Self-Employment Isn't All It's Cracked Up to Be

For whatever reason, a lot of people have a difficult time comprehending that I was self-employed as a real estate agent. As I have explained in the past, I owned my own business. If I didn't feel like going to work - I didn't. If I wanted to take a week of vacation, I just did it. No questions asked.

And I am blaming my blogging absence on the ghost of my real estate past. I made a decision this morning while I was running. After about seven years of usually trying to figure out why I need to get out of my latest relationship, I decided to think about my tax situation and how much it sucks. And I decided that I shouldn't have renewed my Ohio real estate license on March 25th. I spent about two hours filling out the forms after completing my 30 hours of continuing education that I paid for. Then, come to find out that my real estate office insists that I continue to pay for my MLS membership of $180/semi-annually. When I paid in October, I literally threw $180 away. What a waste. Come tax time and nobody seems to understand why mine are so complicated. All those great, large paychecks, yet I still owe more and more money.

Let me spell it out for all of you: 1099!!!! What don't you understand about that? SELF-EMPLOYED. So, the next time someone asks me about my health insurance/life insurance/free office - I will throw up. I was SELF EMPLOYED, people!! I paid a desk fee. I paid for my real estate ads. I paid for my continuing education. I paid, I paid, I paid. Do you want to see my 2008 tax file? It's 16" wide with a lot of papers and receipts called deductions! Unless you make a lot of money while being self-employed, I cannot believe I am saying this - Don't do it!!

Here are the pros:

Our generation works to live, so being self-employed is perfect a lot of the time
You can choose your own hours (sort of)
You can take off whenever you want (sort of)
You will never get fired (sort of)
The sky is the limit (sort of)
You are your own boss (sort of)

What do I mean by the "sort ofs?" Well, your clients sort of run the show. They want you here and now. They need you at midnight to talk them through negotiations. They will refer you to more people. So, they are your boss.

Cons:
Being self-employed, do you know how many people screwed me over? A lot. And I think I am a decent person
You are always worried about every detail of your business
I had to pay for my own crappy health insurance
I had to pay for my own retirement plan
I had to pay for a ton of gasoline at $60 a fill-up
I had to give a percentage of my commission to the brokerage
I still owed money to Uncle Sam last year
There is no regular paycheck

So this is why I recommend that you get a job with an employer:

I was actually jealous of my friends who received regular paychecks and were required to go into an office at a regular set time on a daily basis. They also were guaranteed all those lovely benefits I dreamed of. And I could tell at 5:30 or whenever, they felt like they had put their time in. They looked gratified. Me? I never felt that way. And of course, their taxes are so much easier than mine. So get a job with a W2.

You know, there is something to be said about a job where you can go in for eight or nine hours, do the best you can and enjoy the quality of the end of the day, however you unwind. Yes, sometimes I stay late. Occasionally I check my e-mails late at night for work related things. I don't mind doing any of that. I know I am getting a paycheck. I know the amount and when it's coming. And I have a job with a W2 that I finally look forward to doing. Almost eight years out of college.

Even though you may think it sounds lovely to work for yourself, don't do it!