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.



Want to work for yourself? Cash is King

Cash is King

I recently wrote an article about how you can start your own business while still juggling a day job.  Not only is it possible, it’s also possibly the best way to make the transition from employee to entrepreneur without losing your life savings in the process! 

Budget Planning

Starting small and putting in the effort while you still have a steady income makes a lot of sense.  It’s hard to juggle two jobs – and yes, if you’re actively working on your new business, it is very much your second job – but if you want something bad enough you can make it happen.

Keep Your Eyes on the Prize

One of the items I mention in the article is the importance of staying on top of your budget.  Eventually you’ll get to the point where you want to focus solely on your own business.  Of course you will, because YOUR business is YOUR passion and YOUR dream, and wouldn’t you rather spend every available hour working on your dream rather than working on someone else’s?  The only way to do this is to work for yourself.

In order to work on your dream full-time, you’ll need to quit your job.  And in order to quit your job, you’ll need money in the bank.  Again, the best way to make this transition is to have some customers already buying what you’re selling before you quit your day job to really amp things up.  But how many customers is enough to walk away from your job and still pay your bills?  This is where budgeting comes in.  If you can master your expenses, grow your revenue, and get insight into your financial transition points, you can plan toward making this transition a reality without any unforeseen financial disaster.

Know Your Numbers

What is a financial transition point?  This is what I call a turning point in your financial forecast.  Many people think that the right time to quit their job is when their side business earns them as much money as they would earn as an employee.  Maybe.  This is certainly one potential transition point. But there are others as well, depending on how much risk you want to take, and how much risk you need to avoid.

But you can’t make an informed decision about any of that until you have all of the information.  And there’s no better way to assess your financial position than by taking the time to write down what you spend and how you spend it.  More importantly, what you plan to spend (and earn) in the future will help you realize your business dreams and stay 100% focused on your goals.

Keep it Simple

You don’t need complicated or expensive software to do some basic budgeting and financial forecasting.  Create an inventory and make sure you include all of the money you earn (income, sales) and all of the money you spend (business and personal).  Understanding how your money flows is the first step in turning your dream into an action plan.

If you need a little help, or just want to save yourself some time, sign-up and download my basic budget planning spreadsheet for free.  It’s simple to use and has everything you need to get started today.

The lack of money is the root of all evil.  ~Mark Twain

Learn How Fear Can Motivate You

I recently took my car to a body shop, after losing the car versus snowbank battle that tends to play out in the streets of my city this time of year.  While anxiously waiting to find out the fate of my vehicle, and bank account, I spent some time chatting with the people there.

During the course of conversation, it came up that a new tenant had leased some space in the building next to theirs.  They were in the process of installing 550 cubicles.

550 neat and tidy boxes where 550 people would sit for 1800 hours a year.

Every year.

Until they retire.

Or leave for another cubicle farm.

Or die from lack of individuality.

When I first started working for myself, I was always afraid.  Afraid that I’d run out of money, afraid that the clients who were paying me would suddenly stop paying me, afraid that I’d never get another client.  Afraid that my dream could turn into a nightmare at any moment.

Those same insecurities waft across my brain every now and then, but after these many years of thriving on my own, I’ve learned to acknowledge them for what they are – motivational reminders!  So stop dwelling on the fear itself, and instead consider, really consider, how fear can motivate you.

Know Your Numbers

Instead of staying awake at night trying to mentally calculate how much money is left to pay the bills next month and the month after that, turn this fear into positive action.  Schedule time once a month to review your budget (not just professionally, but personally!).  Make sure you really need all of those things that are costing you money.  Don’t just think about your expenses, actually sit down and make a list of them in Excel, or Google Sheets, or Numbers, or another number crunching tool of choice.  List everything you can think of, and then take a hard look at whether you’re spending your money wisely.  One of the side effects of not having an employer is that you quickly become acquainted with the real value of money. There’s a passive reliance that comes into play when you’re receiving a paycheck every two weeks. It gives a false impression of security.  That’s why it’s such a jolt to suddenly lose it, whether by choice or not.

When you’re working for yourself, and your actions are so tangibly linked to earning every dollar, you take a good hard look at how each of those dollars is spent. Not only that, knowing and managing exactly how much your household and business spend every month is one of the best inputs you’ll have toward peace of mind.

Make More Money

Aside from taking stock of how you spend your money, the absolute best way to guard against running out of money is to make MORE money!   No, I’m not suggesting you start an exciting new counterfeiting business.  I’m also not suggesting that making money is as easy as wishing to do so.  But if you work on it, continually and consistently, you begin to realize that generating revenue is always achievable.  It’s demanding, and a lot of work, and requires a lot of attention; but once you have a solid understanding of what you have to offer, what value you can provide, you’ll find that you can truly discover and connect with people willing to buy what you’re selling.  Connecting with your clients and customers is the first step to making sure you always have an active revenue stream.

