Why Are Many Entrepreneurs Uncomfortable on a Relaxing Vacation?

Why Are Many Entrepreneurs Uncomfortable on a Relaxing Vacation Featured Image

Entrepreneurs often experience discomfort on relaxing vacations because the nature of entrepreneurship requires constant engagement and vigilance. To an entrepreneur, every moment presents an opportunity to improve, expand, or innovate their business. The abrupt shift from a high-energy, problem-solving mindset to one of idle relaxation can be jarring. This lack of constant mental stimulation can cause restlessness, anxiety, and even guilt, as they feel they should always be doing something productive towards their business goals.

Fear of Missing Out

Entrepreneurs may fear that taking time off will cause them to miss out on important opportunities or developments. This “fear of missing out” (FOMO) often stems from the fast-paced environment in which they operate, where timing can be everything.

Constant Connectivity

The modern business landscape is one of continuous connectivity, with emails, phone calls, and messages potentially bringing in new opportunities or the need for immediate problem-solving. Spending time away from these communication channels can lead entrepreneurs to worry they might miss a critical business development.

Competitive Nature

Moreover, entrepreneurs are frequently highly competitive individuals. The thought that their competitors are working while they are not can amplify the fear of losing ground.

Need for Control

Entrepreneurs often invest so much of themselves in their businesses that they develop a strong need for control. Vacations, by nature, can involve elements beyond their control, which can be uncomfortable.

Delegation Difficulty

Delegating tasks is essential while on vacation, but many entrepreneurs struggle with it because they are accustomed to being deeply involved in daily operations. This difficulty with letting go can make it hard for them to relax while away.

Trust Issues

Trust is another factor – entrusting the business to someone else, even temporarily, may raise concerns about things being done differently or incorrectly in their absence.

Habitual Work Mindset

Being an entrepreneur generally entails a non-stop work ethic. The habitual pattern of being always ‘on’ doesn’t shut off easily.

Ingrained Routines

Many entrepreneurs have routines and habits built around their work schedules that become deeply ingrained. Breaking away from these routines can be psychologically uncomfortable.

Identity Tied to Work

For some, their work is a significant part of their identity, and they may feel lost or out of place when not engaged in it. This can lead to a vacation feeling less like a break and more like an identity crisis.

Guilt Over Leisure Time

Taking time off often incites feelings of guilt in entrepreneurs, who might perceive it as indulgence or laziness.

Internal Pressure

The sense that they should be perpetually productive creates an internal pressure that is hard to switch off. Relaxing can then feel like they’re neglecting their business responsibilities.

Cultural Expectations

Additionally, cultural expectations, especially in the sphere of entrepreneurship, often equate constant activity with success. This can make the idea of taking leisure time seem counterintuitive to an entrepreneur’s conception of achievement.

In short, entrepreneurs’ discomfort on relaxing vacations is multifactorial, arising from fears associated with missing out, the need for control, ingrained work habits, and guilt over taking leisure time. Understanding these factors is crucial for entrepreneurs to find a balance that allows them to enjoy well-deserved breaks while ensuring their business thrives.

Strategies for Embracing Relaxation

Despite the challenges, it is important for entrepreneurs to learn how to embrace relaxation to avoid burnout and maintain their overall well-being. Implementing specific strategies can help ease the transition from the work mindset to relaxation mode during vacations.

Scheduled Check-ins

Designating certain times for checking emails or voicemail can satisfy the need to stay connected while limiting it to a manageable level. This ensures entrepreneurs can keep a finger on the pulse of their business without compromising their time off.

Mindfulness and Decompression Techniques

Practicing mindfulness or other relaxation techniques can help entrepreneurs become more comfortable with taking breaks. Meditation, yoga, or simply setting aside time for reflection can enable them to mentally disconnect from work and enjoy moments of peace.

Post-Vacation Integration

Returning from vacation can be just as important as the vacation itself. It’s beneficial for entrepreneurs to plan for a smooth re-entry to their business life.

Buffer Days

Planning a day or two of buffer between vacation and returning to regular work can help ease the transition. Use this time to catch up and prepare for reintegration without the immediate pressure of full-on business activities.

Reflecting on Vacation Benefits

Upon return, reflecting on the positive aspects of taking time off can reinforce the value of breaks. Entrepreneurs should acknowledge any benefits to their mental clarity, creativity, or even strategic thinking that arose from their time away.


How can entrepreneurs minimize guilt when taking vacations?

