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Surviving a Second Job: 10 Moonlighting Tips

Millions of Americans work second jobs to make ends meet or pay debt and save money faster. Of course, it’s mentally and physically exhausting. From four years of working two jobs, here are some tips for surviving a second job.

According to the U.S. Dept. of Labor, about 8 million Americans work second jobs to make ends meet or pay debt and save money faster. Are you included? If so, beware, because moonlighting takes its toll. It’s mentally and physically exhausting and leads to stress at home and at work. But speaking from four years of experience working two jobs, here are some tips for surviving a second job.

1. Do Something Different, or Even Fun – If you’re at a desk all day, avoid computers at night.

You might find that standing at a cash register or the bustle of waiting tables is a refreshing change from your cube. If you can relate your second job to an interest, all the better. Love animals? Try walking dogs. Like music? Usher at concerts.

2. Watch The Stress – Most jobs carry some degree of stress, but if your primary job has you popping antacid tablets like they were tic-tacs, don’t become an air traffic controller by night!

Keep tabs on your on-the-job stress levels at your second job. If you’re a motivated employee (as you probably will be since you’re already willing to work two jobs), you may be targeted for a supervisory role, for example.

Take on additional responsibility with caution. A promotion may mean a few more dollars, but it may not be worth it if your stress level goes through the roof.

3. Tread Carefully at Your Day-Job – To tell your boss, or not to tell?

I’ve always wrestled with this one. On one hand, I didn’t want my boss to think that working a second job would subtract from my ability to do my primary job well, but I always wanted my boss to understand why I was leaving promptly at 5 on certain nights.

Also, I always figured that working a second job was a subtle hint that a raise might be in order! But be cautious if you decide to take on a second job. Many employers won’t allow you to do any sort of extra work if it is remotely related to your day-job, while some employers won’t allow moonlighting at all. Those air traffic controllers, for example, are prohibited by the FAA from moonlighting, lest they be tired on duty and miss two jets converging head-on. If in doubt, ask. I’ve concluded honesty is the best policy here.

4. Find a Flexible Boss – Obviously your full-time job comes first.

So be honest with your second employer if you will need time off to perform well at your primary job. This might include time to take a trip for work or put in the hours needed to do well on a particular project.

While small, independently-owned businesses may be more understanding of your particular position, they may not have the staff levels to accommodate your requests. On the contrary, many large chains offer extremely flexible scheduling, especially if they are able to cover shifts with staff from other nearby locations.

I’ve worked second jobs at both Starbucks and two smaller, locally-owned businesses. While their were benefits to both, I can definitively say I had infinitely more scheduling flexibility with Starbucks.

5. Set Earnings Goals – Before taking a second job, figure out how much extra you want to make each month and only work the hours needed to reach your goal.

If you can, designate your extra income for something tangible, like paying off a credit-card or funding a savings account. Seeing the results of your work will make the grind easier.

6. Keep Your Down Time – Nobody should work 24/7.

Make sure you’re off at least one night and one full day each week. And if you feel like you are missing out on socializing because of extra work, remember that you are saving the dollars you would be spending on drinks or entertainment.

7. Don’t Neglect Relationships – Moonlighting will put stress on you, but it may put even more stress on your relationships.

If you can, talk to your spouse or partner before taking a second job, and be cognizant of how he or she is feeling after you’ve been working the extra hours for a few weeks. Be careful, too, not to neglect social activities. Work too much, and you may find your friends stop calling because they assume you’re unavailable. Bottom line? It’s easier to find other ways to make extra money than it is to find new friends or a new relationship.

8. Beware the Tax Man – If you work limited hours, your second paycheck may not withhold enough in federal taxes each week, even if you select zero exemptions on your W-2.

Take the time to calculate your approximate tax liability with your additional income and specify an additional amount to be withheld each week. Even better, put that money in an interest-bearing account. You will owe Uncle Sam come tax season, but you can pocket the interest!

9. Watch Your Body – I’m not going to preach about healthy lifestyles here (alas, I have a long way to go myself).

I know from experience, however, that the additional fatigue from working two jobs will amplify the effects an unhealthy lifestyle takes on your body. When you work two jobs, you’ll be getting less sleep, though your body actually needs more. You’ll be eating faster and, most likely, less healthfully, when you actually need more nutrition.

Finally, you’ll be tempted to consume more caffeine to get you through the day, when it may keep you from getting the good rest you desperately need. If you can squeeze it in, exercise, a balanced diet, and at least six hours of sleep will make a big difference in your ability to handle a second job.

(I had a friend who would stay up all night and then work a full shift beginning at 5 am on nothing but coffee. Asked how he did it, he said “I took a multivitamin.” Let’s just say I wouldn’t recommend that!)

10. Know When to Stop – Unless you have to work two jobs just to meet the bare necessities, always have an exit strategy.

What has worked well for me is to work a second job for a year, take six months or so off, then start a new second job. I enjoy the challenges of learning something new and meeting new people, but am cautious not to go too long without some downtime.

The beautiful thing about working a second job is it makes you appreciate your free time so much more.

Have you had experience juggling more than one job? I’d love to hear about your experiences and how you survived your second job!

Published or updated on August 3, 2007

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About David Weliver

David Weliver is the founding editor of Money Under 30. He's a cited authority on personal finance and the unique money issues we face during our first two decades as adults. He lives in Maine with his wife and two children.


We invite readers to respond with questions or comments. Comments may be held for moderation and will be published according to our comment policy. Comments are the opinions of their authors; they do not represent the views or opinions of Money Under 30.

