Today’s post is a guest submission from reader Brian Weeks. It’s also a well thought out response to my recent post 5 Reasons Working for the Man isn’t all that bad.

I like to play.  Ask anyone who knows me and they’ll tell you that I’m still a kid at heart.  So, is it any wonder that I shudder at the thought of the 50/50 plan?  Working for someone else for 50 hours a week for 50 years is just not my cup of tea.  Any of you ever feel like that?  If so, here are five reasons to consider taking the risk, striking out on your own, and working for yourself.

1.  More Money

A successful business can reward you with, well, a lot of money.  I know most of you probably aren’t interested in all that being rich stuff so you can skip this point.  For the rest of you, read on.  In a capitalist system, money ultimately flows to owners.  By becoming an entrepreneur you are getting in line with this principle, rather than trying to swim upstream your entire life.  I don’t know about you, but I’m lazy.  Just thinking about swimming upstream my entire life makes me tired.

2.  Passive income

You’re probably starting to realize this, but I don’t like to work.  That’s why everyone calls it “work”.  If we liked it, we would call it “play”.  Owning your own business opens doors to concepts like passive income.  Simply put, passive income is income that you don’t actively have to work for.  Yeah.  Sign me up for that one.  Earning more and more money while having to work less and less?  Why didn’t they teach me that in school?

3.  Freedom/Time

Since owning your own business can reward you with big bucks as well as the ability to make money even while you’re not working, this gives you more free time for whatever you want:  spending time with loved ones, volunteering, sleeping in, or . . . sleeping in.  From my experience and from what I’ve gathered from fellow entrepreneurs, it is this freedom that is the biggest reward of being an entrepreneur.

4.  Taxes

Believe it or not, much of our tax code was written to encourage the growth of capitalism and, therefore, the vast majority of the tax breaks that are available are only available to business owners.  To take advantage of these, find a CPA who knows, understands, and complies with the tax code.  Compliance is just as important if not more important than knowing and understanding the tax code.  I can write off whatever the heck I want on my tax return and pay zero taxes year after year.  It’s only when I’m audited that it matters.  Too many entrepreneurs think they’re getting away with gaming the system when they’re really playing with fire.  Don’t do this.  Be smart.  Play by the rules and you can still save a bunch on taxes.

5.  Control

As the captain of the ship, you can see farther ahead than the if you were in the galley below.  You can see approaching troubled waters and make the needed adjustments.  You would no longer have a limited view and limited control over the solution.  You would be able to steer the ship where you want it to go rather than some stuffy bureaucracy telling you how you how things are going to go down.  This is where your creativity can really shine.

Next steps:

Now, I can hear some of you out there saying, “Brian, I am totally stoked about starting my own business . . . but where do I start?”  Good dang question.  Here are a couple of first steps for those of you ready to make it happen.

Go work for at least six months in a business that is doing what you’re wanting to do.  Not only will you gain invaluable insider knowledge about the inner workings of your potential business, but you will get paid while doing it.  You will come away from this knowing more of what works, what doesn’t work, what pitfalls are out there, and even if this is the right business for you or not.

The next step would be to sit down with your local SCORE advisor who can help you get started for free.  Yep.  Totally free.  SCORE is made up of active and retired entrepreneurs who, out of their passion for entrepreneurship, donate their time and knowledge to help other entrepreneurs where ever they might need help.  They can help you put together a business plan and get the ball rolling.

Welp, there you have it.  My top five reasons why I LOVE being an entrepreneur.  I hope that helps some of you, who might be needing a little nudge, to take that next step.  Now, if it’s cool with you, I’m going back to bed.  

Are you thinking about quitting your day job and working for yourself? What are your hesitations? 

Already own your own business?  What are your favorite things about being the captain of your own ship?

[photos courtesy of  Inga and FusiAsia]