People get too hung up on immediacy.  Success doesn’t happen overnight.  As long as you focus on the long-term, and deliver in the short-term, you can gradually climb the path you need to realize your goals.  Give it time, keep at it, don’t give up.  These are all well-worn tropes.  But maybe there’s a reason for that; maybe they’re so well-known and so often repeated because they represent truths that we’ve gained from experience.

Biggest Fear of All

Lastly, when things get challenging, it’s good to have a conversation like the one I had recently. Because at the end of the day, my biggest fear is that I’ll someday give up and go back to being a cubicle zombie. Who needs more motivation than that?!

When Should I Quit My Job?

The Perfect Time to Quit Your Job

If you’ve ever thought about starting a business or working for yourself, you know just how important it is to wait for the right time.  Wait until you’ve stashed lots of cash as a safety net, until all the bills are paid, until there are no pending financial obligations, and risk is as low as it could possibly be.  That time is called ‘never’.

Saving for a Rainy Day

If only we could line everything up in a neat and tidy row, and then freeze time.  But the world doesn’t work that way.  The world is patently unfair.  Just when you finally make that last car payment, you hear a strange noise coming from the engine; when you have some money saved for a rainy day, something catastrophic happens to your house.  It’s always when you think you’ve finally gotten ahead of the curve that something, some unforeseen event, pops out of nowhere and smacks you back down to reality.

Is there a perfect time to quit your day job? Of course. It’s completely theoretical and has nothing to do with real life, but yes the perfect time to quit your job is when you’ve saved up a year’s worth of income, are 100% sure that you won’t need to spend extra money on emergencies next year, and you are all but certain that your business idea and goals will be achievable in the next twelve months.  When will all of those stars align?  Never.

If It Was Easy

You’ve probably heard that expression, if it was easy, everyone would do it.  It’s very applicable to starting your own business.  But it doesn’t follow that just because something “isn’t easy”, it can’t be done.  Of course it can be done.  I’ve done it!  As have many other successful entrepreneurs, solopreneurs, freelancers, and work-from-home gurus across the globe.  Each with their own unique path and story and, I’d be willing to bet, none that waited for the perfect time.  Waiting for the stars to align is comfortable, safe, and non-productive.  At some point, you need to be willing to make the commitment, and leap.  Look first, certainly, but then leap.  You can build dreams in your imagination, but it takes action to make them a reality.

3 Steps to Take Right Now

Just to be clear, I’m not suggesting that you head into your boss’s office tomorrow morning and quit your job with viral-video-inducing flourish!  There are some steps you can take to do basic due diligence before you take that leap ahead.  The goal here is to stop waiting for the perfect moment, and instead recognize the right moment for you.  Take reasonable action now to set yourself up for successful.

1. Test Your Idea

Whether you have a brilliant idea for the next hot social network or you’ve worked a way to make money from your passion for gardening, the best way to see if people will buy what your selling is to test it.  Ask your friends how much they would pay to buy your service or product.  Ask the market whether they’re interested.  Although you may be interested in buying what you’re selling, the real question is whether anyone else is!

2. Invest Your Free Time

If you want to start your own business, you need to make sure it’s something you care about.  You’ll be pouring inordinate amounts of time and energy into making it work, so don’t sign-up for something that you dread to even think about in the morning.  The simplest way to test your own passion and commitment to your idea is to start working on it in your free time.  Now, as I said above, working on your idea is very different from thinking about your idea.  Thinking, dreaming, imagining…that’s the ultimate fun part!  But working on it requires commitment. After you’ve put in an eight hour day at work, and several more hours attending to your personal obligations, are you still willing to squeeze in that extra hour or two, or even just 30 minutes a day to work on your business?  Building your dream means giving up something, and it’s a choice you make daily. Watch an hour of television, or work on your website?  Meet friends for coffee, or finish your business plan?

3. Work the Side Hustle

This is one of the best steps you can take to making that leap from employee to business owner!  While you’re still toiling away at your day job, start working on the side for yourself.  Evenings, weekends, any moments you can spare, can be spent delivering value to customers and earning money.  It may not necessarily break the bank, but there’s intrinsic value in the side hustle.  You still have your day job to pay the bills, while developing a promotable portfolio and a rich network of happy customers genuinely interested in what you have to offer.  One caution though – be sure to check the terms of your employment, to make sure you’re not restricted from working on the side. Some companies will specify that you can’t offer the same goods or services while in their employment, depending on the industry.

What’s Your Path

Those who know me or have read my blog know that I didn’t exactly leap from my comfortable employment nest, so much as I was pushed.  I was already in it before I began.  But following that initial nudge, I had to make the choice to stay, and the steps above helped me make that commitment.  Of course it also helped that by then I already had a taste of the freedom and empowerment that comes with being “out on your own”.  Everyone’s journey toward realizing their dreams is a little bit different.  What will your path be?