Do You Have What it Takes to Be Self-Employed?

Photo Credit: Dover Publications, Inc. 2008.‘Do You Have What It Takes to Be Self-Employed?’ provides an antidote to the prevailing attitude of ‘be your own boss, set your own hours, work in your pajamas and sit back as clients rush to your doorstep.’

How long have you been self-employed?
Since 1976. I’ve had two ‘regular’ jobs. One lasted eight months, the other a year and a half. Leif has not had a straight job since 1963. His ‘real’ employment lasted four months.

What are some of the major misconceptions about self-employment?
That you are your own boss. I have customers. I have vendors. I have competitors. I have the world, the economy, the IRS, and the State of Colorado. I have a whole bunch of people telling me what to do, and who I have to deal with all the time. I am my own boss in that I choose how to respond. Don’t imagine that being self-employed means you do whatever you want to do, whenever you want to do it.

Say I’m self-employed. Do I have to do everything on my own?
Oh, god no. But we all do it at first, especially starting out – it kind of goes with the hands-on mentality of being self-employed. At first, I did everything, from our taxes, to our marketing, to graphic design. But what I’ve discovered is that if you don’t delegate, or hire tasks out to other skilled professionals, it is difficult to grow your business beyond your fingertips. We have limited time, and it is more productive to focus on those things you do well (what your customers are paying you for). Particularly important is your ‘professional network,’ including your lawyer, accountant, and insurance agent.

What fields are best suited to self-employment?
A simple fact of business is that you need to sell something for more than it cost to produce, and at a profit that makes it worth your time. There has to be a significant margin – you won’t be able to support yourself making and selling something that can be found for less at Target. It’s less about which specific field is good for self-employment and more about the margins; as a one-person operation, even with a strong network, you have less access to economies of scale.

Enthusiasm, persistence, and talent are not enough. Learn to avoid common mistakes with ‘Do You Have What it Takes to be Self-Employed?’

Tip: Engage with your local chamber of commerce. If you are starting out with limited resources, they can provide a wealth of information as well as access to other professionals.


Great all-ages information from the AARP on self-employment

An array of resources at 

And be sure to avoid work-at-home scams