The benefits of working a second job are great. Extra income to help pay off debt or save is fantastic. Plus, it's added security in case you lose your primary job. You are still earning something to get you through.

The New York Times ran this piece about people working four or more jobs to pay the bills.

Not surprisingly, everybody in the story was under 30.

Nor was it surprising that hundreds of readers chimed in to say: “twentysomethings working multiple jobs? Duh!”

This piece is driving home points that you and I already know.

College grads of the last decade:

The following excerpt describes an aspiring actress who works more than four jobs to make ends meet. I think her story may not be all that unusual among twentysomethings:

LOUISE GASSMAN, 28, has a rotating schedule of multiple jobs: as an actress; as an assistant to dance instructors at the Circle in the Square and Juilliard schools; as a baby-sitter; and in a variety of administrative roles and as a spinning instructor at SoulCycle, an indoor cycling studio in New York.

Ms. Gassman’s monthly income, which can vary greatly depending on whether she books an acting job, ranges from $1,800 to $4,000. Some months, almost all of her income goes to the $1,450 rent on her 290-square-foot studio on the Upper West Side of Manhattan. Whatever is left after essentials goes toward paying off her remaining $16,000 in college loans.

“I worry about money all the time,” Ms. Gassman said. “I live on a really tight budget, and I live paycheck to paycheck.”

Periodically, the accountant who cuts her check at SoulCycle reminds her that someone her age should be putting away $300 a paycheck for retirement, an amount that is sometimes almost half of her pay. “I’m like, retirement?” she asks. “Then I have the ‘Oh my God, Oh my God’ feelings.”

I know many of you will immediately want to set Ms. Gassman straight.

  • “What are you doing living in a Manhattan studio on that kind of pay? Get roommates, or at least move to Jersey.”
  • “Please tell me you at least have an emergency fund? And health insurance!!”
  • “What do you expect for wanting to be an actress? Get a real job.”

But here’s the reality: while these things occur immediately to regular readers of personal finance blogs (like the accountant prosthelytizing for retirement contributions), most people do not think so pragmatically.

Most of us hate thinking about money, so we don’t

I can’t prove this. (Yet.) But there are indicators. Like the fact that over half of Americans couldn’t scrounge together $2,000 in an emergency if they had to.

I also suspect this because for the first half-decade of my adulthood, I was one of these people.

I was 22. Retirement wasn’t on my radar. Neither was health insurance. (Isn’t that for old, sick people?) Saving for tomorrow was something a few of my friends did, but they were math and business majors, and they graduated without debt. I was lucky to be working at all, and if I had money in my pocket for drinks on Friday night and a bus fare to visit my girlfriend, that’s all I needed.  When emergency expenses came up (and they did), well, that’s what credit cards are for, right?

This is how many, many people think. Especially in our twenties.

If you’re one of these people, you get it. But the problem is, you’re probably not reading my blog. Most of you who are reading have emergency funds and 5-figure IRAs at 25, and unless you’re reformed like me, the concept of ignoring your finances is alien. Confounding. Terrifying.

I wish more people who don’t think about their money would read this blog, but I can’t force them.

Getting personal finance advice is like going to AA. An alcoholic isn’t going to get sober until he’s ready to get sober. When that happens, AA is there for him. In the same way, when you realize you need to get a grip on your finances, personal finance blogs are here for you.  But we can’t force you to start an emergency fund any more than a concerned family member can force an addict to quit.

So what the hell does all this have to do with working multiple jobs?


Second jobs solve financial problems

When you can’t make ends meet and can no longer cut back, you must earn more money. And second jobs are the easiest way for most people to do that. Even if you’re totally unwilling to make a budget, cut back on spending, automate your savings, stop using credit cards, you can get at least get a second job.

The upside of Ms. Gassman’s situation is that she’s doing what it takes to pay her bills…working a crazy number of odd part-time jobs.

Not everybody is willing to do that.

But the ones that do get ahead.

Second jobs are what started me on the road out of debt and to financial security. And in one way or another, I’ve been working multiple jobs for the last five years.

In my mid-twenties, I worked nights and weekends at a Starbucks in addition to my 9-5 job. Later, when blogging grew into a business, I traded actual second jobs for self-employment in addition to my regular employment.

Later this month, I’m going to publish a post offering a behind-the-scenes look at what the business of blogging looks like and how I now make full-time money from this blog spending only a couple hours a week working on it. If you don’t believe me—I understand—I can still hardly believe it, too. But it’s true. (Subscribe if you don’t want to miss it.) In that post, I’m also going to explain why I still have a day job and why I have no intentions of leaving it.

But here’s a hint: Two incomes are better than one.

When you take on a second job, you get:

  • Extra money to pay down debt, start saving, or just get by.
  • Income diversification. You can lose one job and “still have something”.
  • Additional networks and career opportunities. Sometimes, an extra job may turn into something more.

Best Side Hustles

Now that you understand the benefit of getting a second income, here are some of the best side hustles to supplement those impulse buys and help you save for emergencies:


It’s a huge new industry, and it’s only getting bigger. If you have a car, you can make money on the side. It’s just sitting there anyway while you’re at work, so let your car earn its keep! Check out Uber or Lyft for some of the best rates and policies anywhere. These services also take the leg work out of ridesharing, matching you with passengers who are ideally suited for you.


Whether it’s babysitting at night, caring for the elderly on the weekends, or picking up kids from school, people will pay you a lot for these easy jobs that generally don’t take a lot of time.

Pet sitters/dog walkers

The only thing people love more than their kids are their pets. And people will pay astronomical amounts to have their four-legged friends cared for properly. If you have a penchant for furry friends, this could be a lucrative business for you. Imagine, you can charge $20 to go for a walk with one pup. Now, imagine you are taking five dogs at the same time: $20*5= $100 for the same walk you were taking anyway!

Household care and personal assistant

There are plenty of people who are just too busy to get basic tasks done on their own and are willing to pay well to have someone else do it for them. From picking up the groceries to tidying up after the morning rush or getting the mail organized, there are so many easy to do jobs that people will hand over to you for a price.

Like what you’re hearing? Here are some more side hustles that are easy to do and will earn you the extra cash you want.

The downside of working multiple jobs

Obviously, working multiple jobs requires the one resource more precious than money, our time.

I’m not saying go out and work 100 hours a week. Balance is important. But working 60 hours a week never killed anybody, especially when you’re young and/or single.

In my moonlighting days, I certainly felt a bit of a stigma to working two jobs. (In fact, I chose the Starbucks I worked at because it was a good 30 minutes away from my office; still, I occasionally bumped into a coworker there.) I’m under the impression this may have changed in light of how hard the economy’s been, which would be great. I’d love to hear your input in a comment—how much of a stigma is there to working multiple jobs or working service jobs with a college degree? Is it changing?

Why I’m telling you this

Simply put, today’s twentysomethings have lousy starting positions for life. Choosing to work multiple jobs for a defined period of time (when you’re young and have the time), is a great way to catapult yourself ahead.

Nobody should work their life away, and that’s not what I’m recommending.

BUT…a few extra hours on the clock today can get you out of debt faster or on track to saving faster. In short, it can pave the way to more secure future. Heck, if Louise Glassman keeps it up, she might even be able to sock something away for retirement.

What about you? Do you work multiple jobs? How’s it helped you? What are the drawbacks? Are there any stigmas to working more than one job or certain kind of jobs? Share your story in a comment.

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