4 questions to ask before taking a second job

By Jennifer Rose Hale

With a few independently wealthy exceptions, most of us could use extra money at one time or another. If you're thinking that now is one of those times, a surefire way to increase your income is to take a second job.

Before you start looking for "Help Wanted" signs, ask yourself these four questions: What do you want to do? How much time can you give it? Who can help you get started? And what will you do with the extra money?

1. What do you want to do?

As a child, you were often asked, "What do you want to be when you grow up?" Whether you're 22, 42 or 62, you never stop growing, so it's always a good question to ask.

Lots of jobs that appealed to us as teenagers are easy to start again -- babysitting, for example. Parents will always have a need for good child-care providers -- especially the ones who have real-world experience. Can you look after kids in the neighborhood on the weekend?

Do you enjoy photography? Do friends wear your handmade jewelery or ask for your handyman skills? You might find someone willing to give you a chance if you set a competitive introductory price, and that chance could turn into a referral.

In addition to generating more income, a second job can provide experience, skills and contacts necessary to pursue a new career. If it's something you enjoy doing, a second job can feel less like work and more like a hobby.

2. How much time can you give it?

Don't diss your day job if it pays your bills and puts food on your table. Double-check your employer's policies on outside work. Many companies have specific policies about not working for competitors. Others require you to notify your boss of any outside work you're doing. It's better to be safe than sorry: your boss wants to know you're doing the job you're being paid for.

And while it may be tempting to use the office copier to make your fliers, making the extra effort to find the copier at the library or a packing store is not only ethically more sound, but it will also help you track expenses related to your side work.

3. Who can help you get started?

Starting a second job can be as easy as sending an e-mail to your friends and family, setting up a website or talking to a mentor. It's not that hard to find people willing to help you -- whether it's reaching for a lifelong dream or just paying off those credit cards a little earlier.

You may also find newer services on-line that help -- Etsy, for example, for selling handmade goods, or Sittercity.com for babysitting.

4. What will you do with the extra money?

Another important factor: Be ready to take care of your income. Those extra dollars can get lost in your household expenses quickly.

Consider setting up a separate checking account or high-interest savings account. Then you'll be able to track every dollar from your side business. This can be particularly helpful if you generate enough income to file quarterly estimated taxes. It will also help you answer the question, "Is this worth my time?"

For more inspiration, take a look at this Forbes.com piece, "Taking On a Second Job," and find more resources at the Get Rich Slowly post "How to Supercharge Your Income."