Working for yourself can be awesome if you are prepared for it. Have all your ducks in a row and have a strategy.
An FKD Feature exclusive

Ready to hang up your suit and throw on a pair of jeans? Feel like you can no longer take your boss breathing over you while micromanaging your work, all of those awkward water-cooler conversations and the endless office politics? Many people give up working a traditional job for just those reasons.

Working in an office can sometimes feel like working in a jungle. A jungle not full of lions and tigers and bears (oh my!) but one full of sharks that are out for your job or something that you have got that they don’t (hooray for pun work!) Want to trade in that jungle for your apartment? Well, for one, it might not be that simple. And two, self-employment is no cake-walk. Regardless of the field in which you desire self-employment, there are a few hard and fast things you must do to ensure that it works out well for you. And there are also some things you should try and stay away from.

You are your own boss

Yes, that’s exciting. It means that you get to do what you want, money aside. Having said that, if you do certain bad things, you will find yourself throwing quite a lot of money aside. (Yay for further wordplay!) Yes, you can watch television instead of critiquing that manuscript or working on that new graphic or tattoo sketch. But is it a good idea? The key word here is discipline. Do you have it? If not, get some because one of the benefits of having a boss breathing down your neck is that they keep you in line. That is their job. But now it is your job!

Learn to say “no”

Many people don’t know — or don’t acknowledge — the difference between self-employment and “just chilling.” It is probably because they have seen so many “self-employed” people not being self-employed “well.” And they assume you are doing it similarly lazily and wrong. But just like it is your job to discipline yourself, it is also your job to make some things abundantly clear to family and friends: No, you are not free. No, you can’t do them a favor or pick something up for them. And yes, yes you are working, despite what they may think. Would they come to your office and ask you to deliver a gift to a friend for them because they needed to go to work? No, that would be absurd! Because you yourself would be at work. Which is exactly what you’re doing. Working. So set those boundaries, and stick to them.

Not just boundaries, but schedules

Ya know that daytime talk-show that you want to watch? Well, would you have been able to watch it if you were at your old job? No? Then you probably shouldn’t be flipping on the television right now. But that’s not to say that your work hours cannot be eccentric. That is one of the perks of being self-employed, after all. Although you absolutely must have a schedule, you can make it your own. But it should be consistent and rigorous. (Always challenge yourself!) Choose from the hours that you find yourself to be the most productive, as a rule of thumb. Morning. Evening. Midnight. Doesn’t matter. As long as you stick to it, and you are productive and working hard within that time frame. Not working? No money.

Where’s your workspace?

Huh? Workspace? It really matters! Designating a workspace is important because it tricks your brain into working when you enter that space and conversely trains your brain to think of the rest of the spaces in your home as leisure areas. It is a bad idea to intermingle these spaces because then you will feel anxious at the wrong time and lazy at other wrong times. First off, the couch is not an office. Invest in a desk, lamp, definitely a pen holder. But that’s just for starters. To whet your appetite and creativity, make the space your own, but make it conducive to work. Don’t place an Xbox in your workspace, in other words, unless you’re a game developer.

Go outside. Right now.

If you are on the opposite side of things and find yourself working far too much, then somebody needs to tell you that this is a surefire way to burn out and collapse into a month of complete and total indolence and non-productivity. Wait! That person is me! You might be able to work long hours without sleep for a while, but eventually, it will bite you in the butt. Instead, give yourself what are called “micro-breaks.” A good way not to burn out is to go outside every once in a while. Don’t get stuck in your workspace and suddenly, Monday through Friday have gone by without leaving your laptop. Take a break and go listen to the birds sing in the park. Even if you just go around the corner to the coffee shop or take a walk around the block, it’ll be worth it.

Back to this frisky business about social boundaries

You must set boundaries with people. That is definitely true. You also must not shut people out or forget to have human contact. That is not good for work productivity or for your mood. If you spiral into a depression, you won’t be getting much work done anyway.

Get Dressed!

This is much like developing a workspace. Yes, you can work anywhere. But will you really be working? Do you really believe you can work lying down on your couch in a dimly lit room that looks like Dracula’s den? Well, the same psychological theory is behind changing for work, even if you aren’t going anywhere. It tells your mind that it is time for work. Remember: we are just a mass of chemicals. So you have to play that up and learn how to master your brain’s functioning processes to optimize work productivity. So ditch the pajamas and wear something more work-like. You don’t have to wear a suit! Because, then, what’s the point of being self-employed? But maybe a pair of jeans and a shirt would be nice. Is that too much to ask? (Hear the last sentence in your mother’s voice).

Still on the fence?

Not sure if you want to make the switch? It really isn’t for everyone. But if your fears primarily are in regards to changes in income, then know this: You will save a lot of money on expenses. So you might have less reason to be afraid of the pay-cut than you believe. Plus, freedom and dedication to the work that you truly love have a chance of yielding far better results down the road, by virtue of the fact that you truly love what you’re doing now. Certain expenses you might find being severely reduced are coffee runs, lunches out, and Ubers and taxis. Also, new suits and work-clothing to keep your boss thinking you’re fly can go!


Going from employed to self-employed is a big step. It is more than doable, though. If you have a field of expertise, you are off to a good start. In fact, a field of expertise is the prerequisite that makes self-employment even a possibility for you (obviously). But it is not all that you need. Without a strategy, some good habits, and the sloughing off of your bad habits, your self-employment situation likely will crash and burn.

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Header image: ShutterStock


Posted 06.06.2018 - 12:00 pm EST