How One Musician Turned Into a Successful Entrepreneur

It’s not easy being a master of all trades—but that doesn’t stop us from trying. To help you in the ever-ongoing pursuit of thriving in your career, your personal life, and beyond, we’re debuting a new series called Keep It 100 in partnership with Dole Packaged Foods. In this weekly installment, we’ve shared productivity hacks for the workweek as well as real-mom advice on balance. This week, we’re featuring a woman whose whole life is a balancing act in this new video series where a musician-turned-entrepreneur shares how she keeps it 100 every day.

Director, Ronald Schnetke; Creative Director, Amy Osburn; Prop Stylist, Aneta Florczyk; Wardrobe Stylist, Lisa Mosko; Hair & Makeup, Hayley Farrington; Photographer, Edward Negron

It’d be difficult to assign 34-year-old Caitlin Crosby a singular title—entrepreneur, philanthropist, mom, and musician would all be wholly accurate. For Crosby, life seems to be a balancing act between two primary passions: her love for music and creativity, and her passion for helping the homeless. Somehow, one love led to the other. Her origin story begins, like many, on Hollywood Boulevard. After a show, Crosby ran into a homeless couple who she not only invited over for dinner but subsequently hired for her startup, The Giving Keys, a company that employs people who are transitioning out of homelessness.

Above, watch as Crosby shares how she manages to Keep It 100 in every element of her life. From founding a company to becoming a mom to changing the world one key at a time, this enterprising slashie is figuring out how it all fits together.