I’ve been self employed since October 2009 when I was fired from my day job. Long time readers will know that it was a massive blessing in disguise because in my first full year of self employment I nearly tripled my income. After working for myself for over 18 months I’d like to share why at times self employment can suck:

1. Extra Stress

I have a younger brother and an older brother. My 31 year old older brother has no gray hair and my dad didn’t get gray hair until he was nearly 40. On the other hand, I’m “only” 27 and started getting gray hair as soon almost as soon as I started running my own business. Yes it could be a coincidence but I’m near certain it is from the added stresses of being self employed.

I know a lot of the stress is self enforced, because I feel like if I don’t grow my business by at least 50% year over year that I’m doing something wrong. With these type of growth goals I feel like everything I do has to be successful and because I’m trying so many things unfortunately not every project I’ve worked on has been a success.

2. Lack Of Social Interaction

I used to work in a sales job and really enjoyed the people I worked with. We’d take occasional breaks to play Foosball, go out to lunch and occasionally hang out after work. Now the only people I communicate with are over the phone or on Skype. I believe this lack of social interaction is partly why I’m pushing myself so hard to grow my business because I’d actually like to have an office with several employees that I could go to each day. I never minded the office life, I just hated having stupid leaders telling me what to do only because they’d been with the company for 10 years.

3. Paycheck Varies Every Month

This is a double edged sword, obviously my paychecks are larger than when I was working my full time day job but it’s still stressful to have huge swings in the money I’m earning. I had a massive “pay check” in November when I sold one of my websites for six figures but then of course my monthly income took a hit so although I received a huge cash influx I had to think about which other projects I needed to start working on.

4. No Set Hours

I can be lazy from time to time, and this was true both before and after I was working on my online business full time. In fact, some of my friends would argue that the only reason why I worked so hard on my business was so that when I succeeded I could work less (lol). Having a day job is easy because you know that from 9 to 5 you’re in work mode and busy earning a pay check. Now that I work for myself I don’t have any set hours. I will occasionally work 12 – 16 hours in a single day and only get up a couple times to eat food. Sometimes I will also feel compelled to work on weekends for a few hours a day. On the other hand, I don’t have anyone cracking a whip at me so I will work shorter hours on occasion because I can.

5. Most New Businesses Fail

Making it through my first year of self employment was a big confidence booster, but the fact remains that most businesses fail over the long run (see small business facts here). Businesses like mine that technically don’t have “employee’s” (I use contractors) fail at a rate three times higher than other businesses do. I feel confident that my business will be around for years unless it’s acquired, but the odds truly are stacked against you as a self employed individual.

6. Deciding What To Work On

I make money in a variety of different ways, but I’m at the stage in my business where even though I enjoy solid base hits like selling a website for six figures I also want to hit a grand slam and work on something where I can exit for several million dollars (preferably with enough to buy the Guthrie Castle before my 20 year deadline). The toughest thing for me to do is to decide what to work on to help me achieve my financial goals, set new challenges and enjoy doing it all at the same time.

7. People Saying “Get A Real Job”

The worst part about being self employed is the fact that all of my friends and family that know what I do for a living think I don’t have a real job. Because I don’t have a real job I must always be able drive people to the air port and perform other menial tasks right? Any other self employed person will agree that this is one of the most annoying aspects of being self employed.

Self Employment Is Still Better Than The Alternative:

Even with all of these negative drawbacks I still wouldn’t have it any other way. The same freedom that causes me stress is what makes working for myself so much more enjoyable and challenging than anything I did in any of my past jobs. I’m a huge fan of this life style and building online businesses. In the coming weeks I’ll be changing several things about my blog to make it even better for people looking to succeed at building their own online business. In the mean time, feel free to read my suggestions on how to quit your day job. Just remember, that being self employed isn’t always awesome.

Stay tuned…