Working Solo: A Self Employment Reality Check

The Pros and Cons of Self EmploymentGraduating from college is a huge accomplishment, and for most people, an incredibly expensive undertaking that often leads to a level of expectation that may or may not be realistic.  Every field and every higher education institution obviously affords different opportunities, but as the search for a job gets frustrating, and as you get a grasp on what’s really out there, your sense of entitlement can easily get crushed.

That said, I think the following thoughts hold true for most graduates across the board once they get that first job:  “Are you serious?”“Is that all you think I’m worth?”“How am I ever going to pay off that huge debt I just took on for my education with that kind of pay?”  

You can’t help but think of the financial sacrifice you made for the sake of having a better lifestyle – and wonder if you’ll ever achieve your dreams.

The reality of the “real world” of employment is that you often have to start from the bottom, and once you’ve grasped that concept and sucked up your pride, you have another hurdle to get over once you see how much that new salary is reduced after taxes, insurance, Social Security, and other benefits.

For me personally, earning a bachelor’s degree in communications from a mediocre college left me with a few options.

  • I could continue to live in with roommates and work my way up a ladder that I had zero control over.
  • I could “marry well” and then have less control of my life.
  • Or, I could go back to school for four more years for my Master’s or Ph.D., incurring even more student loan debt, only to graduate into the unknown once again.

I think these options work well for many people, and if one of them works for you, you should go with it. But at this point in my life and career, my choice has been to work in a commission-only sales position in an industry that evokes all sorts of negative reactions: real estate!

I have chosen to work for myself selling real estate during the 10 years since I graduated from college, and it’s involved the good and the bad. From the initial job search right after graduation to the market crash in the last couple of years, to the strain of just plain having a bad week (and wanting to say “screw it”), I think I may have enough experience on both sides of the coin to give you some of the pros and cons of working for yourself.

Pro #1: Control Over Your Finances

If I am feeling a pinch in my wallet or am having a new fantasy, be it a new car, vacation etc., I know for a fact that I have the option of putting my nose to the grindstone to earn it. Whether it becoming up with new creative marketing ideas or simply dialing for dollars, I know it’s going to pay off in either the short term or the long term. If you are working in a conventional “corporate” job, you can work late at the office and kiss the boss’ ass, but at the end of the day, it is really all a gamble since you are at the mercy of company policies and financials.

Pro #2: Working With People You Like

This one is big for me. People either exude positive energy and inspire you to grow, or they can be what I like to call “energy sucking vampires.” If these vampires are your coworkers or worse, your boss, unless you’re Buddha, you’re screwed. What’s so great about working for yourself is you can make the conscious choice: are these individuals worth the money? Or would I prefer them not to be in my life at all? Brilliant! The minute I get a vibe this person is going to be a giant pain in the rear, I have the flexibility to decide if I want to work with them or not.

Pro #3: Professional and Social Flexibility

At this point in my life, I don’t have any children, but if I did, I would be able to make it to a few more parent teacher meetings, baseball games, etc. I am a single girl, so the option to fly out to meet friends out of town or take the day off when I need it is always available – as long as I recognize that I still have to meet the obligations that I have set for myself, and my clients.


Sounds great, right? But like most things, there are some also some very important cons to take into consideration.

Con #1: Financial Responsibility (and the IRS!)

Some people are very fiscally responsible and for them this may not be an issue, but if you have a hard time getting a check and not putting a very large portion away for a rainy day, WATCH OUT! April 15th can be torture. Trust me when I tell you that the IRS is not an institution that can be charmed into forgiving you. They will show up at your door, take your money, and put a lien on your house and car if you make a critical error. (And you thought the credit companies were scandalous.) As you consider a business in which you have to account for everything, including your taxes, please keep this in mind.

Con #2: The Fine Line Between Friends and Clients

Anyone that says that they can keep their real estate business separate from their personal life is lying. For people with “regular jobs” who can clock out, it’s awesome if you can separate your private life and your work business! You don’t get to do that when you run a business, especially if your friends happen to be clients, and vice-versa. The feeling that someone is always watching and judging you can be exhausting.

Con # 3: Hard to Take Off Time

Even though there is flexibility to the hours, it is very difficult to take time off from being self-employed. Of course you always have that option of saying no thanks, especially when you feel tired and overwhelmed. However, you still have bills to pay and dreams to fulfill, and with every call every call you send to voicemail, you could be throwing a few thousand dollars down the drain.  So the challenge you are faced with is this: is my quality personal time worth the potential loss of income from making a client happy? This doesn’t necessarily make for the healthiest relationships or the healthiest mindset.


Of course, these are just my opinions, based on my own life experiences. But I hope that weighing the pros and cons gives you a different perspective on both sides as you go about choosing your career path!

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