EP #293 How the Best Companies Beat Entrepreneurship

There is a lot of talk about leaving corporate life…

…quitting your job, and “betting on yourself” as the only path to freedom. In this episode, I ask a different question, is corporate life really broken, or are most workplaces just not generous enough yet to give people what they are craving.

I share why we do not need every talented person to become a solo entrepreneur, and how generous workplace cultures can offer the same things people think they have to leave to find, ownership of time, presence at home, optionality, purpose, and meaningful impact.

We’ll walk through twelve signs that often push people toward the entrepreneurial leap, things like wanting to own your calendar, desiring more purpose than politics, seeking freedom over titles, and wanting to grow your own brand and skills. Instead of telling you to quit, I show how the best companies are building environments where you can have those things while still working with a team, with resources, and with stability. You’ll also four practical solutions you can start using right now to make your organization more generous, whether you are the official leader or you are leading from within.

If you have ever thought, “Maybe I need to leave corporate to feel fulfilled,” this episode will help you see another path. You will learn how to build or seek out a generous culture where you can be present for your family, own more of your time, grow like an entrepreneur, and still enjoy the support of a healthy organization.

*Enroll in the “Feeling Generous” Email course 📧

Have a generous week of business. 📈

What You'll Learn in Today's Episode:

  • Why people feel pulled toward entrepreneurship and whether corporate life is really “broken” or just lacking generosity.

  • How generous workplace culture gives people many of the same benefits they hope to find by leaving, autonomy, purpose, flexibility, growth, and meaningful impact. ​

  • The twelve signs that you are ready for more freedom and purpose at work, and how to interpret them without automatically assuming you need to quit.

  • How the best organizations are designing roles, schedules, and processes so people can own their calendars, be present at home, and still contribute at a high level.

  • Practical ways leaders can turn employees into “intrapreneurs,” giving them room to innovate, grow their skills, and take risks inside the company.

  • Four concrete practices you can implement, or ask for, right now to move your existing company closer to generous culture instead of starting over somewhere else.

Quotes Worth Sharing:

“Is corporate life broken, or is it just not generous enough yet to give people what they are craving.”

  • Bob DePasquale

“We do not need everyone to leave corporate and go solo. We need more generous organizations where people actually want to stay.”

  • Bob DePasquale

“Generous cultures give people what they would otherwise chase as solo entrepreneurs, freedom, purpose, and the chance to make something great together.”

  • Bob DePasquale

“You might not need a new career. You might need a new environment, or to help create one, where your gifts can actually be used.”

  • Bob DePasquale

“When people feel like they own their time and their contribution, they stop counting the hours and start caring about the impact.”

  • Bob DePasquale

“You can build a life where you are present at home, fulfilled at work, and surrounded by a team, without having to do it all by yourself.”

  • Bob DePasquale

“The future belongs to organizations that treat people like they are capable entrepreneurs, but give them the security and support corporate can offer.”

  • Bob DePasquale

Resources from Today’s Episode:

  • My socials: LinkedIn - X - Substack

  • On Corporate Life, Entrepreneurship, and Satisfaction

    Why Employees Are Quitting To Start A Business – Forbes
    Explores key reasons people leave corporate to start businesses, like wanting more autonomy, flexibility, and the chance to address needs they care about.​
    Helps frame why people are tempted by entrepreneurship and what generous companies must offer if they want to retain high potential people.​

    Americans’ Job Satisfaction in 2024 – Pew Research Center
    Provides fresh data on how satisfied workers are with their jobs, relationships at work, and how respected they feel by supervisors and coworkers.
    Underscores how factors like purpose, relationships, and respect drive satisfaction, and how improving culture inside companies can keep people from feeling forced to leave.

Related Episodes:

Robert DePasquale

Lover of Stewardship

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EP #292 The 5 Things Wasting Most of Your Time