Becoming your own boss can be a liberating and exciting experience, or potentially a complete nightmare. Depending on your temperament and how solid and realistic your plans are, the decision to start a business or go freelance can be the beginning of a lucrative career beyond the shackles of being a wage slave, but without proper planning and testing the waters before diving in, success may be difficult to achieve. Here are five questions to ask yourself before deciding to become your own boss.

Can You Afford Things To Go Wrong?
Of course, no one can predict the future, but deciding to work for yourself can potentially be disastrous if you don’t have backup finances in case things don’t go as planned. While you’ll obviously have decided how much you need to invest in your venture, you’ll also want to be sure you can still support yourself in case sales are slow or unexpected costs build up. A safety net to fall back on is essential for any entrepreneur.

Have You Factored in Loss of Perks?
While there are many advantages to working for yourself, you’re also likely to lose a lot of perks by quitting your day job. Health insurance, pension contributions and sometimes even free food and transport are among the perks offered to many employees, so make sure you’ve got a plan for how to take care of those yourself.

Will the Different Working Style Suit You?
Many people envisage being their own boss as like taking an early retirement. However, while you can usually set your own hours and place of work, without a boss breathing down your neck you’ll have to be extra disciplined in staying productive. Working for yourself may also be far more isolating, which can be difficult for many people to handle every day.

Are You Prepared to Work More Hours?
While this varies massively, on the whole many entrepreneurs find they work more hours than they did as employees. As well as doing the actual job, you may have to take care of your own marketing, research and accounts, so be sure to factor all that in to your expectations. Many people find that working more hours for themselves so they don’t have to spend any time toiling for someone else is worth it, but be sure to evaluate your priorities beforehand.

Would You Rather Be a High Achiever Than Have More Power?
Again, this depends on your field, but it’s likely that as a successful entrepreneur you’ll achieve more and do it independently, but you won’t necessarily have more power. Climbing the traditional corporate ladder generally means having more control over people in the traditional sense, while running a successful business by yourself means making unique achievements, but the power is generally limited to your own life. That said, if you really make it big, you could have more power than could be possible as a manager or executive in someone else’s company.

Overall, deciding to be your own boss is a personal decision, and is not to be taken lightly. While it’s easy to imagine that life is simple when you don’t have a manager to report to, the reality is that you’ll have to work a lot harder to make sure you’re succeeding independently. Many people achieve great things with entrepreneurship, but it takes a lot of dedication and an honest look at what’s realistically possible to truly succeed as your own boss.

Jason Felts

Jason Felts is the CEO of Advanced Merchant Services. Starting out of his home in 1998, he has led his company to the corporate enterprise it is today. Jason has a dedicated passion to motivate others to pursue their entrepreneurial goals and become successful.