level, I want them to feel so seen and cared for as an individual. When they are interacting with any of the content I’ve made, is it just another video to scroll past or is there an opportunity to learn something that generally gets overlooked?

Just as I prioritize therapy for my personal well-being and working out for my physical health, I am currently participating in a year-long mastermind program with a fabulous group of women from around the world. We get IN THE WEEDS of what’s both helping and hindering us with our businesses and how we can grow. Through these past few months, I’ve discovered the significant correlation between my internal state and what I produce in work.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
The Pacific Northwest is truly the most magical place in the Summer months. I always recommend a Mariners game, then a sandwich from Market Grill in Pikes Place. Having boat day on Lake Washington then boating to dinner at White Swan Public house or Bowriders on Lake Union then after, dessert at Hot Cakes in Ballard. But of course eating it in the boat watching the sun set. If you have the time, a long weekend in the San Juan Islands. You will never have a better salmon sandwich then the one from San Juan Brewery. I recommend driving onto the ferry (get a reservation) so that you can explore the Island(s). The most beautiful light houses, beaches and whale watching.

Who else deserves some credit and recognition?
While it may not be the conventional response, my therapist has been instrumental in my journey. Over the course of seven plus years (and counting), she has encouraged me to view myself and my capabilities through a different lens, granting me the freedom to pursue my desires. What I once saw as an obstacle, parts of me I thought I needed to hide, has now evolved into my most valuable strength and the things I’m most proud of!

Website: makeupbyannadawson.com

Instagram: @makeupbyannadawson

Linkedin: www.linkedin.com/in/makeupbyannadawson

Facebook: https://www.facebook.com/makeupbyannadawson

Other: tiktok @makeupbyannadawson

Image Credits
@kmat.jpg @perenchiophotoco @will_har @wearismax

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