Battle of the Bosses: Self-Employment vs. a Traditional Job

March 17, 2007

Posted in Small Business.

Starting your own business is a hell of a decision. You hold an internal debate about the pros and cons. It can keep you paralyzed, analyzing hundreds of scenarios. You can read up on all of these topics, but you’ll see a blindingly obvious trend: the people who promote self-employment will defend self-employment across the board. But it’s ludicrous to think that self-employment wins out each time.

Starting today, we’ll go over a list of variables—money, stability, etc.—that may factor into your decision to quit your day job and start a business. I want to explore these factors and give you a chance to consider them from your own perspective, not from someone trying to hawk a book or brag about how much money they make from their website. This is a personal decision that can affect your whole life. It doesn’t make sense for me to tell you what to do as if I somehow know best.

The Showdown

Each variable will be listed with the pros and cons – arguments for and against – of both self-employment and working for a boss. For our purposes, we’ll use self-employment to describe any job where you answer to yourself or your partners. A “boss” means you have a job working for an organization that you don’t own and have no control over. It should be pretty clear which one you’re in.

A final note before I go on: I do both of these. I work at a university and own a web design company. I’ve done each exclusively, but for now I do both concurrently. Considering these factors in my own situation, I decided to work both angles. And as I said before, these are variables – not constants – and you’re going to need to evaluate these within the context of your own situation.


How reliable your paycheck and position is
How much financial compensation you receive
What kind of non-financial compensation you receive
How stressful the position is
Career Potential
What the future could hold for you in terms of work
Your freedom in what you do and how you do it
How difficult your work is and your influence over it
How you directly interact with others
How much time your work requires and your influence over it
Commute and Travel
The distance and time spent traveling for work
The impact of work on your family
I’ll keep coming back to update this post and link to the showdowns when a new one is up. Enjoy!