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Meet Silverlake Makeup Artist & Hairstylist: Jen Winning

Today we’d like to introduce you to Jen Winning.

Jen, please share your story with us. How did you get to where you are today?
I became a makeup artist at STRIIIKE and a freelance makeup artist + hairstylist in LA by the wonderful cocktail of choosing the path of must, hard work, persistence, trust in myself, accountability, kindness, and travel.

I was born and raised in Salt Lake City, UT, but I never felt a connection with the city. I was always drawn to California and knew that I would move there at some point in my life even though I didn’t how or when. Fast forward to dropping out of college to signing up for cosmetology school to another 4 years when I basically told my family I got a job as a makeup artist with Bobbi Brown cosmetics in Orange County and that I was moving in 48hrs. That became the most liberating and unknown adventure to endless possibilities in my life, which was so exciting for me.

Since then I have been graced with the opportunity to learn and work side by side with Danny Moon – hair color and glitter magician at Andy LeCompte Salon and Ramirez Tran Salon to today, betting on myself as a freelance artist and having a home base at STRIIIKE as their makeup artist.

I am very grateful for all the opportunities I have had and continue to have, without them my life wouldn’t be this fun.

Has it been a smooth road?
Not at all. When you choose the life as a creative, you’re going to love and hate your work/life. When you’re busy and creating cool stuff, you’re on cloud 9. Then you hit the slow period where you’re not creating and you think you should crawl in under a rock and never come out. Mix that with bouts of longing for your old comfortable life and being broke and that rock is looking mighty cozy. But you remind yourself you left for a reason and that everything comes in and out of your life like the ebb and flow of the ocean.

What is the most difficult part of what you do?
I think the one hardest part of being in this business is being my own worst critic. It doesn’t help with social media either. You see all the great work your friends, peers, and idols are creating (which you are 100% happy & amazed by), but you look at your own work and think it falls flat in comparison. It is incredibly difficult to not compare yourself to others when you are on this creative path since you don’t get instructions or a mapped out plan like you would with a traditional career choice.

Also, having patience with myself – I’m the worst! We live in a world where you can be successful overnight. I so badly want to get to point B! But I keep reminding myself that there will always be a point B and that the magical part of it all is how I get there.

What are you striving for, what criteria or markers have you set as indicators of success?
I’ll let you know when I am actually successful?! It’s a win in my book when I can pay all my bills and buy groceries for myself every month while having a little extra spending money for a little getaway! LA is expensive hahaha

So, what’s next? Any big plans?
I get to be on set more and create cool stuff with my friends! I look forward to gaining representation by an agency in the next year or two, live in a foreign country for a few months to a year or indefinitely (life is unpredictable!!) for work and/or leisure (particularly in Japan), more adventures, space travel, and having longer hair!

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