Why Doesn’t Everyone Quit Their Job

Quitting Your JobIf it’s so great, why doesn’t everybody do it?

If that thought has ever crossed your mind while considering working for yourself, you’re not alone. I get asked this question time and again. Even more frequently, people don’t ask, they just skeptically assume that I do what I do as a temporary measure, until I ‘find a real job’. Well, it’s been 12 years, so I guess their definition of temporary is a little different than mine.

5 Obstacles to Being Your Own Boss

People cling to the 9-to-5 paycheck for a few reasons. And those reasons are not insignificant. They’re exactly what distinguishes the non-employed (but not unemployed) from the employed.

The Comfort Zone

It’s all they know, and they’re comfortable with the model. A paycheck appears every two weeks that pays JUST enough to pay the bills. Or, for those at the top of the food chain, pays the bills and affords them a comfortable lifestyle. Not rich, never rich, but comfortable.

Let’s not understate the harsh reality of self-employment. There is no paycheck. Ever. The only money you get is the money you generate from the work that you generate. That’s a considerable downside for many people.

The upside? The amount of money you get is the amount of money you generate from the amount of work that you generate. You don’t need to wait for a bonus, or a promotion, or the benevolence of someone above you on the corporate ladder. And there will always be someone above you on the corporate ladder.

You don’t need to perpetually bite your tongue or swallow your opinions to ensure that you’re always “on the good side” of your boss. If you quit your job and work for yourself, the amount of money you make is only limited by how hard you’re willing to work.

The Fear Factor That Kills Solopreneurship

The primary reason people stay exactly in the place they’ve been put in or stumbled into is that they’re afraid of change. Why? Because change doesn’t guarantee success, or improvement, or a better result. Change only guarantees difference. And difference may be good, but it can also be bad. Very, very bad. Why take a leap forward in the dark, when you can stay exactly where you are? Miserable, maybe, but it’s a known misery.

If you quit your job, what happens next? No one knows. Pretend you have a friend or colleague who quit their job to become a virtual project manager. They start slowly, get a few steady clients, and eventually build up their reputation and network over time. They get so busy that they start contracting out some of the work to take on even more clients. Success!

So you decide, great, and you quit your job to start an online business. Will you be successful? I don’t know. Maybe. Online work is on the rise and is expected to continue to increase over the next number of years. That would indicate a good chance of success.

But then again, maybe not. Maybe you’re not very good at what you do. Maybe you don’t work as hard as your friend. Maybe you haven’t thought about how to deliver your services efficiently and effectively.

The point is, when you work for yourself, it’s all on you. Does that thought scare you, or reassure you? That’s the inner voice you should be listening to. Do you want to be taken care of, or do you want to take care of yourself?

Commitment Needed to Be Your Own Boss

People know it requires more effort than they’re willing to give. They don’t necessarily admit this to themselves, but ultimately this is the root cause of a lot of inaction. Committment equals effort, and lack of effort is easier.

The path of least resistance will never travel parallel to the path to success.

The good news is that if you have the committment, you can reap the reward. Go to Google and search for successful entrepreneurs and read their stories. I bet you won’t find any that say “it was really easy, I was literally an overnight success, and it didn’t take an ounce of hard work”.

Commitment is something you need to assess at the outset, and then constantly revisit if you quit your job to work for yourself. You won’t have the luxury of calling in sick when you don’t feel like working; or taking a few weeks vacation and ignoring your email and voice messages while you’re gone.

Are you the type of person that leaves the office at 5pm every day, regardless of what you’re in the middle of doing?  Do you take a sick day every couple of months, whether you need it or not?  That isn’t reality when you work for yourself.

Criticism is Easier Than Ownership

It’s easier to sit on the sidelines and criticize. Always. Something I’ve noticed is that the biggest cynics, your biggest critics, aren’t those who have tried and failed, but those who have never even tried. Why?

No one likes to admit to cowardice. Much better to say that they had the “insight” to avoid a mistake, than to admit they were too afraid to make the attempt.

Admitting that you want this, that you really want this, but you’re afraid to try will help you take those next steps.  What are you afraid of?  Write it down. Then break it down.

Afraid of failure?  How do you define failure?  Not becoming a millionaire?  Not being able to pay your bills?  Not getting even one client?  How do you mitigate failure?  Start with clients and customers.  Work on securing your first sale before you’ve left the safety of your current nest.  Write it down.  Develop a plan.

A Little Narcissism is a Good Thing

If you’ve decided to spread your wings and go out on your own, then yes, you need to be a little narcissistic. Frankly if you spend too much time thinking about others and not enough time dwelling on yourself, you’re not going to be in the business of building a business. Think Donald Trump. But dialed back to reasonable scale. You’re just trying to build a life for yourself after all, not an empire.

There’s also an inherent danger in too much narcissism. Some people are stopped in their tracks from pursuing their dreams because they’re too focused on their own specialness. They truly believe that their circumstances are so incredibly unique, and so incredibly difficult, and so incredibly complex, that they can’t possibly do what others have done because those others just have it so much easier than them.

Really? Business owners don’t have spouses and children and parents and siblings and family commitments? Business owners aren’t busy? They don’t work hard? They don’t go to the gym or play hockey or go to their kids’ soccer games or have social obligations?

The truth is, you’re not that special. Neither am I. Neither are most people that are making a living working for themselves, working from home, running online businesses, running small businesses, freelancing, and otherwise generating their own income.  That’s good news.  It means there’s no reason that you can’t do the same.  If you want it, you can do it.


The biggest barriers to starting your own business aren’t external. It’s not money and resources and time that stop you before you even get out of the gate. It’s our own internal fears and doubts and constructs and rationalizations that keep us tethered to a situation. Breaking down those mental barriers are usually your first challenge.

It’s a little more complicated than “believe in yourself”, but being honest with yourself, examining what makes you tick, admitting your fears, and challenging your assumptions will move you forward. Get unstuck. Or, at the very least, conclude that maybe being stuck is where you’re happiest.



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