The Thrive Questionnaire With Alyssa Raine

The Interim Chief Marketing Officer at Walgreens opens up about waking up before sunrise, taking breaks from her phone, and the one change she made that boosted her success when first starting out.

When you have the opportunity to ask some of the most interesting people in the world about their lives, sometimes the most fascinating answers come from the simplest questions. The Thrive Questionnaire is an ongoing series that gives an intimate look inside the lives of some of the world’s most successful people.

Alyssa Raine is the Interim Chief Marketing Officer and DVP Brand Marketing at Walgreens.  She has led marketing at a variety of organizations, from start-ups to 100 year old brands, and built ecommerce. In her Thrive Questionnaire, she opens up about waking up before sunrise, taking breaks from her phone, and the one change that boosted her success when she was first starting out.

TG: What’s the first thing you do when you get out of bed? 

AR: I love the mornings and typically wake up before 5am.  I sneak a check in on my three kids (love the sounds of their soft sleeping), go for a run if I can, and call my grandma.  We are usually the only ones awake.  

TG: What gives you energy?

AR: Looking at my kids and wanting to provide a good life for them, both in a caring, safe home and in a caring, safe world.  We have a short, wonderful, and sometimes challenging time on this earth.  I want mine to have meant something, to have made people’s lives a smidge better.  And I want to enjoy it.  So every single day I am exceptionally thankful that I get to spend time with my family, that I get to work on a meaningful purpose – to champion the health and wellbeing of every community in America, and that I get to connect with amazing people at Walgreens and with our many incredible partners.    

TG: What’s your secret life hack?

AR: I have two. First, is my phone.  I use it to manage most everything in my life – from buying groceries to maintaining friendships, finding sitters to filling prescriptions on Walgreen’s app. Massive kudos to the moms who were able to run their households pre-mobile – I have no idea how they did it! Second, is putting down my phone. I love to enjoy people and the world around me. The best moments of our lives are not on a screen. Those moments are what really brings me joy.

TG: Name a book that changed your life.

AR: Difficult to name just one as reading is a massive passion of mine. I typically read two to three books at a time, and a mix of business (makes me better at my job), British lit (my mental candy), and child development (makes me a better mom).

TG: Tell us about your relationship with your phone. Does it sleep with you?

AR: Does the bedside table count?

TG: How do you deal with email?

AR: To be effective, make sure your inbox isn’t by default your priority list.  You won’t get much done and you won’t enjoy the work you do.  Email is one of many communication tools – know what you want to accomplish, and decide when email will help facilitate executing those goals.  Also know that any email you send could create additional work for others that you did not intend, or could be misread in tonality.  So think before you hit send.  

TG: You unexpectedly find 15 minutes in your day, what do you do with it?

AR: Go outside and wander.  I love our new Walgreen’s offices in both Deerfield and downtown Chicago, but I absolutely love to be outside and explore.  I love to be in nature – I’m a mountain girl – but I also love to wander cities – whether it’s Chicago, SF, London, or Beijing.   

TG: When was the last time you felt burned out and why?

AR: First year at business school.  My section mates were incredibly smart, and to keep up, I felt like I had to work around the clock.  So, I did, and I only slept 2-4 hours a night for the entire year.  The result was that I performed average as a student, and I ended up feeling lousy. So, second year I forced myself to sleep 7-8 hours a night.  I felt much better and I performed much better, graduating in the top 15% of the class.

TG: When was the last time you felt you failed and how did you overcome it?

AR: A few years ago, I didn’t fully internalize that each organization has their own DNA.  When you enter a new corporation, you need to listen, learn, and respect that DNA to be absorbed into the organization.  If you don’t you will not be able to effectively get things done.  I listen and learn intently and then earn the right to push at the appropriate time.

TG: Share a quote that you love and that gives you strength or peace.

AR: It had long since come to my attention that people of accomplishment rarely sat back and let things happen to them. They went out and happened to things.”    – Leonardo da Vinci

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