The Entrepreneur Lifestyle – What’s it Really Like? And How to Help it Go Smoothly

Many people dream of being an entrepreneur, but don’t have a clear idea of what it is all about. The most common misconceptions are that: entrepreneurs make lots of money, they have a lot of freedom in their job, they aren’t accountable to the whims of anybody else.

Many people dream of being an entrepreneur, but don’t have a clear idea of what it is all about.

But is being a successful entrepreneur everything you believe it to be? Are there any unexpected surprises? Is it a lifestyle that can suite anyone, or you in particular? Let’s take a little closer look at what it really means to be an entrepreneur.


Target by Jasper Johns

First and foremost being an entrepreneur means you have to bring your ‘A’ game a lot of the time, and that you need to be constantly ‘on’. If you’re an entrepreneur then you’re the first and last word on the success of your business, and that’s why it’s so crucial that you make sure you’re working at your best all the time. It’s no good just showing up and doing your time so you can go home – your salary is dependent on how well you work and that means you’ll likely work harder when you’re working for yourself

Besides being more emotionally invested because it’s your business, you’ll be more economically invested, you’ll be taking big risks with your money. While that is exciting and can be greatly rewarding when it works out, most of the time you will be in a state where it hasn’t worked out yet and you’ll probably be a lot more worried about losing everything than about hitting the home run. Don’t be surprised then if your entrepreneurial lifestyle leads you to become somewhat obsessive, which can sometimes lead to difficulties with your partner or family.

Lonely at the Top

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Often at the beginning, every entrepreneur starts out with an idea by himself, or with a partner or two, working at home and rarely meeting others. When there is a meeting, it is usually for a business relationship, which don’t often lead to casual, fun peer-to-peer get togethers. The comraderie of hanging out with your buddies by the office water cooler isn’t an easy thing to replace.

As you grow, you will, usually, be at the top of your own organization, so people will be looking and relating to you the way you used to relate to the CEO of the company you used to work for. It can be rewarding, but it is often a bit lonely.

A nice thing happening nowadays is that more and more people are starting their own small businesses, so there are communities popping up at local coffee shops, incubators, and shared workspaces where you can connect with others on a personal, carefree level. Those people usually seem to be pretty interesting and diverse as well.



While it seems like the person at the top has all the freedom you could want, it seems quite different when you get there. In fact, good CEO’s are the ones who balance the needs of all of their relationships most effectively. As an engineer or product manager you might only have to please your boss, and a handful of other people in your department.

As the CEO it’s your job to keep all the employees happy, the customers happy, the investors happy…basically anybody that is involved in your business. Going around with a hard-nosed, it’s my way or the highway, kind of attitude is a sure way to alienate those people that are critical to your success. While there is certainly some flexibility in decision making, the end result is that if anybody isn’t happy, it’s your fault.

Choose the Lifestyle


Probably the most important predictor of your success as an entrepreneur is whether or not you will enjoy the lifestyle. It’s not for everybody. In fact, it’s not for most people. It’s takes a lot of self-motivation, determination, ability to manage stressful situations (both from a business and personal sense), independence, a strong desire to see things through, and I think a certain yearning to feel that sensation of elation when it all works out. If you’re not sure that it’s the kind of lifestyle you are looking for, then it probably isn’t.

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