Working On The Side – How To Do It Effectively

Freelancing. Consulting. Outside employment. Moonlighting at a second job. Whatever you call it, working on the side is something many of us do to fuel our passion or just to make ends meet.

Here’s some advice on how to do your side job effectively. In fact, if you’re lucky, it could become the best occupation you ever had.

1) How to start – Some of us contemplate starting a new job for years. Some ease into it for a few hours a day or a week. To be most effective, ask all of your friends through sites like for a referral to someone in your chosen field. Send letters or make cold calls to ask for an informational interview. Search for an internship online to learn from the ground up. Or apply for a grant in that field.

2) Hit the ground running – I suddenly became a freelance writer about 15 years ago after I was laid off from a high-level advertising agency job. I immediately started interviewing for full-time jobs during the day but working at night to generate income. I learned how to ride the emotional and financial roller coasters, to control my destiny, and to forge a freelance career. So can you.

3) How much to focus – If you’re finding that you love the side job more than your 9-to-5 gig, start exploring full-time opportunities in that field. Contact an executive search firm. Visit job sites like Craigslist,, or You may have to take a substantial pay cut to become a pastry chef, a musician, or running a day care center, but if happiness is more important to you than money, follow your heart.

4) Know when to say when – Not all side jobs work out. If it turns out you’re unhappy pursuing your dream, you have to know when to give it up. Also, if you find the side job interfering with your day job to the point where you’re worried about a bad performance review or getting fired, it’s probably time to scale back. As well, be wary of conflicts of interest between the side job and your regular work. It’s one thing to get fired; it’s another thing altogether to get sued because of your outside employment.

5) When to resign your day job – The best scenario of working a side job is gaining enough expertise so you can kiss your regular job goodbye and become a full-timer in what you prefer to do with your career. Only you know when you hit this point, so constantly evaluate where you’re at.

About Gil Zeimer

Gil Zeimer is the Creative Director of Zeimer's Advertising Shoppe. As a consultant with 25 years of advertising and blogging experience, he is a Mad Man who works with businesses large and small. Read his marketing musings at
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