Stop “Shoulding” Yourself: How to Build a Business That Actually Fits Your Life | Jess Wass
4/16/202636 min
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 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
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Clips
Transcript preview
First 90 secondsJustin Colby· Host0:00
What is up The Entrepreneur DNA family? This is gonna be incredible. Now, as always, I bring on the best of the best guests, and they are gonna be the advisors to the school community, skool.com/theentrepreneurDNA. That's where you can learn directly from them, not just on a podcast, but learn their expertise, engage with them, ask their questions. So if you want to grow as a business owner, get to school, skool.com/theentrepreneurDNA, so you can listen to my next guest, who she is an expert at managing 360. She's an expert in corporate leadership. Jess Wass is here. How are you?
Jess Wass· Guest0:39
Hi. How are you? I'm so excited to be chatting with you again.
Justin Colby· Host0:42
I know. Now, if you guys are watching this, the bummer is we just found out she's in, in Brooklyn, and I think I'm headed to Brooklyn in, like, 10 days. So we could've been doing this live, but we will still make it work no matter what, right?
Jess Wass· Guest0:54
Yeah. We got the magic no matter what.
Justin Colby· Host0:57
That's right. So listen, you're very much an expert about what I believe is a great term, managing 360. Tell us more about that.
Jess Wass· Guest1:06
Yeah. So when I say managing 360, I'm talking about managing up, so this is more for folks who are still working in corporate, where they have to manage up to people higher than them. How do you make sure that you're being seen, heard, and appreciated, and valued so you can get promoted? And then managing down, which is very relevant to this community in particular. How do we manage everyone underneath us? How do we lead? And then what I call managing