Break and Entrepreneurship: Love- Hate Relationship?

I was going through someone’s LinkedIn profile yesterday, and I came across this quote, and it stuck with me:

Entrepreneurship gives you the freedom to take a day off any day. But a founder often dares not to take it.

Entrepreneurship is often viewed as the ultimate path to freedom and money. The idea of being your boss and having the ability to take a day off whenever you desire sounds enticing. However, the reality for many founders is far more complex and challenging. As a first-time founder of EntrePi, it had at one point become impossible to not think about work. It still sometimes is. Even though the founders may technically have the freedom to take a day off, the pressure to succeed, the fear of failure, and the constant demands of running a business make it incredibly difficult.

What stops founders?

Freedom vs. responsibility: Entrepreneurship promises the freedom to create your schedule and take time off as needed. On the other hand, founders often feel a deep sense of responsibility towards their work, team, customers, and investors, making them hesitant to step away, even briefly.

The ultimate battle between long-term and short-term needs: Founders are often driven by a long-term vision for their business, which requires significant dedication and hard work in the initial stages. This long-term focus may conflict with the desire to take a day off and relax in the short term.

FOMO vs. fear of failure: Founders may fear missing out on crucial opportunities if they take time off, which could be detrimental to their business’s growth. At the same time, the fear of failure and the belief that no one else can handle their responsibilities as well as they can often keep them from taking a break.

Why is this?

Many entrepreneurs and business leaders advocate for a hustle culture, glorifying long working hours and constant dedication to the business. This culture can perpetuate the belief that taking time off shows weakness or lack of commitment. Additionally, the competitive nature of entrepreneurship can create an environment where founders fear that any break might put them at a disadvantage compared to their competitors.

While the hustle culture is required at some point, it is temporary. There will be moments in my startup journey where I have to push myself every day, and I look forward to them (at least as of now :p), but I also have to know that is not permanent.

Like Naval Ravikanth has said, train like an athlete. Sprint, rest, analyse. Then repeat.

Having a hustle mindset and following the hustle culture are very different things. A hustler’s perspective is always on the lookout for the next opportunity and chance but also realises the needs and limits of the human body and the importance of analysis and reflection.

Founders must recognise that caring for their physical and mental well-being is essential for long-term success. By setting clear boundaries and prioritising self-care, they can recharge and be more effective in their roles.

As I write this article, I will be taking a break from work next week due to some other unavoidable commitments. Am I OK with it? Hell no.

Can I do anything about it?

During the break, no, excepting taking stress that would neither lead to the other work being fruitful or something groundbreaking happening here. And I am certainly not signing up for it. So to mitigate this, I proactively planned for the time off, ensuring things would be in motion when I would not be around.

This made me feel tons better.

Planning ahead combined with delegation takes one’s toll. It allows for a more well-rested, mentally balanced founder who is more likely to make sound decisions and lead their business to tremendous success.

To all the people reading this without reading the previous articles, I am in the middle of making a startup-themed board game. I am documenting my progress as I move forward. I keep discussing the various roadblocks, the attempted solutions and my next step through these articles.

If you want to playtest Startup High, please join this Whatsapp Group. I update this group with regular playtests for everyone to be a part of it!

The game aims to get entrepreneurship and startup into the mainstream; board games are an excellent way to do it. If you like the idea or want to contribute, please visit entrepi.world and contact us!