Leading with Love: A Candid Conversation with Ally Love

A conversation with

Ally Love

CEO of Love Squad,
Today Show on-air contributor,
Peloton instructor, host and speaker

Annie Diamond

Executive Director, New England
Regional Sales Manager,
Morgan Stanley

Love and diamonds are typically a winning combination. When Annie Diamond, Executive Director and New England Regional Sales Manager at Morgan Stanley, sat down with Ally Love, CEO/Founder of Love Squad, Today Show on-air contributor, Peloton Instructor and in-arena Host of the Brooklyn Nets, it was no exception. Their frank conversation about "progress over perfection," motivation and health and wellness will inspire all those who aspire to "boss up."

Annie Diamond: I am thrilled about this latest installment of Morgan Stanley's Lessons in Leadership featuring Ally Love, a multi-talented leader whose words of empowerment inspire hundreds of thousands of people to live happier, healthier and fuller lives. Can you share a bit about how you founded Love Squad in 2016?

Ally Love: As a young woman living in New York City, I didn't have the resources to network and seek out the conversations required to navigate my career. So, I created this rinky-dink website called "Love Squad." I put a call to action out to my 3,000 Instagram followers to join a free event about personal and professional branding and within 15 seconds, the slots were filled. The aha, sticky moment happened when we held the event and I realized that this can become the catalyst for change in at least one person's trajectory.

Diamond: What does it mean to be a boss and boss up?

Love: During my first few months as a Peloton instructor, I wanted to be the boss of the bike, clip in and make people feel good. Throughout class, I tested it out, saying "let's boss up." It's about reclaiming agency, taking back power and redefining what being a boss means. You have that power by simply bringing your energy into any room.

Diamond: "Progress, not perfection" is an "Allyism." What does that mean to you?

Love: During class, when I say "progress over perfection," you think I'm saying it to you, but I'm also saying it to myself. It's a reminder for me to take some pressure off of myself, that I'm here, progressing and moving forward. It helps me be more mindful of how I use my energy and focus on my daily priorities.

Diamond: How do you balance your professional and personal responsibilities with self-care?

Love: I've stopped saying that I am very busy and started saying that I'm productive. By saying, "I'm so busy," I was feeding a negative narrative that made work and life feel laborious and heavy. We can communicate with our personal and professional counterparts to let them know what our current priorities are and that in this moment, this is where the energy is going.

Diamond: What tools do you use to stay motivated and positive?

Love: I believe in incorporating rituals within personal routines. My advice to anyone struggling or dealing with the fact that you don't have time to breathe is to commit to getting up five minutes earlier. Even when I have to teach at 6 a.m., I do this and just sit in my chair in the dark, drinking my water and breathing, taking that five minutes that's just mine to own.

Diamond: What would you say is the biggest failure that helped you learn the most?

Love: One really pops out—I was modeling while in college and got a phone call from my agent that a long-term client no longer wanted to work with me. At that moment, I felt terrible and rushed into signing my modeling contract, which was up for renegotiation. I allowed myself to compromise my self-worth in this instance, but my self-worth is non-negotiable and everyone deserves respect, kindness and consideration.

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