An Entrepreneur’s Long Holiday Weekend: Balancing Business, Rest, and Relationships

Long weekends such as those three consecutive days away from work for holidays such as Memorial Day and Labor Day are the perfect time for rest, relaxation, and reconnecting with loved ones. But what about for entrepreneurs, those tireless individuals often consumed with the passion for their enterprise? Can they carve out time for themselves and their family amidst the demands of their ambitious endeavors?

The answer is complex, shaped by the individual’s work habits, their business demands, and the nature of entrepreneurship itself. However, a healthy blend of leisure, creativity, and minimal work can often be the recipe for an entrepreneur’s long holiday weekend.

The Rest

These three-day weekends for entrepreneurs should ideally involve downtime. A rest period is essential to replenish energy levels, improve productivity, and stimulate creative thinking. Entrepreneurs are well-known for their work ethic, but there’s a growing understanding that constant work without breaks can lead to burnout. It’s crucial for entrepreneurs to take time to recharge physically, mentally, and emotionally.

Rest can take different forms for different people. Some entrepreneurs may choose to unwind by engaging in physical activities like sports, hiking, or yoga. Others might opt for quieter pursuits, such as reading, meditating, or simply catching up on sleep. The key is to step away from work-related activities and let the mind relax and reset.

The Relationships

Long holiday weekends often provide entrepreneurs with a valuable opportunity to spend quality time with loved ones. It’s a time for family outings, catching up with friends, and rekindling relationships that might have taken a backseat due to demanding work schedules. This interpersonal connection not only enriches their personal lives but can also contribute to their professional success by reducing stress and providing emotional support.

The Work

While it might be ideal for an entrepreneur to completely disconnect from work during a holiday weekend, it’s often not practical or even desirable. Some entrepreneurs thrive on their work, finding it a source of joy and fulfillment. They might choose to spend some time during their holiday brainstorming new ideas, reading industry-related articles, or jotting down strategies for upcoming projects.

However, there’s a distinction between obsessively checking emails and doing a little work that feels invigorating or fulfilling. Setting clear boundaries between work and rest is crucial to avoid encroaching on the time meant for relaxation and relationships.

The Creativity

Entrepreneurs are often creative individuals, and a break from routine work can often lead to an outpouring of new ideas and innovation. This could involve anything from brainstorming sessions on the beach to casually discussing new business strategies over a barbeque.

Long holiday weekends can be a particularly fruitful time for these creative insights. When the mind is relaxed, it’s often more open to novel ideas and approaches. Taking a step back from the daily grind allows entrepreneurs to see the bigger picture and potentially come up with groundbreaking ideas that they wouldn’t have thought of in the midst of a busy work week.


In essence, an entrepreneur’s long holiday weekend is a delicate balance between rest, family time, minimal work, and creative thinking. While the entrepreneurial drive makes it challenging to entirely switch off, incorporating leisure and relaxation is not only beneficial for personal well-being but also for the long-term success of the business. The trick is to find a balance that respects both the demands of entrepreneurship and the human need for rest and connection.

Make it a great long holiday weekend. Make it happen. Make it count!