7 Crucial Qualities That Will Ensure Your Success As Your Own Boss

Working as your own boss is a dream for many, what with all the worthwhile benefits that come with it. You can choose the time you work. Plan your own vacations whenever it suits you. You can handpick the projects you work on. Not to mention that you can save money since you don’t have to buy corporate clothes or commute to work.

I could spout off a few more advantages, but you probably get the drift by now.

Personally, I believe being self-employed should be the norm. I want to see more people enjoying their lives and careers with more time and autonomy.

But the thing is, you have to know what it takes to successfully work for yourself. For some, they won’t know until they try it. While some could already glean from knowing themselves. Charting your own business or freelance career typically involves significant risk, as well as possible losses in time and effort. Not to mention the cost of not being able to bank on stability.

If you’ve been thinking for some time whether to start working independently, this article is for you. Below are just some the things that can help you ensure your success as your own boss.

Combine the Right Drive With the Willingness to Work

There are a good number of people out there who think being self-employed equals slacking off. But this is just a myth.

In fact, a 2012 freelance report by Ed Gandia attests to this where it revealed that only virtual assistants and photographers are able to get the most free time once they start working independently.

Those in the freelance IT and software positions have less free time compared to when they were regularly employed. For business consultants, editors, and illustrators, it’s roughly just the same. It was also disclosed that at least one-third (29%) of freelancers work more than 40 hours a week while a good 27% worked the typical 40 hours.

This just goes to show that working for yourself doesn’t mean you could take things easy. It doesn’t mean you can’t in the future. But you have to put in the work first, even if it means working more than you ever did in your life at times or when necessary.

Nonetheless, there are few other forms of livelihood out there where you can enjoy a great deal of freedom, flexibility, and autonomy. However, working independently still comes with the usual obligations that come with any job. This means there are deadlines to meet, clients to appease, and requirements to follow.

With the average employee in U.S. working 47 hours a week, it’s more ambitious to think what you could do with all those hours when geared toward your own goals.

If you look at being self-employed as a stepping stone for bigger things and not just an easy way out of the 9 to 5 grind, then you my friend, are one step closer to success.

Be Able to Deal With Financial Uncertainties


With every benefit comes a drawback. In the case of being self-employed, there will always be a certain amount of uncertainty in terms of your monthly income. In fact, in Gandia’s report, the foremost challenges majority of freelancers experience is finding clients and getting consistent, steady work.

A separate survey by Contently says the same thing and that as much as 35% of independent workers think that the biggest obstacle for them is securing sufficient work. In the survey, full-time freelancers also reportedly had a median income of $30,000. Compared to those who had a traditional job, the income from being self-employed is comparatively smaller in the data they published.

Many freelancers often claim a feast-or-famine cycle in this field. There will invariably be times you’ll get droves of work that you have to start turning down projects and at times. There will also be times you’ll have no project for weeks on end.

This could be why 55% of freelancers surveyed in the report are willing to go back the 9 to 5 route. Or at least think about it if the right options come along.

So if you can deal with this and can live your life decently despite a fluctuating monthly income, then you just met another essential skill set for thriving in this field.

Have the Discipline to Work on Your Own

Discipline has been hailed as one of the building foundations of success. Studies such as the Marshmallow Test and other follow-up studies to it have all led to the conclusion that it’s a crucial factor if you want to succeed in most aspects of life—whether on a personal or professional level.

Working for yourself requires a tremendous amount of self-discipline. You have to get things done within a specific timeframe even when no one’s breathing down your neck to do it.

Moreover, working in this field means that you get the burden of doing everything alone—from networking to prospecting and doing the actual work. All of these takes time (sometimes months or up to a year). If you can develop the self-discipline to get everything in working order then you can pretty much make it through most obstacles in this field.

Once you’re past that phase, you’ll still need a hefty amount of self-discipline to sustain whatever you’ve managed to build thus far. After all, you wouldn’t want to let all that work go to waste, right?

If you have the wherewithal to consistently improve your capacity for self-discipline even without someone pressuring you to do so or even when there seem to be no tangible benefits, then you’ll no doubt geared for success.

Handle Long-Term Difficulties


Just like any endeavor worth pursuing, you have to be able to see the good with the bad aspects in order to accurately assess whether something is a good fit for you.

Statistics show that around 35% of freelancers think that the self-employment field is bound to get difficult in the next 10 years. Understandably so, since independent workers are expected to rise as much as 40% by 2020 according to Intuit’s report so competition is about to get stiff.