  1. Emily Nghiem says:

    I started working two jobs in 2008, to replace my overtime I was depending on to
    pay for community programs. Now it exceeds my salary just to pay the monthly costs of loans to several nonprofits
    that I had been juggling and transferring back and forth from one credit card to the next.

    The stress level went so far off the scale, I numbed out and don’t think about it in order not to react.
    So I worried I would develop the brain of a sociopath by turning off whatever emotional sensor or red flag would normally be triggered constantly.

    The worst part of all, is when people take this for granted, and think I can just pay extra expenses for them
    because I work two jobs while they barely work part time or volunteer and don’t make enough money to pay their bills.

    It seems the only people who understand are other people working two jobs trying to keep the community going
    while other people have no clue how much it costs, and how hard it is to work two jobs to pay the costs.

    It is like my sense of economic scale is never going to be like other people’s.
    The value of time, relations and resources are always going to be different for me.

    It has changed my entire perspective when I took on responsibility for
    paying for debts and damages in my community caused by govt abuses that nobody else was
    holding officials accountable for. When you try to pay for things yourself, that govt officials do not
    consider a wrong that needs to be corrected, and you work two jobs to pay for that;
    this tends to conflict with other people
    * who don’t believe in holding govt responsible (so they don’t think what I’m doing is right or necessary but COMPLAIN about what I am doing, when they aren’t doing a thing to fix the problem and won’t complain about the real abuses)
    — arguments about whose fault it is, and who should be fixing it but isn’t, can go in circles and end up in public yell wars —
    * other people who don’t work two jobs, don’t understand my impossible time schedule and stress level,
    * and who complain when I don’t return calls, don’t follow up, am late getting things done, etc.
    or when I blow up at them from stress because I don’t have time to talk on the phone or do all the things they want me to.

    I was hoping to find a support group for people working two jobs,
    before i start a third job on the weekend. I need to pay for my
    health insurance which will go up 300 a month after my job ends.

    Thanks to the insurance mandate, I may have to give up the place
    I was renting if I cannot physically and mentally handle a third job.

    I would have to give up one of the three things I need a third job to pay for:
    * insurance at 300 a month
    * rent at 300 a month
    * the van I am paying for at 300 month
    for the nonprofit community volunteers to use.

    Thanks to the health care mandate, I’m going to need three
    jobs in order to “keep my insurance.”

    If you know of any forums or support groups for people working 2-3 jobs, I’d like to join!

  2. kmanguru666 says:

    It’s all about the monnnnayyyyyyyyyyyyyy $$$$$$$$$$$$$$$$$$$$$ hahahahaha evil laugh evil laugh

  3. […] more good advice:try and do something different, watch your stress levels, take care of your health, try to keep […]

  4. […] work.  But for some people, that one job just is not enough.  In many instances, men and women take on a second position in order to provide some much needed additional income for their families.  Other times, though, […]

  5. CJ says:

    I have recently started a second job working overnight as a grocery stocker at a grocery store for about 30 hours a week. I also work at a gas station for 40 hours a week and go to school for about 16 hours a week. Plus I am married. lol So luckily I have a loving wife to use as motivation. But if at all possibly I’d love to here some extra tips other than sleep and nutrition.

  6. […] Money Under 30 has 10 good tips for making moonlighting work. Tags: abundance, friendship, inspiration, M.J. Ryan, Mity Nice, Motivation, multiple streams of income, slash career, Success tools, The economy, thrive, thriving […]

  7. ohToLiveInSanity says:

    while i did not work two jobs, i did work full time & go to school full time for graphic design. my major requires me to spend a little extra time on homework because we have projects to build or create such as a 24″x36″ painting or build a series of packages for advertising assignment. anywho, it was just like a second job to me because of the lack of sleep & the increased stress & number of commitments. let me tell u, i had a saturday class for 3 straight semesters & this class lasted for 5 hours and i just got off work 4 hours before. it was pure hellllllll. but when u have determination u get through it. no matter what. i knew of people who’s schedules were worse & they made it so that helped me to know that. always, always get sleep when u can. skip the facebooking, myspace, surfing the net. skip it & eat or sleep instead. feel like you’re missing out on hanging with friends? if u get a scheduled lunch break: meet a friend somewhere for lunch (or in between classes if your “2nd job” is actually school. have a support system, too. tell people, “hey i have class nearby, can i crash here for a nap so i dont have to drive all the way home & back in an hour?”. hope this helps.

  8. Should you take a second job? says:

    […] Su&#114&#118iging a second &#106o&#98 […]

  9. […] Money Under 30 discusses Surviving a Second Job: 10 Moonlighting Tips. If you need some extra income and are considering a 2nd job, be sure to read this post. […]

  10. Jason says:

    One more tip for choosing a second job… it’s not a bad idea to get something where you have the potential to make new friends. I balanced a record store job with several other full time jobs for some time, and I found that I wanted to hang onto the camaraderie of my co-workers more than I even wanted the money from the job! It was quite a benefit and it meant it felt less like “working” and more like “socializing,” even though I was building up my savings account at the time.

    However, I found something that DIDN’T work for me, also. I was a full-time realtor for awhile, and later found a perfect day full-time day job (since I was never terribly fond of real estate) but decided to continue realtoring part-time. It seemed it would be easy–you could just work your network and actually “work” only rarely, when something came up. The drawback was that “things”–which were very stressful and time consuming–had a way of coming up at the worst times, and eating up an entire weekend last-minute. If you’re serious about that kind of second job, you really have to be willing to cancel your weekend plans in favor of your lucrative second job. Plenty of people can do this but it wasn’t for me; I’m glad I no longer have to worry each time my cell phone rings that it’s a work call.

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