Stop “Shoulding” Yourself: How to Build a Business That Actually Fits Your Life | Jess Wass

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In this episode, I sat down with Jess Wass to break down what it really means to build a business and life that actually aligns with who you are. We talked about her “Managing 360” framework, why so many entrepreneurs feel stuck or overwhelmed, and how most of us are chasing success based on what we think we “should” want instead of what truly matters to us. We got into values, decision-making, comparison, and even when quitting is the right move. This episode is a deep dive into how to stop living someone else’s version of success and start building a life that actually fulfills you. Jess Wass Bio Jess Wass is a Career Coach, Organizational Development Consultant, and the Founder & CEO of Reworkit, a transformational coaching company that helps high-achieving individuals and organizations build careers and cultures with intention. With over 15 years of experience across finance, consulting, hospitality, and startups, Jess specializes in helping professionals and leaders navigate career transitions, lead high-performing teams, and overcome the internal and external barriers holding them back. She holds a Master’s degree in Social-Organizational Psychology from Columbia University and is a Certified Professional Co-Active Coach (CPCC). Jess blends behavioral psychology with real-world leadership experience to deliver practical frameworks that drive clarity, alignment, and results. Jess has been featured in major publications including The New York Times, The Wall Street Journal, Bloomberg, and Fast Company, and is known for her expertise in helping overachievers who feel stuck design careers and lives that actually work for them. Socials & Links Website: https://www.jesswass.com/Company: https://www.reworkit.co/LinkedIn: https://www.linkedin.com/in/jesswass/ About Justin: Justin Colby is the host of The Entrepreneur DNA and The Science of Flipping podcasts and a best-selling author. He is a serial entrepreneur with over and a seasoned real estate investor with over 20 years of experience. Driven by a passion to he