More than just the competition, part of the difficulties of working for yourself is that you’ll largely be operating alone. If you crave socializing and schmoozing with your officemates or hustle and bustle of the corporate atmosphere, then either it might take you a while to get used to having only yourself around or you come to hate being self-employed.

Aside from just the social aspect, be ready to forego the usual benefits you’re used to getting from your regular job.

When you’re employed, your company takes on the bulk of handling your benefits and other forms of social assistance. As a freelancer, you have to take on payments for your health care and retirement plans.

These are just a few of the challenges that come with being an independent worker. If you think you can handle most, or all of the above, let alone manage multiple challenges at once then this might just be the path where you can flourish.

Be Assertive When it Comes to Negotiating

Part of being your own boss is that a lot of it rides on your ability to look out for yourself. To do that, you need to be assertive especially when someone’s lowballing you to the depths of bargain pricing hell. Once you’re able to get your worth, you also have to be assertive enough to point out when a project’s working scope becomes out of bounds of your contractual limits.

Sending a client an invoice won’t necessarily guarantee you payment, but if that happens, can you also stand up for yourself and follow up a late payment?

Research has shown that assertiveness is an important trait if you want to be able to achieve a positive financial outcome for yourself. Being assertive means being able to get what you’re worth and sticking up to the kind of value you can give.

Out in this field (or in life in general), if you act like a prey, you get treated like a prey. My favorite proverb all the more attests to this by saying, “You won’t get anywhere in life if you let people walk all over you.”

This is true whether in a personal or professional context. So if this is an aspect you have or are willing to develop, then you’ll undoubtedly thrive being your own boss.

Be Capable of Wearing Different Hats


To succeed working for yourself, you have to be able to juggle different roles throughout your career.

From your workload to filing your taxes and arranging your overall finances, making sure that everything gets done can be a tricky balancing act.

Your task doesn’t stop at just finding clients—you have to be able to keep them as well. This means spending enough time building your professional relationships so that they’ll want to have repeat business with you in the future.

Being self-employed also often means you’re not just tied to one job and you get to work on multiple projects at once. If you’re the type who can easily handle different tasks and enjoy doing a broad range of things then you have a bright future ahead of you in this field.

Sooner down the line, you might also find that you need to diversify your freelance career with other skills in order to grow professionally. Although a lot of people prefer sticking to their strengths, a little learning or additional knowledge never hurt anybody.

Without growth, you’ll be stuck in the same level of skill set and income you started with. Regardless of whether you have another mouth to feed or you just upgraded your lifestyle.

Can Handle Unpredictability and Freedom to Work On Your Own

People have different versions of what freedom means for them. For many of today’s self-employed peeps, it usually means autonomy and being free of rote, dull work.

In a recently published IBM report, it was revealed that one of the things that independent workers value is autonomy. Autonomy is the capacity to work even without anyone telling you what to do for the most part.

Even though it’s a good thing that you can freely choose the kind of work that you do, you’re also the only person who has to deliver the work that you choose. With great power, comes great possibility indeed (pardon for using this cliched Spiderman quote).

Since you don’t have any traditional boss watching everything you do, you have to have the initiative of meeting deadlines and abiding by the project’s standards.

For many, having a sense of control in the work that they do is paramount for their job satisfaction. If this is the case for you, you might just find success working for yourself.

Weighing the Pros and Cons


Success is an elusive, relative thing. It’s rarely the case that it lands on your lap with little to no work and success isn’t success until it fulfills your most significant goals in life. This is why the success rate for reaching one’s goals is absurdly minuscule—only 3% in fact.

This is why it’s always helpful to figure out first if you’d be a good fit working for yourself. In the end, you wouldn’t want your life or your years of tenure at your job to go to waste with the sudden realization that this isn’t what you wanted after all.

There are a lot of advantages to being an independent worker. To be able to reap the benefits that come with the job, you also have to know if it’s a good fit for your overall goals, skills, and personality.

There are a lot of responsibility riding if it’s just you manning the ship. So make sure this lifestyle is really something you’d want for yourself.

Know that independence doesn’t always guarantee success. If anything, it actually entails being more accountable and responsible for your own working habits and output.

At the end of the day, your decision shouldn’t just reflect what you want, but an honest assessment of your skills and willingness. If you know yourself enough, you’ll know what the right decision is for you and whether you really have what it takes to succeed in this field.

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Also published on Medium.

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