Why Founders Should Live Life Like a Vacation

Diving deeper into my unpopular opinions, I assert that success doesn’t have to come with suffering.

Yes, you heard that right: Entrepreneurs don’t need to turn their everyday lives into a stressful grind to find success. In fact, it’s entirely possible — and advisable — for founders to cultivate enjoyable experiences daily, irrespective of their business's current stage.

At the party, someone inquired, "Do you have big plans for your birthday?"

I replied that it’s tough to plan anything major when every day feels like a birthday. This prompted her to wonder if I had already celebrated extensively. But for me, it isn't about traditional celebrations; it's about creating a life where I don’t need those milestones to feel fulfilled.

Living the "Everyday Vacation" Lifestyle

I began my journey towards an "everyday vacation" lifestyle while living in a cramped, lead- and asbestos-filled apartment near the ocean. Despite the lack of extravagant celebrations or gifts, I made it a point to find excitement and fulfillment in each day.

Red flags in my previous (failed) ventures began to appear when I started to dread Monday mornings and eagerly awaited Friday nights. If you find yourself feeling this way as a founder or entrepreneur, it might indicate that something is amiss.

What Hustle Culture Gets Wrong

It's important to clarify: launching a business and steering it toward success is no small feat. It requires immense effort and dedication. However, the reason entrepreneurs persist through challenges is that they find joy in their work — or in the vision they are pursuing.

Hustle culture falters when individuals become trapped in exhausting work schedules for ventures they lack passion for.

Having been in such situations myself, I can confidently say that if you are pursuing something you genuinely care about, each day can feel rewarding and enjoyable, akin to indulging in a guilty pleasure.

In contrast, if your business or daily responsibilities leave you feeling anxious or unhappy, it’s likely a sign that you are chasing the wrong goals. A change of direction might be necessary.

Reevaluating the Need for Vacations

The real issue with vacations, weekends, and occasional celebrations is that they imply escaping reality is preferable to living joyfully every day. I find this notion disheartening and counterproductive.

Society often promotes the idea that we should:

• Endure the workweek to enjoy the weekend
• Go without during the year to receive gifts or celebrate birthdays
• Slog through the school year to reach summer break
• Endure months of work for a brief tropical getaway

It doesn’t take much to realize that squeezing the most out of life doesn’t align with these conventional beliefs. Moreover, this fixation on vacations and celebrations fosters an unhealthy relationship with daily life and work — which occupies most of our time.

Why limit enjoyment to just two days of the week? Or to a mere fraction of the year for a birthday celebration?

As entrepreneurs, our lives and work can — and should — be more fulfilling than that. If entrepreneurship feels like an escape from the 9 to 5 grind, it’s crucial to assess your current structure and ensure you’re not just recreating the very confines you sought to break free from.

You don’t need validation from a boss, a large bank account, or a formal holiday to make every day feel special.

There’s no need to suffer to prove your dedication. If you can work smart and enjoy the journey while building your startup on a budget, why not create a life where every day feels like a vacation? I would choose that lifestyle over two weeks of paid time off any day — and I do.

This video titled "How I feel about hustle culture + other unpopular opinions" delves into the complexities of hustle culture, exploring why it often leads to burnout and how to find joy in everyday entrepreneurial activities.