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

Take the 5 minute Get a GRIP Leadership Assessment today! Go to: https://www.reworkit.co/grip  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 the Founder & CEO of Reworkit, a transformational coaching company that helps leaders and their teams break through the "hidden drag" holding back growth, whether that's communication breakdowns burning time and money, teams that can't execute, or leadership habits getting in the way of results. With over 15 years leading teams of up to 100+ employees across finance, consulting, hospitality, and tech startups, Jess knows the chaos of scaling and high performance firsthand. She blends expertise in organizational psychology with real-world leadership experience to help clients manage their teams, manage themselves, and build operations that actually run without constant firefighting. Jess works with entrepreneurs, executives, and organizations across industries. She is a sought-after voice whose insights have been featured in The New York Times, The Wall Street Journal, Bloomberg, and Fast Company. You can learn more about her and her work at www.reworkit.co Socials & Links Website: https://www.jesswass.com/Company: https://www.reworkit.co/LinkedIn: https://www.linkedin.com/in/jesswasserman 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 help entrepreneurs thrive, Justin created the Entrepreneur DNA community to support business owners in building wealth, systems, and long-term freedom. Through his podcasts, books, education platforms, and hands-on mentorship, he continues to help entrepreneurs scale with clarity and confidence. Connect with Justin: Instagram: @thejustincolby YouTube: Justin Colby TikTok: @justincolbytsof LinkedIn: Justin Colby Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.