Are you considering getting an extra job to earn some extra income? You’re not alone—39% percent of workers ages 18-24 and 44% of workers ages 25-34 reported earning extra cash on the side.

The biggest reason to look for a second job? If you’re like many young adults, you may be facing student loan debt and wondering if the career you’ve chosen is going to be enough to pay the bills and set you up for the life you want 10, 20, and even 50 years from now.

So, where to start? For many of us in our 20s and 30s, the answer is to find side hustle jobs that can help us clear out debt in a fun way while not interfering with our career goals.

Sound like you? Then read on. If you can answer yes to the questions below about a potential side hustle gig, chances are it’s an income opportunity you should pursue.

5 Questions To Ask About Your Side Hustle Job

1. Is it flexible?

I’m betting this one ranks high. Flexibility is a big deal—especially if you’re at a point in your life where you have a full-time job that isn’t quite as flexible. You need a way to earn good money while still being able to work when it’s convenient for you. And you may also be juggling other commitments and responsibilities, so finding a side hustle job that you can do on your own schedule is important.


Interested in becoming a Wine Guide? Here are five good reasons you should join Traveling Vineyard.


One of our Traveling Vineyard Wine Guides came to our organization because she was trying to figure out how to make extra income herself. She had a career after college, but she was working for a boss she really didn’t like, and she wanted to be on her own schedule. She found that being a Wine Guide was not only a great way to supplement her full-time job—she actually turned her side hustle job into her full-time career! Now, she’s doing what she wants—on her own schedule—as her own boss.

2. Will I make more money than it costs me to do it?

Something many people don’t think about until it’s too late is that some side hustle jobs cost a lot just to get started. If you’re looking for a side hustle to make money, you don’t want to spend everything you’ll make just to get started (or each month after that to “pay back” your company).

Here are some practical questions to investigate:

  • How much of what you make will go back to the company?
  • How much does the starter kit cost?
  • Will you have to buy a ton of inventory to get started? What happens if it doesn’t sell?
  • Will you need any additional or specialized training before you start, and what is the cost?
  • Will you need permits or licenses?
  • Does it involve costly wear and tear on your vehicle or property?
3. Can I make enough to pay off debt?

Many millennials are looking for side hustle jobs specifically to pay off student loans and consumer debt.

Two stats from Forbes show why people are looking for side hustle ideas to make money: Student loan debt is now the second highest consumer debt category (behind only mortgage debt)—higher than both credit cards and auto loans. The average student who graduated in 2016 has $37,172 in student loan debt.

Instead of waiting decades to pay these loans or other debts back, students are taking the advice of financial advisors and taking on second and third jobs to do whatever they can to knock their debts out.

This is one reason Traveling Vineyard stands out. Our millennial Wine Guides choose to partner with Traveling Vineyard instead of other extra income opportunities because they can see the needle moving with every wine tasting they lead.

And they know that their friends, who tend to be foodies and wine enthusiasts, will be game to see what their side hustle is all about, too, whether as Hosts or Guests at a tasting or as Wine Guides themselves. It helps them in their quest toward financial freedom, and it’s fun—which leads us to the fourth question:

4. Is it something I’ll enjoy doing?

We are social creatures. But we all know this intrinsically—we don’t need a study to show us that being in community with others makes us feel good. Your side hustle job should give you the opportunity to:

  • Collaborate with like-minded people.
  • Learn from your peers.
  • Raise the “high-water mark” by surrounding yourself with people who teach you and help you improve.

Doing work we enjoy with people we like—even in a part-time setting—means we’re more likely to stick with a job. Culturally, that is one reason being a Wine Guide is so much fun.

Wine Guides definitely do hard work—but they get to do it while among friends. (Read some of their stories here.) They enjoy the social aspect of wine tastings without the pressure of doing work they don’t believe in or can’t enjoy. And it’s fun! Wine Guides are active across social media—Instagram, Facebook, and Twitter—because their excitement about their “jobs” naturally makes them want to share. And that leads to wider social circles with greater opportunities and new friendships!

5. Will it help me reach my goals?

Whether you’re looking to pay down debt, improve your financial security, meet new people, or do work that is meaningful, a side hustle job isn’t worth pursuing if it doesn’t help you reach your goals. And side hustle jobs that can do all of those things do exist!


Find a Wine Guide

Before you can place an order you’ll need to get a local wine guide, to help you with future purchases or to participate in wine tastings.