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08 Dec 2014
Be Your Own Boss

Infographic: Do You Have What It Takes To Be Your Own Boss?

With startups popping up left and right, it seems fair to also assume that there must be a respective increase in the number of self-employed entrepreneurs that were acting as their own “bosses”.

However, studies in this year have shown that self-employment is actually down 5% from last year, and may decrease further.

It isn’t hugely surprising when you factor in the significant failure rate of individuals who set out to run their own company. On average, ⅓ of self-started entrepreneurs fail within the first two years, and a staggering 60% fail by the fourth. This means the decrease in entrepreneur “bosses” might simply be a reaction to a hugely difficult undertaking that is increasingly difficult to pull off. There are many factors that come into play here – on top of navigating a tough economic climate, self-employers are faced with increasing competition, a very significant rise in outsourcing, and all kinds of other factors that make it exceedingly difficult to run a new business – especially if you’re helming all of the boss’s duties.

Here are the main reasons why self-employed people fail – and why some self-employers might not be ready to call themselves “boss.”

Trouble With The IRS

Self-employed individuals are one of the most frequently targeted demographics for tax audits. It is believed that self-employed taxpayers have the highest rate of tax fraud – from declaring the wrong amount of income to taking unnecessary deductions, like those they actually didn’t pay for or shouldn’t be deducted in the first place.

To avoid this pitfall, the answer is simple: be honest. Don’t claim or deduct anything you don’t truly believe you can claim or deduct, and if you’re ever uncertain, hire a tax specialist that can help. While you might want to avoid the cost, it’s much cheaper than the fines you’ll ensue if you’re caught doing your taxes incorrectly – and the IRS is especially harsh on individuals who work for themselves.

They Actually Need A Boss

While being your own boss might sound fantastic, it’s more beneficial for those who have goals that would otherwise be thwarted if they were under someone else’s thumb. For people who simply dislike structure, authority, and want to try working without having a supervisor looming over their heads, they might still need some external incentive to get the work done and do it well. Some people need leadership to bring out their most productive work ethic.

If you feel like you’d have trouble regulating yourself – getting up at the same time every day, completing tasks in a timely manner, and exerting your networking skills to make new contacts and meet new clients – you might look for a good job with a company that will help do that for you.

They’re Invested In One Aspect Of The Company, And Not The Rest

A common example of a startup that frequently fails – as a matter of fact, it has the second highest failure rate of any industry – is the salon business. This usually happens simply because a beauty guru sets out to make the world beautiful, without brushing up on proper business plans, accounting material, loan planning, and employment training.

While passion should drive what you do, it cannot sustain your company on it’s own. To truly be your own boss, you have to be prepared to dip your toes into less familiar water – more frequently, to dive in headfirst. The boss runs everything – it’s an all-or-nothing endeavor if you want to take on the title. This means understanding the books, supervising customer service, checking in with staff and salespeople, and directing maintenance workers and interns. There are many facets to a business, and the boss knows them like the back of his or her hand.

They Give Up

The benefits of being a boss come with the responsibilities, too. No matter how much planning can do into your company, all kinds of things can go wrong, and you have to be thorough, versatile, and tenacious to keep up with them all at once. Many people eventually find it’s simply easier to find a job through a company and relinquish the throne.

This is why to truly employ yourself, you have to do it out of a drive to pull through all obstacles that are thrown your way, and not simply because you don’t like working with people, or resent having bosses and supervisors.

Still need more guidance? Take this test to see if you’re up to the challenge of being your own boss.

Be Your Own Boss


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Search engine marketing expert with 15 years of experience in the industry, working with small mom and pop shops as well as large corporate websites. I have experience with all aspects of inbound marketing, including SEO, Link Building, Social Shares, Usability, Conversions, PPC, Email Marketing, and more.