I’ve been working for myself for 10 years now, celebrating my anniversary in June. At this point I think it makes me at least a specialist in the pros and cons of trying to work for oneself. Trust me, it’s not easy, and the dichotomy that comes up can be mind numbing. Let me show you why.


1. Marketing can be challenging. Marketing is what separates those who will make it and those who will struggle. At some point we all have to try to come to grips with this and figure out what works best for us. In my case, I’ve done the bulk of my work as a subcontractor, so I’ve marketed myself to people who act on my behalf better than going directly to a customer base.

2. You sometimes work longer hours. When I was first in business I found myself regularly working 16 to 18 hours a day, even on the weekends. This is when working a 9-5 looks really good, getting paid, coming home to watch TV, and being able to take a paid vacation 2 or 3 times a year. You have to make yourself work to get things done because no one else will do it.

3. Money is inconsistent. For someone who likes to budget, it’s tough budgeting when income changes from month to month. And the swing in income can be drastic, since your clients really don’t owe you anything except to pay you for work you’ve done.


1. When you find your rhythm, there’s great freedom in when and how long you can decide to work. I tend to do my best work in the evenings so I concentrate on being ready then more than earlier in the day. I go out to lunch at least twice a week, and if I need to get something else done during day hours it’s pretty easy to just go get it done.

2. You can decide how you want to dress. Even if you work out of your home for yourself, since it’s your business you might decide you won’t want to wear a tie except on special occasion. When you work from home you don’t even have to go that far.

3. You might have some great years. For a 3 year period in the mid 2000’s I made more money than I’d made in the previous 14 years total. You pretty much get to set your rate and if you can get enough people to pay it, or even a long term contract, life is really sweet. And even when things aren’t at that level you still have many other options in figuring out how to make money for yourself. Freedom does come at a cost, but sometimes that cost is reached pretty quickly.

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