Should I moonlight — and how do I go about doing it?

Question: “Should I moonlight — get a second job — and how do I go about doing it?”

by Randall S. Hansen, Ph.D.

Somewhere between 7-8 million Americans hold a second or third job… and most do so to simply earn a living or to help earn extra money. Moonlighting is tough — it’s hardest on you (because you will have no free time) and your family and friends (because they will never see you).

Here are some moonlighting strategies — for finding and surviving a second job:

  1. Check your main employer’s policies. Before you even consider looking for a second job, take the time to check your current employer’s policies about holding outside employment.
  2. Understand your reasons for taking a second job. If it’s purely monetary, you may be able to talk to your current employer to pick up extra shifts rather than take a second job.
  3. Consider a trial basis. Moonlighting in short doses — to accomplish some short-term goals — usually works better than working multiple jobs for long stretches of time.
  4. Find a job that interests you. Perhaps you have a boring office job as your main job, so try something fun like being a tour guide or other more unusual job for your second one.
  5. Consider second jobs that are less stressful. If your first job is a pressure-cooker, find a second one that is relaxing to you, such as pet-sitting or tutoring.
  6. Find jobs that are geographically close to each other — or to your home. Your time will be limited enough without adding a long commute to your second job.
  7. Seek out new opportunities with new employers. If you are contemplating a career change, but are not sure of your next career, use second jobs to test out some of your career ideas.
  8. Reduce your load. If you are working multiple jobs, it’s probably time to cut some of those extracurricular activities.
  9. Carve out time for significant others. You must find a way to schedule some time with your family and friends or those relationships will suffer… and if you have a partner, be sure s/he is okay with your plans.
  10. Know when it’s time to quit. Whether it’s when you reach your financial goal or when you are beginning to mentally or physically breakdown, you must reduce your load… though that does not necessarily mean quitting your second job (if it has become your new career passion).

Read more in my latest article published on Quintessential Careers: Moonlighting in America: Strategies for Managing Working Multiple Jobs.

This article is part of a series from The Career Doctor’s Cures & Remedies to Quintessentially Perplexing Career and Job-Hunting Ailments. Read more.

See a list of all the most common college, career, and job questions — and Dr. Hansen’s solutions.

Who is the Career Doctor? Learn more, read his current career column, or browse the column archives when you visit the Career Doctor’s homepage. Founder Dr. Randall Hansen Dr. Randall S. Hansen is a nationally recognized career and job-search expert. He is founder of Quintessential Careers, one of the oldest and most comprehensive career development sites on the Web, as well CEO of He is also founder of and He is publisher of Quintessential Careers Press, including the Quintessential Careers electronic newsletter, QuintZine. Dr. Hansen is also a published author, with several books, chapters in books, and hundreds of articles. He’s often quoted in the media and conducts empowering workshops around the country. Finally, Dr. Hansen is also an educator, having taught at the college level for more than 15 years. Visit his personal Website or reach him by email at randall(at) Check out Dr. Hansen on GooglePlus.

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