Taking Care of Business... with Rachael Krutchkoff

We’re passing the mic to some of our favorite freelancers who make Wingspan’s community thrive, and who remind us everyday that there are no wrong ways to take care of business. Want to be featured? Submit yourself here!

Rachael is a freelance makeup artist whose clients include Marc Jacobs, Parade, Susan Alexandra, Milk Makeup, Refinery29, Man Repeller, The Cut, Office, King Princess, Teen Vogue, Vogue Spain, Apple, and Thrillist.

In your own words, what do you do?

Makeup Artist!  

Where do you call home?


What’s the first thing you do when you wake up?

Spritz my face with rosewater, feed my cat Bill, and check my emails / DMs for jobs!

What’s your favorite thing about freelancing?

All the new, inspiring people I get to meet at each new job. I am always learning from them and becoming a better artist through the diverse variety of people I get to collaborate with.

What’s the best advice you’ve ever gotten?

Be careful comparing myself to others and focus on my own path. Especially on social media.

What’s your biggest challenge as an independent professional?

Finding a balance and knowing when to give yourself time off. There are no weekends or set vacation days for freelancers. Also not knowing where your next paycheck is coming from (like during a pandemic) and getting yourself paid on time is really challenging. (Shameless editor promo: our Wingspan payment product helps freelancers get paid on time! Sign up for one month free here)

What’s your favorite freelance project you’ve worked on?

Keying makeup at NYFW shows!

What’s your best hot-take / unpopular opinion?

Brunch is better on weekdays.

What do you wish you’d known 10 years ago?

That fear just gets in the way of thriving!

Most iconic work role model?

Jane Goodall. She just really gave it her all with those chimpanzees.

How do you deal with difficult clients?

I try to meet difficult clients with patience and compassion as sometimes they are being difficult due to the stress of the situation. I will finish the job and once it’s over decide if that client is worth my time and effort again.

What–or who–is your go-to source for inspiration?

Nature, The Metropolitan Museum of Art, current fellow artists/designers, makeup artists from the past.

Best workday lunch?

Brain boosting food! Salmon, avocado, almonds, coffee, turmeric, eggs, green tea, etc…

What’s your anthem?


What’s your email sign off?

I personalize it for everyone! But you can’t go wrong with ‘Thank you so much for having me, Rocky’

Where can people find you?

I’m @rocky_mua on Instagram!

Want to be our next featured freelancer? Submit here!

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