Entrepreneurs, Long Weekends, and the Power of Choice
Rethinking the Myth: Entrepreneurs and Time Off
As we settle into the middle day of a long holiday weekend, I’m giving myself permission to hit pause—not just on work, but on the pressure to do. Instead of focusing on what needs to be done, I’m shifting my attention toward what I enjoy—maybe something I’m passionate about but haven’t had the time or headspace to explore. Even if it’s loosely tied to work, if it fuels my soul or sparks my creativity, that’s good enough for me.
Like many of you, I’m taking these couple of days to slow down, recharge, and embrace the rare gift of not having to do anything—at least not anything I have to do. Instead, I’m choosing what I want to do. And that, in itself, is a luxury. Because when we really think about it, freedom is the ability to choose. And the power of that choice? It defines so much of what entrepreneurship is all about.
But before I let my mind fully drift into weekend mode, I want to share some thoughts I’ve written about before—thoughts on entrepreneurs and long holiday weekends. It still resonates deeply every time this kind of weekend arrives.
Entrepreneurs and Long Holiday Weekends
There’s a widely held belief that entrepreneurs never take time off. That they work around the clock, miss family gatherings, and are constantly absorbed in the grind. People often ask me—Is that really true?
The answer is: not entirely. Yes, there’s truth to the idea that many entrepreneurs push their limits. Some do pull all-nighters and grind their way through weekends. But much of the mythology is just that—myth. We tend to romanticize the sleepless, overworked entrepreneur like some kind of modern superhero. But let’s not forget: entrepreneurs are human. We need rest, recovery, and time away to clear our minds and reconnect with what matters.
What separates successful entrepreneurs from the rest isn’t their ability to power through without sleep—it’s their ability to choose. To choose when to lean in, and when to step back. To decide how to spend their time, energy, and attention. That’s the real power behind entrepreneurship: the ability to create space for freedom and flexibility on your own terms.
Entrepreneur and best-selling author Richie Norton summed it up perfectly:
“Entrepreneurs don’t have weekends or birthdays or holidays. Every day is my weekend, my birthday, my holiday. OR every day is my workday. Mostly it’s a choice.”
That word—choice—is so important.
One of my favorite insights comes from Strategic Coach, a world-class organization dedicated to helping entrepreneurs succeed. In one of their blog posts, they pose a simple but profound question:
“Why did you decide to become an entrepreneur?”
For most of us, the answer is freedom—freedom of time, freedom to earn what we’re worth, freedom to work with who we choose, and freedom to live with purpose.
Another organization I greatly admire is The Lonely Entrepreneur, founded by Michael Dermer. What I love about Michael’s work is how deeply he understands the emotional rollercoaster of entrepreneurship. His perspective is raw, honest, and relatable.
In his piece “What is an Entrepreneur? Dealing with the Holidays,” there’s a line that always comes to mind as a long weekend approaches:
“As entrepreneurs, we have enough stress throughout the year trying to win customers, bring on employees, raise money and sign deals with vendors. We may have enjoyed, or even taken advantage of these breaks in our ‘past lives,’ but once you become an entrepreneur, we can’t understand how this ever made sense.”
Both Dermer and Dan Sullivan, founder of Strategic Coach, have had a tremendous influence on me. They come at things from different perspectives, but both speak from deep experience and a genuine desire to see entrepreneurs thrive. I’ve learned a lot from each of them—and I continue to.
Their work constantly reminds me of the importance of three foundational principles that anchor my own entrepreneurial journey:
Freedom. Choice. Balance.
Freedom – the power to act, speak, or think without constraint.
Choice – the ability to decide between two or more possibilities.
Balance – the ability to maintain the right proportion between competing priorities.
That’s what entrepreneurship is really about—not just building businesses, but building lives that we love. And in that sense, holiday weekends aren’t just pauses in our schedule. They’re reminders of why we do what we do.
So however you’re spending this weekend—working on your passion, lounging in the sun, catching up with loved ones, or simply doing absolutely nothing—I hope it fills your cup. And I hope it reminds you that rest isn’t retreat. It’s an investment in your long-term energy, clarity, and purpose.
Make this a great weekend. Make it happen. Make it count. AND… Make it meaningful. Make it yours.
About the Author
Paul Segreto brings over four decades of hands-on experience in franchising, restaurants, and small business development. A passionate advocate for entrepreneurship, Paul has helped countless individuals turn their visions into thriving ventures. Ready to take your next step in business or looking for expert insight to overcome today’s challenges? Reach out directly to Paul at paul@acceler8success.com — your path to success may be one conversation away.
About Your Entrepreneurial Success (YES)
Your Entrepreneurial Success (YES) is a dedicated platform created for aspiring entrepreneurs, family business stakeholders, and the next generation of partners and leaders. Recently launched, YES is designed to deliver the insight, strategy, and inspiration needed to successfully navigate — and thrive — throughout the entrepreneurial journey.
If you’re thinking of business ownership for yourself and learning how the choice of a franchise, startup or acquisition can “jump-start” both the process AND your earning potential, please visit OwnABizness.com. If interested in taking a deeper dive into how to succeed as an entrepreneur, please visit AccelerateSuccessCoaching.com.