Entrepreneurs can minimize guilt by recognizing that breaks are a crucial component of long-term productivity and success. Before leaving, they should remind themselves of the importance of rest for their health and well-being. Setting clear goals for what they wish to accomplish before the vacation can provide a sense of completion and permission to truly disconnect. Furthermore, communicating the importance of the break to their teams can help establish an understanding environment that values the well-being of everyone, including the leader.

What can entrepreneurs do to prepare their team for their absence?

Entrepreneurs should ensure that their team is well-prepared for any eventualities during their absence. This involves providing thorough training, comprehensive guidelines, and clear expectations. They can also designate a responsible individual or a temporary leader who can make decisions in their stead. Scheduled check-ins can be planned ahead of time, providing reassurance and guidance without completely disrupting the vacation. By empowering their team, entrepreneurs can create a resilient structure that functions effectively, even in their absence.

Is it beneficial for entrepreneurs to unplug completely from work while on vacation?

Completely unplugging from work can be highly beneficial for entrepreneurs, as it allows for a full mental and emotional reset. It can lead to increased creativity, new perspectives on business challenges, and improved overall well-being. However, the feasibility of totally disconnecting varies depending on the individual and their business. Some may prefer scheduled times to check in, which can alleviate anxiety without significantly impeding relaxation.

How does vacation time impact an entrepreneur’s long-term business performance?

Taking vacation time can significantly enhance long-term business performance by mitigating burnout and fostering creativity and fresh perspectives. After a period of rest, entrepreneurs often return to work with renewed energy, clearer thinking, and heightened motivation—all of which are essential for strategic decision-making, leadership, and driving business growth. Regularly scheduled breaks can lead to a more sustainable work-life balance, increasing the likelihood of long-term success and satisfaction in both personal and professional realms.

How should entrepreneurs deal with the workload that accumulates during their vacation?

Upon return, entrepreneurs should prioritize tasks and delegate where possible to manage the accumulated workload effectively. A buffer period can prove advantageous, allowing them to sort through emails and updates before diving into the more demanding aspects of their role. Approaching post-vacation work with a structured plan will help channel efforts productively, reduce stress, and maintain the benefits gained from the vacation.

Can entrepreneurs benefit from shorter breaks instead of extended vacations?

Shorter breaks, such as long weekends or mini-vacations, can be very effective for entrepreneurs. These can provide quick bouts of rest without the stress of being away for too long. Mini-breaks can serve as regular intervals of relaxation to recharge while ensuring the entrepreneur is not removed from critical operations for an extended period. The frequency and timing of these breaks should align with the natural ebb and flow of the business to maximize their effectiveness.

What are some signals that an entrepreneur should take a break?

Signs that an entrepreneur needs a vacation include constant fatigue, irritation, decreased productivity, lack of creativity, difficulty focusing, and a feeling of burnout. If regular tasks begin to feel overwhelming, or if they are making more mistakes than usual, it may be time to take a break. Additionally, if personal relationships start to suffer due to continuous work stress, this is a strong indicator that it is time to step back and recharge.

How can entrepreneurs foster a company culture that supports taking vacations?

Entrepreneurs can lead by example by prioritizing their well-being and openly scheduling and taking vacations. By doing so, they signal to their employees that taking breaks is not only accepted but encouraged. Creating policies that ensure ample vacation time, promoting a work culture that values life outside of work, and recognizing the benefits of rest for productivity and creativity are all steps toward fostering a supportive environment. Transparent communication about the importance of recharging and how it contributes to the company’s success can help instill a culture that embraces vacations.


The article provides insights into why entrepreneurs find it difficult to enjoy relaxing vacations, including key challenges and strategies for overcoming them.

Key Takeaways:

  • Entrepreneurial FOMO and competitiveness can make detaching from work difficult.
  • Many entrepreneurs have a strong need for control and face difficulty in trusting others with their business.
  • Ingrained work routines and identities tied to work contribute to entrepreneurs’ discomfort with relaxation.
  • Feelings of guilt about leisure time are exacerbated by internal pressure and cultural expectations.
  • Strategies such as scheduled check-ins and mindfulness can help mitigate the anxiety of taking a break.
  • Planning buffer days and reflecting on the benefits of vacation can ease the post-vacation transition.

By understanding these points, entrepreneurs can better navigate the balance between their commitment to their business and taking the well-deserved rest necessary for long-term success.

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*Based on a survey of small businesses using QuickBook Online conducted September 2018.