Is Becoming Self-Employed the Best Idea for You?

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For workers who toil all day in an office at the bottom of an endless river of in-office memos and all-caps-filled emails from their bosses, the idea of being self-employed and being your own boss working on your own schedule is nothing more than a day dream, like the kind you get when staring at the Hawaiian sunset calendar hanging on your cubicle wall. A lie many tell themselves is that becoming self-employed just doesn’t sound doable, and is probably not as safe or reliable as a regular office job could be.

With a huge portion of our working population providing services for individual gigs and contracts whenever they feel is needed, being self-employed in 2016 has become a norm that is as widely accepted as it has become popular. Becoming self-employed is no picnic, but the pros and cons that follow are definitely worth considering if you are looking for a paradigm shift for how you work.

Here are some points to consider for those of you who are looking into becoming a full time self-employed worker and freelancer.


Test the waters first.

The idea of moving from a safe and employed position into a self-employment role can be a terrifying thought, but shifting via a gradual transition is proven to be the best route to calming any fears. By working a day job and taking on side gigs (also called “Moonlighting”), you can test the waters to see how successful you just might be at taking gigs, as well as gaining more and more practice at whatever it is you are looking to move over into full time with.

Making the shift from “full time day job” into “full time self-employed” freelance can be a liberating and confidence affirming move, but feeling out the extent and range of your abilities is key:

  • Can your skill at the gigs at hand be enough to help you keep work flowing enough to equal if not eventually surpass your income being earned in your day job?
  • Do you think your skills at providing gig and contract work will be in enough demand if you were to move into full time self-employment rather than at the hands of another employer?

These questions and more are put into a kind of test run when they are started while still continuing a day job, that way if you change your mind and want to keep your day job and keep your gigs just on the side, no harm no foul.


You really are your own boss.

There is a vast amount of freedoms that come with being self-employed, with the biggest and most popular detail being that you are your own boss. Not having your own boss is one of the biggest selling points when it comes to being self-employed, but little is said about what it means to really be your own boss and supervisor.

The role of a “boss” is to provide work, set deadlines, and keep production moving at an even and steady pace. Only when that enforcement is taken away do we realize just how big of an asset and tool a boss and supervisor actually is when it comes to keeping things done on time and correctly.

As a self-employed worker, you no longer have a boss because that boss is now you. Keeping focused and self-motivated can be a stretch for people who are otherwise used to having the figurative whip cracked on them, but keeping yourself focused and dialed in on your own is a skill that can be acquired and refined with enough practice, and enough reason to do so.


“Work whenever you want”.

Another big selling point is that you can work whenever you want, and that you can set your own schedule when it suits you best. While this is very true, it should also be said that when you don’t work, that is time that you are not being payed, so keep that in mind when you want to take a week vacation without so much as looking at your email once.

If you are self-employed, gone are the days of the paid vacation. While you do have the power to take a day off at will, you must consider the tradeoff that comes with taking a day versus taking on gigs, contracts and assignments.

A possible solution: Being self-employed, you more than likely work via telecommute, which means that you can work from absolutely anywhere with an internet connection. Looking to travel? Just work during pockets of time during your vacation. It may not be ideal, but it will quell any fears of losing too much time.


You’re always on call.

Although being your own boss means that you get to set your own hours, be aware that you will not always have this privilege, even when you are self-employed. Depending on the kind of contracts, gigs, and assignments your work allows you to take on, there are often deadlines and communicational situations that force you to have to be on call for whenever your client needs you to take on work.

For example, if you are self-employed and you pick up a client that will provide you with contracts and gigs, but they are in another international time zone, that means that the principle time that you will communicate with them will be at what their convenience is, be that in the middle of the night your time, or the early morning. Depending on the kind of work that you are looking to procure that will establish and allow you to work full time as a self-employed worker, let it be known that you will be most likely placed in a mindset of always being on-call. So keep that smartphone close to check emails and other chat platforms on the go.


Dry spells, droughts, and possible work famines.

A panic that often sets in and deters employees seeking other options that could eventually lead to full time self-employment is that of the unsecured income. A misconception is that you never will have a stable and promised workload that pays as a self-employed worker. While this is half-true, you work as much as you can receive work, and if you are established and put in the time to build yourself up, then finding that much work to fill your work hours with should not be a problem.

Even though you can easily find work, there will be periods of time that you may not have that phone ring. When that happens, it is easy to have self-employed workers enter into a period of panic, and reconsider if it really was so bad having a boss constantly send emails in all caps about a report that was already filed a month ago.

In periods of drought, don’t panic, but remember what you did to receive the assignments you needed in the past and try to duplicate them. Work comes in waves, and isn’t always steady, but it always bounces back again. Even the most successful self-employed workers and freelancers have dry spells. How do they combat this? Stay calm, tighten your financial belt until more work rolls in, and keep those thoughts of self-doubt at bay. Nothing good comes from you beginning to panic and doubt your abilities. You’ve come this far, don’t stop now just because of a dry spell.


Being self-employed is not a matter that needs to be feared, just shared about and made transparent about to expect. For many, it can be liberating and confidence boosting to know that what you really desire to have fill your time and thoughts is something you can make a living doing. For others, phasing out a day job in favor for being self-employed can cause panic, anxiety, and nervousness due to the risk of insecurity of not having a promised income and set workload. This kind of life certainly not for everyone, but for some, it’s just the challenge that they have always wanted.

Would you ever consider becoming self-employed in favor of your day job? Sound off in the comments below!



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