Back in 2021, I went to put in my notice at my full-time job and came out with "entrepreneurial leave".

While you may not have heard of this benefit, if you're seeking creative ways to retain top talent, this is the underrated benefit you've been searching for. It gives ambitious employees the chance to explore new ideas without severing ties with your company, and builds lasting loyalty in the process.

Here’s how it worked, why it mattered, and what other employers can learn from it.

​Read this on the web | Subscribe​

Why I Was Ready to Quit (Even Though I Loved My Job)

From 2018-2021, I successfully juggled my full-time leadership role at a tech company with growing Remote Work Prep, my business dedicated to helping remote teams work better.

Balancing both wasn’t easy, but I chose this path intentionally:

• Financial stability – My job allowed me to never have to make business choices based on money. Every choice I made was value-driven, and I found it liberating.
• Better user research – I was working inside my ideal audience every day. The best way to make something valuable is to be an insider. It was a win-win for my FT company too, because they got my best ideas first.
• Peace of mind – I never felt pressure to “make it” as an entrepreneur overnight.
• A team I loved – I wasn’t looking to escape a toxic workplace. I genuinely enjoyed my colleagues and the work I did.

But as my business grew, so did the demands on my time. I was preparing to launch a live course on mastering remote leadership, and I realized I simply couldn’t do it all.

I wasn’t burned out. I was out of bandwidth. And I knew that if I kept trying to do both, something (or someone) would eventually suffer.

That’s when I made the tough decision to put in my notice.

The Unexpected Offer: Entrepreneurial Leave

When I sat down with my CEO to resign, I expected a straightforward conversation. Instead, he surprised me with an alternative:

I was stunned. I had never heard of entrepreneurial leave before, but it was the perfect solution:

✅ More time – I could fully focus on my business without feeling torn between two demanding roles
✅ No burned bridges – Leaving a job I loved was one of the hardest parts of my decision. This gave me flexibility
✅ A chance to test the waters – Instead of going all-in overnight, I could see what full-time entrepreneurship felt like before making a permanent decision

In that moment, I realized how rare this kind of flexibility and support was, and how much of a difference it makes in employee loyalty.

The Power of Flexible Leadership

My CEO didn’t have to offer me this. He could have just accepted my resignation and moved on. But great leaders think long-term.

By creating an environment where employees feel valued, supported, and trusted, he built a team with high retention and strong loyalty. I’d seen him do this time and time again, and it’s a lesson I’ve tried to carry into my own leadership style.

When September rolled around, I switched from an employer to client relationship with that company until they sold. As for the CEO, we still talk regularly, and I’ve had the opportunity to support him in return over the years. Even four years later, I would still drop everything to help this leader if they ever needed it.

Leaders who want to retain top talent recognize that supporting growth isn’t optional. It’s a competitive advantage.

How Companies Can Benefit from Entrepreneurial Leave

Most employers couldn't fathom offering entrepreneurial leave, but forward-thinking companies should consider it. Offering this kind of flexibility benefits organizations by:

• Encouraging growth – Employees who take time to build their own ventures develop new skills that they bring back to the company. By supporting personal and professional growth, companies create a workforce that is more adaptable and forward-thinking.
• Retaining top talent – Instead of losing valuable employees to entrepreneurship, companies can offer a middle ground that keeps them engaged and loyal.
• Building a culture of innovation – Encouraging employees to explore entrepreneurial pursuits fosters creativity and fresh perspectives that can benefit the company in unexpected ways.

Companies that embrace entrepreneurial leave don’t just support their employees, they future-proof their workforce. By giving employees space to grow, companies gain a more skilled, loyal, and motivated workforce that’s better equipped to solve future challenges.

Entrepreneurial leave is more than a benefit. It’s a vote of confidence in your people. When you show you believe in their growth, they’ll show up for your company in ways that matter most.

​

If you’ve ever taken (or offered) entrepreneurial leave, I’d love to hear your story. Hit reply and share your experience.

​

Quote of the Week

- Confucius

​

In Other News

Tim Ferriss @tferriss Doing less meaningless work, so that you can focus on things of greater personal importance, is NOT laziness. This is hard for most to accept, because our culture tends to reward personal sacrifice instead of personal productivity. 9:15 AM • Mar 17, 2025 415 Retweets 3401 Likes Read 143 replies

​

In Case You Missed It

​March Favorites
​Last week, I shared my favorite lessons, reads, and shares of March.

​AI Recipe: Daily Mind Dump for Mental Clarity​
In a recent Idea Kitchen article, I broke down how to use NotebookLM’s new Mind Map feature to organize your thinking. It’s a fast, visual way to bring clarity to your ideas. Definitely worth trying out.

Work Forward Society Want to meet others who do work differently? Join us in making 2025 your year of less meetings and more real work! Join The Work Forward Society →

​

What did you think of this issue? What do you hope to see in the next one? Hit reply and let me know. I read every response. I truly appreciate you taking the time to read this. Hope you have a lovely day! Marissa ​Founder, Remote Work Prep​ P.S. Did you enjoy this issue? Share the article with a friend. Struggling with a remote work problem? Book a coaching call. If you liked this, consider supporting this free newsletter by leaving a testimonial. ​

​