Why Your Job is a Dead End (and How to Re-Energize Your Life)

“Go to college, major in something marketable, then get a good job in a secure field.” Sound familiar? It’s what most of us have been told.

But now that you’ve been out in the real world for a while, something doesn’t quite seem right about that advice.

Maybe you feel like:

  • you’re not being paid what you’re worth, or
  • you’re not challenged, or
  • you’re afraid you’ll get laid off/down-sized/right-sized, or
  • you’re overwhelmed and stressed with the demands of your job, or
  • you wish you could do something that truly interests you.

Maybe you’ve even switched jobs–several times–trying to find something better. Or maybe you’ve read career books to help give you some direction.

That’s OK. See, the problem isn’t you.

The problem is that we’re conditioned to believe that a job can create the kind of lifestyle you want.

What’s wrong with having a job?

Well, plenty actually. Your job has some huge fundamental flaws that make it a dead end:

  • Financial security:

Over the past few decades, we’ve seen downsizing, rightsizing, doing more with less, and working smarter not harder, which have all created less job stability for workers.

With a job, you’re entire financial livelihood is dependent upon a single source of income. If you lose your job, how will you pay for food, rent, and your eBay addiction?

  • Scalability:

You work hard, but how much can you do?

Have you scaled yourself? Cloning is now a medical reality, but you don’t really want to pay a surrogate to bear a half-dozen mini-me’s that you can raise up and train into your personal worker-bee posse.

  • Free to be me:

Now, this is admittedly a bit touchy-feely, but it’s actually the most important piece.

Do you get up every morning excited about your job? Do you–in Warren Buffett’s words–“tap dance to work”? Not likely.

What’s the toll of working for years–or decades–at a job or jobs where you feel bored, unfulfilled, and dispassionate?

What if you liked–no, LOVED–what you did? How much richer would your life be if you were passionate about your work and if it energized you?

What’s the alternative?

The alternative is something that roughly 1 out of 7 workers is already doing: working for yourself.

Wait–did you feel it? You probably just felt something like:

  • discouraged at the prospect of working hard for something that isn’t guaranteed, or
  • doubtful that you can succeed, or even
  • fear that you’d fail.

But guess what? That’s just the job talking, trying to convince you it’s actually a really great deal–when, in fact, it’s not.

See, a job isn’t your friend. It’s actually the enemy of the kind of lifestyle you really want. It just looks good because you’ve been conditioned to think that way–regardless of the facts.

Let’s see how working for yourself looks compared to a job

With a job:

  • You’re told when to arrive at work, when to take breaks, and when you can leave.
  • You’re told what work to do, and often, how to do it.
  • If you disagree with your boss, too bad–you just have to deal with it.
  • You have little control over how much you’re paid, how much time off you can have, and what your benefits are.

The whole thing is pretty restrictive.

Now, let’s take a look at working for yourself. I’ve been self-employed since I ditched my day job in 2008, and here’s what self-employment looks like:

  • No one tells me when to work, how long to work, or how to do my job.
  • I get assignments from my clients, and if I don’t want the project or client, I don’t have to take it.
  • I control how much I earn, how much time off I take and when I take it, and have benefits (healthcare, retirement, etc.) that are equivalent to most “real” jobs.

You might think that money’s not that important. But how would an extra $1,000, $2,000, or $5,000 each month change your life?  After quitting my day job, I was able to QUADRUPLE my former salary, and I continue to boost my revenue each and every year.

Would you turn down a 400{54c12dad2cc2b53ae830e39915b1a3e70288dbcbbeb8bbf8395437c5dc3c512c} raise? I didn’t think so.

Now, let’s look at some of the other aspects of working for yourself:

  • Financial security: If one of your clients/customers has no work, it’s not a big deal, since your revenue comes from multiple customers–not a single employer.
  • Scalability: Yes, there is only one you, but you can subcontract, hire employees, and automate processes. Try asking if you can subcontract your job, and see where that gets you. Probably something like: “Do you want to pack your things now, or shall we send them to you–along with your final paycheck?”
  • Personal fulfillment: Working for yourself means having control over your destiny. As an employee, I complained a lot–a LOT–but as a business owner, I feel empowered and continually see new opportunities.
  • Fringe benefits: More flexibility, equivalent health & retirement benefits, and less stress round out some of the other benefits of working for yourself.

Don’t quit your job–yet

Before you hand in your resignation, you need to know the right way to do it.

Start your business part-time on the side, and keep your day job–let your job fund your new business. Use the skills and experience you already have, and provide value to clients. Find out how to specialize so you can charge MORE for your expertise instead of competing with people around the globe who are eager to work for burger-flipping wages.

There’s a way to become self-employed WITHOUT being risky, and without struggling.


Greg Miliates started his consulting business in 2007, QUADRUPLED his former day-job salary, and teaches how to ditch your day job on his blog


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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