Taking the Leap to Be Your Own Boss

Elaine Welteroth

Lesson time 06:38 min

What are the questions you should ask yourself before venturing out on your own? This lesson is for creative entrepreneurs, side hustlers, and mid-career pivoters who are ready to take the leap.

Students give MasterClass an average rating of 4.7 out of 5 stars

Topics include: Taking the Leap to Be Your Own Boss • Don’t Let Fear Dictate Your Direction •


- We've talked about identifying your zone of genius. We've talked about excavating, you know, answers to what it is you really want out of your career and your life. And we've mapped out a game plan to get there. But how do you really know if you're ready to quit your job and take a bet on yourself? This is the question you have to ask yourself. [MUSIC PLAYING] You should be getting something in return for the investment of your time, your energy, and your hard work into your career or into your job. And I will tell you there-- there are times that I've come to in my career where I'm like, I'm quitting today. Today's the day. I've had enough. I'm walking out. I'm not coming back. They don't appreciate me. They don't pay me enough. This is too damn hard. I don't have enough resources to do what I need to do. This person is standing in my way. I could do better on my own, right? Like you feel me. You've been there, right? Like we've all been there. We're like, I had enough of this one. Or-- there goes my ring. I'm throwing shit. I'm taking off earrings. I'm ready to fight. Sometimes, you get there. And before you make any rash decisions from that place, I beg you to stop yourself, take a breath, and ask, have I reached the point of diminishing returns? Is there something that I have yet to learn? Is there a skill that I'm still honing here that I'm going to need in my next chapter? Is there a financial goal that I have yet to hit? Really, take the time to go through the pillars that we've talked about and ask yourself, is there more for you to get that you would be cheating yourself if you walked away from it all today? Would you have any regrets? You have this question in your back pocket that is just there waiting for you for those moments to pull out and to really sit with yourself and grapple with whether or not it's really your time. [MUSIC PLAYING] I think it's really important that we acknowledge how scary it is to walk away from a known entity, to walk away from an identity that has been defined by a particular role within a company. It's difficult to walk away from a steady paycheck. The sheer notion of leaving that all behind is enough to keep people stuck in a place where you're no longer growing for the rest of your life. And I think the reason that you're even in this class, the reason that you and I are even connecting right now, is because you are the kind of person that is looking to live a different kind of life, a life that is fulfilling. And I have to tell you fear is going to be part of the process. We all feel fear. We have to become friends with it. We have to figure out how to dance with fear and not to allow fear to dictate where we go or where we end up stuck. When I was grappling with this extremely scary decision of whether it was time to leave this big job at "Teen Vogue" that had come to define me in the public eye, that other p...

About the Instructor

After a decade in her dream job as editor in chief of Teen Vogue, award-winning journalist Elaine Welteroth realized she had other dreams worth pursuing. Now, the New York Times bestselling author, multimedia trailblazer, and judge on the new Project Runway is teaching you how to get out of your comfort zone and harness your personal values, passions, and skills to custom design a career path as unique as you are.

Featured MasterClass Instructor

Elaine Welteroth

Former Teen Vogue editor in chief and multimedia icon Elaine Welteroth teaches you how to harness your values, skills, and passions to create your dream career path.

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